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UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 10-Q

(Mark One)

☒ | QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the Quarterly Period Ended June 30, 2023

OR

☐ | TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the transition period from to

Commission File Number 000-24435

MICROSTRATEGY INCORPORATED

(Exact name of registrant as specified in its charter)

Delaware

(State or other jurisdiction of incorporation or organization)

51-0323571

(I.R.S. Employer

Identification Number)

1850 Towers Crescent Plaza, Tysons Corner, VA

(Address of Principal Executive Offices)

22182

(Zip Code)

(703) 848-8600

(Registrant’s telephone number, including area code)

Securities registered pursuant to Section 12(b) of the Act:

Title of Each Class |  | Trading Symbol |  | Name of Each Exchange on which Registered
Class A common stock, par value $0.001 per share |  | MSTR |  | The Nasdaq Global Select Market

Indicate by check mark whether the registrant,: (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☒ No ☐

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☒ No ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

Large accelerated filer | ☒ |  | Accelerated filer | ☐
Non-accelerated filer | ☐ |  | Smaller reporting company | ☐
|  |  | Emerging growth company | ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes ☐ No ☒

As of July 25, 2023, the registrant had 12,121,369 and 1,964,025 shares of class A common stock and class B common stock outstanding, respectively.

MICROSTRATEGY INCORPORATED

FORM 10-Q

TABLE OF CONTENTS

|  |  | Page
PART I. |  | FINANCIAL INFORMATION | 1
Item 1. |  | Financial Statements (unaudited) | 1
|  | Consolidated Balance Sheets as of June 30, 2023 and December 31, 2022 | 1
|  | Consolidated Statements of Operations for the Three and Six Months Ended June 30, 2023 and 2022 | 2
|  | Consolidated Statements of Comprehensive Income (Loss) for the Three and Six Months Ended June 30, 2023 and 2022 | 3
|  | Consolidated Statements of Stockholders’ Equity (Deficit) as of June 30, 2023 | 4
|  | Consolidated Statements of Cash Flows for the Six Months Ended June 30, 2023 and 2022 | 5
|  | Notes to Consolidated Financial Statements | 6
Item 2. |  | Management’s Discussion and Analysis of Financial Condition and Results of Operations | 23
Item 3. |  | Quantitative and Qualitative Disclosures About Market Risk | 44
Item 4. |  | Controls and Procedures | 44
PART II. |  | OTHER INFORMATION | 46
Item 1. |  | Legal Proceedings | 46
Item 1A. |  | Risk Factors | 46
Item 2. |  | Unregistered Sales of Equity Securities and Use of Proceeds | 73
Item 5. |  | Other Information | 73
Item 6. |  | Exhibits | 73

PART I - FINANCI AL INFORMATION

Item 1. Financi al Statements

MICROSTRATEGY INCORPORATED

CONSOLIDATED B ALANCE SHEETS

(in thousands, except per share data)

|  | June 30, |  |  | December 31, |
|  | 2023 |  |  | 2022 |
|  | (unaudited) |  |  |  |
Assets |  |  |  |  |  |
Current assets: |  |  |  |  |  |
Cash and cash equivalents |  | $ | 65,968 |  |  | $ | 43,835 |
Restricted cash |  |  | 2,085 |  |  |  | 7,033 |
Accounts receivable, net |  |  | 121,901 |  |  |  | 189,280 |
Prepaid expenses and other current assets |  |  | 19,680 |  |  |  | 24,418 |
Total current assets |  |  | 209,634 |  |  |  | 264,566 |
Digital assets |  |  | 2,323,252 |  |  |  | 1,840,028 |
Property and equipment, net |  |  | 30,507 |  |  |  | 32,311 |
Right-of-use assets |  |  | 58,264 |  |  |  | 61,299 |
Deposits and other assets |  |  | 22,421 |  |  |  | 23,916 |
Deferred tax assets, net |  |  | 719,026 |  |  |  | 188,152 |
Total assets |  | $ | 3,363,104 |  |  | $ | 2,410,272 |
Liabilities and Stockholders’ Equity (Deficit) |  |  |  |  |  |
Current liabilities: |  |  |  |  |  |
Accounts payable, accrued expenses, and operating lease liabilities |  | $ | 33,660 |  |  | $ | 42,976 |
Accrued compensation and employee benefits |  |  | 41,492 |  |  |  | 53,716 |
Accrued interest |  |  | 1,493 |  |  |  | 2,829 |
Current portion of long-term debt, net |  |  | 468 |  |  |  | 454 |
Deferred revenue and advance payments |  |  | 195,817 |  |  |  | 217,428 |
Total current liabilities |  |  | 272,930 |  |  |  | 317,403 |
Long-term debt, net |  |  | 2,177,974 |  |  |  | 2,378,560 |
Deferred revenue and advance payments |  |  | 11,244 |  |  |  | 12,763 |
Operating lease liabilities |  |  | 63,814 |  |  |  | 67,344 |
Other long-term liabilities |  |  | 17,826 |  |  |  | 17,124 |
Deferred tax liabilities |  |  | 198 |  |  |  | 198 |
Total liabilities |  |  | 2,543,986 |  |  |  | 2,793,392 |
Commitments and Contingencies |  |  |  |  |  |
Stockholders’ Equity (Deficit) |  |  |  |  |  |
Preferred stock undesignated, $0.001 par value; 5,000 shares authorized; no shares issued or outstanding |  |  | 0 |  |  |  | 0 |
Class A common stock, $0.001 par value; 330,000 shares authorized; 20,803 shares issued and 12,119 shares outstanding, and 18,269 shares issued and 9,585 shares outstanding, respectively |  |  | 21 |  |  |  | 18 |
Class B convertible common stock, $0.001 par value; 165,000 shares authorized; 1,964 shares issued and outstanding, and 1,964 shares issued and outstanding, respectively |  |  | 2 |  |  |  | 2 |
Additional paid-in capital |  |  | 2,559,268 |  |  |  | 1,841,120 |
Treasury stock, at cost; 8,684 shares and 8,684 shares, respectively |  |  | (782,104 | ) |  |  | (782,104 | )
Accumulated other comprehensive loss |  |  | (13,150 | ) |  |  | (13,801 | )
Accumulated deficit |  |  | (944,919 | ) |  |  | (1,428,355 | )
Total stockholders’ equity (deficit) |  |  | 819,118 |  |  |  | (383,120 | )
Total liabilities and stockholders’ equity (deficit) |  | $ | 3,363,104 |  |  | $ | 2,410,272 |

The accompanying notes are an integral part of these Consolidated Financial Statements.

1

MICROSTRATEGY INCORPORATED

CONSOLIDATED STATEM ENTS OF OPERATIONS

(in thousands, except per share data)

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
|  | (unaudited) |  |  | (unaudited) |  |  | (unaudited) |  |  | (unaudited) |
Revenues: |  |  |  |  |  |  |  |  |  |  |  |
Product licenses |  | $ | 15,522 |  |  | $ | 20,129 |  |  | $ | 32,934 |  |  | $ | 36,642 |
Subscription services |  |  | 19,878 |  |  |  | 14,017 |  |  |  | 38,688 |  |  |  | 26,862 |
Total product licenses and subscription services |  |  | 35,400 |  |  |  | 34,146 |  |  |  | 71,622 |  |  |  | 63,504 |
Product support |  |  | 66,081 |  |  |  | 66,521 |  |  |  | 131,562 |  |  |  | 133,672 |
Other services |  |  | 18,919 |  |  |  | 21,406 |  |  |  | 39,131 |  |  |  | 44,174 |
Total revenues |  |  | 120,400 |  |  |  | 122,073 |  |  |  | 242,315 |  |  |  | 241,350 |
Cost of revenues: |  |  |  |  |  |  |  |  |  |  |  |
Product licenses |  |  | 444 |  |  |  | 431 |  |  |  | 978 |  |  |  | 908 |
Subscription services |  |  | 7,216 |  |  |  | 5,498 |  |  |  | 15,072 |  |  |  | 10,908 |
Total product licenses and subscription services |  |  | 7,660 |  |  |  | 5,929 |  |  |  | 16,050 |  |  |  | 11,816 |
Product support |  |  | 5,816 |  |  |  | 5,127 |  |  |  | 11,584 |  |  |  | 10,318 |
Other services |  |  | 13,645 |  |  |  | 14,148 |  |  |  | 27,428 |  |  |  | 28,747 |
Total cost of revenues |  |  | 27,121 |  |  |  | 25,204 |  |  |  | 55,062 |  |  |  | 50,881 |
Gross profit |  |  | 93,279 |  |  |  | 96,869 |  |  |  | 187,253 |  |  |  | 190,469 |
Operating expenses: |  |  |  |  |  |  |  |  |  |  |  |
Sales and marketing |  |  | 37,660 |  |  |  | 36,862 |  |  |  | 73,766 |  |  |  | 70,102 |
Research and development |  |  | 29,354 |  |  |  | 31,790 |  |  |  | 60,712 |  |  |  | 65,313 |
General and administrative |  |  | 28,830 |  |  |  | 28,502 |  |  |  | 56,736 |  |  |  | 55,208 |
Digital asset impairment losses |  |  | 24,143 |  |  |  | 917,838 |  |  |  | 43,054 |  |  |  | 1,087,929 |
Total operating expenses |  |  | 119,987 |  |  |  | 1,014,992 |  |  |  | 234,268 |  |  |  | 1,278,552 |
Loss from operations |  |  | (26,708 | ) |  |  | (918,123 | ) |  |  | (47,015 | ) |  |  | (1,088,083 | )
Interest expense, net |  |  | (11,095 | ) |  |  | (13,187 | ) |  |  | (26,025 | ) |  |  | (24,226 | )
Gain on debt extinguishment |  |  | 0 |  |  |  | 0 |  |  |  | 44,686 |  |  |  | 0 |
Other (expense) income, net |  |  | (250 | ) |  |  | 5,120 |  |  |  | (1,693 | ) |  |  | 7,345 |
Loss before income taxes |  |  | (38,053 | ) |  |  | (926,190 | ) |  |  | (30,047 | ) |  |  | (1,104,964 | )
(Benefit from) provision for income taxes |  |  | (60,296 | ) |  |  | 136,108 |  |  |  | (513,483 | ) |  |  | 88,085 |
Net income (loss) |  | $ | 22,243 |  |  | $ | (1,062,298 | ) |  | $ | 483,436 |  |  | $ | (1,193,049 | )
Basic earnings (loss) per share (1) |  | $ | 1.68 |  |  | $ | (94.01 | ) |  | $ | 41.18 |  |  | $ | (105.64 | )
Weighted average shares outstanding used in computing basic earnings (loss) per share |  |  | 13,247 |  |  |  | 11,300 |  |  |  | 11,739 |  |  |  | 11,294 |
Diluted earnings (loss) per share (1) |  | $ | 1.52 |  |  | $ | (94.01 | ) |  | $ | 33.56 |  |  | $ | (105.64 | )
Weighted average shares outstanding used in computing diluted earnings (loss) per share |  |  | 16,095 |  |  |  | 11,300 |  |  |  | 14,534 |  |  |  | 11,294 |

(1) Basic and fully diluted earnings (loss) per share for class A and class B common stock are the same.

The accompanying notes are an integral part of these Consolidated Financial Statements.

2

MICROSTRATEGY INCORPORATED

CONSOLIDATED STATEMENTS OF COMPREHENSIVE INCOME (LOSS)

(in thousands)

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
|  | (unaudited) |  |  | (unaudited) |  |  | (unaudited) |  |  | (unaudited) |
Net income (loss) |  | $ | 22,243 |  |  | $ | (1,062,298 | ) |  | $ | 483,436 |  |  | $ | (1,193,049 | )
Other comprehensive (loss) income, net of applicable taxes: |  |  |  |  |  |  |  |  |  |  |  |
Foreign currency translation adjustment |  |  | (87 | ) |  |  | (4,113 | ) |  |  | 651 |  |  |  | (6,122 | )
Total other comprehensive (loss) income |  |  | (87 | ) |  |  | (4,113 | ) |  |  | 651 |  |  |  | (6,122 | )
Comprehensive income (loss) |  | $ | 22,156 |  |  | $ | (1,066,411 | ) |  | $ | 484,087 |  |  | $ | (1,199,171 | )

The accompanying notes are an integral part of these Consolidated Financial Statements.

3

MICROSTRATEGY INCORPORATED

CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (DEFICIT)

(in thousands, unaudited)

|  |  |  |  | Class A |  |  | Class B Convertible |  |  | Additional |  |  |  |  |  |  |  |  | Accumulated Other |  |  | (Accumulated Deficit) |
|  |  |  |  | Common Stock |  |  | Common Stock |  |  | Paid-in |  |  | Treasury Stock |  |  | Comprehensive |  |  | Retained |
|  | Total |  |  | Shares |  |  | Amount |  |  | Shares |  |  | Amount |  |  | Capital |  |  | Shares |  |  | Amount |  |  | Loss |  |  | Earnings |
Balance at January 1, 2022 |  | $ | 978,958 |  |  |  | 18,006 |  |  | $ | 18 |  |  |  | 1,964 |  |  | $ | 2 |  |  | $ | 1,727,143 |  |  |  | (8,684 | ) |  | $ | (782,104 | ) |  | $ | (7,543 | ) |  | $ | 41,442 |
Net loss |  |  | (130,751 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (130,751 | )
Other comprehensive loss |  |  | (2,009 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (2,009 | ) |  |  | 0 |
Issuance of class A common stock upon exercise of stock options |  |  | 288 |  |  |  | 2 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 288 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock under employee stock purchase plan |  |  | 2,805 |  |  |  | 7 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 2,805 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock upon vesting of restricted stock units, net of withholding taxes |  |  | (501 | ) |  |  | 3 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (501 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Share-based compensation expense |  |  | 14,209 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 14,209 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Balance at March 31, 2022 |  | $ | 862,999 |  |  |  | 18,018 |  |  | $ | 18 |  |  |  | 1,964 |  |  | $ | 2 |  |  | $ | 1,743,944 |  |  |  | (8,684 | ) |  | $ | (782,104 | ) |  | $ | (9,552 | ) |  | $ | (89,309 | )
Net loss |  |  | (1,062,298 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (1,062,298 | )
Other comprehensive loss |  |  | (4,113 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (4,113 | ) |  |  | 0 |
Issuance of class A common stock upon exercise of stock options |  |  | 423 |  |  |  | 3 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 423 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock upon vesting of restricted stock units, net of withholding taxes |  |  | (49 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (49 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Share-based compensation expense |  |  | 15,970 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 15,970 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Balance at June 30, 2022 |  | $ | (187,068 | ) |  |  | 18,021 |  |  | $ | 18 |  |  |  | 1,964 |  |  | $ | 2 |  |  | $ | 1,760,288 |  |  |  | (8,684 | ) |  | $ | (782,104 | ) |  | $ | (13,665 | ) |  | $ | (1,151,607 | )
Net loss |  |  | (27,079 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (27,079 | )
Other comprehensive loss |  |  | (4,514 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (4,514 | ) |  |  | 0 |
Issuance of class A common stock upon exercise of stock options |  |  | 621 |  |  |  | 4 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 621 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock under employee stock purchase plan |  |  | 1,668 |  |  |  | 9 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 1,668 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock upon vesting of restricted stock units, net of withholding taxes |  |  | (642 | ) |  |  | 4 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (642 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Share-based compensation expense |  |  | 16,725 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 16,725 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Balance at September 30, 2022 |  | $ | (200,289 | ) |  |  | 18,038 |  |  | $ | 18 |  |  |  | 1,964 |  |  | $ | 2 |  |  | $ | 1,778,660 |  |  |  | (8,684 | ) |  | $ | (782,104 | ) |  | $ | (18,179 | ) |  | $ | (1,178,686 | )
Net loss |  |  | (249,669 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (249,669 | )
Other comprehensive income |  |  | 4,378 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 4,378 |  |  |  | 0 |
Issuance of class A common stock upon exercise of stock options |  |  | 61 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 61 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock upon vesting of restricted stock units, net of withholding taxes |  |  | (1,021 | ) |  |  | 12 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (1,021 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock under public offerings, net of issuance costs |  |  | 46,219 |  |  |  | 219 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 46,219 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Share-based compensation expense |  |  | 17,201 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 17,201 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Balance at December 31, 2022 |  | $ | (383,120 | ) |  |  | 18,269 |  |  | $ | 18 |  |  |  | 1,964 |  |  | $ | 2 |  |  | $ | 1,841,120 |  |  |  | (8,684 | ) |  | $ | (782,104 | ) |  | $ | (13,801 | ) |  | $ | (1,428,355 | )
Net income |  |  | 461,193 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 461,193 |
Other comprehensive income |  |  | 738 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 738 |  |  |  | 0 |
Issuance of class A common stock upon exercise of stock options |  |  | 6,750 |  |  |  | 44 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 6,750 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock under employee stock purchase plan |  |  | 2,380 |  |  |  | 13 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 2,380 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock upon vesting of restricted stock units, net of withholding taxes |  |  | (514 | ) |  |  | 4 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (514 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock under public offerings, net of issuance costs |  |  | 338,962 |  |  |  | 1,349 |  |  |  | 2 |  |  |  | 0 |  |  |  | 0 |  |  |  | 338,960 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Share-based compensation expense |  |  | 16,822 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 16,822 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Balance at March 31, 2023 |  | $ | 443,211 |  |  |  | 19,679 |  |  | $ | 20 |  |  |  | 1,964 |  |  | $ | 2 |  |  | $ | 2,205,518 |  |  |  | (8,684 | ) |  | $ | (782,104 | ) |  | $ | (13,063 | ) |  | $ | (967,162 | )
Net income |  |  | 22,243 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 22,243 |
Other comprehensive loss |  |  | (87 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (87 | ) |  |  | 0 |
Issuance of class A common stock upon exercise of stock options |  |  | 5,354 |  |  |  | 39 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 5,354 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock upon vesting of restricted stock units, net of withholding taxes |  |  | (242 | ) |  |  | 6 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | (242 | ) |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Issuance of class A common stock under public offerings, net of issuance costs |  |  | 333,494 |  |  |  | 1,079 |  |  |  | 1 |  |  |  | 0 |  |  |  | 0 |  |  |  | 333,493 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Share-based compensation expense |  |  | 15,145 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 15,145 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Balance at June 30, 2023 |  | $ | 819,118 |  |  |  | 20,803 |  |  | $ | 21 |  |  |  | 1,964 |  |  | $ | 2 |  |  | $ | 2,559,268 |  |  |  | (8,684 | ) |  | $ | (782,104 | ) |  | $ | (13,150 | ) |  | $ | (944,919 | )

The accompanying notes are an integral part of these Consolidated Financial Statements.

4

MICROSTRATEGY INCORPORATED

CONSOLIDATED STATEM ENTS OF CASH FLOWS

(in thousands)

|  | Six Months Ended |
|  | June 30, |
|  | 2023 |  |  | 2022 |
|  | (unaudited) |  |  | (unaudited) |
Operating activities: |  |  |  |  |  |
Net income (loss) |  | $ | 483,436 |  |  | $ | (1,193,049 | )
Adjustments to reconcile net income (loss) to net cash provided by operating activities: |  |  |  |  |  |
Depreciation and amortization |  |  | 6,661 |  |  |  | 4,767 |
Reduction in carrying amount of right-of-use assets |  |  | 4,320 |  |  |  | 3,990 |
Credit losses and sales allowances |  |  | 438 |  |  |  | 606 |
Deferred taxes |  |  | (530,628 | ) |  |  | 76,109 |
Release of liabilities for unrecognized tax benefits |  |  | (102 | ) |  |  | 0 |
Share-based compensation expense |  |  | 33,049 |  |  |  | 29,688 |
Digital asset impairment losses |  |  | 43,054 |  |  |  | 1,087,929 |
Amortization of issuance costs on long-term debt |  |  | 4,400 |  |  |  | 4,297 |
Gain on debt extinguishment |  |  | (44,686 | ) |  |  | 0 |
Changes in operating assets and liabilities: |  |  |  |  |  |
Accounts receivable |  |  | 17,737 |  |  |  | 9,281 |
Prepaid expenses and other current assets |  |  | 4,861 |  |  |  | (7,077 | )
Deposits and other assets |  |  | 1,189 |  |  |  | (6,578 | )
Accounts payable and accrued expenses |  |  | (9,400 | ) |  |  | (10,216 | )
Accrued compensation and employee benefits |  |  | (15,559 | ) |  |  | (9,802 | )
Accrued interest |  |  | (1,336 | ) |  |  | 776 |
Deferred revenue and advance payments |  |  | 26,952 |  |  |  | 36,945 |
Operating lease liabilities |  |  | (5,233 | ) |  |  | (4,835 | )
Other long-term liabilities |  |  | (228 | ) |  |  | 32 |
Net cash provided by operating activities |  |  | 18,925 |  |  |  | 22,863 |
Investing activities: |  |  |  |  |  |
Purchases of digital assets |  |  | (526,278 | ) |  |  | (225,500 | )
Purchases of property and equipment |  |  | (1,138 | ) |  |  | (1,519 | )
Net cash used in investing activities |  |  | (527,416 | ) |  |  | (227,019 | )
Financing activities: |  |  |  |  |  |
Proceeds from secured term loan, net of lender fees |  |  | 0 |  |  |  | 204,693 |
Issuance costs paid for secured term loan, excluding lender fees |  |  | 0 |  |  |  | (107 | )
Repayments of secured term loan and third-party extinguishment costs |  |  | (160,033 | ) |  |  | 0 |
Proceeds from other long-term secured debt |  |  | 0 |  |  |  | 11,100 |
Issuance costs paid for other long-term secured debt |  |  | 0 |  |  |  | (174 | )
Repayments of other long-term secured debt |  |  | (254 | ) |  |  | 0 |
Proceeds from sale of common stock under public offerings |  |  | 676,068 |  |  |  | 0 |
Issuance costs paid related to sale of common stock under public offerings |  |  | (3,628 | ) |  |  | 0 |
Proceeds from exercise of stock options |  |  | 12,104 |  |  |  | 711 |
Proceeds from sales under employee stock purchase plan |  |  | 2,380 |  |  |  | 2,805 |
Payment of withholding tax on vesting of restricted stock units |  |  | (726 | ) |  |  | (541 | )
Net cash provided by financing activities |  |  | 525,911 |  |  |  | 218,487 |
Effect of foreign exchange rate changes on cash, cash equivalents, and restricted cash |  |  | (235 | ) |  |  | (3,224 | )
Net increase in cash, cash equivalents, and restricted cash |  |  | 17,185 |  |  |  | 11,107 |
Cash, cash equivalents, and restricted cash, beginning of period |  |  | 50,868 |  |  |  | 64,434 |
Cash, cash equivalents, and restricted cash, end of period |  | $ | 68,053 |  |  | $ | 75,541 |

The accompanying notes are an integral part of these Consolidated Financial Statements.

5

MICROSTRATEGY INCORPORATED

NOTES TO CONSOLIDATED FINANCIAL STATEMENTS

(unaudited)

(1) Summary of Significant Accounting Policies

(a) Basis of Presentation

The accompanying Consolidated Financial Statements of MicroStrategy Incorporated (“MicroStrategy” or the “Company”) are unaudited. In the opinion of management, all adjustments necessary for a fair statement of financial position and results of operations have been included. All such adjustments are of a normal recurring nature, unless otherwise disclosed. Interim results are not necessarily indicative of results for a full year.

The Consolidated Financial Statements and Notes to Consolidated Financial Statements are presented as required by the United States Securities and Exchange Commission (“SEC”) and do not contain certain information included in the Company’s annual financial statements and notes. These financial statements should be read in conjunction with the Company’s audited financial statements and the notes thereto filed with the SEC in the Company’s Annual Report on Form 10-K for the year ended December 31, 2022. There have been no significant changes in the Company’s accounting policies since December 31, 2022, except for those related to the Company’s new share-settled performance stock unit awards as described further in Note 8, Share-based Compensation, to the Consolidated Financial Statements.

The accompanying Consolidated Financial Statements include the accounts of the Company and its subsidiaries. All significant intercompany accounts and transactions have been eliminated in consolidation.

(2) Digital Assets

The Company accounts for its digital assets, which are comprised solely of bitcoin, as indefinite-lived intangible assets in accordance with Accounting Standards Codification (“ASC”) 350, Intangibles—Goodwill and Other. The Company’s digital assets are initially recorded at cost. Subsequently, they are measured at cost, net of any impairment losses incurred since acquisition. Impairment losses are recognized as “Digital asset impairment losses” in the Company’s Consolidated Statement of Operations in the period in which the impairment occurs. Gains (if any) are not recorded until realized upon sale, at which point they are presented net of any impairment losses in the Company’s Consolidated Statements of Operations. In determining the gain to be recognized upon sale, the Company calculates the difference between the sales price and carrying value of the specific bitcoins sold immediately prior to sale.

The following table summarizes the Company’s digital asset holdings (in thousands, except number of bitcoins), as of:

|  | June 30, |  |  | December 31, |
|  | 2023 |  |  | 2022 |
Approximate number of bitcoins held |  |  | 152,333 |  |  |  | 132,500 |
Digital assets carrying value |  | $ | 2,323,252 |  |  | $ | 1,840,028 |
Cumulative digital asset impairment losses |  | $ | 2,196,216 |  |  | $ | 2,153,162 |

The carrying value on the Company’s Consolidated Balance Sheet at each period-end represents the lowest fair value (based on Level 1 inputs in the fair value hierarchy) of the bitcoins at any time since their acquisition. Therefore, these fair value measurements were made during the period from their acquisition through June 30, 2023 or December 31, 2022, respectively, and not as of June 30, 2023 or December 31, 2022, respectively.

The following table summarizes the Company’s digital asset purchases and digital asset impairment losses (in thousands, except number of bitcoins) for the periods indicated. The Company did not sell any of its bitcoins during the three and six months ended June 30, 2023 or 2022, respectively.

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Approximate number of bitcoins purchased |  |  | 12,333 |  |  |  | 481 |  |  |  | 19,833 |  |  |  | 5,308 |
Digital asset purchases |  | $ | 347,003 |  |  | $ | 10,000 |  |  | $ | 526,278 |  |  | $ | 225,500 |
Digital asset impairment losses |  | $ | 24,143 |  |  | $ | 917,838 |  |  | $ | 43,054 |  |  | $ | 1,087,929 |

6

From time to time, the Company may be extended short-term credits from Coinbase or other execution partners to purchase bitcoin in advance of using cash funds in the Company’s trading account. The trade credits are due and payable in cash within days after they are extended. As of June 30, 2023, the Company had no outstanding trade credits payable.

As of June 30, 2023, approximately 15,264 of the bitcoins held by the Company, which had a carrying value of approximately $239.5 million on the Company’s Consolidated Balance Sheet as of June 30, 2023, serve as part of the collateral for the Company’s 6.125% Senior Secured Notes due 2028 (the “2028 Secured Notes”), as further described in Note 4, Long-term Debt, to the Consolidated Financial Statements. All of the Company’s bitcoins previously serving as collateral for a $205.0 million term loan (the “2025 Secured Term Loan”) issued to MacroStrategy LLC (“MacroStrategy”), a wholly-owned subsidiary of the Company, by Silvergate Bank (“Silvergate”) were released from collateral upon the repayment of the 2025 Secured Term Loan during the first quarter of 2023. Refer to Note 4, Long-term Debt, to the Consolidated Financial Statements for further details of the 2025 Secured Term Loan and its repayment.

(3) Contract Balances

The Company invoices its customers in accordance with billing schedules established in each contract. The Company’s rights to consideration from customers are presented separately in the Company’s Consolidated Balance Sheets depending on whether those rights are conditional or unconditional.

The Company presents unconditional rights to consideration from customers within “Accounts receivable, net” in its Consolidated Balance Sheets. All of the Company’s contracts are generally non-cancelable and/or non-refundable, and therefore an unconditional right generally exists when the customer is billed or amounts are billable per the contract.

Accounts receivable (in thousands) consisted of the following, as of:

|  | June 30, |  |  | December 31, |
|  | 2023 |  |  | 2022 |
Billed and billable |  | $ | 124,595 |  |  | $ | 191,844 |
Less: allowance for credit losses |  |  | (2,694 | ) |  |  | (2,564 | )
Accounts receivable, net |  | $ | 121,901 |  |  | $ | 189,280 |

Changes in the allowance for credit losses were not material for the three and six months ended June 30, 2023.

Rights to consideration that are subject to a condition other than the passage of time are considered contract assets until they are expected to become unconditional and transfer to accounts receivable. Current contract assets included in “Prepaid expenses and other current assets” in the Consolidated Balance Sheets consist of $0.9 million and $0.6 million, as of June 30, 2023 and December 31, 2022, respectively, related to accrued sales and usage-based royalty revenue and performance obligations or services being rendered in advance of future invoicing associated with multi-year contracts. In royalty-based arrangements, consideration is not billed or billable until the royalty reporting is received, generally in the subsequent quarter, at which time the contract asset transfers to accounts receivable and a true-up adjustment is recorded to revenue. These true-up adjustments are generally not material. Non-current contract assets included in “Deposits and other assets” in the Consolidated Balance Sheets consisted of $1.1 million and $0.7 million, as of June 30, 2023 and December 31, 2022, respectively, related to performance obligations or services being rendered in advance of future invoicing associated with multi-year contracts. During the three and six months ended June 30, 2023 and 2022, there were no significant impairments to the Company’s contract assets, nor were there any significant changes in the timing of the Company’s contract assets being reclassified to accounts receivable.

Contract liabilities are amounts received or due from customers in advance of the Company transferring the software or services to the customer. In the case of multi-year service contract arrangements, the Company generally does not invoice more than one year in advance of services and does not record deferred revenue for amounts that have not been invoiced. Revenue is subsequently recognized in the period(s) in which control of the software or services is transferred to the customer. The Company’s contract liabilities are presented as either current or non-current “Deferred revenue and advance payments” in the Consolidated Balance Sheets, depending on whether the software or services are expected to be transferred to the customer within the next year.

The Company’s “Accounts receivable, net” and “Deferred revenue and advance payments” balances in the Consolidated Balance Sheets include unpaid amounts related to contracts under which the Company has an enforceable right to invoice the customer for non-cancelable and/or non-refundable software and services. Changes in accounts receivable and changes in deferred revenue and advance payments are presented net of these unpaid amounts in “Operating activities” in the Consolidated Statements of Cash Flows.

7

Deferred revenue and advance payments (in thousands) from customers consisted of the following, as of:

|  | June 30, |  |  | December 31, |
|  | 2023 |  |  | 2022 |
Current: |  |  |  |  |  |
Deferred product licenses revenue |  | $ | 974 |  |  | $ | 2,825 |
Deferred subscription services revenue |  |  | 49,898 |  |  |  | 51,861 |
Deferred product support revenue |  |  | 141,605 |  |  |  | 155,366 |
Deferred other services revenue |  |  | 3,340 |  |  |  | 7,376 |
Total current deferred revenue and advance payments |  | $ | 195,817 |  |  | $ | 217,428 |
Non-current: |  |  |  |  |  |
Deferred product licenses revenue |  | $ | 2,493 |  |  | $ | 2,742 |
Deferred subscription services revenue |  |  | 2,888 |  |  |  | 3,030 |
Deferred product support revenue |  |  | 5,340 |  |  |  | 6,387 |
Deferred other services revenue |  |  | 523 |  |  |  | 604 |
Total non-current deferred revenue and advance payments |  | $ | 11,244 |  |  | $ | 12,763 |

During the three and six months ended June 30, 2023, the Company recognized revenues of $62.3 million and $143.1 million, respectively, from amounts included in the total deferred revenue and advance payments balances at the beginning of 2023. During the three and six months ended June 30, 2022, the Company recognized revenues of $58.9 million and $133.8 million, respectively, from amounts included in the total deferred revenue and advance payments balances at the beginning of 2022. For the three and six months ended June 30, 2023 and 2022, there were no significant changes in the timing of revenue recognition on the Company’s deferred balances.

The Company’s remaining performance obligation represents all future revenue under contract and includes deferred revenue and advance payments and billable non-cancelable amounts that will be invoiced and recognized as revenue in future periods. The remaining performance obligation excludes contracts that are billed in arrears, such as certain time and materials contracts. The portions of multi-year contracts that will be invoiced in the future are not presented on the balance sheet within accounts receivable and deferred revenues and are instead included in the following remaining performance obligation disclosure. As of June 30, 2023, the Company had an aggregate transaction price of $294.3 million allocated to the remaining performance obligation related to product support, subscription services, product licenses, and other services contracts. The Company expects to recognize $229.1 million within the next 12 months and the remainder thereafter.

(4) Long-term Debt

The net carrying value of the Company’s long-term debt (in thousands) consisted of the following, as of:

|  | June 30, 2023 |  |  | December 31, 2022 |
2025 Convertible Notes |  | $ | 642,405 |  |  | $ | 640,888 |
2027 Convertible Notes |  |  | 1,035,290 |  |  |  | 1,033,277 |
2028 Secured Notes |  |  | 490,356 |  |  |  | 489,547 |
2025 Secured Term Loan |  |  | 0 |  |  |  | 204,688 |
Other long-term secured debt |  |  | 9,923 |  |  |  | 10,160 |
Total |  | $ | 2,177,974 |  |  | $ | 2,378,560 |

Convertible Senior Notes

In December 2020, the Company issued $650.0 million aggregate principal amount of 0.750% Convertible Senior Notes due 2025 (the “2025 Convertible Notes”) in a private offering. The 2025 Convertible Notes are senior unsecured obligations of the Company and bear interest at a fixed rate of 0.750% per annum, payable semiannually in arrears on June 15 and December 15 of each year, beginning on June 15, 2021. Holders of the 2025 Convertible Notes may receive additional interest under specified circumstances as outlined in the indenture relating to the issuance of the 2025 Convertible Notes. The 2025 Convertible Notes will mature on December 15, 2025, unless earlier converted, redeemed, or repurchased in accordance with their terms.

In February 2021, the Company issued $1.050 billion aggregate principal amount of 0% Convertible Senior Notes due 2027 (the “2027 Convertible Notes”) in a private offering. The 2027 Convertible Notes are senior unsecured obligations of the Company and do not bear regular interest. However, holders of the 2027 Convertible Notes may receive special interest under specified circumstances as outlined

8

in the indenture relating to the issuance of the 2027 Convertible Notes. Any special interest is payable semiannually in arrears on February 15 and August 15 of each year, beginning on August 15, 2021. The 2027 Convertible Notes will mature on February 15, 2027, unless earlier converted, redeemed, or repurchased in accordance with their terms.

The terms of the 2025 Convertible Notes and 2027 Convertible Notes (collectively, the “Convertible Notes”) are discussed more fully in Note 8, Long-term Debt, to the Consolidated Financial Statements of the Company’s Annual Report on Form 10-K for the year ended December 31, 2022.

There have been no adjustments to the initial conversion rates for each of the Convertible Notes as of June 30, 2023. As of June 30, 2023, the maximum number of shares into which the Convertible Notes could be potentially converted if the conversion features are triggered are 1,633,190 and 733,005 shares for the 2025 Convertible Notes and 2027 Convertible Notes, respectively.

During the six months ended June 30, 2023, the 2025 Convertible Notes were not convertible at any time. During the six months ended June 30, 2022, the 2025 Convertible Notes were convertible at the option of the holders of the 2025 Convertible Notes during the first quarter of 2022 only. During the six months ended June 30, 2023 and 2022, the 2027 Convertible Notes were not convertible at any time. No conversions of the Convertible Notes occurred during the six months ended June 30, 2023 or 2022. The Convertible Notes may be convertible in future periods if one or more of the conversion conditions is satisfied during future measurement periods.

As of June 30, 2023 and December 31, 2022, the net carrying value of the Convertible Notes was classified as a long-term liability in the “Long-term debt, net” line item in the Company’s Consolidated Balance Sheets.

The following is a summary of the Company’s convertible debt instruments as of June 30, 2023 (in thousands):

|  | June 30, 2023
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2025 Convertible Notes |  | $ | 650,000 |  |  | $ | (7,595 | ) |  | $ | 642,405 |  |  | $ | 710,232 |  |  | Level 2
2027 Convertible Notes |  |  | 1,050,000 |  |  |  | (14,710 | ) |  |  | 1,035,290 |  |  |  | 672,000 |  |  | Level 2
Total |  | $ | 1,700,000 |  |  | $ | (22,305 | ) |  | $ | 1,677,695 |  |  | $ | 1,382,232 |  |  |

The following is a summary of the Company’s convertible debt instruments as of December 31, 2022 (in thousands):

|  | December 31, 2022
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2025 Convertible Notes |  | $ | 650,000 |  |  | $ | (9,112 | ) |  | $ | 640,888 |  |  | $ | 364,000 |  |  | Level 2
2027 Convertible Notes |  |  | 1,050,000 |  |  |  | (16,723 | ) |  |  | 1,033,277 |  |  |  | 394,800 |  |  | Level 2
Total |  | $ | 1,700,000 |  |  | $ | (25,835 | ) |  | $ | 1,674,165 |  |  | $ | 758,800 |  |  |

The fair value of the Convertible Notes is determined using observable market data other than quoted prices, specifically the last traded price at the end of the reporting period of identical instruments in the over-the-counter market (Level 2).

For the three months ended June 30, 2023 and 2022, interest expense related to the Convertible Notes was as follows (in thousands):

|  | Three Months Ended June 30, 2023 |  |  | Three Months Ended June 30, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2025 Convertible Notes |  | $ | 1,219 |  |  | $ | 760 |  |  | $ | 1,979 |  |  | $ | 1,219 |  |  | $ | 750 |  |  | $ | 1,969 |
2027 Convertible Notes |  |  | 0 |  |  |  | 1,007 |  |  |  | 1,007 |  |  |  | 0 |  |  |  | 1,003 |  |  |  | 1,003 |
Total |  | $ | 1,219 |  |  | $ | 1,767 |  |  | $ | 2,986 |  |  | $ | 1,219 |  |  | $ | 1,753 |  |  | $ | 2,972 |

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For the six months ended June 30, 2023 and 2022, interest expense related to the Convertible Notes was as follows (in thousands):

|  | Six Months Ended June 30, 2023 |  |  | Six Months Ended June 30, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2025 Convertible Notes |  | $ | 2,438 |  |  | $ | 1,517 |  |  | $ | 3,955 |  |  | $ | 2,438 |  |  | $ | 1,498 |  |  | $ | 3,936 |
2027 Convertible Notes |  |  | 0 |  |  |  | 2,013 |  |  |  | 2,013 |  |  |  | 0 |  |  |  | 2,005 |  |  |  | 2,005 |
Total |  | $ | 2,438 |  |  | $ | 3,530 |  |  | $ | 5,968 |  |  | $ | 2,438 |  |  | $ | 3,503 |  |  | $ | 5,941 |

For each of the three and six months ended June 30, 2023, the Company paid $2.4 million in interest related to the 2025 Convertible Notes. For each of the three and six months ended June 30, 2022, the Company paid $2.4 million in interest related to the 2025 Convertible Notes. The Company has no t paid any additional interest or special interest related to the 2025 Convertible Notes or the 2027 Convertible Notes, respectively, to date.

Senior Secured Notes

On June 14, 2021, the Company issued $500.0 million aggregate principal amount of 2028 Secured Notes in a private offering. The 2028 Secured Notes bear interest at a fixed rate of 6.125% per annum, payable semiannually in arrears on June 15 and December 15 of each year, beginning on December 15, 2021. The 2028 Secured Notes have a stated maturity date of June 15, 2028, unless earlier redeemed or repurchased in accordance with their terms and subject to a springing maturity date of September 15, 2025 or November 16, 2026 as discussed further below.

The 2028 Secured Notes include a springing maturity feature that will cause the stated maturity date to spring ahead to: (1) September 15, 2025 (the “First Springing Maturity Date”), unless on the First Springing Maturity Date (i) the Company has Liquidity (as defined in the 2028 Secured Notes Indenture) in excess of 130% of the amount required to pay in full in cash the then outstanding aggregate principal amount of, and accrued interest on, the 2025 Convertible Notes or (ii) less than $100,000,000 of the aggregate principal amount of the 2025 Convertible Notes remains outstanding, (2) November 16, 2026 (the “Second Springing Maturity Date”), unless on the Second Springing Maturity Date (i) the Company has Liquidity in excess of 130% of the amount required to pay in full in cash the then outstanding aggregate principal amount of, and accrued interest on, the 2027 Convertible Notes or (ii) less than $100,000,000 of the aggregate principal amount of the 2027 Convertible Notes remains outstanding, or (3) the date (such date, an “FCCR Springing Maturity Date”) that is 91 days prior to the maturity date of any future convertible debt that we may issue that is then outstanding (the “FCCR Convertible Indebtedness”), unless on the FCCR Springing Maturity Date (i) the Company has Liquidity in excess of 130% of the amount required to pay in full in cash the then outstanding aggregate principal amount of and accrued interest on such FCCR Convertible Indebtedness or (ii) less than $100,000,000 of the aggregate principal amount of such FCCR Convertible Indebtedness remains outstanding. As of June 30, 2023, for purposes of calculating Liquidity, the Company and its Restricted Subsidiaries (as defined in the indenture for the 2028 Secured Notes) owned approximately 92,079 unencumbered Existing Digital Assets (as defined in the indenture for the 2028 Secured Notes).

The terms of the 2028 Secured Notes are discussed more fully in Note 8, Long-term Debt, to the Consolidated Financial Statements of the Company’s Annual Report on Form 10-K for the year ended December 31, 2022.

The 2028 Secured Notes are governed by an indenture containing certain covenants with which the Company must comply, including covenants with respect to limitations on (i) additional indebtedness, (ii) liens, (iii) certain payments and investments, (iv) the ability to merge or consolidate with another person, or sell or otherwise dispose of substantially all the Company’s assets, and (v) certain transactions with affiliates. The Company was in compliance with its debt covenants as of June 30, 2023.

As of June 30, 2023 and December 31, 2022, the net carrying value of the 2028 Secured Notes was classified as a long-term liability in the “Long-term debt, net” line item in the Company’s Consolidated Balance Sheets.

The following is a summary of the 2028 Secured Notes as of June 30, 2023 (in thousands):

|  | June 30, 2023
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2028 Secured Notes |  | $ | 500,000 |  |  | $ | (9,644 | ) |  | $ | 490,356 |  |  | $ | 448,835 |  |  | Level 2

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The following is a summary of the 2028 Secured Notes as of December 31, 2022 (in thousands):

|  | December 31, 2022
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2028 Secured Notes |  | $ | 500,000 |  |  | $ | (10,453 | ) |  | $ | 489,547 |  |  | $ | 369,800 |  |  | Level 2

The fair value of the 2028 Secured Notes is determined using observable market data other than quoted prices, specifically the last traded price at the end of the reporting period of identical instruments in the over-the-counter market (Level 2).

For the three months ended June 30, 2023 and 2022, interest expense related to the 2028 Secured Notes was as follows (in thousands):

|  | Three Months Ended June 30, 2023 |  |  | Three Months Ended June 30, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2028 Secured Notes |  | $ | 7,656 |  |  | $ | 408 |  |  | $ | 8,064 |  |  | $ | 7,656 |  |  | $ | 382 |  |  | $ | 8,038 |

For the six months ended June 30, 2023 and 2022, interest expense related to the 2028 Secured Notes was as follows (in thousands):

|  | Six Months Ended June 30, 2023 |  |  | Six Months Ended June 30, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2028 Secured Notes |  | $ | 15,312 |  |  | $ | 809 |  |  | $ | 16,121 |  |  | $ | 15,312 |  |  | $ | 758 |  |  | $ | 16,070 |

For each of the three and six months ended June 30, 2023, the Company paid $15.3 million in interest related to the 2028 Secured Notes. For each of the three and six months ended June 30, 2022, the Company paid $15.3 million in interest related to the 2028 Secured Notes.

Secured Term Loan

On March 23, 2022, MacroStrategy, a wholly-owned subsidiary of the Company, entered into a Credit and Security Agreement (the “Credit and Security Agreement”) with Silvergate pursuant to which Silvergate issued the $205.0 million 2025 Secured Term Loan to MacroStrategy. The terms of the 2025 Secured Term Loan are discussed more fully in Note 8, Long-term Debt, to the Consolidated Financial Statements of the Company’s Annual Report on Form 10-K for the year ended December 31, 2022. On March 24, 2023, MacroStrategy and Silvergate entered into a Prepayment, Waiver and Payoff to Credit and Security Agreement, pursuant to which MacroStrategy voluntarily prepaid Silvergate approximately $161.0 million (the “Payoff Amount”), in full repayment, satisfaction, and discharge of the 2025 Secured Term Loan and all other obligations under the Credit and Security Agreement. Upon Silvergate’s receipt of the Payoff Amount on March 24, 2023, the Credit and Security Agreement was terminated and Silvergate released its security interest in all of MacroStrategy’s assets collateralizing the 2025 Secured Term Loan, including the bitcoin that was serving as collateral.

The Payoff Amount consisted of a $159.9 million payment to repay the full $205.0 million outstanding principal amount of the 2025 Secured Term Loan as of March 24, 2023 and a $1.1 million payment for accrued unpaid interest on the 2025 Secured Term Loan as of March 24, 2023. The Company also incurred $0.1 million in third party fees in connection with the repayment of the 2025 Secured Term Loan. The net carrying value of the 2025 Secured Term Loan as of March 24, 2023, immediately prior to the loan’s repayment, was $204.7 million, which resulted in a $44.7 million gain on debt extinguishment recognized in the Company’s Consolidated Statement of Operations in the first quarter of 2023.

MacroStrategy previously maintained a $5.0 million cash reserve account (the “Reserve Account”) with Silvergate to serve as additional collateral for the 2025 Secured Term Loan. On March 24, 2023, the $5.0 million then held in the Reserve Account was applied against the Payoff Amount, reducing the amount of additional funds that were required to be paid by MacroStrategy to Silvergate in connection with the payoff of the 2025 Secured Term Loan.

As of December 31, 2022, the net carrying value of the 2025 Secured Term Loan was classified as a long-term liability in the “Long-term debt, net” line item in the Company’s Consolidated Balance Sheet.

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The following is a summary of the 2025 Secured Term Loan as of December 31, 2022 (in thousands):

|  | December 31, 2022
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2025 Secured Term Loan |  | $ | 205,000 |  |  | $ | (312 | ) |  | $ | 204,688 |  |  | $ | 205,000 |  |  | Level 3

The outstanding principal amount of the 2025 Secured Term Loan approximated its fair value as of December 31, 2022 as the 2025 Secured Term Loan bore interest at a floating rate and was over-collateralized (the Company was required to maintain an LTV ratio of less than 50%). Additionally, the Company had approximately 82,991 unencumbered bitcoins that were available to be pledged as additional collateral at December 31, 2022.

No interest expense related to the 2025 Secured Term Loan was recognized after the debt was repaid in full during the first quarter of 2023. For the six months ended June 30, 2023, interest expense related to the 2025 Secured Term Loan was as follows (in thousands):

|  | Six Months Ended June 30, 2023 |
|  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2025 Secured Term Loan |  | $ | 3,781 |  |  | $ | 31 |  |  | $ | 3,812 |

For the three and six months ended June 30, 2022, interest expense related to the 2025 Secured Term Loan was as follows (in thousands):

|  | Three Months Ended June 30, 2022 |  |  | Six Months Ended June 30, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2025 Secured Term Loan |  | $ | 2,207 |  |  | $ | 33 |  |  | $ | 2,240 |  |  | $ | 2,383 |  |  | $ | 36 |  |  | $ | 2,419 |

The Company paid a final $5.1 million in interest related to the 2025 Secured Term Loan during the first quarter of 2023, $1.1 million of which was included in the Payoff Amount. The Company paid $1.6 million in interest related to the 2025 Secured Term Loan during each of the three and six months ended June 30, 2022.

Other long-term secured debt

In June 2022, the Company, through a wholly-owned subsidiary, entered into a secured term loan agreement in the amount of $11.1 million, bearing interest at an annual rate of 5.2%, and maturing in June 2027. The loan is secured by certain non-bitcoin assets of the Company that are not otherwise serving as collateral for any of the Company’s other indebtedness. As of June 30, 2023, the loan had a net carrying value of $10.4 million and an outstanding principal balance of $10.6 million, after monthly payments made under the terms of the agreement. As of June 30, 2023, $0.5 million of the net carrying value is short-term and is presented in “Current portion of long-term debt, net” in the Consolidated Balance Sheet.

Maturities

The following table shows the maturities of the Company’s debt instruments as of June 30, 2023 (in thousands). The principal payments related to the 2028 Secured Notes are included in the table below based on the First Springing Maturity Date of September 15, 2025, as if the springing maturity feature discussed above were triggered. As of June 30, 2023, the Company expects to be able to satisfy the requirements in the 2028 Secured Notes Indenture to avoid triggering the springing maturity feature of the 2028 Secured Notes.

Payments due by period ended June 30, |  | 2025 Convertible Notes |  |  | 2027 Convertible Notes |  |  | 2028 Secured Notes |  |  | Other long-term secured debt |  |  | Total |
2024 |  | $ | 0 |  |  | $ | 0 |  |  | $ | 0 |  |  | $ | 525 |  |  | $ | 525 |
2025 |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 555 |  |  |  | 555 |
2026 |  |  | 650,000 |  |  |  | 0 |  |  |  | 500,000 |  |  |  | 584 |  |  |  | 1,150,584 |
2027 |  |  | 0 |  |  |  | 1,050,000 |  |  |  | 0 |  |  |  | 8,937 |  |  |  | 1,058,937 |
2028 |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Thereafter |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Total |  | $ | 650,000 |  |  | $ | 1,050,000 |  |  | $ | 500,000 |  |  | $ | 10,601 |  |  | $ | 2,210,601 |

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(5) Commitments and Contingencies

(a) Commitments

From time to time, the Company enters into certain types of contracts that require it to indemnify parties against third-party claims. These contracts primarily relate to agreements under which the Company assumes indemnity obligations for intellectual property infringement, as well as other obligations from time to time depending on arrangements negotiated with customers and other third parties. The conditions of these obligations vary. Thus, the overall maximum amount of the Company’s indemnification obligations cannot be reasonably estimated. Historically, the Company has not been obligated to make significant payments for these obligations and does not currently expect to incur any material obligations in the future. Accordingly, the Company has not recorded an indemnification liability on its Consolidated Balance Sheets as of June 30, 2023 or December 31, 2022.

(b) Contingencies

Following an internal review initiated in 2018, the Company believes that its Brazilian subsidiary failed or likely failed to comply with local procurement regulations in conducting business with certain Brazilian government entities.

On February 6, 2020, the Company learned that a Brazilian court authorized the Brazilian Federal Police to use certain investigative measures in its investigation into alleged corruption and procurement fraud involving certain government officials, pertaining to a particular transaction. The transaction at issue is part of the basis of the previously reported failure or likely failure of the Company’s Brazilian subsidiary to comply with local procurement regulations. The Company is not aware of any allegations that any former employee or the Company made any payments to Brazilian government officials. The Brazilian Federal Police expanded the investigation to include other possible cases of procurement fraud involving Brazilian government entities. Criminal penalties may be imposed against individuals; however, neither employees of the Company’s Brazilian subsidiary nor the subsidiary itself have been targets of the Federal Police investigation.

The Company has also learned that Brazil’s Federal Comptroller General filed an administrative action against the Company’s Brazilian subsidiary with respect to the alleged procurement violations. These matters remain the subject of investigation by Brazilian authorities. The Company is taking measures to attempt to resolve these matters.

On January 18, 2023, Brazil’s General Superintendence of the Administrative Council for Economic Defense (“SG/CADE”) launched an administrative proceeding to investigate potentially anticompetitive conduct, naming various individuals and companies as defendants including the Company’s Brazilian subsidiary. The proceeding involves conduct relating to transactions with certain Brazilian public and private entities that is part of the basis of the foregoing failure or likely failure of the Brazilian subsidiary to comply with local procurement regulations. The proceeding was precipitated by the Company’s Brazilian subsidiary’s voluntary disclosure of information to SG/CADE that arose out of the internal review initiated in 2018, and the Company’s Brazilian subsidiary has secured a leniency agreement with SG/CADE. If at the end of the proceeding, CADE’s Tribunal confirms that the leniency agreement obligations have been fulfilled, the Company’s Brazilian subsidiary will receive full immunity from fines.

The Company believes that a loss is probable in connection with these Brazilian matters. In the second quarter of 2023, the Company was able to reasonably estimate a minimum loss of $1.2 million in respect of these matters and accrued $1.0 million in its consolidated financial statements for the three months ended June 30, 2023, which amount is in addition to the $0.2 million it had previously accrued with respect to such matters. However, given the stage of these matters, the Company remains unable to reasonably estimate a range of loss beyond such minimum loss at this time. The aggregate accrued amount for these matters is included as a component of “Accounts payable, accrued expenses, and operating lease liabilities” in the Consolidated Balance Sheet as of June 30, 2023. The final outcome of these matters may result in a loss that is significantly greater than this accrued amount. Any loss associated with the final outcome of these matters may result in a material impact on the Company’s earnings and financial results for the period in which any such additional liability is accrued. However, the Company believes that any loss associated with the final outcome of these matters will not have a material effect on the Company’s financial position.

On November 4, 2020, a complaint was filed against the Company in the U.S. District Court for the Eastern District of Virginia by a patent assertion entity called Daedalus Blue, LLC (“Daedalus”). In its complaint, Daedalus alleges that the Company has infringed U.S. Patent Nos. 8,341,172 (the “’172 Patent”) and 9,032,076 (the “’076 Patent”) based on specific functionality in the MicroStrategy platform. The ’172 Patent relates to a method for providing aggregate data access in response to a query, whereas the ’076 Patent relates to a role-based access control system.

On March 1, 2021, Daedalus provided its formal infringement contentions which included additional accused functionality as part of its infringement allegations from the complaint, materially expanding the scope of its case. The Company has filed a motion to dismiss the complaint with prejudice, asking the court to rule that the asserted claims are invalid as being directed to patent ineligible matter. The

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court conducted a claim construction hearing on July 15, 2021. The court appointed a special master on October 28, 2021 and directed the special master to submit a Report and Recommendation as to the issue of claim construction and the pending motion to dismiss by February 1, 2022. On January 21, 2022, the special master issued two separate Reports and Recommendations. The first Report and Recommendation recommended constructions of certain patent claim terms and the second Report and Recommendation recommended, without reaching the merits, dismissing the Company’s motion to dismiss without prejudice to re-filing after discovery ends. The parties filed their respective objections to the special master’s Reports and Recommendations on February 4, 2022, and their oppositions to the other party’s objections on February 18, 2022. On March 9, 2022, the court issued an order overruling all parties’ objections and adopting the special master’s Reports and Recommendations in full. As per court order, the parties submitted a joint proposed schedule, which the court adopted on April 7, 2022, providing new deadlines for the close of fact discovery, expert reports, expert discovery, and dispositive motions. Fact discovery reopened on April 18, 2022 and closed on June 1, 2022. In July 2022, the case proceeded to expert discovery and the parties exchanged their opening expert reports on issues for which they bear the burden of proof on July 1, 2022, their rebuttal reports on July 29, 2022, and their reply reports on August 12, 2022. The parties engaged in expert depositions the weeks of August 22 and August 29, 2022. On September 21, 2022, the parties filed their respective motions for summary judgment, and on October 12, 2022 and October 19, 2022, the parties filed their opposition and reply briefs. The court also re-appointed the special master to assist in addressing the parties’ motions for summary judgment and other pending pre-trial motions. The special master has provided his Reports and Recommendations for the parties’ evidentiary motions and summary judgment motions. The court also ordered a mediation, which the Company expects to occur in August 2023. The outcome of this matter is not presently determinable.

On August 31, 2022, the District of Columbia (the “District”), through its Office of the Attorney General, filed a civil complaint in the Superior Court of the District of Columbia naming as defendants (i) Michael J. Saylor, the Chairman of the Company’s Board of Directors and the Company’s Executive Chairman, in his personal capacity, and (ii) the Company. The District sought, among other relief, monetary damages under the District’s False Claims Act for the alleged failure of Mr. Saylor to pay personal income taxes to the District over a number of years together with penalties, interest, and treble damages. The complaint alleged that the amount of personal income taxes purportedly involved was more than $25 million. The complaint also alleged in the sole claim against the Company that it violated the District’s False Claims Act by conspiring to assist Mr. Saylor’s alleged failure to pay personal income taxes. On October 26, 2022, the Company filed a motion to dismiss the District’s complaint. On February 28, 2023, the court ruled on the motion to dismiss, dismissing the sole claim against the Company as well as a claim against Mr. Saylor alleging that Mr. Saylor violated the District’s False Claims Act. The court did not dismiss claims against Mr. Saylor alleging that Mr. Saylor failed to pay personal income taxes, interest and penalties due. On April 13, 2023, the District, through its Office of the Attorney General, filed a motion to amend its complaint to attempt to restore claims under the False Claims Act against both Mr. Saylor and the Company. On May 10, 2023, the court granted the District’s motion to amend its complaint, reinstating the Company as a defendant in the case. The amended complaint alleges that the Company violated the District’s False Claims Act by making and using false records and statements in the form of false withholding filings with the District Office of Tax and Revenue. The amended complaint also alleges that Mr. Saylor violated the District’s False Claims Act by making and using false records and statements and by causing the Company to make and use false records and statements. On June 7, 2023, Mr. Saylor and the Company filed a motion to dismiss the District’s amended complaint with prejudice. On July 5, 2023, the District filed an opposition to the motion to dismiss made by Mr. Saylor and the Company. On July 19, 2023, Mr. Saylor and the Company filed a reply in support of their motion to dismiss. On July 31, 2023, the court denied Mr. Saylor’s and the Company’s motion to dismiss the amended complaint. The final outcome of this matter is not presently determinable.

The Company is also involved in various legal proceedings arising in the normal course of business. Although the outcomes of these legal proceedings are inherently difficult to predict, management does not expect the resolution of these legal proceedings to have a material adverse effect on the Company’s financial position, results of operations, or cash flows.

The Company has contingent liabilities that, in management’s judgment, are not probable of assertion. If such unasserted contingent liabilities were to be asserted, or become probable of assertion, the Company may be required to record significant expenses and liabilities in the period in which these liabilities are asserted or become probable of assertion.

(6) Treasury Stock

The Board of Directors previously authorized the Company’s repurchase of up to an aggregate of $800.0 million of its class A common stock from time to time on the open market through April 29, 2023 (the “Share Repurchase Program”). The Share Repurchase Program expired by its own terms on April 29, 2023, and no shares of the Company’s class A common stock remain available for repurchase under the Share Repurchase Program. At the time of expiration, the Company had repurchased an aggregate of 5,674,226 shares of its class A common stock at an average price per share of $104.13 and an aggregate cost of $590.9 million pursuant to the Share Repurchase Program. The average price per share and aggregate cost amounts disclosed above include broker commissions. During 2023 and 2022, the Company did no t repurchase any shares of its class A common stock pursuant to the Share Repurchase Program.

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(7) Income Taxes

The Company computes its year-to-date provision for (benefit from) income taxes by applying the estimated annual effective tax rate to year-to-date pretax income or loss and adjusts the provision for (benefit from) income taxes for discrete tax items recorded in the period. The estimated effective tax rate is subject to fluctuation based on the level and mix of earnings and losses by tax jurisdiction, foreign tax rate differentials, and the relative impact of permanent book to tax differences. Each quarter, a cumulative adjustment is recorded for any fluctuations in the estimated annual effective tax rate as compared to the prior quarter. As a result of these factors, and due to potential changes in the Company’s period-to-period results, fluctuations in the Company’s effective tax rate and respective tax provisions or benefits may occur. For the six months ended June 30, 2023, the Company recorded a benefit from income taxes of $513.5 million on a pretax loss of $30.0 million, which resulted in an effective tax rate of 1,708.9%. For the six months ended June 30, 2022, the Company recorded a provision for income taxes of $88.1 million on a pretax loss of $1.105 billion, which resulted in an effective tax rate of (8.0)%. The change in the effective tax rate, as compared to the same period in the prior year, is primarily due to the release of the remaining valuation allowance on the Company's deferred tax asset related to the impairment on its bitcoin holdings, attributable to the increase in market value of bitcoin as of June 30, 2023 compared to December 31, 2022.

As of June 30, 2023, the Company had a valuation allowance of $2.6 million primarily related to certain foreign tax credit carryforwards that, in the Company’s present estimation, more likely than not will not be realized. If the market value of bitcoin declines or the Company is unable to maintain profitability in future periods, the Company may be required to increase the valuation allowance against its deferred tax assets, which could result in a charge that would materially adversely affect net income (loss) in the period in which the charge is incurred. The Company will continue to regularly assess the realizability of deferred tax assets.

The Company records liabilities related to its uncertain tax positions. As of June 30, 2023, the Company had total gross unrecognized tax benefits, including accrued interest, of $6.1 million, all of which was recorded in “Other long-term liabilities” in the Company’s Consolidated Balance Sheet. As of December 31, 2022, the Company had total gross unrecognized tax benefits of $6.1 million, including accrued interest, all of which was recorded in “Other long-term liabilities” in the Company’s Consolidated Balance Sheet.

(8) Share-based Compensation

Stock Incentive Plans

On May 24, 2023, the Company’s stockholders approved the Company’s 2023 Equity Incentive Plan (the “2023 Equity Plan”) and the 2023 Equity Plan became effective as of such date. No awards may be granted under the 2023 Equity Plan more than 10 years after the 2023 Equity Plan’s effective date. No new awards will be granted under the Company’s 2013 Stock Incentive Plan (as amended, the “2013 Equity Plan”) following the date of such approval, though awards previously granted under the 2013 Equity Plan will remain outstanding in accordance with their terms. Under the 2023 Equity Plan and the 2013 Equity Plan (together, the “Stock Incentive Plans”), the Company’s employees, officers, directors, and other eligible participants may be (with respect to the 2023 Equity Plan) and have been (with respect to the 2013 Equity Plan) awarded various types of share-based compensation, including options to purchase shares of the Company’s class A common stock, restricted stock units, and other stock-based awards. Under the 2023 Equity Plan, awards may now also be granted that are subject to the achievement of one or more performance measures established by the Company’s Board of Directors or a duly authorized committee thereof. Any shares issued under the Stock Incentive Plans may consist in whole or in part of authorized but unissued shares or treasury shares.

With the exception of awards granted subject to the achievement of a performance measure (as discussed further below), the accounting policies in place for awards granted under the 2023 Equity Plan are the same as those for the awards previously granted under the 2013 Equity Plan. With the exception of awards to non-employee members of the Company’s Board of Directors which vest in full after one year, and awards whose vesting is subject to the achievement of a performance measure (as discussed further below), awards granted under the 2023 Equity Plan generally vest over four years.

An aggregate of up to 1,932,703 shares of the Company’s class A common stock were authorized for issuance under the 2023 Equity Plan, comprised of (i) 200,000 shares of the Company’s class A common stock authorized under the 2023 Equity Plan and (ii) up to an aggregate of 1,732,703 shares of the Company’s class A common stock consisting of: (a) the shares of class A common stock reserved for issuance under the 2013 Equity Plan that remained available for grant as of May 23, 2023, and (b) shares of class A common stock subject to awards granted under the 2013 Equity Plan that were outstanding as of May 23, 2023 and which subsequently expire, terminate or are otherwise surrendered, cancelled or forfeited or repurchased by the Company at their original issuance price pursuant to a contractual repurchase right, including shares subject to awards granted under the 2013 Equity Plan that are delivered (either by actual delivery, attestation or net exercise) to the Company by a participant to (x) purchase shares upon the exercise of such award or (y) satisfy tax withholding obligations with respect to such awards, including shares retained from the award creating the tax obligation, subject, in the case of incentive stock options, to any limitations under the Internal Revenue Code of 1986, as amended. As of June 30, 2023, there were 171,066 shares of class A common stock reserved and available for future issuance under the 2023 Equity Plan.

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Stock option awards

As of June 30, 2023, there were options to purchase 1,440,696 shares of class A common stock outstanding under the Stock Incentive Plans.

The following table summarizes the Company’s stock option activity (in thousands, except per share data and years) for the six months ended June 30, 2023:

|  | Stock Options Outstanding |
|  |  |  |  | Weighted Average |  |  | Aggregate |  |  | Weighted Average |
|  |  |  |  | Exercise Price |  |  | Intrinsic |  |  | Remaining Contractual |
|  | Shares |  |  | Per Share |  |  | Value |  |  | Term (Years) |
Balance as of January 1, 2023 |  |  | 1,577 |  |  | $ | 288.30 |  |  |  |  |  |  |
Granted |  |  | 36 |  |  | $ | 284.06 |  |  |  |  |  |  |
Exercised |  |  | (83 | ) |  | $ | 145.15 |  |  | $ | 11,675 |  |  |  |
Forfeited/Expired |  |  | (89 | ) |  | $ | 400.57 |  |  |  |  |  |  |
Balance as of June 30, 2023 |  |  | 1,441 |  |  | $ | 289.58 |  |  |  |  |  |  |
Exercisable as of June 30, 2023 |  |  | 880 |  |  | $ | 238.07 |  |  | $ | 140,690 |  |  |  | 3.7 |
Expected to vest as of June 30, 2023 |  |  | 561 |  |  | $ | 370.46 |  |  | $ | 35,325 |  |  |  | 8.3 |
Total |  |  | 1,441 |  |  | $ | 289.58 |  |  | $ | 176,015 |  |  |  | 5.5 |

Stock options outstanding as of June 30, 2023 are comprised of the following range of exercise prices per share (in thousands, except per share data and years):

|  | Stock Options Outstanding at June 30, 2023 |
|  |  |  |  | Weighted Average |  |  | Weighted Average |
|  |  |  |  | Exercise Price |  |  | Remaining Contractual |
Range of Exercise Prices per Share |  | Shares |  |  | Per Share |  |  | Term (Years) |
$121.43 - $200.00 |  |  | 807 |  |  | $ | 136.99 |  |  |  | 3.4 |
$200.01 - $300.00 |  |  | 113 |  |  | $ | 252.02 |  |  |  | 9.4 |
$300.01 - $400.00 |  |  | 3 |  |  | $ | 301.63 |  |  |  | 9.9 |
$400.01 - $500.00 |  |  | 287 |  |  | $ | 409.16 |  |  |  | 8.3 |
$600.01 - $691.23 |  |  | 231 |  |  | $ | 691.23 |  |  |  | 7.2 |
Total |  |  | 1,441 |  |  | $ | 289.58 |  |  |  | 5.5 |

An aggregate of 163,500 stock options with an aggregate grant date fair value of $44.5 million vested during the six months ended June 30, 2023. The weighted average grant date fair value of stock option awards using the Black-Scholes valuation model was $190.86 and $219.79 for each share subject to a stock option granted during the six months ended June 30, 2023 and 2022, respectively, based on the following assumptions:

|  | Six Months Ended
|  | June 30,
|  | 2023 |  | 2022
Expected term of award in years |  | 5.5 - 6.3 |  | 6.3
Expected volatility |  | 71.8% - 74.1% |  | 58.4% - 69.5%
Risk-free interest rate |  | 3.7% - 3.9% |  | 1.9% - 2.9%
Expected dividend yield |  | 0.0% |  | 0.0%

For the three and six months ended June 30, 2023, the Company recognized approximately $10.5 million and $23.4 million, respectively, in share-based compensation expense from stock options granted under the Stock Incentive Plans. For the three and six months ended June 30, 2022, the Company recognized approximately $12.3 million and $22.7 million, respectively, in share-based compensation expense from stock options granted under the Stock Incentive Plans. As of June 30, 2023, there was approximately $98.2 million of total unrecognized share-based compensation expense related to unvested stock options, which the Company expects to recognize over a weighted average vesting period of approximately 2.4 years.

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Share-settled restricted stock units

As of June 30, 2023, there were 210,969 share-settled restricted stock units outstanding under the Stock Incentive Plans. The following table summarizes the Company’s share-settled restricted stock unit activity (in thousands) for the periods indicated:

|  | Share-Settled Restricted Stock Units Outstanding |
|  |  |  |  | Aggregate |
|  | Units |  |  | Intrinsic Value |
Balance as of January 1, 2023 |  |  | 120 |  |  |  |
Granted |  |  | 112 |  |  |  |
Vested |  |  | (13 | ) |  | $ | 3,690 |
Forfeited |  |  | (8 | ) |  |  |
Balance as of June 30, 2023 |  |  | 211 |  |  |  |
Expected to vest as of June 30, 2023 |  |  | 211 |  |  | $ | 72,240 |

During the six months ended June 30, 2023, 12,847 share-settled restricted stock units having an aggregate grant date fair value of $5.1 million vested, and 2,792 shares were withheld to satisfy tax obligations, resulting in 10,055 issued shares. The weighted average grant date fair value of share-settled restricted stock units granted during the six months ended June 30, 2023 and 2022 was $277.59 and $272.82, respectively, based on the fair value of the Company’s class A common stock.

For the three and six months ended June 30, 2023, the Company recognized approximately $3.9 million and $7.3 million, respectively, in share-based compensation expense from share-settled restricted stock units granted under the Stock Incentive Plans. For the three and six months ended June 30, 2022, the Company recognized approximately $3.2 million and $6.4 million, respectively, in share-based compensation expense from share-settled restricted stock units granted under the Stock Incentive Plans. As of June 30, 2023, there was approximately $58.8 million of total unrecognized share-based compensation expense related to unvested share-settled restricted stock units, which the Company expects to recognize over a weighted average vesting period of approximately 3.1 years.

Share-settled performance stock units

During the second quarter of 2023, the Company granted performance stock units under the 2023 Equity Plan. Performance stock units entitle recipients to receive a number of shares of the Company’s class A common stock at a specified date in the future based on achievement of one or more performance measures, as specified in the applicable performance stock unit agreement. Although the Company may in its sole discretion elect to pay fully or partially in cash in lieu of settling solely in shares, it does not currently intend to do so.

The vesting of each performance stock unit granted is subject to the Company’s achievement of a relative total shareholder return (“TSR”) performance goal over a three-year performance period with the number of performance stock units granted representing the number of performance stock units that would vest based on target performance. As more fully specified in the applicable grant agreements, the number of performance stock units that will vest will be based on the percentile ranking of the Company’s TSR over the three-year performance period as compared to the TSR of the members of the Nasdaq Composite Index over the same period (the “TSR Goal”), with the payout factor ranging from 0% to 200% of the number of performance stock units granted. The performance stock units, to the extent vested, will vest on the date the Compensation Committee of the Company’s Board of Directors certifies the level of achievement of the TSR Goal

Vesting of the performance stock units is also generally subject to the provision of service through the vesting date of the award (unless accelerated in connection with a termination following a change in control event as set forth in the applicable performance stock unit agreement or otherwise in accordance with provisions of the 2023 Equity Plan or applicable performance stock unit agreement).

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The TSR Goal is considered a “market condition” under ASC 718, Compensation—Stock Compensation. The Company uses a Monte Carlo simulation model to determine the grant date fair value of performance awards with a market condition. The Monte Carlo simulation takes into consideration the assumptions noted below, in addition to the probability that the market condition will be achieved based on predicted stock price paths compared to peer companies in the Nasdaq Composite Index. The Company did not grant any performance awards prior to June 2023. The weighted average grant date fair value of performance stock units using the Monte-Carlo simulation model was $486.18 for each performance stock unit granted during the six months ended June 30, 2023 based on the following assumptions:

|  | Six Months Ended |
|  | June 30, |
|  | 2023 |
Expected term of award in years |  |  | 3.0 |
Expected volatility |  |  | 95.6 | %
Risk-free interest rate |  |  | 4.1 | %
Expected dividend yield |  |  | 0.0 | %

Since the Company continues to account for forfeitures as they occur, as long as the performance stock unit recipient provides service to the Company during the requisite service period, share-based compensation expense associated with the grant date fair value of the performance stock units is recognized ratably over the performance period, regardless of the Company’s actual level of achievement against the TSR Goal.

As of June 30, 2023, there were 26,737 performance stock units outstanding under the 2023 Equity Plan. The following table summarizes the Company’s performance stock unit activity (in thousands) for the periods indicated:

|  | Share-Settled Performance Stock Units Outstanding |
|  |  |  |  | Aggregate |
|  | Units |  |  | Intrinsic Value |
Balance as of January 1, 2023 |  |  | 0 |  |  |  |
Granted |  |  | 27 |  |  |  |
Vested |  |  | 0 |  |  | $ | 0 |
Forfeited |  |  | 0 |  |  |  |
Balance as of June 30, 2023 |  |  | 27 |  |  |  |
Expected to vest as of June 30, 2023 |  |  | 27 |  |  | $ | 18,311 |

No performance stock units vested during the three and six months ended June 30, 2023. For the three and six months ended June 30, 2023, the Company recognized approximately $0.3 million in share-based compensation expense from performance stock units granted under the 2023 Equity Plan. As of June 30, 2023, there was approximately $12.7 million of total unrecognized share-based compensation expense related to unvested performance stock units, which the Company expects to recognize over a weighted average vesting period of approximately 3.0 years.

Other stock-based awards and cash-settled restricted stock units

From time to time the Company has granted “other stock-based awards” and “cash-settled restricted stock units” under the 2013 Equity Plan. Other stock-based awards are similar to stock options, and cash-settled restricted stock units are similar to the Company’s share-settled restricted stock units, except in each case these awards are settled in cash only and not in shares of the Company’s class A common stock. Due to their required cash settlement feature, these awards are classified as liabilities in the Company’s Consolidated Balance Sheets and the fair value of the awards is remeasured each quarterly reporting period. For the three and six months ended June 30, 2023, the Company recognized approximately $0.4 million and $1.1 million, respectively, in share-based compensation expense from other stock-based awards and cash-settled restricted stock units. For the three and six months ended June 30, 2022, the Company recognized a reduction of approximately $0.7 million and $0.5 million, respectively, in share-based compensation expense from other stock-based awards and cash-settled restricted stock units. As of June 30, 2023, there was approximately $0.8 million of total unrecognized share-based compensation expense related to other stock-based awards and cash-settled restricted stock units, which the Company expects to recognize over a weighted average vesting period of approximately 1.7 years, subject to additional fair value adjustments through the earlier of settlement or expiration.

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2021 ESPP

The Company also maintains the 2021 Employee Stock Purchase Plan (the “2021 ESPP”). The purpose of the 2021 ESPP is to provide eligible employees of the Company and certain of its subsidiaries with opportunities to purchase shares of the Company’s class A common stock in 6-month offering periods commencing on each March 1 and September 1. An aggregate of 100,000 shares of the Company’s class A common stock has been authorized for issuance under the 2021 ESPP. During the six months ended June 30, 2023, 12,672 shares of class A common stock were issued in connection with the 2021 ESPP. As of June 30, 2023, 66,791 shares of the Company’s class A common stock remained available for issuance under the 2021 ESPP.

For the three and six months ended June 30, 2023, the Company recognized approximately $0.4 million and $1.0 million, respectively, in share-based compensation expense related to the 2021 ESPP. For the three and six months ended June 30, 2022, the Company recognized approximately $0.5 million and $1.1 million, respectively, in share-based compensation expense related to the 2021 ESPP. As of June 30, 2023, there was approximately $0.3 million of total unrecognized share-based compensation expense related to the 2021 ESPP, which the Company expects to recognize over a period of approximately 0.2 years.

Tax Benefits Related to Equity Plans

The following table summarizes the tax (benefit) expense related to the Company’s equity plans (in thousands) for the three and six months ended June 30, 2023 and 2022:

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Tax (benefit) expense related to: |  |  |  |  |  |  |  |  |  |  |  |
Share-based compensation expense |  | $ | (2,754 | ) |  | $ | (3,343 | ) |  | $ | (5,979 | ) |  | $ | (6,240 | )
Exercises of stock options and vesting of share-settled restricted stock units |  |  | 370 |  |  |  | 57 |  |  |  | 285 |  |  |  | 110 |
Total tax benefit related to the Company's equity plans |  | $ | (2,384 | ) |  | $ | (3,286 | ) |  | $ | (5,694 | ) |  | $ | (6,130 | )

(9) Basic and Diluted Earnings (Loss) per Share

The Company has two classes of common stock: class A common stock and class B common stock. Holders of class A common stock generally have the same rights, including rights to dividends, as holders of class B common stock, except that holders of class A common stock have one vote per share while holders of class B common stock have ten votes per share. Each share of class B common stock is convertible at any time, at the option of the holder, into one share of class A common stock. As such, basic and fully diluted earnings per share for class A common stock and for class B common stock are the same. The Company has never declared or paid any cash dividends on either class A or class B common stock. As of June 30, 2023 and December 31, 2022, there were no shares of preferred stock issued or outstanding.

The impact from potential shares of common stock on the diluted earnings per share calculation are included when dilutive. Potential shares of class A common stock issuable upon the exercise of outstanding stock options, the vestin g of restricted stock units and performance stock units considered probable of achievement, and in connection with the 2021 ESPP are computed using the treasury stock method. Potential shares of class A common stock issuable upon conversion of the Convertible Notes are computed using the if-converted method. In computing diluted earnings per share, the Company first calculates the earnings per incremental share (“EPIS”) for each class of potential shares of common stock and ranks the classes from the most dilutive (i.e., lowest EPIS) to the least dilutive (i.e., highest EPIS). Basic earnings per share is then adjusted for the effect of each class of shares, in sequence and cumulatively, until a particular class no longer produces further dilution.

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The following table sets forth the computation of basic and diluted earnings (loss) per share (in thousands, except per share data) for the periods indicated:

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Numerator: |  |  |  |  |  |  |  |  |  |  |  |
Net income (loss) - Basic |  | $ | 22,243 |  |  | $ | (1,062,298 | ) |  | $ | 483,436 |  |  | $ | (1,193,049 | )
Effect of dilutive shares on net income (loss): |  |  |  |  |  |  |  |  |  |  |  |
Interest expense on 2025 Convertible Notes, net of tax |  |  | 1,424 |  |  |  | 0 |  |  |  | 2,838 |  |  |  | 0 |
Interest expense on 2027 Convertible Notes, net of tax |  |  | 725 |  |  |  | 0 |  |  |  | 1,445 |  |  |  | 0 |
Net income (loss) - Diluted |  | $ | 24,392 |  |  | $ | (1,062,298 | ) |  | $ | 487,719 |  |  | $ | (1,193,049 | )
Denominator: |  |  |  |  |  |  |  |  |  |  |  |
Weighted average common shares of class A common stock |  |  | 11,283 |  |  |  | 9,336 |  |  |  | 9,775 |  |  |  | 9,330 |
Weighted average common shares of class B common stock |  |  | 1,964 |  |  |  | 1,964 |  |  |  | 1,964 |  |  |  | 1,964 |
Total weighted average shares of common stock outstanding - Basic |  |  | 13,247 |  |  |  | 11,300 |  |  |  | 11,739 |  |  |  | 11,294 |
Effect of dilutive shares on weighted average common shares outstanding: |  |  |  |  |  |  |  |  |  |  |  |
Stock options |  |  | 441 |  |  |  | 0 |  |  |  | 398 |  |  |  | 0 |
Restricted stock units |  |  | 37 |  |  |  | 0 |  |  |  | 29 |  |  |  | 0 |
Performance stock units |  |  | 3 |  |  |  | 0 |  |  |  | 2 |  |  |  | 0 |
Employee stock purchase plan |  |  | 1 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
2025 Convertible Notes |  |  | 1,633 |  |  |  | 0 |  |  |  | 1,633 |  |  |  | 0 |
2027 Convertible Notes |  |  | 733 |  |  |  | 0 |  |  |  | 733 |  |  |  | 0 |
Total weighted average shares of common stock outstanding - Diluted |  |  | 16,095 |  |  |  | 11,300 |  |  |  | 14,534 |  |  |  | 11,294 |
Earnings (loss) per share: |  |  |  |  |  |  |  |  |  |  |  |
Basic earnings (loss) per share (1) |  | $ | 1.68 |  |  | $ | (94.01 | ) |  | $ | 41.18 |  |  | $ | (105.64 | )
Diluted earnings (loss) per share (1) |  | $ | 1.52 |  |  | $ | (94.01 | ) |  | $ | 33.56 |  |  | $ | (105.64 | )

(1) Basic and fully diluted earnings (loss) per share for class A and class B common stock are the same.

For the three and six months ended June 30, 2023 and 2022, the following weighted average shares of potential class A common stock were excluded from the diluted earnings (loss) per share calculation because their impact would have been anti-dilutive (in thousands):

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Stock options |  |  | 643 |  |  |  | 1,474 |  |  |  | 677 |  |  |  | 1,393 |
Restricted stock units |  |  | 35 |  |  |  | 116 |  |  |  | 39 |  |  |  | 111 |
Performance stock units |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Employee stock purchase plan |  |  | 0 |  |  |  | 5 |  |  |  | 2 |  |  |  | 4 |
2025 Convertible Notes |  |  | 0 |  |  |  | 1,633 |  |  |  | 0 |  |  |  | 1,633 |
2027 Convertible Notes |  |  | 0 |  |  |  | 733 |  |  |  | 0 |  |  |  | 733 |
Total |  |  | 678 |  |  |  | 3,961 |  |  |  | 718 |  |  |  | 3,874 |

(10) At-the-Market Equity Offerings

On September 9, 2022, the Company entered into a Sales Agreement (the “2022 Sales Agreement”) with Cowen and Company LLC and BTIG, LLC, as agents (collectively, the “2022 Sales Agents”), pursuant to which the Company could issue and sell shares of its

20

class A common stock having an aggregate offering price of up to $500.0 million from time to time through the 2022 Sales Agents. The Company agreed to pay the 2022 Sales Agents commissions for their services in acting as agents in the sale of the shares in the amount of up to 2.0% of gross proceeds from the sale of shares pursuant to the 2022 Sales Agreement. The Company also agreed to provide the 2022 Sales Agents with customary indemnification and contribution rights.

On May 1, 2023, the Company terminated the 2022 Sales Agreement and entered into a new Sales Agreement (the “2023 Sales Agreement”) with Cowen and Company, LLC and Canaccord Genuity LLC, as agents (collectively, the “2023 Sales Agents”), pursuant to which the Company may issue and sell shares of its class A common stock having an aggregate offering price of up to $625.0 million from time to time through the 2023 Sales Agents.

The Company agreed to pay the 2023 Sales Agents commissions for their services in acting as agents in the sale of the shares in the amount of up to 2.0% of gross proceeds from the sale of shares pursuant to the 2023 Sales Agreement. The Company also agreed to provide the 2023 Sales Agents with customary indemnification and contribution rights.

The Company did not sell any shares of its class A common stock under the 2022 Sales Agreement during the three months ended June 30, 2023. During the six months ended June 30, 2023, the Company issued and sold 1,348,855 shares of class A common stock under the 2022 Sales Agreement for aggregate net proceeds (less sales commissions and expenses) of approximately $339.0 million. At termination of the 2022 Sales Agreement on May 1, 2023, the Company had issued and sold an aggregate of 1,567,430 shares under the 2022 Sales Agreement for aggregate net proceeds (less sales commissions and expenses) of approximately $385.2 million.

During the three and six months ended June 30, 2023, the Company issued and sold 1,079,170 shares of class A common stock under the 2023 Sales Agreement for aggregate net proceeds (less sales commissions and expenses) of approximately $333.5 million. As of June 30, 2023, approximately $290.0 million of the Company’s class A common stock remained available for issuance and sale pursuant to the 2023 Sales Agreement.

The sales commissions and expenses related to the 2022 Sales Agreement and 2023 Sales Agreement are considered direct and incremental costs and are charged against “Additional paid-in capital” on the Consolidated Balance Sheet in the period in which the related shares are issued and sold.

(11) Segment Information

The Company manages its business in one reportable operating segment. The Company’s one reportable operating segment is engaged in the design, development, marketing, and sales of its software platform through licensing arrangements and cloud subscriptions and related services. The following table presents total revenues, gross profit, and long-lived assets (in thousands) according to geographic region. Long-lived assets are comprised of right-of-use assets and property and equipment, net.

Geographic regions: |  | U.S. |  |  | EMEA |  |  | Other Regions |  |  | Consolidated |
Three months ended June 30, 2023 |  |  |  |  |  |  |  |  |  |  |  |
Total revenues |  | $ | 71,427 |  |  | $ | 37,109 |  |  | $ | 11,864 |  |  | $ | 120,400 |
Gross profit |  | $ | 56,780 |  |  | $ | 28,809 |  |  | $ | 7,690 |  |  | $ | 93,279 |
Three months ended June 30, 2022 |  |  |  |  |  |  |  |  |  |  |  |
Total revenues |  | $ | 74,172 |  |  | $ | 35,578 |  |  | $ | 12,323 |  |  | $ | 122,073 |
Gross profit |  | $ | 61,108 |  |  | $ | 27,335 |  |  | $ | 8,426 |  |  | $ | 96,869 |
Six months ended June 30, 2023 |  |  |  |  |  |  |  |  |  |  |  |
Total revenues |  | $ | 141,104 |  |  | $ | 75,129 |  |  | $ | 26,082 |  |  | $ | 242,315 |
Gross profit |  | $ | 110,969 |  |  | $ | 58,506 |  |  | $ | 17,778 |  |  | $ | 187,253 |
Six months ended June 30, 2022 |  |  |  |  |  |  |  |  |  |  |  |
Total revenues |  | $ | 141,638 |  |  | $ | 74,866 |  |  | $ | 24,846 |  |  | $ | 241,350 |
Gross profit |  | $ | 115,437 |  |  | $ | 58,037 |  |  | $ | 16,995 |  |  | $ | 190,469 |
As of June 30, 2023 |  |  |  |  |  |  |  |  |  |  |  |
Long-lived assets |  | $ | 78,687 |  |  | $ | 6,936 |  |  | $ | 3,148 |  |  | $ | 88,771 |
As of December 31, 2022 |  |  |  |  |  |  |  |  |  |  |  |
Long-lived assets |  | $ | 83,279 |  |  | $ | 6,466 |  |  | $ | 3,865 |  |  | $ | 93,610 |

21

The EMEA region includes operations in Europe, the Middle East, and Africa. The other regions include all other foreign countries, generally comprising Latin America, the Asia Pacific region, and Canada. For the three and six months ended June 30, 2023 and 2022, no individual foreign country accounted for 10% or more of total consolidated revenues.

For the three and six months ended June 30, 2023 and 2022, no individual customer accounted for 10% or more of total consolidated revenues.

As of June 30, 2023 and December 31, 2022, no individual foreign country accounted for 10% or more of total consolidated assets.

(12) Related Party Transactions

On June 24, 2022, concurrently with binding directors and officers (“D&Os”) liability insurance policies (the “Initial Commercial Policies”) with several third-party carriers, the Company and Michael J. Saylor, the Company’s Chairman of the Board of Directors and Executive Chairman, entered into (i) an indemnification agreement (the “Excess Agreement”) for Mr. Saylor to provide $10 million in excess indemnity coverage payable only after the exhaustion of the Initial Commercial Policies, and (ii) an indemnification agreement (the “Tail Agreement”) for Mr. Saylor to provide $40 million in indemnity coverage for claims made at any time based on actions or omissions occurring prior to the inception date of the Initial Commercial Policies. The Company paid Mr. Saylor $600,000 for a one-year term under the Excess Agreement, and $150,000 for a 90-day term under the Tail Agreement. At the option of the Company, the Company was permitted to extend the term under the Tail Agreement for up to a total of twenty-three additional 90-day periods, for $150,000 per additional 90-day term. The Company elected to extend the term of the Tail Agreement for three consecutive additional 90-day periods and paid Mr. Saylor $150,000 for each extension.

On August 30, 2022, the Company bound additional D&O liability insurance policies (the “Excess Commercial Policies”) with third-party carriers for excess coverage payable only after the exhaustion of the Initial Commercial Policies. Effective as of the same date, the Company and Mr. Saylor executed an amendment (the “Amendment”) to the Excess Agreement to limit Mr. Saylor’s obligation to provide indemnification under the Excess Agreement to claims made during the term of the Excess Agreement which arise from wrongful acts occurring upon or after the commencement of the Excess Agreement but prior to the effective date of the Amendment. In connection with the Amendment, Mr. Saylor refunded $489,863 to the Company, representing the pro rata portion of the $600,000 originally paid by the Company to Mr. Saylor under the Excess Agreement attributable to the period from the date of the Amendment through the end of the original term of the Excess Agreement.

On June 12, 2023, the Company bound new D&O liability insurance policies (the “2023 Commercial Policies”) with third-party carriers that provide coverage substantially equivalent to the aggregate coverage provided under the Initial Commercial Policies and the Excess Commercial Policies for a policy period running from June 12, 2023 through June 12, 2024 except that the 2023 Commercial Policies also provide coverage for claims made with respect to wrongful acts or omissions occurring prior to the binding of the Initial Commercial Policies subject to exclusions with respect to claims previously noticed to and accepted by an earlier D&O insurer, claims related to acts or omissions giving rise to such claims, and demands, investigations, suits or other proceedings entered against an insured prior to June 24, 2022, as well as future interrelated wrongful acts.

On June 12, 2023, the Company entered into a new indemnification agreement with Mr. Saylor (the “2023 Tail Agreement”) pursuant to which Mr. Saylor agreed to provide coverage that is similar to the coverage provided under the Tail Agreement, but only for matters excluded from coverage under the 2023 Commercial Policies for an initial one-year term for a payment of $157,000. The Company may elect, at its option, to extend the term under the 2023 Tail Agreement for up to a total of four additional one-year periods, for $157,000 per additional one-year term.

The Excess Agreement, Tail Agreement and other related party transactions between the Company and Mr. Saylor are described more fully in Note 17 to the Consolidated Financial Statements of the Company's Annual Report on Form 10-K for the year ended December 31, 2022.

(13) Subsequent Events

Since June 30, 2023 through the date immediately preceding the filing of this Quarterly Report, the Company has purchased approximately 467 bitcoins for $14.4 million, or approximately $30,788 per bitcoin. All of these approximately 467 bitcoins serve as part of the collateral for the 2028 Secured Notes. See Note 2, Digital Assets, to the Consolidated Financial Statements for further detail on accounting for digital assets.

22

Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations

Forward-Looking Information

This Quarterly Report on Form 10-Q (this “Quarterly Report”) contains forward-looking statements within the meaning of Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). For this purpose, any statements contained herein that are not statements of historical fact, including without limitation, certain statements regarding industry prospects and our results of operations or financial position, may be deemed to be forward-looking statements. Without limiting the foregoing, the words “believes,” “anticipates,” “plans,” “expects,” and similar expressions are intended to identify forward-looking statements. The important factors discussed under “Part II. Item 1A. Risk Factors,” among others, could cause actual results to differ materially from those indicated by forward-looking statements made herein and presented elsewhere by management from time to time. Such forward-looking statements represent management’s current expectations and are inherently uncertain. Investors are warned that actual results may differ from management’s expectations.

Business Overview

MicroStrategy® pursues two corporate strategies in the operation of its business. One strategy is to acquire and hold bitcoin and the other strategy is to grow our enterprise analytics software business. We believe that undertaking these two, interdependent corporate strategies serves as a key differentiator for our business, as our bitcoin acquisition strategy has raised our profile with certain potential software customers while our enterprise analytics software business has provided stable cash flows that allow us to acquire and hold bitcoin for the long-term.

Our Bitcoin Acquisition Strategy

Our bitcoin acquisition strategy generally involves acquiring bitcoin with our liquid assets that exceed working capital requirements, and from time to time, subject to market conditions, issuing debt or equity securities or engaging in other capital raising transactions with the objective of using the proceeds to purchase bitcoin. We view our bitcoin holdings as long-term holdings and expect to continue to accumulate bitcoin. We have not set any specific target for the amount of bitcoin we seek to hold, and we will continue to monitor market conditions in determining whether to engage in additional financings to purchase additional bitcoin. This overall strategy also contemplates that we may (i) periodically sell bitcoin for general corporate purposes, including to generate cash for treasury management or in connection with strategies that generate tax benefits in accordance with applicable law, (ii) enter into additional capital raising transactions that are collateralized by our bitcoin holdings, and (iii) consider pursuing additional strategies to create income streams or otherwise generate funds using our bitcoin holdings.

We believe that bitcoin is attractive because it can serve as a store of value, supported by a robust and public open-source architecture, that is untethered to sovereign monetary policy. We also believe that, due to its limited supply, bitcoin offers the opportunity for appreciation in value if its adoption increases and has the potential to serve as a hedge against inflation in the long-term. In addition, we believe that our bitcoin acquisition strategy is complementary to our enterprise analytics software business, as we believe that our bitcoin and related activities in support of the bitcoin network enhance awareness of our brand. We are also exploring opportunities to integrate features into our software offerings that leverage the Lightning Network – a decentralized second-layer payment protocol built on top of the Bitcoin blockchain that is intended to enable fast and less costly transactions.

Under our Treasury Reserve Policy, our treasury reserve assets consist of:

•
cash and cash equivalents and short-term investments (“Cash Assets”) held by us that exceed working capital requirements; and
•
bitcoin held by us, with bitcoin serving as the primary treasury reserve asset on an ongoing basis, subject to market conditions and anticipated needs of the business for Cash Assets.

During 2022 and 2023, we used proceeds from various capital raising transactions to purchase bitcoin. As of June 30, 2023, we held an aggregate of approximately 152,333 bitcoins, with 15,264 bitcoins held directly by MicroStrategy Incorporated and 137,069 bitcoins held by MacroStrategy LLC (“MacroStrategy”), a wholly-owned subsidiary of MicroStrategy. As of June 30, 2023, all of the approximately 15,264 bitcoins held directly by MicroStrategy Incorporated, which had a market value of $463.4 million based on the $30,361.51 market price of one bitcoin on the Coinbase exchange at 4:00 p.m. Eastern Time on June 30, 2023, are held in a separate custodial account from those held by MacroStrategy and serve as part of the collateral securing our 2028 Secured Notes. See below for further disclosure surrounding market value calculations of our bitcoin.

23

The following table presents a roll-forward of our bitcoin holdings, including additional information related to our bitcoin purchases, sales, and digital asset impairment losses within the respective periods:

|  | Source of Capital Used to Purchase Bitcoin |  | Digital Asset Original Cost Basis (in thousands) |  |  | Digital Asset Impairment Losses (in thousands) |  |  | Digital Asset Carrying Value (in thousands) |  |  | Approximate Number of Bitcoins Held (Disposed) |  |  | Approximate Average Purchase or Sale Price Per Bitcoin |
Balance at December 31, 2021 |  |  |  | $ | 3,751,529 |  |  | $ | (901,319 | ) |  | $ | 2,850,210 |  |  |  | 124,391 |  |  | $ | 30,159 |
Digital asset purchases |  | (a) |  |  | 215,500 |  |  |  |  |  |  | 215,500 |  |  |  | 4,827 |  |  |  | 44,645 |
Digital asset impairment losses |  |  |  |  |  |  |  | (170,091 | ) |  |  | (170,091 | ) |  |  |  |  |  |
Balance at March 31, 2022 |  |  |  | $ | 3,967,029 |  |  | $ | (1,071,410 | ) |  | $ | 2,895,619 |  |  |  | 129,218 |  |  | $ | 30,700 |
Digital asset purchases |  | (b) |  |  | 10,000 |  |  |  |  |  |  | 10,000 |  |  |  | 481 |  |  |  | 20,790 |
Digital asset impairment losses |  |  |  |  |  |  |  | (917,838 | ) |  |  | (917,838 | ) |  |  |  |  |  |
Balance at June 30, 2022 |  |  |  | $ | 3,977,029 |  |  | $ | (1,989,248 | ) |  | $ | 1,987,781 |  |  |  | 129,699 |  |  | $ | 30,664 |
Digital asset purchases |  | (c) |  |  | 5,978 |  |  |  |  |  |  | 5,978 |  |  |  | 301 |  |  |  | 19,860 |
Digital asset impairment losses |  |  |  |  |  |  |  | (727 | ) |  |  | (727 | ) |  |  |  |  |  |
Balance at September 30, 2022 |  |  |  | $ | 3,983,007 |  |  | $ | (1,989,975 | ) |  | $ | 1,993,032 |  |  |  | 130,000 |  |  | $ | 30,639 |
Digital asset purchases |  | (d) |  |  | 56,443 |  |  |  |  |  |  | 56,443 |  |  |  | 3,204 |  |  |  | 17,616 |
Digital asset impairment losses |  |  |  |  |  |  |  | (198,557 | ) |  |  | (198,557 | ) |  |  |  |  |  |
Digital asset sales * |  |  |  |  | (46,260 | ) |  |  | 35,370 |  |  |  | (10,890 | ) |  |  | (704 | ) |  |  | 16,786 |
Balance at December 31, 2022 |  |  |  | $ | 3,993,190 |  |  | $ | (2,153,162 | ) |  | $ | 1,840,028 |  |  |  | 132,500 |  |  | $ | 30,137 |
Digital asset purchases |  | (e) |  |  | 179,275 |  |  |  |  |  |  | 179,275 |  |  |  | 7,500 |  |  |  | 23,903 |
Digital asset impairment losses |  |  |  |  |  |  |  | (18,911 | ) |  |  | (18,911 | ) |  |  |  |  |  |
Balance at March 31, 2023 |  |  |  | $ | 4,172,465 |  |  | $ | (2,172,073 | ) |  | $ | 2,000,392 |  |  |  | 140,000 |  |  | $ | 29,803 |
Digital asset purchases |  | (f) |  |  | 347,003 |  |  |  |  |  |  | 347,003 |  |  |  | 12,333 |  |  |  | 28,136 |
Digital asset impairment losses |  |  |  |  |  |  |  | (24,143 | ) |  |  | (24,143 | ) |  |  |  |  |  |
Balance at June 30, 2023 |  |  |  | $ | 4,519,468 |  |  | $ | (2,196,216 | ) |  | $ | 2,323,252 |  |  |  | 152,333 |  |  | $ | 29,668 |

* During the fourth quarter of 2022, we sold approximately 704 bitcoins having an original cost basis of $46.3 million and cumulative digital asset impairment losses of $35.4 million, resulting in a carrying value of $10.9 million at the time of sale. The approximately 704 bitcoins were sold for cash proceeds of $11.8 million, net of fees and expenses, resulting in gains on sale of $0.9 million.

(a)
In the first quarter of 2022, we purchased bitcoin using $190.5 million of the net proceeds from the issuance of the 2025 Secured Term Loan and Excess Cash.
(b)
In the second quarter of 2022, we purchased bitcoin using Excess Cash.
(c)
In the third quarter of 2022, we purchased bitcoin using Excess Cash.
(d)
In the fourth quarter of 2022, we purchased bitcoin using $44.6 million of the net proceeds from our sale of class A common stock under our at-the-market offering program and $11.8 million in proceeds from sales of bitcoin.
(e)
In the first quarter of 2023, we purchased bitcoin using $179.3 million of the net proceeds from our sale of class A common stock under our at-the-market offering program.
(f)
In the second quarter of 2023, we purchased bitcoin using $336.9 million of the net proceeds from our sale of class A common stock under our at-the-market offering program, and Excess Cash.

Excess Cash refers to cash in excess of the minimum Cash Assets that we are required to hold under our Treasury Reserve Policy, which may include cash generated by operating activities and cash from the proceeds of financing activities.

24

The following table shows the approximate number of bitcoins held at the end of each respective period, as well as market value calculations of our bitcoin holdings based on the lowest, highest, and ending market prices of one bitcoin on the Coinbase exchange (our principal market) for each respective quarter, as further defined below:

|  | Approximate Number of Bitcoins Held at End of Quarter |  |  | Lowest Market Price Per Bitcoin During Quarter (a) |  |  | Market Value of Bitcoin Held at End of Quarter Using Lowest Market Price (in thousands) (b) |  |  | Highest Market Price Per Bitcoin During Quarter (c) |  |  | Market Value of Bitcoin Held at End of Quarter Using Highest Market Price (in thousands) (d) |  |  | Market Price Per Bitcoin at End of Quarter (e) |  |  | Market Value of Bitcoin Held at End of Quarter Using Ending Market Price (in thousands) (f) |
December 31, 2021 |  |  | 124,391 |  |  | $ | 42,333.00 |  |  | $ | 5,265,844 |  |  | $ | 69,000.00 |  |  | $ | 8,582,979 |  |  | $ | 45,879.97 |  |  | $ | 5,707,055 |
March 31, 2022 |  |  | 129,218 |  |  | $ | 32,933.33 |  |  | $ | 4,255,579 |  |  | $ | 48,240.00 |  |  | $ | 6,233,476 |  |  | $ | 45,602.79 |  |  | $ | 5,892,701 |
June 30, 2022 |  |  | 129,699 |  |  | $ | 17,567.45 |  |  | $ | 2,278,481 |  |  | $ | 47,469.40 |  |  | $ | 6,156,734 |  |  | $ | 18,895.02 |  |  | $ | 2,450,665 |
September 30, 2022 |  |  | 130,000 |  |  | $ | 18,153.13 |  |  | $ | 2,359,907 |  |  | $ | 25,214.57 |  |  | $ | 3,277,894 |  |  | $ | 19,480.51 |  |  | $ | 2,532,466 |
December 31, 2022 |  |  | 132,500 |  |  | $ | 15,460.00 |  |  | $ | 2,048,450 |  |  | $ | 21,478.80 |  |  | $ | 2,845,941 |  |  | $ | 16,556.32 |  |  | $ | 2,193,712 |
March 31, 2023 |  |  | 140,000 |  |  | $ | 16,490.00 |  |  | $ | 2,308,600 |  |  | $ | 29,190.04 |  |  | $ | 4,086,606 |  |  | $ | 28,468.44 |  |  | $ | 3,985,582 |
June 30, 2023 |  |  | 152,333 |  |  | $ | 24,750.00 |  |  | $ | 3,770,242 |  |  | $ | 31,443.67 |  |  | $ | 4,789,909 |  |  | $ | 30,361.51 |  |  | $ | 4,625,060 |

(a)
The "Lowest Market Price Per Bitcoin During Quarter" represents the lowest market price for one bitcoin reported on the Coinbase exchange during the respective quarter, without regard to when we purchased any of our bitcoin.
(b)
The "Market Value of Bitcoin Held at End of Quarter Using Lowest Market Price" represents a mathematical calculation consisting of the lowest market price for one bitcoin reported on the Coinbase exchange during the respective quarter multiplied by the number of bitcoins we held at the end of the applicable period.
(c)
The "Highest Market Price Per Bitcoin During Quarter" represents the highest market price for one bitcoin reported on the Coinbase exchange during the respective quarter, without regard to when we purchased any of our bitcoin.
(d)
The "Market Value of Bitcoin Held at End of Quarter Using Highest Market Price" represents a mathematical calculation consisting of the highest market price for one bitcoin reported on the Coinbase exchange during the respective quarter multiplied by the number of bitcoins we held at the end of the applicable period.
(e)
The "Market Price Per Bitcoin at End of Quarter" represents the market price of one bitcoin on the Coinbase exchange at 4:00 p.m. Eastern Time on the last day of the respective quarter.
(f)
The "Market Value of Bitcoin Held at End of Quarter Using Ending Market Price" represents a mathematical calculation consisting of the market price of one bitcoin on the Coinbase exchange at 4:00 p.m. Eastern Time on the last day of the respective quarter multiplied by the number of bitcoins we held at the end of the applicable period.

The amounts reported as “Market Value” in the above table represent only a mathematical calculation consisting of the price for one bitcoin reported on the Coinbase exchange (our principal market) in each scenario defined above multiplied by the number of bitcoins held by us at the end of the applicable period. The Securities and Exchange Commission has previously stated that there has not been a demonstration that (i) bitcoin and bitcoin markets are inherently resistant to manipulation or that the spot price of bitcoin may not be subject to fraud and manipulation; and (ii) adequate surveillance-sharing agreements with bitcoin-related markets are in place, as bitcoin-related markets are either not significant, not regulated, or both. Accordingly, the Market Value amounts reported above may not accurately represent fair market value, and the actual fair market value of our bitcoin may be different from such amounts and such deviation may be material. Moreover, (i) the bitcoin market historically has been characterized by significant volatility in price, limited liquidity and trading volumes compared to sovereign currencies markets, relative anonymity, a developing regulatory landscape, potential susceptibility to market abuse and manipulation, compliance and internal control failures at exchanges, and various other risks that are, or may be, inherent in its entirely electronic, virtual form and decentralized network and (ii) we may not be able to sell our bitcoins at the Market Value amounts indicated above, at the market price as reported on the Coinbase exchange (our principal market) on the date of sale, or at all.

Our digital asset impairment losses have significantly contributed to our operating expenses. During the three months ended June 30, 2023, digital asset impairment losses of $24.1 million represented 20.1% of our operating expenses, compared to digital asset impairment losses of $917.8 million, representing 90.4% of our operating expenses, during the three months ended June 30, 2022. During the six months ended June 30, 2023, digital asset impairment losses of $43.1 million represented 18.4% of our operating expenses, compared to digital asset impairment losses of $1.088 billion, representing 85.1% of our operating expenses, during the six months ended June 30, 2022.

As of July 31, 2023, we held approximately 152,800 bitcoins that were acquired at an aggregate purchase price of $4.534 billion and an average purchase price of approximately $29,672 per bitcoin, inclusive of fees and expenses. As of July 31, 2023, at 4:00 p.m. Eastern Time, the market price of one bitcoin reported on the Coinbase exchange was $29,158.43.

25

Our Enterprise Analytics Software Strategy

MicroStrategy is a global leader in enterprise analytics software and services. Our vision is to enable Intelligence Everywhere™ by providing world-class software and services that empower enterprise users with actionable insights.

The MicroStrategy Platform is an enterprise analytics software platform that incorporates a comprehensive suite of software offerings that are packaged and configured to meet customer requirements. The MicroStrategy Platform empowers organizations to leverage the immense value of their data. The platform enables users to connect to, sort and cleanse a wide variety of data. Sitting at the top of a technology stack, it can blend a myriad of sources to provide organizations with a comprehensive view of their business.

In addition, the platform elevates an organization’s relationship with data so they can build high-performance, governed, and secure applications at scale. The platform enables users to create visualizations, customize apps, and embed analytics directly into workflows to unlock insights and promote a culture of data. Users can access insights via a web or mobile client, desktop applications, and cards that instantly surface contextual information on top of a web browser or web application.

Our customers benefit from a variety of powerful platform services. These include access to in-memory cubes of data—increasing application performance and expanding analytical capabilities. Users can also subscribe to and receive reports, dossiers, or alerts, directly to screens or devices based on customized thresholds or specified parameters. And to enhance collaboration, users can exchange messages, tag individuals, and share pre-filtered views via a chat function in a dossier.

With 200+ connectors to popular drivers and gateways to enterprise data sources on premise and in the cloud, the platform provides the open architecture and flexibility necessary to stay agile in a rapidly changing business landscape. In addition, organizations can utilize a library of comprehensive APIs that streamline embedding the platform into packaged and custom applications, workflows, and devices.

Our customers include leading companies from a wide range of industries, including retail, banking, technology, consulting, manufacturing, insurance, healthcare, telecommunications, as well as the public sector.

The analytics market is highly competitive. Our future success depends on the effectiveness with which we can differentiate our offerings from those offered by large software vendors that provide products across multiple lines of business, including one or more products that directly compete with our offerings, and other potential competitors across analytics implementation projects of varying sizes. We believe a key differentiator of MicroStrategy is our modern, open, comprehensive enterprise platform that can be extended to other tools and systems, can scale across the enterprise, is optimized for cloud or on-premises deployments, and can be combined with unique packages of our expert services and education offerings.

26

Operating Highlights

The following table sets forth certain operating highlights (in thousands) for the three and six months ended June 30, 2023 and 2022:

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Revenues |  |  |  |  |  |  |  |  |  |  |  |
Product licenses |  | $ | 15,522 |  |  | $ | 20,129 |  |  | $ | 32,934 |  |  | $ | 36,642 |
Subscription services |  |  | 19,878 |  |  |  | 14,017 |  |  |  | 38,688 |  |  |  | 26,862 |
Total product licenses and subscription services |  |  | 35,400 |  |  |  | 34,146 |  |  |  | 71,622 |  |  |  | 63,504 |
Product support |  |  | 66,081 |  |  |  | 66,521 |  |  |  | 131,562 |  |  |  | 133,672 |
Other services |  |  | 18,919 |  |  |  | 21,406 |  |  |  | 39,131 |  |  |  | 44,174 |
Total revenues |  |  | 120,400 |  |  |  | 122,073 |  |  |  | 242,315 |  |  |  | 241,350 |
Cost of revenues |  |  |  |  |  |  |  |  |  |  |  |
Product licenses |  |  | 444 |  |  |  | 431 |  |  |  | 978 |  |  |  | 908 |
Subscription services |  |  | 7,216 |  |  |  | 5,498 |  |  |  | 15,072 |  |  |  | 10,908 |
Total product licenses and subscription services |  |  | 7,660 |  |  |  | 5,929 |  |  |  | 16,050 |  |  |  | 11,816 |
Product support |  |  | 5,816 |  |  |  | 5,127 |  |  |  | 11,584 |  |  |  | 10,318 |
Other services |  |  | 13,645 |  |  |  | 14,148 |  |  |  | 27,428 |  |  |  | 28,747 |
Total cost of revenues |  |  | 27,121 |  |  |  | 25,204 |  |  |  | 55,062 |  |  |  | 50,881 |
Gross profit |  |  | 93,279 |  |  |  | 96,869 |  |  |  | 187,253 |  |  |  | 190,469 |
Operating expenses |  |  |  |  |  |  |  |  |  |  |  |
Sales and marketing |  |  | 37,660 |  |  |  | 36,862 |  |  |  | 73,766 |  |  |  | 70,102 |
Research and development |  |  | 29,354 |  |  |  | 31,790 |  |  |  | 60,712 |  |  |  | 65,313 |
General and administrative |  |  | 28,830 |  |  |  | 28,502 |  |  |  | 56,736 |  |  |  | 55,208 |
Digital asset impairment losses |  |  | 24,143 |  |  |  | 917,838 |  |  |  | 43,054 |  |  |  | 1,087,929 |
Total operating expenses |  |  | 119,987 |  |  |  | 1,014,992 |  |  |  | 234,268 |  |  |  | 1,278,552 |
Loss from operations |  | $ | (26,708 | ) |  | $ | (918,123 | ) |  | $ | (47,015 | ) |  | $ | (1,088,083 | )

We have incurred and may continue to incur significant impairment losses on our digital assets, and we have recognized and may continue to recognize gains upon sale of our digital assets in the future, which are presented net of any impairment losses within operating expenses. In addition, we base our internal operating expense forecasts on expected revenue trends and strategic objectives in our enterprise analytics software business. Many of our expenses, such as office leases and certain personnel costs, are relatively fixed. Accordingly, any decrease in the price of bitcoin during any quarter, any sales by us of our bitcoin at prices above their then current carrying costs or any shortfall in revenue in our software business may cause significant variation in our operating results. We therefore believe that quarter-to-quarter comparisons of our operating results may not be a good indication of our future performance.

Employees

As of June 30, 2023, we had a total of 2,099 employees, of whom 684 were based in the United States and 1,415 were based internationally. The following table summarizes employee headcount as of the dates indicated:

|  | June 30, |  |  | December 31, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2022 |
Subscription services |  |  | 113 |  |  |  | 110 |  |  |  | 83 |
Product support |  |  | 172 |  |  |  | 183 |  |  |  | 164 |
Consulting |  |  | 436 |  |  |  | 447 |  |  |  | 428 |
Education |  |  | 13 |  |  |  | 16 |  |  |  | 36 |
Sales and marketing |  |  | 427 |  |  |  | 434 |  |  |  | 457 |
Research and development |  |  | 674 |  |  |  | 688 |  |  |  | 728 |
General and administrative |  |  | 264 |  |  |  | 274 |  |  |  | 262 |
Total headcount |  |  | 2,099 |  |  |  | 2,152 |  |  |  | 2,158 |

27

Share-based Compensation Expense

As discussed in Note 8, Share-based Compensation, to the Consolidated Financial Statements, we have outstanding stock options to purchase shares of our class A common stock, restricted stock units, performance stock units, and certain other stock-based awards under our Stock Incentive Plans. Each restricted stock unit and performance stock unit represents a contingent right to receive a share of our class A common stock upon the satisfaction of applicable vesting requirements. We also provide opportunities for eligible employees to purchase shares of our class A common stock under our 2021 ESPP. Share-based compensation expense (in thousands) from these awards was recognized in the following cost of revenues and operating expense line items for the periods indicated:

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Cost of subscription services revenues |  | $ | 84 |  |  | $ | 34 |  |  | $ | 153 |  |  | $ | 141 |
Cost of product support revenues |  |  | 525 |  |  |  | 522 |  |  |  | 1,032 |  |  |  | 972 |
Cost of consulting revenues |  |  | 455 |  |  |  | 439 |  |  |  | 888 |  |  |  | 815 |
Cost of education revenues |  |  | 23 |  |  |  | 54 |  |  |  | 44 |  |  |  | 106 |
Sales and marketing |  |  | 4,211 |  |  |  | 4,444 |  |  |  | 9,311 |  |  |  | 8,727 |
Research and development |  |  | 2,211 |  |  |  | 3,126 |  |  |  | 6,157 |  |  |  | 6,440 |
General and administrative |  |  | 7,985 |  |  |  | 6,675 |  |  |  | 15,464 |  |  |  | 12,487 |
Total share-based compensation expense |  | $ | 15,494 |  |  | $ | 15,294 |  |  | $ | 33,049 |  |  | $ | 29,688 |

Share-based compensation expense did not materially change during the three months ended June 30, 2023 as compared to the same period in the prior year, primarily due to the expansion of our equity award program worldwide and the revaluation of certain liability-classified stock-based awards, substantially offset by the forfeiture of certain stock awards. The $3.4 million increase in share-based compensation expense during the six months ended June 30, 2023, as compared to the same period in the prior year, was primarily due to the expansion of our equity award program worldwide and the revaluation of certain liability-classified stock-based awards, partially offset by the forfeiture of certain stock awards. As of June 30, 2023, we estimated that an aggregate of approximately $170.8 million of additional share-based compensation expense associated with the Stock Incentive Plans and the 2021 ESPP will be recognized over a remaining weighted average period of 2.7 years.

Critical Accounting Estimates

Our discussion and analysis of our financial condition and results of operations are based on our Consolidated Financial Statements, which have been prepared in accordance with GAAP. The preparation of our Consolidated Financial Statements requires us to make estimates and judgments that affect the reported amounts of assets, liabilities, and equity, the disclosure of contingent assets and liabilities at the date of the financial statements, and the reported amounts of revenues and expenses during the reporting period. Actual results and outcomes could differ from these estimates and assumptions.

Critical accounting estimates involve a significant level of estimation uncertainty and are estimates that have had or are reasonably likely to have a material impact on our financial condition or results of operations. We consider certain estimates and judgments related to revenue recognition to be critical accounting estimates for us, as discussed under “Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations—Critical Accounting Estimates” included in our Annual Report on Form 10-K for the fiscal year ended December 31, 2022. There have been no significant changes in such estimates and judgments since December 31, 2022.

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Results of Operations

Comparison of the three and six months ended June 30, 2023 and 2022

Revenues

Except as otherwise indicated herein, the term “domestic” refers to operations in the United States and Canada and the term “international” refers to operations outside of the United States and Canada.

Product licenses and subscription services revenues. The following table sets forth product licenses and subscription services revenues (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Product Licenses and Subscription Services Revenues: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Product Licenses |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Domestic |  | $ | 10,416 |  |  | $ | 15,165 |  |  |  | -31.3 | % |  | $ | 19,066 |  |  | $ | 25,009 |  |  |  | -23.8 | %
International |  |  | 5,106 |  |  |  | 4,964 |  |  |  | 2.9 | % |  |  | 13,868 |  |  |  | 11,633 |  |  |  | 19.2 | %
Total product licenses revenues |  |  | 15,522 |  |  |  | 20,129 |  |  |  | -22.9 | % |  |  | 32,934 |  |  |  | 36,642 |  |  |  | -10.1 | %
Subscription Services |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Domestic |  |  | 12,867 |  |  |  | 10,061 |  |  |  | 27.9 | % |  |  | 25,203 |  |  |  | 19,159 |  |  |  | 31.5 | %
International |  |  | 7,011 |  |  |  | 3,956 |  |  |  | 77.2 | % |  |  | 13,485 |  |  |  | 7,703 |  |  |  | 75.1 | %
Total subscription services revenues |  |  | 19,878 |  |  |  | 14,017 |  |  |  | 41.8 | % |  |  | 38,688 |  |  |  | 26,862 |  |  |  | 44.0 | %
Total product licenses and subscription services revenues |  | $ | 35,400 |  |  | $ | 34,146 |  |  |  | 3.7 | % |  | $ | 71,622 |  |  | $ | 63,504 |  |  |  | 12.8 | %

The following table sets forth a summary, grouped by size, of the number of recognized product licenses transactions for the periods indicated:

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Product Licenses Transactions with Recognized Licenses Revenue in the Applicable Period: |  |  |  |  |  |  |  |  |  |  |  |
More than $1.0 million in licenses revenue recognized |  |  | 2 |  |  |  | 2 |  |  |  | 4 |  |  |  | 3 |
Between $0.5 million and $1.0 million in licenses revenue recognized |  |  | 3 |  |  |  | 4 |  |  |  | 7 |  |  |  | 7 |
Total |  |  | 5 |  |  |  | 6 |  |  |  | 11 |  |  |  | 10 |
Domestic: |  |  |  |  |  |  |  |  |  |  |  |
More than $1.0 million in licenses revenue recognized |  |  | 2 |  |  |  | 2 |  |  |  | 3 |  |  |  | 3 |
Between $0.5 million and $1.0 million in licenses revenue recognized |  |  | 3 |  |  |  | 4 |  |  |  | 5 |  |  |  | 6 |
Total |  |  | 5 |  |  |  | 6 |  |  |  | 8 |  |  |  | 9 |
International: |  |  |  |  |  |  |  |  |  |  |  |
More than $1.0 million in licenses revenue recognized |  |  | 0 |  |  |  | 0 |  |  |  | 1 |  |  |  | 0 |
Between $0.5 million and $1.0 million in licenses revenue recognized |  |  | 0 |  |  |  | 0 |  |  |  | 2 |  |  |  | 1 |
Total |  |  | 0 |  |  |  | 0 |  |  |  | 3 |  |  |  | 1 |

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The following table sets forth the recognized revenue (in thousands) attributable to product licenses transactions, grouped by size, and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Product Licenses Revenue Recognized in the Applicable Period: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
More than $1.0 million in licenses revenue recognized |  | $ | 2,202 |  |  | $ | 7,432 |  |  |  | -70.4 | % |  | $ | 5,473 |  |  | $ | 8,557 |  |  |  | -36.0 | %
Between $0.5 million and $1.0 million in licenses revenue recognized |  |  | 2,880 |  |  |  | 3,185 |  |  |  | -9.6 | % |  |  | 5,417 |  |  |  | 5,138 |  |  |  | 5.4 | %
Less than $0.5 million in licenses revenue recognized |  |  | 10,440 |  |  |  | 9,512 |  |  |  | 9.8 | % |  |  | 22,044 |  |  |  | 22,947 |  |  |  | -3.9 | %
Total |  |  | 15,522 |  |  |  | 20,129 |  |  |  | -22.9 | % |  |  | 32,934 |  |  |  | 36,642 |  |  |  | -10.1 | %
Domestic: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
More than $1.0 million in licenses revenue recognized |  |  | 2,202 |  |  |  | 7,432 |  |  |  | -70.4 | % |  |  | 3,978 |  |  |  | 8,557 |  |  |  | -53.5 | %
Between $0.5 million and $1.0 million in licenses revenue recognized |  |  | 2,880 |  |  |  | 3,185 |  |  |  | -9.6 | % |  |  | 4,086 |  |  |  | 4,628 |  |  |  | -11.7 | %
Less than $0.5 million in licenses revenue recognized |  |  | 5,334 |  |  |  | 4,548 |  |  |  | 17.3 | % |  |  | 11,002 |  |  |  | 11,824 |  |  |  | -7.0 | %
Total |  |  | 10,416 |  |  |  | 15,165 |  |  |  | -31.3 | % |  |  | 19,066 |  |  |  | 25,009 |  |  |  | -23.8 | %
International: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
More than $1.0 million in licenses revenue recognized |  |  | 0 |  |  |  | 0 |  |  | n/a |  |  |  | 1,495 |  |  |  | 0 |  |  | n/a |
Between $0.5 million and $1.0 million in licenses revenue recognized |  |  | 0 |  |  |  | 0 |  |  | n/a |  |  |  | 1,331 |  |  |  | 510 |  |  |  | 161.0 | %
Less than $0.5 million in licenses revenue recognized |  |  | 5,106 |  |  |  | 4,964 |  |  |  | 2.9 | % |  |  | 11,042 |  |  |  | 11,123 |  |  |  | -0.7 | %
Total |  | $ | 5,106 |  |  | $ | 4,964 |  |  |  | 2.9 | % |  | $ | 13,868 |  |  | $ | 11,633 |  |  |  | 19.2 | %

Product licenses revenues decreased $4.6 million and $3.7 million for the three and six months ended June 30, 2023, respectively, as compared to the same periods in the prior year. For the three months ended June 30, 2023 and 2022, product licenses transactions with more than $0.5 million in recognized revenue represented 32.7% and 52.7%, respectively, of our product licenses revenues. For the six months ended June 30, 2023, our top three product licenses transactions totaled $4.4 million in recognized revenue, or 13.3% of total product licenses revenues, compared to $8.6 million, or 23.4% of total product licenses revenues, for the six months ended June 30, 2022. Our product licenses revenues may experience declines in future periods as we continue to promote our cloud offering to new and existing customers.

Domestic product licenses revenues. Domestic product licenses revenues decreased $4.7 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a decrease in the average deal size of transactions with more than $1.0 million in recognized revenue and a decrease in the number of transactions with more than $0.5 million and less than $1.0 million in recognized revenue, partially offset by an increase in the average deal size of transactions with less than $1.0 million in recognized revenue. Domestic product licenses revenues decreased $5.9 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a decrease in the average deal size of transactions with more than $1.0 million in recognized revenue and a decrease in the number of transactions with less than $1.0 million in recognized revenue.

International product licenses revenues. International product licenses revenues did not materially change for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to an increase in the average deal size of transactions with less than $0.5 million in recognized revenue, substantially offset by a $0.7 million unfavorable foreign currency exchange impact. International product licenses revenues increased $2.2 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to an increase in the number of transactions with more than $0.5 million in recognized revenue, partially offset by a $1.7 million unfavorable foreign currency exchange impact.

Subscription services revenues. Subscription services revenues are derived from our MCE cloud subscription service and are recognized ratably over the service period in the contract. Subscription services revenues increased $5.9 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to an increase in the use of subscription services by existing customers, conversions to cloud-based subscriptions from existing on-premises customers, and sales contracts with new customers,

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partially offset by certain non-renewing customers. Subscription services revenues increased $11.8 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to conversions to cloud-based subscriptions from existing on-premises customers, an increase in the use of subscription services by existing customers, and sales contracts with new customers, partially offset by certain non-renewing customers and a $1.1 million unfavorable foreign currency exchange impact. We expect our subscription services revenues to continue to grow in future periods as we continue to promote our cloud offering to new and existing customers.

Product support revenues. The following table sets forth product support revenues (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Product Support Revenues: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Domestic |  | $ | 39,735 |  |  | $ | 39,403 |  |  |  | 0.8 | % |  | $ | 79,554 |  |  | $ | 78,486 |  |  |  | 1.4 | %
International |  |  | 26,346 |  |  |  | 27,118 |  |  |  | -2.8 | % |  |  | 52,008 |  |  |  | 55,186 |  |  |  | -5.8 | %
Total product support revenues |  | $ | 66,081 |  |  | $ | 66,521 |  |  |  | -0.7 | % |  | $ | 131,562 |  |  | $ | 133,672 |  |  |  | -1.6 | %

Product support revenues are derived from providing technical software support and software updates and upgrades to customers. Product support revenues are recognized ratably over the term of the contract, which is generally one year. Product support revenues did not materially change for the three months ended June 30, 2023, as compared to the same period in the prior year. Product support revenues decreased $2.1 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a $1.5 million unfavorable foreign currency exchange impact and certain existing customers converting from perpetual product licenses with separate support contracts to our subscription services or term product licenses offerings. Our product support revenues may experience declines in future periods as we continue to promote our cloud offering to new and existing customers.

Other services revenues. The following table sets forth other services revenues (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Other Services Revenues: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Consulting |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Domestic |  | $ | 8,849 |  |  | $ | 9,743 |  |  |  | -9.2 | % |  | $ | 18,247 |  |  | $ | 19,324 |  |  |  | -5.6 | %
International |  |  | 9,131 |  |  |  | 10,530 |  |  |  | -13.3 | % |  |  | 19,070 |  |  |  | 22,384 |  |  |  | -14.8 | %
Total consulting revenues |  |  | 17,980 |  |  |  | 20,273 |  |  |  | -11.3 | % |  |  | 37,317 |  |  |  | 41,708 |  |  |  | -10.5 | %
Education |  |  | 939 |  |  |  | 1,133 |  |  |  | -17.1 | % |  |  | 1,814 |  |  |  | 2,466 |  |  |  | -26.4 | %
Total other services revenues |  | $ | 18,919 |  |  | $ | 21,406 |  |  |  | -11.6 | % |  | $ | 39,131 |  |  | $ | 44,174 |  |  |  | -11.4 | %

Consulting revenues. Consulting revenues are derived from helping customers plan and execute the deployment of our software. Consulting revenues decreased $2.3 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a decrease in billable hours worldwide, partially offset by an increase in average bill rates. Consulting revenues decreased $4.4 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a decrease in billable hours worldwide and a $0.9 million unfavorable foreign currency exchange impact, partially offset by an increase in average bill rates.

Education revenues. Education revenues are derived from the education and training that we provide to our customers to enhance their ability to fully utilize the features and functionality of our software. These offerings include self-tutorials, custom course development, joint training with customers’ internal staff, and standard course offerings, with pricing dependent on the specific offering delivered. Education revenues did not materially change for the three months ended June 30, 2023, as compared to the same period in the prior year. Education revenues decreased $0.7 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to lower sales in prior quarters of annual subscriptions to training courses.

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Costs and Expenses

Cost of revenues. The following table sets forth cost of revenues (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Cost of Revenues: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Product licenses and subscription services: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Product licenses |  | $ | 444 |  |  | $ | 431 |  |  |  | 3.0 | % |  | $ | 978 |  |  | $ | 908 |  |  |  | 7.7 | %
Subscription services |  |  | 7,216 |  |  |  | 5,498 |  |  |  | 31.2 | % |  |  | 15,072 |  |  |  | 10,908 |  |  |  | 38.2 | %
Total product licenses and subscription services |  |  | 7,660 |  |  |  | 5,929 |  |  |  | 29.2 | % |  |  | 16,050 |  |  |  | 11,816 |  |  |  | 35.8 | %
Product support |  |  | 5,816 |  |  |  | 5,127 |  |  |  | 13.4 | % |  |  | 11,584 |  |  |  | 10,318 |  |  |  | 12.3 | %
Other services: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Consulting |  |  | 13,180 |  |  |  | 12,837 |  |  |  | 2.7 | % |  |  | 26,192 |  |  |  | 26,137 |  |  |  | 0.2 | %
Education |  |  | 465 |  |  |  | 1,311 |  |  |  | -64.5 | % |  |  | 1,236 |  |  |  | 2,610 |  |  |  | -52.6 | %
Total other services |  |  | 13,645 |  |  |  | 14,148 |  |  |  | -3.6 | % |  |  | 27,428 |  |  |  | 28,747 |  |  |  | -4.6 | %
Total cost of revenues |  | $ | 27,121 |  |  | $ | 25,204 |  |  |  | 7.6 | % |  | $ | 55,062 |  |  | $ | 50,881 |  |  |  | 8.2 | %

Cost of product licenses revenues. Cost of product licenses revenues consists of referral fees paid to channel partners, the costs of product manuals and media, and royalties paid to third-party software vendors. Cost of product licenses revenues did not materially change for the three and six months ended June 30, 2023, as compared to the same periods in the prior year.

Cost of subscription services revenues. Cost of subscription services revenues consists of equipment, facility and other related support costs (including cloud hosting infrastructure costs), and personnel and related overhead costs. Subscription services headcount increased 36.1% to 113 at June 30, 2023 from 83 at June 30, 2022. Cost of subscription services revenues increased $1.7 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a $1.2 million increase in cloud hosting infrastructure costs, which is a result of the increased usage by new and existing cloud subscription services customers. Cost of subscription services revenues increased $4.2 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $3.0 million increase in cloud hosting infrastructure costs, which is a result of the increased usage by new and existing cloud subscription services customers, (ii) a $0.5 million increase in employee salaries primarily attributable to an increase in average staffing levels, (iii) a $0.3 million increase in facility and other related support costs, and (iv) a $0.3 million increase in variable compensation. Included in cost of subscription services revenues for the six months ended June 30, 2023 is an aggregate $0.5 million favorable foreign currency exchange impact.

Cost of product support revenues. Cost of product support revenues consists of personnel and related overhead costs, including those under our Enterprise Support program. Our Enterprise Support program utilizes primarily consulting personnel to provide product support to our customers at our discretion. Compensation related to personnel providing Enterprise Support services is reported as cost of product support revenues. Product support headcount increased 4.9% to 172 at June 30, 2023 from 164 at June 30, 2022. Cost of product support revenues increased $0.7 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a $0.8 million increase in compensation and related costs attributable to non-product support personnel providing an increased level of Enterprise Support services. Cost of product support revenues increased $1.3 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a $1.4 million increase in compensation and related costs attributable to non-product support personnel providing an increased level of Enterprise Support services. Included in cost of product support revenues for the six months ended June 30, 2023 is an aggregate $0.7 million favorable foreign currency exchange impact.

Cost of consulting revenues. Cost of consulting revenues consists of personnel and related overhead costs, excluding those under our Enterprise Support program, which are allocated to cost of product support revenues. Consulting headcount increased 1.9% to 436 at June 30, 2023 from 428 at June 30, 2022. Cost of consulting revenues did not materially change for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $1.0 million increase in variable compensation and (ii) a $0.6 million increase in employee salaries primarily attributable to an increase in average staffing levels, substantially offset by (iii) a $0.8 million decrease in compensation and related costs attributable to consulting personnel providing an increased level of Enterprise Support services and (iv) a $0.7 million decrease in in subcontractor costs. Cost of consulting revenues did not materially change for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $1.6 million increase in variable compensation, (ii) a $0.7 million increase in employee salaries primarily attributable to an increase in average staffing levels, and (iii) a $0.4 million increase in facility and other related support costs, substantially offset by (iv) a $1.4 million decrease in compensation and related costs attributable to consulting personnel providing an increased level of Enterprise Support services and (v)

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a $1.3 million decrease in in subcontractor costs. Included in cost of consulting revenues for the six months ended June 30, 2023 is an aggregate $0.9 million favorable foreign currency exchange impact.

Cost of education revenues. Cost of education revenues consists of personnel and related overhead costs. Education headcount decreased 63.9% to 13 at June 30, 2023 from 36 at June 30, 2022. Cost of education revenues decreased $0.8 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $0.4 million decrease in employee salaries primarily attributable to a decrease in average staffing levels and (ii) a $0.3 million decrease in variable compensation. Cost of education revenues decreased $1.4 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $0.8 million decrease in employee salaries primarily attributable to a decrease in average staffing levels and (ii) a $0.3 million decrease in variable compensation.

Sales and marketing expenses. Sales and marketing expenses consist of personnel costs, commissions, office facilities, travel, advertising, public relations programs, and promotional events, such as trade shows, seminars, and technical conferences. Sales and marketing headcount decreased 6.6% to 427 at June 30, 2023 from 457 at June 30, 2022. The following table sets forth sales and marketing expenses (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Sales and marketing expenses |  | $ | 37,660 |  |  | $ | 36,862 |  |  |  | 2.2 | % |  | $ | 73,766 |  |  | $ | 70,102 |  |  |  | 5.2 | %

Sales and marketing expenses increased $0.8 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $1.5 million increase in marketing costs due to the return of in-person events, (ii) a $1.4 million increase in travel and entertainment expenditures due to the return of in-person events and meetings, and (iii) a $0.3 million increase in facility and other related support costs, partially offset by (iv) a $1.6 million decrease in variable compensation primarily attributable to a decrease in commissions earned, partially offset by a decrease in net capitalized commissions and increases in other personnel costs and employee relations expenses, (v) a $0.7 million decrease in employee salaries primarily attributable to a decrease in average staffing levels, partially offset by wage increases, and (vi) a $0.2 million net decrease in share-based compensation expense primarily attributable to the forfeiture of certain awards, partially offset by the fair value remeasurement of certain liability-classified awards at the end of the reporting period and the grant of additional awards under the Stock Incentive Plans. Included in sales and marketing expenses for the three months ended June 30, 2023 is an aggregate $0.7 million favorable foreign currency exchange impact.

Sales and marketing expenses increased $3.7 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $2.1 million increase in travel and entertainment expenditures due to the return of in-person events and meetings, (ii) a $1.2 million increase in marketing costs due to the return of in-person events, (iii) a $0.8 million increase in variable compensation primarily attributable to a decrease in net capitalized commissions and increases in employee relations expenses and other personnel costs, partially offset by a decrease in commissions earned, (iv) a $0.6 million net increase in share-based compensation expense primarily attributable to the grant of additional awards under the Stock Incentive Plans and the fair value remeasurement of certain liability-classified awards at the end of the reporting period, partially offset by the forfeiture of certain awards, and (v) a $0.5 million increase in facility and other related support costs, partially offset by (vi) a $1.5 million decrease in employee salaries primarily attributable to a decrease in average staffing levels, partially offset by wage increases. Included in sales and marketing expenses for the six months ended June 30, 2023 is an aggregate $2.0 million favorable foreign currency exchange impact.

Research and development expenses. Research and development expenses consist of the personnel costs for our software engineering personnel, depreciation of equipment, and other related costs. Research and development headcount decreased 7.4% to 674 at June 30, 2023 from 728 at June 30, 2022. The following table summarizes research and development expenses (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Research and development expenses |  | $ | 29,354 |  |  | $ | 31,790 |  |  |  | -7.7 | % |  | $ | 60,712 |  |  | $ | 65,313 |  |  |  | -7.0 | %

Research and development expenses decreased $2.4 million for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $0.9 million decrease in employee salaries primarily attributable to a decrease in average staffing levels, partially offset by wage increases, (ii) a $0.9 million net decrease in share-based compensation expense primarily attributable to the forfeiture of certain awards, partially offset by the fair value remeasurement of certain liability-classified awards at the end of the reporting period and the grant of additional awards under the Stock Incentive Plans, and (iii) a $0.3 million decrease in variable compensation.

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Research and development expenses decreased $4.6 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $1.9 million decrease in employee salaries primarily attributable to a decrease in average staffing levels, partially offset by wage increases, (ii) a $0.8 million decrease in variable compensation, (iii) a $0.6 million decrease in facility and other related support costs, (iv) a $0.5 million decrease in recruiting costs, (v) a $0.4 million decrease in subcontractor costs, and (vi) a $0.3 million net decrease in share-based compensation expense primarily attributable to the forfeiture of certain awards, partially offset by the grant of additional awards under the Stock Incentive Plans and the fair value remeasurement of certain liability-classified awards at the end of the reporting period. Included in research and development expenses for the six months ended June 30, 2023 is an aggregate $1.1 million favorable foreign currency exchange impact.

General and administrative expenses. General and administrative expenses consist of personnel and related overhead costs, and other costs of our executive, finance, human resources, information systems, and administrative departments, as well as third-party consulting, legal, and other professional fees. General and administrative headcount increased 0.8% to 264 at June 30, 2023 from 262 at June 30, 2022. The following table sets forth general and administrative expenses (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
General and administrative expenses |  | $ | 28,830 |  |  | $ | 28,502 |  |  |  | 1.2 | % |  | $ | 56,736 |  |  | $ | 55,208 |  |  |  | 2.8 | %

General and administrative expenses did not materially change for the three months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $1.3 million net increase in share-based compensation expense primarily attributable to the grant of additional awards under the Stock Incentive Plans, (ii) a $1.0 million increase in the estimated minimum loss with respect to the Brazilian matters noted in Note 5, Commitments and Contingencies, to the Consolidated Financial Statements, (iii) a $0.4 million increase in directors and officers liability insurance expense, and (iv) a $0.3 million increase in variable compensation, substantially offset by (v) a $2.3 million decrease in costs related to the maintenance and operations of our corporate aircraft, (vi) a $0.5 million decrease in non-income taxes, and (vii) a $0.3 million decrease in recruiting costs.

General and administrative expenses increased $1.5 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) a $3.0 million net increase in share-based compensation expense primarily attributable to the grant of additional awards under the Stock Incentive Plans, partially offset by certain awards that became fully vested, (ii) a $1.2 million increase in the estimated minimum loss with respect to the Brazilian matters noted in Note 5, Commitments and Contingencies, to the Consolidated Financial Statements, and (iii) a $0.9 million increase in directors and officers liability insurance expense, partially offset by (iv) a $2.0 million decrease in costs related to the maintenance and operations of our corporate aircraft, (v) a $0.7 million decrease in custodial fees incurred on our bitcoin holdings, and (vi) a $0.7 million decrease in recruiting costs. Included in general and administrative expenses for the six months ended June 30, 2023 is an aggregate $0.6 million favorable foreign currency exchange impact.

Digital asset impairment losses. Digital asset impairment losses are recognized when the carrying value of our digital assets exceeds their lowest fair value at any time since their acquisition. Impaired digital assets are written down to fair value at the time of impairment, and such impairment loss cannot be recovered for any subsequent increases in fair value. Gains (if any) are not recorded until realized upon sale. The following table sets forth digital asset impairment losses (in thousands) and related percentage changes for the periods indicated:

|  | Three Months Ended |  |  |  |  |  | Six Months Ended |  |  |  |
|  | June 30, |  |  | % |  |  | June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |  |  | 2023 |  |  | 2022 |  |  | Change |
Digital asset impairment losses |  | $ | 24,143 |  |  | $ | 917,838 |  |  |  | -97.4 | % |  | $ | 43,054 |  |  | $ | 1,087,929 |  |  |  | -96.0 | %

We did not sell any of our digital assets during the three and six months ended June 30, 2023 and 2022. We may continue to incur significant digital asset impairment losses in the future.

Interest Expense, Net

For the three and six months ended June 30, 2023, interest expense, net, of $11.1 million and $26.0 million were primarily related to the contractual interest expense and amortization of issuance costs related to our long-term debt arrangements. For the three and six months ended June 30, 2022, interest expense, net, of $13.2 million and $24.2 million, respectively, were primarily related to the contractual interest expense and amortization of issuance costs related to our long-term debt arrangements. Interest expense for future periods in 2023 is expected to continue to decrease compared to the same periods in 2022 as a result of the repayment of the 2025 Secured Term Loan in March 2023. Refer to Note 4, Long-term Debt, to the Consolidated Financial Statements for further information.

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Gain on Debt Extinguishment

For the six months ended June 30, 2023, the $44.7 million gain on debt extinguishment resulted from the repayment of the 2025 Secured Term Loan. Refer to Note 4, Long-term Debt, to the Consolidated Financial Statements for further information.

Other (Expense) Income, Net

For the three and six months ended June 30, 2023, other expense, net, of $0.3 million and $1.7 million, were comprised primarily of foreign currency transaction net losses. For the three and six months ended June 30, 2022, other income, net, of $5.1 million and $7.3 million, respectively, were comprised primarily of foreign currency transaction net gains.

(Benefit From) Provision For Income Taxes

We recorded a benefit from income taxes of $513.5 million on a pretax loss of $30.0 million that resulted in an effective tax rate of 1,708.9% for the six months ended June 30, 2023, as compared to a provision for income taxes of $88.1 million on a pretax loss of $1.105 billion that resulted in an effective tax rate of (8.0)% for the six months ended June 30, 2022. Our benefit from income taxes increased from the same period in the prior year primarily due to the release of the remaining valuation allowance on our deferred tax asset related to the impairment on our bitcoin holdings, attributable to the increase in market value of bitcoin as of June 30, 2023 compared to December 31, 2022.

As of June 30, 2023, we had a valuation allowance of $2.6 million primarily related to certain foreign tax credit carryforwards that, in our present estimation, more likely than not will not be realized. If the market value of bitcoin declines or we are unable to maintain profitability in future periods, we may be required to increase the valuation allowance against our deferred tax assets, which could result in a charge that would materially adversely affect net income (loss) in the period in which the charge is incurred. We will continue to regularly assess the realizability of deferred tax assets.

Our effective tax rate may fluctuate due to changes in our domestic and foreign earnings and losses, material discrete tax items, or a combination of these factors resulting from transactions or events.

Deferred Revenue and Advance Payments

Deferred revenue and advance payments represent amounts received or due from our customers in advance of our transferring our software or services to the customer. In the case of multi-year service contract arrangements, we generally do not invoice more than one year in advance of services and do not record deferred revenue for amounts that have not been invoiced. Revenue is subsequently recognized in the period(s) in which control of the software or services is transferred to the customer.

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The following table summarizes deferred revenue and advance payments (in thousands), as of:

|  | June 30, |  |  | December 31, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2022 |
Current: |  |  |  |  |  |  |  |  |
Deferred product licenses revenue |  | $ | 974 |  |  | $ | 2,825 |  |  | $ | 754 |
Deferred subscription services revenue |  |  | 49,898 |  |  |  | 51,861 |  |  |  | 40,295 |
Deferred product support revenue |  |  | 141,605 |  |  |  | 155,366 |  |  |  | 143,524 |
Deferred other services revenue |  |  | 3,340 |  |  |  | 7,376 |  |  |  | 3,525 |
Total current deferred revenue and advance payments |  | $ | 195,817 |  |  | $ | 217,428 |  |  | $ | 188,098 |
Non-current: |  |  |  |  |  |  |  |  |
Deferred product licenses revenue |  | $ | 2,493 |  |  | $ | 2,742 |  |  | $ | 0 |
Deferred subscription services revenue |  |  | 2,888 |  |  |  | 3,030 |  |  |  | 2,639 |
Deferred product support revenue |  |  | 5,340 |  |  |  | 6,387 |  |  |  | 5,272 |
Deferred other services revenue |  |  | 523 |  |  |  | 604 |  |  |  | 586 |
Total non-current deferred revenue and advance payments |  | $ | 11,244 |  |  | $ | 12,763 |  |  | $ | 8,497 |
Total current and non-current: |  |  |  |  |  |  |  |  |
Deferred product licenses revenue |  | $ | 3,467 |  |  | $ | 5,567 |  |  | $ | 754 |
Deferred subscription services revenue |  |  | 52,786 |  |  |  | 54,891 |  |  |  | 42,934 |
Deferred product support revenue |  |  | 146,945 |  |  |  | 161,753 |  |  |  | 148,796 |
Deferred other services revenue |  |  | 3,863 |  |  |  | 7,980 |  |  |  | 4,111 |
Total current and non-current deferred revenue and advance payments |  | $ | 207,061 |  |  | $ | 230,191 |  |  | $ | 196,595 |

The portions of multi-year contracts that will be invoiced in the future are not presented on the balance sheet in “Accounts receivable, net” and “Deferred revenue and advance payments” and instead are included in the remaining performance obligation disclosure below. Total deferred revenue and advance payments decreased $23.1 million as of June 30, 2023, as compared to December 31, 2022, primarily due to the timing of product support and subscription services renewals and an increase in revenue recognized from previously deferred other services, subscription services, and product licenses. Total deferred revenue and advance payments increased $10.5 million as of June 30, 2023, as compared to June 30, 2022, primarily due to an increase in deferred revenue from subscription services contracts and an increase in deferred product license revenue from the early renewal of a large multi-year term license deal in the fourth quarter of 2022, partially offset by a decrease in deferred product support revenue from an increase in conversions from on-premises to subscription services contracts. Included in our international deferred revenue balances at June 30, 2023 is a $1.1 million favorable foreign currency impact from the general weakening of the U.S. dollar compared to June 30, 2022.

Our remaining performance obligation represents all future revenue under contract and includes deferred revenue and advance payments and billable non-cancelable amounts that will be invoiced and recognized as revenue in future periods. The remaining performance obligation excludes contracts that are billed in arrears, such as certain time and materials contracts. As of June 30, 2023, we had an aggregate transaction price of $294.3 million allocated to the remaining performance obligation related to product support, subscription services, product licenses, and other services contracts. We expect to recognize approximately $229.1 million of the remaining performance obligation over the next 12 months and the remainder thereafter. However, the timing and ultimate recognition of our deferred revenue and advance payments and other remaining performance obligations depend on our satisfaction of various performance obligations, and the amount of deferred revenue and advance payments and remaining performance obligations at any date should not be considered indicative of revenues for any succeeding period.

Liquidity and Capital Resources

Liquidity. Our principal sources of liquidity are cash and cash equivalents and on-going collection of our accounts receivable. Cash and cash equivalents may include holdings in bank demand deposits, money market instruments, certificates of deposit, and U.S. Treasury securities. Under our Treasury Reserve Policy and bitcoin acquisition strategy, we use a significant portion of our cash, including cash generated from capital raising transactions, to acquire bitcoins, which are classified as indefinite-lived intangible assets. In September 2022, we commenced an at-the-market equity offering under the 2022 Sales Agreement, pursuant to which we issued and sold 1,567,430 shares of our class A common stock for aggregate net proceeds (net of sales commissions and expenses) of $385.2 million through the first quarter of 2023. We terminated the 2022 Sales Agreement in May 2023 and commenced a new at-the-market equity offering under the 2023 Sales Agreement, pursuant to which we may from time to time issue and sell shares of our class A common stock having an aggregate offering price of up to $625.0 million. As of June 30, 2023, we had issued and sold 1,079,170 shares of our class A common stock for aggregate net proceeds (net of sales commissions and expenses) of $333.5 million and approximately $290.0 million of our

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class A common stock remained available for issuance and sale pursuant to the 2023 Sales Agreement. For additional information, see “—At-the-Market Equity Offerings” below.

As of June 30, 2023 and December 31, 2022, the amount of cash and cash equivalents held by our U.S. entities was $17.3 million and $14.8 million, respectively, and by our non-U.S. entities was $48.7 million and $29.0 million, respectively. We earn a significant amount of our revenues outside the United States. We repatriated foreign earnings and profits of $44.7 million during 2022. We did not repatriate any foreign earnings and profits during the six months ended June 30, 2023.

Our material contractual obligations and cash requirements consist of:

•
principal and interest payments related to our long-term debt;
•
rent payments under noncancellable operating leases;
•
payments related to the mandatory deemed repatriation transition tax (the “Transition Tax”) under the U.S. Tax Cuts and Jobs Act (the “Tax Act”);
•
payments under various purchase agreements, primarily related to third-party software supporting our products, marketing, and operations; and
•
ongoing personnel-related expenditures and vendor payments.

The above items are explained in further detail in Note 4, Long-term Debt, to the Consolidated Financial Statements included in this Quarterly Report as well as under “Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations—Liquidity and Capital Resources” included in our Annual Report on Form 10-K for the fiscal year ended December 31, 2022 and in the Notes to the Consolidated Financial Statements included therein. Other than the payoff of the 2025 Secured Term Loan described more fully below and in Note 4, Long-term Debt, to the Consolidated Financial Statements included in this Quarterly Report, and new purchase commitments for third-party cloud hosting services totaling $135.0 million to be spent over the next four years, there have been no changes to our material contractual obligations and cash requirements since December 31, 2022.

We believe that existing cash and cash equivalents held by us and cash and cash equivalents anticipated to be generated by us are sufficient to meet working capital requirements, anticipated capital expenditures, and contractual obligations for at least the next 12 months. Beyond the next 12 months, our long-term cash requirements are primarily for obligations related to our long-term debt. We have principal due upon maturity of our long-term debt instruments in the aggregate of $2.208 billion in addition to $2.4 million in coupon interest due each semi-annual period for the 2025 Convertible Notes, $15.3 million in coupon interest due each semi-annual period for the 2028 Secured Notes, and $0.1 million due monthly in principal and interest related to our other long-term secured debt. We also have long-term cash requirements for obligations related to our operating leases, the Transition Tax, and our various purchase agreements. As of June 30, 2023, we do not expect cash and cash equivalents generated by our enterprise analytics software business to be sufficient to satisfy these obligations. As a result, we would seek to satisfy these obligations through various options that we expect to be available to us, such as refinancing our debt or generating cash from other sources, which may include the issuance and sale of shares of our class A common stock, borrowings collateralized by bitcoin, or the sale of our bitcoin. Furthermore, if certain conditions are met, we may have the right to elect to settle the Convertible Notes upon a conversion of such Convertible Notes in shares of our class A common stock, or a combination of cash and shares of class A common stock, which may enable us to reduce the amount of our cash obligations under the Convertible Notes.

The 2028 Secured Notes have a stated maturity date of June 15, 2028, but include a springing maturity feature that will cause the stated maturity date to spring ahead to the date that is (i) 91 days prior to the existing maturity date of the 2025 Convertible Notes (which is September 15, 2025), (ii) 91 days prior to the existing maturity date of the 2027 Convertible Notes (which is November 16, 2026), or (iii) the maturity date of any future convertible debt that we may issue that is then outstanding, unless on such dates we meet specified liquidity requirements or less than $100,000,000 of aggregate principal amount of the 2025 Convertible Notes, the 2027 Convertible Notes, or such future convertible debt, as applicable, remains outstanding.

As of June 30, 2023, we held approximately 152,333 bitcoins, of which approximately 137,069 are unencumbered. We do not believe we will need to sell or engage in other transactions with respect to any of our bitcoins within the next twelve months to meet our working capital requirements, although we may from time to time sell or engage in other transactions with respect to our bitcoins as part of treasury management operations, as noted above. The bitcoin market historically has been characterized by significant volatility in its price, limited liquidity and trading volumes compared to sovereign currencies markets, relative anonymity, a developing regulatory landscape, susceptibility to market abuse and manipulation, compliance and internal control failures at exchanges, and various other risks inherent in its entirely electronic, virtual form and decentralized network. During times of instability in the bitcoin market, we may not be able to sell our bitcoins at reasonable prices or at all. As a result, our bitcoins are less liquid than our existing cash and cash equivalents and may not be able to serve as a source of liquidity for us to the same extent as cash and cash equivalents. In addition, upon

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sale of our bitcoin, we may incur additional taxes related to any realized gains or we may incur capital losses as to which the tax deduction may be limited.

The following table sets forth a summary of our cash flows (in thousands) and related percentage changes for the periods indicated:

|  | Six Months Ended June 30, |  |  | % |
|  | 2023 |  |  | 2022 |  |  | Change |
Net cash provided by operating activities |  | $ | 18,925 |  |  | $ | 22,863 |  |  |  | -17.2 | %
Net cash used in investing activities |  | $ | (527,416 | ) |  | $ | (227,019 | ) |  |  | 132.3 | %
Net cash provided by financing activities |  | $ | 525,911 |  |  | $ | 218,487 |  |  |  | 140.7 | %

Net cash provided by operating activities. The primary source of our cash provided by operating activities is cash collections of our accounts receivable from customers following the sales and renewals of our product licenses, subscription services and product support, as well as consulting and education services. Our primary uses of cash in operating activities are for personnel-related expenditures for software development, personnel-related expenditures for providing consulting, education, and subscription services, and for sales and marketing costs, general and administrative costs, interest expense related to our long-term debt arrangements, and income taxes. Non-cash items to further reconcile net income (loss) to net cash provided by operating activities consist primarily of depreciation and amortization, reduction in the carrying amount of operating lease right-of-use assets, credit losses and sales allowances, deferred taxes, release of liabilities for unrecognized tax benefits, share-based compensation expense, digital asset impairment losses, amortization of the issuance costs on our long-term debt, and gain on extinguishment of debt.

Net cash provided by operating activities decreased $3.9 million for the six months ended June 30, 2023, as compared to the same period in the prior year, due to a $1.691 billion decrease in non-cash items (principally related to changes in digital asset impairment losses, deferred taxes, and a gain on extinguishment of debt in the first quarter of 2023), which was partially offset by a $1.676 billion increase in net income and a $10.5 million increase from changes in operating assets and liabilities.

Net cash used in investing activities. The changes in net cash used in investing activities primarily relate to purchases of digital assets and expenditures on property and equipment. Net cash used in investing activities increased $300.4 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to a $300.8 million increase in purchases of bitcoins. During the six months ended June 30, 2023, we purchased $526.3 million of bitcoin using the net proceeds from the sale of class A common stock under the 2022 Sales Agreement and the 2023 Sales Agreement, and Excess Cash, while during the six months ended June 30, 2022, we purchased $225.5 million of bitcoin using net proceeds from the issuance of the 2025 Secured Term Loan and Excess Cash.

Net cash provided by financing activities. The changes in net cash provided by (used in) financing activities primarily relate to the sale of class A common stock under our at-the-market offering program, the issuance and subsequent repayment of our long-term debt, the exercise or vesting of certain awards under the 2013 Equity Plan, and the sales of class A common stock under the 2021 ESPP. Net cash provided by financing activities increased $307.4 million for the six months ended June 30, 2023, as compared to the same period in the prior year, primarily due to (i) $672.4 million in net proceeds from the sale of class A common stock under our at-the-market offering program during the six months ended June 30, 2023, (ii) a $11.4 million increase in proceeds from the exercise of stock options under the Equity Plans in the six months ended June 30, 2023, as compared to the same period in the prior year, partially offset by (iii) a $215.5 million decrease in long-term debt proceeds, net of lender fees and issuance costs, during the six months ended June 30, 2023 as compared to the same period in the prior year, and (iv) the $160.0 million repayment of the 2025 Secured Term Loan and related third-party extinguishment costs during the six months ended June 30, 2023, which was repaid using proceeds from our sale of class A common stock offered under our at-the-market offering program.

Long-term Debt

The terms of each of the long-term debt instruments are discussed more fully in Note 4, Long-term Debt to the Consolidated Financial Statements included in this Quarterly Report as well as Note 8, Long-term Debt, to the Consolidated Financial Statements of our Annual Report on Form 10-K for the fiscal year ended December 31, 2022.

In December 2020, we issued $650.0 million aggregate principal amount of the 2025 Convertible Notes and in February 2021, we issued $1.050 billion aggregate principal amount of the 2027 Convertible Notes. We used the net proceeds from the issuance of the Convertible Notes to acquire bitcoin. For each of the three and six months ended June 30, 2023, we paid $2.4 million in interest to holders of the 2025 Convertible Notes. For each of the three and six months ended June 30, 2022, we paid $2.4 million in interest to holders of the 2025 Convertible Notes. The 2027 Convertible Notes do not bear regular interest and we have not paid any special interest to holders of the 2027 Convertible Notes to date.

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In June 2021, we issued $500.0 million aggregate principal amount of the 2028 Secured Notes. We used the net proceeds from the issuance of the 2028 Secured Notes to acquire bitcoin. As of June 30, 2023, approximately 15,264 of the bitcoins held by the Company serve as part of the collateral for the 2028 Secured Notes. For each of the three and six months ended June 30, 2023, we paid $15.3 million in interest to holders of the 2028 Secured Notes. For each of the three and six months ended June 30, 2022, we paid $15.3 million in interest to holders of the 2028 Secured Notes.

In March 2022, MacroStrategy, our wholly-owned subsidiary, entered into a Credit and Security Agreement with Silvergate Bank, pursuant to which Silvergate Bank issued the $205.0 million 2025 Secured Term Loan to MacroStrategy. We used $190.5 million of the net proceeds from the issuance of the 2025 Secured Term Loan to acquire bitcoin, used $5.0 million of the net proceeds to maintain a reserve account that served as collateral for the 2025 Secured Term Loan, and used the remaining net proceeds to pay fees, interest, and expenses related to the 2025 Secured Term Loan. On March 24, 2023, MacroStrategy and Silvergate Bank entered into a Prepayment, Waiver and Payoff to Credit and Security Agreement, pursuant to which MacroStrategy voluntarily prepaid Silvergate approximately $161.0 million (the “Payoff Amount”), in full repayment, satisfaction, and discharge of the 2025 Secured Term Loan and all other obligations under the Credit and Security Agreement. Upon Silvergate’s receipt of the Payoff Amount on March 24, 2023, the Credit and Security Agreement was terminated, and Silvergate released its security interest in all of MacroStrategy’s assets collateralizing the 2025 Secured Term Loan, including the bitcoin that was serving as collateral. During the first quarter of 2023, we made a final $5.1 million interest payment to Silvergate, $1.1 million of which was included in the Payoff Amount. For each of the three and six months ended June 30, 2022, we paid $1.6 million in interest to Silvergate.

In June 2022, we, through one of our wholly-owned subsidiaries, entered into a secured term loan agreement in the amount of $11.1 million, bearing interest at an annual rate of 5.2%, and maturing in June 2027. During the three and six months ended June 30, 2023, we paid $0.3 million and $0.5 million, respectively, in principal and interest to the lender. During the three and six months ended June 30, 2022, we did not pay any principal or interest to the lender.

At-the-Market Equity Offerings

On September 9, 2022, we entered into the 2022 Sales Agreement with the 2022 Sales Agents, pursuant to which we could issue and sell shares of our class A common stock having an aggregate offering price of up to $500.0 million from time to time through the 2022 Sales Agents.

On May 1, 2023, we terminated the 2022 Sales Agreement and entered into a new Sales Agreement (the “2023 Sales Agreement”) with the 2023 Sales Agents, pursuant to which we may issue and sell shares of our class A common stock having an aggregate offering price of up to $625.0 million from time to time through the 2023 Sales Agents.

The terms of the 2022 Sales Agreement and 2023 Sales Agreement are discussed more fully in Note 10, At-the-Market Equity Offerings, to the Consolidated Financial Statements.

We did not sell any shares of our class A common stock under the 2022 Sales Agreement during the three months ended June 30, 2023. During the six months ended June 30, 2023, we issued and sold 1,348,855 shares of class A common stock under the 2022 Sales Agreement for aggregate net proceeds (less sales commissions and expenses) of approximately $339.0 million. At termination of the 2022 Sales Agreement on May 1, 2023, we had issued and sold an aggregate of 1,567,430 shares under the 2022 Sales Agreement for aggregate net proceeds (less sales commissions and expenses) of approximately $385.2 million.

During the three and six months ended June 30, 2023, we issued and sold 1,079,170 shares of our class A common stock under the 2023 Sales Agreement, for aggregate net proceeds (less sales commissions and expenses) of approximately $333.5 million. As of June 30, 2023, approximately $290.0 million of our class A common stock remained available for issuance and sale pursuant to the 2023 Sales Agreement

Debt Repurchases and Prepayments.

During the first quarter of 2023, MacroStrategy voluntarily prepaid Silvergate the Payoff Amount in full repayment, satisfaction, and discharge of the 2025 Secured Term Loan and all other obligations under the Credit and Security Agreement. During the three months ended June 30, 2023 and the three and six months ended June 30, 2022, we did not repurchase or prepay any of our other outstanding debt. We or our affiliates may, at any time and from time to time, seek to retire or purchase our outstanding debt through cash purchases and/or exchanges for equity or debt, in open-market purchases, privately negotiated transactions or otherwise. Such repurchases or exchanges, if any, will be upon such terms and at such prices as we may determine, and will depend on prevailing market conditions, our liquidity requirements, contractual restrictions and other factors. We may also prepay our outstanding indebtedness. The amounts involved in any such repurchase or prepayment may be material. We may effect debt repurchases or prepayments using proceeds from

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the sale of our class A common stock pursuant to the 2023 Sales Agreement (under which approximately $290.0 million remains available for sale as of the date hereof).

Non-GAAP Financial Measures

We are providing supplemental non-GAAP financial measures below which management uses internally to help understand, manage, and evaluate our business performance and to help make operating decisions. We believe that these non-GAAP financial measures are also useful to investors and analysts in comparing our performance across reporting periods on a consistent basis. We also believe the use of these non-GAAP financial measures can facilitate comparison of our operating results to those of our competitors. These supplemental financial measures are not measurements of financial performance under generally accepted accounting principles in the United States (“GAAP”) and, as a result, these supplemental financial measures may not be comparable to similarly titled measures of other companies.

Non-GAAP financial measures are subject to material limitations as they are not measurements prepared in accordance with GAAP, and are not a substitute for such measurements. For example, we expect that share-based compensation expense, which is excluded from certain of the non-GAAP financial measures below, will continue to be a significant recurring expense over the coming years and is an important part of the compensation provided to certain employees, officers, and directors. Similarly, we expect that interest expense arising from the amortization of debt issuance costs on our long-term debt, which is excluded from certain of the non-GAAP financial measures below, will continue to be a recurring expense over the terms of our long-term debt arrangements. Our non-GAAP financial measures are not meant to be considered in isolation and should be read only in conjunction with our Consolidated Financial Statements, which have been prepared in accordance with GAAP. We rely primarily on such Consolidated Financial Statements to understand, manage, and evaluate our business performance and use the non-GAAP financial measures only supplementally.

Non-GAAP loss from operations

Non-GAAP loss from operations excludes share-based compensation expense, which is a significant non-cash expense that we believe is not reflective of our general business performance, and for which the accounting requires management judgment. Consequently, our accounting for share-based compensation expense could vary significantly in comparison to other companies. The following is a reconciliation of our non-GAAP loss from operations to loss from operations, its most directly comparable GAAP measure, (in thousands) for the periods indicated:

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Reconciliation of non-GAAP loss from operations: |  |  |  |  |  |  |  |  |  |  |  |
Loss from operations |  | $ | (26,708 | ) |  | $ | (918,123 | ) |  | $ | (47,015 | ) |  | $ | (1,088,083 | )
Share-based compensation expense |  |  | 15,494 |  |  |  | 15,294 |  |  |  | 33,049 |  |  |  | 29,688 |
Non-GAAP loss from operations |  | $ | (11,214 | ) |  | $ | (902,829 | ) |  | $ | (13,966 | ) |  | $ | (1,058,395 | )

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Non-GAAP net income (loss) and non-GAAP diluted earnings (loss) per share

Non-GAAP net income (loss) and non-GAAP diluted earnings (loss) per share each exclude the impact of (i) share-based compensation expense, (ii) interest expense arising from the amortization of debt issuance costs on our long-term debt, (iii) gain on extinguishment of debt, and (iv) related income taxes. We believe non-GAAP net income (loss) and non-GAAP diluted earnings (loss) per share offer management and investors insight as they exclude significant non-cash expenses, gains on debt extinguishment, and their related income tax effects. The following are reconciliations of our non-GAAP net income (loss) and non-GAAP diluted earnings (loss) per share to net income (loss) and diluted earnings (loss) per share, respectively, their most directly comparable GAAP measures (in thousands, except per share data), for the periods indicated:

|  | Three Months Ended |  |  | Six Months Ended |
|  | June 30, |  |  | June 30, |
|  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2022 |
Reconciliation of non-GAAP net income (loss): |  |  |  |  |  |  |  |  |  |  |  |
Net income (loss) |  | $ | 22,243 |  |  | $ | (1,062,298 | ) |  | $ | 483,436 |  |  | $ | (1,193,049 | )
Share-based compensation expense |  |  | 15,494 |  |  |  | 15,294 |  |  |  | 33,049 |  |  |  | 29,688 |
Interest expense arising from amortization of debt issuance costs |  |  | 2,190 |  |  |  | 2,168 |  |  |  | 4,400 |  |  |  | 4,297 |
Gain on debt extinguishment |  |  | 0 |  |  |  | 0 |  |  |  | (44,686 | ) |  |  | 0 |
Income tax effects (1) |  |  | (2,998 | ) |  |  | (3,898 | ) |  |  | 5,768 |  |  |  | (7,342 | )
Non-GAAP net income (loss) |  | $ | 36,929 |  |  | $ | (1,048,734 | ) |  | $ | 481,967 |  |  | $ | (1,166,406 | )
Reconciliation of non-GAAP diluted earnings (loss) per share (2): |  |  |  |  |  |  |  |  |  |  |  |
Diluted earnings (loss) per share |  | $ | 1.52 |  |  | $ | (94.01 | ) |  | $ | 33.56 |  |  | $ | (105.64 | )
Share-based compensation expense (per diluted share) |  |  | 0.96 |  |  |  | 1.35 |  |  |  | 2.27 |  |  |  | 2.63 |
Interest expense arising from amortization of debt issuance costs (per diluted share) (3) |  |  | 0.03 |  |  |  | 0.19 |  |  |  | 0.06 |  |  |  | 0.38 |
Gain on debt extinguishment (per diluted share) |  |  | 0.00 |  |  |  | 0.00 |  |  |  | (3.07 | ) |  |  | 0.00 |
Income tax effects (per diluted share) (3) |  |  | (0.16 | ) |  |  | (0.34 | ) |  |  | 0.46 |  |  |  | (0.65 | )
Non-GAAP diluted earnings (loss) per share |  | $ | 2.35 |  |  | $ | (92.81 | ) |  | $ | 33.28 |  |  | $ | (103.28 | )

(1)
Income tax effects reflect the net tax effects of share-based compensation expense, which includes tax benefits and expenses on exercises of stock options and vesting of share-settled restricted stock units, interest expense for amortization of debt issuance costs, and gain on debt extinguishment.
(2)
For reconciliation purposes, the non-GAAP diluted earnings (loss) per share calculations use the same weighted average shares outstanding as that used in the GAAP diluted earnings (loss) per share calculations for the same period. For example, in periods of GAAP net loss, otherwise dilutive potential shares of common stock from our share-based compensation arrangements and Convertible Notes are excluded from the GAAP diluted loss per share calculation as they would be antidilutive, and therefore are also excluded from the non-GAAP diluted earnings or loss per share calculation.
(3)
For the three and six months ended June 30, 2023, interest expense from the amortization of issuance costs of the Convertible Notes has been added back to the numerator in the GAAP diluted earnings per share calculation (as disclosed in Note 9, Basic and Diluted Earnings (Loss) per Share, to the Consolidated Financial Statements), and therefore the per diluted share effects of the amortization of issuance costs of the Convertible Notes have been excluded from the “Interest expense arising from amortization of debt issuance costs (per diluted share)” and “Income tax effects (per diluted share)” lines in the above reconciliation for the three and six months ended June 30, 2023.

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Non-GAAP Constant Currency Revenues, Cost of Revenues, and Operating Expenses

We present certain of our revenues, cost of revenues, and operating expenses on a non-GAAP constant currency basis, which excludes changes resulting from fluctuations in foreign currency exchange rates. These non-GAAP constant currency metrics allow our management and investors to compare operating results to the same period in the prior year without the effects of changes in foreign currency exchange rates, which are not reflective of our general business performance and may vary significantly between periods. The following are reconciliations our non-GAAP constant currency revenues, cost of revenues, and operating expenses to their most directly comparable GAAP measures (in thousands) for the periods indicated:

|  | Three Months Ended |
|  | June 30, |
|  | GAAP |  |  | Foreign Currency Exchange Rate Impact (1) |  |  | Non-GAAP Constant Currency (2) |  |  | GAAP |  |  | GAAP % Change |  |  | Non-GAAP Constant Currency % Change (3) |
|  | 2023 |  |  | 2023 |  |  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2023 |
Product licenses revenues |  | $ | 15,522 |  |  | $ | (658 | ) |  | $ | 16,180 |  |  | $ | 20,129 |  |  |  | -22.9 | % |  |  | -19.6 | %
Subscription services revenues |  |  | 19,878 |  |  |  | (328 | ) |  |  | 20,206 |  |  |  | 14,017 |  |  |  | 41.8 | % |  |  | 44.2 | %
Product support revenues |  |  | 66,081 |  |  |  | 34 |  |  |  | 66,047 |  |  |  | 66,521 |  |  |  | -0.7 | % |  |  | -0.7 | %
Other services revenues |  |  | 18,919 |  |  |  | (147 | ) |  |  | 19,066 |  |  |  | 21,406 |  |  |  | -11.6 | % |  |  | -10.9 | %
Cost of product support revenues |  |  | 5,816 |  |  |  | (319 | ) |  |  | 6,135 |  |  |  | 5,127 |  |  |  | 13.4 | % |  |  | 19.7 | %
Cost of other services revenues |  |  | 13,645 |  |  |  | (185 | ) |  |  | 13,830 |  |  |  | 14,148 |  |  |  | -3.6 | % |  |  | -2.2 | %
Sales and marketing expenses |  |  | 37,660 |  |  |  | (733 | ) |  |  | 38,393 |  |  |  | 36,862 |  |  |  | 2.2 | % |  |  | 4.2 | %
Research and development expenses |  |  | 29,354 |  |  |  | (370 | ) |  |  | 29,724 |  |  |  | 31,790 |  |  |  | -7.7 | % |  |  | -6.5 | %
General and administrative expenses |  |  | 28,830 |  |  |  | (188 | ) |  |  | 29,018 |  |  |  | 28,502 |  |  |  | 1.2 | % |  |  | 1.8 | %
|  | GAAP |  |  | Foreign Currency Exchange Rate Impact (1) |  |  | Non-GAAP Constant Currency (2) |  |  | GAAP |  |  | GAAP % Change |  |  | Non-GAAP Constant Currency % Change (3) |
|  | 2022 |  |  | 2022 |  |  | 2022 |  |  | 2021 |  |  | 2022 |  |  | 2022 |
Product licenses revenues |  | $ | 20,129 |  |  | $ | (608 | ) |  | $ | 20,737 |  |  | $ | 22,151 |  |  |  | -9.1 | % |  |  | -6.4 | %
Subscription services revenues |  |  | 14,017 |  |  |  | (483 | ) |  |  | 14,500 |  |  |  | 10,342 |  |  |  | 35.5 | % |  |  | 40.2 | %
Product support revenues |  |  | 66,521 |  |  |  | (3,000 | ) |  |  | 69,521 |  |  |  | 71,027 |  |  |  | -6.3 | % |  |  | -2.1 | %
Other services revenues |  |  | 21,406 |  |  |  | (1,365 | ) |  |  | 22,771 |  |  |  | 21,831 |  |  |  | -1.9 | % |  |  | 4.3 | %
Cost of product support revenues |  |  | 5,127 |  |  |  | (236 | ) |  |  | 5,363 |  |  |  | 4,862 |  |  |  | 5.5 | % |  |  | 10.3 | %
Cost of other services revenues |  |  | 14,148 |  |  |  | (1,130 | ) |  |  | 15,278 |  |  |  | 13,947 |  |  |  | 1.4 | % |  |  | 9.5 | %
Sales and marketing expenses |  |  | 36,862 |  |  |  | (1,505 | ) |  |  | 38,367 |  |  |  | 40,321 |  |  |  | -8.6 | % |  |  | -4.8 | %
Research and development expenses |  |  | 31,790 |  |  |  | (447 | ) |  |  | 32,237 |  |  |  | 28,548 |  |  |  | 11.4 | % |  |  | 12.9 | %
General and administrative expenses |  |  | 28,502 |  |  |  | (414 | ) |  |  | 28,916 |  |  |  | 22,917 |  |  |  | 24.4 | % |  |  | 26.2 | %

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|  | Six Months Ended |
|  | June 30, |
|  | GAAP |  |  | Foreign Currency Exchange Rate Impact (1) |  |  | Non-GAAP Constant Currency (2) |  |  | GAAP |  |  | GAAP % Change |  |  | Non-GAAP Constant Currency % Change (3) |
|  | 2023 |  |  | 2023 |  |  | 2023 |  |  | 2022 |  |  | 2023 |  |  | 2023 |
Product licenses revenues |  | $ | 32,934 |  |  | $ | (1,715 | ) |  | $ | 34,649 |  |  | $ | 36,642 |  |  |  | -10.1 | % |  |  | -5.4 | %
Subscription services revenues |  |  | 38,688 |  |  |  | (1,062 | ) |  |  | 39,750 |  |  |  | 26,862 |  |  |  | 44.0 | % |  |  | 48.0 | %
Product support revenues |  |  | 131,562 |  |  |  | (1,458 | ) |  |  | 133,020 |  |  |  | 133,672 |  |  |  | -1.6 | % |  |  | -0.5 | %
Other services revenues |  |  | 39,131 |  |  |  | (986 | ) |  |  | 40,117 |  |  |  | 44,174 |  |  |  | -11.4 | % |  |  | -9.2 | %
Cost of product support revenues |  |  | 11,584 |  |  |  | (694 | ) |  |  | 12,278 |  |  |  | 10,318 |  |  |  | 12.3 | % |  |  | 19.0 | %
Cost of other services revenues |  |  | 27,428 |  |  |  | (951 | ) |  |  | 28,379 |  |  |  | 28,747 |  |  |  | -4.6 | % |  |  | -1.3 | %
Sales and marketing expenses |  |  | 73,766 |  |  |  | (2,033 | ) |  |  | 75,799 |  |  |  | 70,102 |  |  |  | 5.2 | % |  |  | 8.1 | %
Research and development expenses |  |  | 60,712 |  |  |  | (1,087 | ) |  |  | 61,799 |  |  |  | 65,313 |  |  |  | -7.0 | % |  |  | -5.4 | %
General and administrative expenses |  |  | 56,736 |  |  |  | (592 | ) |  |  | 57,328 |  |  |  | 55,208 |  |  |  | 2.8 | % |  |  | 3.8 | %
|  | GAAP |  |  | Foreign Currency Exchange Rate Impact (1) |  |  | Non-GAAP Constant Currency (2) |  |  | GAAP |  |  | GAAP % Change |  |  | Non-GAAP Constant Currency % Change (3) |
|  | 2022 |  |  | 2022 |  |  | 2022 |  |  | 2021 |  |  | 2022 |  |  | 2022 |
Product licenses revenues |  | $ | 36,642 |  |  | $ | (1,096 | ) |  | $ | 37,738 |  |  | $ | 43,431 |  |  |  | -15.6 | % |  |  | -13.1 | %
Subscription services revenues |  |  | 26,862 |  |  |  | (688 | ) |  |  | 27,550 |  |  |  | 20,368 |  |  |  | 31.9 | % |  |  | 35.3 | %
Product support revenues |  |  | 133,672 |  |  |  | (4,699 | ) |  |  | 138,371 |  |  |  | 141,676 |  |  |  | -5.6 | % |  |  | -2.3 | %
Other services revenues |  |  | 44,174 |  |  |  | (2,167 | ) |  |  | 46,341 |  |  |  | 42,778 |  |  |  | 3.3 | % |  |  | 8.3 | %
Cost of product support revenues |  |  | 10,318 |  |  |  | (367 | ) |  |  | 10,685 |  |  |  | 9,674 |  |  |  | 6.7 | % |  |  | 10.5 | %
Cost of other services revenues |  |  | 28,747 |  |  |  | (1,816 | ) |  |  | 30,563 |  |  |  | 27,568 |  |  |  | 4.3 | % |  |  | 10.9 | %
Sales and marketing expenses |  |  | 70,102 |  |  |  | (2,317 | ) |  |  | 72,419 |  |  |  | 78,519 |  |  |  | -10.7 | % |  |  | -7.8 | %
Research and development expenses |  |  | 65,313 |  |  |  | (430 | ) |  |  | 65,743 |  |  |  | 58,031 |  |  |  | 12.5 | % |  |  | 13.3 | %
General and administrative expenses |  |  | 55,208 |  |  |  | (655 | ) |  |  | 55,863 |  |  |  | 44,646 |  |  |  | 23.7 | % |  |  | 25.1 | %

(1)
The “Foreign Currency Exchange Rate Impact” reflects the estimated impact of fluctuations in foreign currency exchange rates on international components of our Consolidated Statements of Operations. It shows the increase (decrease) in material international revenues or expenses, as applicable, from the same period in the prior year, based on comparisons to the prior year quarterly average foreign currency exchange rates. The term “international” refers to operations outside of the United States and Canada.
(2)
The “Non-GAAP Constant Currency” reflects the current period GAAP amount, less the Foreign Currency Exchange Rate Impact.
(3)
The “Non-GAAP Constant Currency % Change” reflects the percentage change between the current period Non-GAAP Constant Currency amount and the GAAP amount for the same period in the prior year.

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Item 3. Quantitative and Qualitat ive Disclosures About Market Risk

The following discussion about our market risk exposures involves forward-looking statements. Actual results could differ materially from those projected in the forward-looking statements.

We are exposed to the impact of market price changes in bitcoin and foreign currency fluctuations.

Market Price Risk of Bitcoin. We have used a significant portion of our cash, including cash generated from capital raising transactions, to acquire bitcoin and, as of June 30, 2023, we held approximately 152,333 bitcoins. The carrying value of our bitcoins as of June 30, 2023 was $2.323 billion, which reflects cumulative impairments of $2.196 billion, on our Consolidated Balance Sheet. We account for our bitcoin as indefinite-lived intangible assets, which are subject to impairment losses if the fair value of our bitcoin decreases below their carrying value at any time since their acquisition. Impairment losses cannot be recovered for any subsequent increase in fair value. For example, the market price of one bitcoin on the Coinbase exchange (our principal market for bitcoin) ranged from a low of $16,490.00 to a high of $31,443.67 during the six months ended June 30, 2023, but the carrying value of each bitcoin we held at the end of the reporting period reflects the lowest price of one bitcoin quoted on the active exchange at any time since its acquisition. Therefore, negative swings in the market price of bitcoin could have a material impact on our earnings and on the carrying value of our digital assets. Positive swings in the market price of bitcoin are not reflected in the carrying value of our digital assets and impact earnings only when the bitcoin is sold at a gain. For the six months ended June 30, 2023, we incurred an impairment loss of $43.1 million on our bitcoin.

Foreign Currency Risk. We conduct a significant portion of our business in currencies other than the U.S. dollar, the currency in which we report our Consolidated Financial Statements. International revenues accounted for 40.7% and 39.2% of our total revenues for the three months ended June 30, 2023 and 2022, respectively, and 41.8% and 41.3% of our total revenue for the six months ended June 30, 2023 and 2022, respectively. We anticipate that international revenues will continue to account for a significant portion of our total revenues. The functional currency of each of our foreign subsidiaries is generally the local currency.

Assets and liabilities of our foreign subsidiaries are translated into U.S. dollars at exchange rates in effect as of the applicable Balance Sheet date and any resulting translation adjustments are included as an adjustment to stockholders’ equity. Revenues and expenses generated from these subsidiaries are translated at average monthly exchange rates during the quarter in which the transactions occur. Transaction gains and losses arising from transactions denominated in a currency other than the functional currency of the entity involved are included in the results of operations.

As a result of transacting in multiple currencies and reporting our Consolidated Financial Statements in U.S. dollars, our operating results may be adversely impacted by currency exchange rate fluctuations in the future. The impact of foreign currency exchange rate fluctuations on current and comparable periods is described in the “Non-GAAP Financial Measures” section under “Part I. Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations.”

We cannot predict the effect of exchange rate fluctuations upon our future results. We attempt to minimize our foreign currency risk by converting our excess foreign currency held in foreign jurisdictions to U.S. dollar-denominated cash and investment accounts.

As of June 30, 2023 and December 31, 2022, a 10% adverse change in foreign currency exchange rates versus the U.S. dollar would have decreased our aggregate reported cash and cash equivalents by 4.6% and 4.5%, respectively. If average exchange rates during the six months ended June 30, 2023 had changed unfavorably by 10%, our revenues for the six months ended June 30, 2023 would have decreased by 3.7%. During the six months ended June 30, 2023, our revenues were lower by 2.1% as a result of a 3.5% unfavorable change in weighted average exchange rates, as compared to the same period in the prior year.

Item 4. Controls and Procedures

Evaluation of Disclosure Controls and Procedures. Our management, with the participation of our Chief Executive Officer and Chief Financial Officer, evaluated the effectiveness of our disclosure controls and procedures (as defined in Rules 13a-15(e) and 15d-15(e) under the Exchange Act) as of the end of the period covered by this Quarterly Report. Management recognizes that any controls and procedures, no matter how well designed and operated, can provide only reasonable assurance of achieving their objectives, and management necessarily applies its judgment in evaluating the cost-benefit relationship of possible controls and procedures. Our disclosure controls and procedures are designed to provide reasonable assurance of achieving their control objectives. Based on the evaluation of our disclosure controls and procedures as of the end of the period covered by this Quarterly Report, our Chief Executive Officer and Chief Financial Officer concluded that, as of such date, our disclosure controls and procedures were effective at the reasonable assurance level.

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Changes in Internal Controls. No change in our internal control over financial reporting (as defined in Rules 13a-15(f) and 15d-15(f) under the Exchange Act) occurred during the three months ended June 30, 2023 that has materially affected, or is reasonably likely to materially affect, our internal control over financial reporting.

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PART II - OTHE R INFORMATION

Item 1. Legal Proceedings

We are involved in various legal proceedings arising in the normal course of business, including the matter described below. Although the outcomes of these legal proceedings are inherently difficult to predict, we do not expect the resolution of these legal proceedings to have a material adverse effect on our financial position, results of operations, or cash flows.

On August 31, 2022, the District, through its Office of the Attorney General, filed a civil complaint in the Superior Court of the District of Columbia naming as defendants (i) Michael J. Saylor, the Chairman of our Board of Directors and our Executive Chairman, in his personal capacity, and (ii) MicroStrategy. The District sought, among other relief, monetary damages under the District’s False Claims Act for the alleged failure of Mr. Saylor to pay personal income taxes to the District over a number of years together with penalties, interest, and treble damages. The complaint alleged that the amount of personal income taxes purportedly involved was more than $25 million. The complaint also alleged in the sole claim against us that we violated the District’s False Claims Act by conspiring to assist Mr. Saylor’s alleged failure to pay personal income taxes. On October 26, 2022, we filed a motion to dismiss the District’s complaint. On February 28, 2023, the court ruled on the motion to dismiss, dismissing the sole claim against us as well as a claim against Mr. Saylor alleging that Mr. Saylor violated the District’s False Claims Act. The court did not dismiss claims against Mr. Saylor alleging that Mr. Saylor failed to pay personal income taxes, interest and penalties due. On April 13, 2023, the District, through its Office of the Attorney General, filed a motion to amend its complaint to attempt to restore claims under the False Claims Act against both Mr. Saylor and MicroStrategy. On May 10, 2023, the court granted the District’s motion to amend its complaint, reinstating MicroStrategy as a defendant in the case. The amended complaint alleges that MicroStrategy violated the District’s False Claims Act by making and using false records and statements in the form of false withholding filings with the District Office of Tax and Revenue. The amended complaint also alleges that Mr. Saylor violated the District’s False Claims Act by making and using false records and statements and by causing MicroStrategy to make and use false records and statements. On June 7, 2023, Mr. Saylor and MicroStrategy filed a motion to dismiss the District’s amended complaint with prejudice. On July 5, 2023, the District filed an opposition to the motion to dismiss made by Mr. Saylor and MicroStrategy. On July 19, 2023, Mr. Saylor and MicroStrategy filed a reply in support of their motion to dismiss. On July 31, 2023, the court denied Mr. Saylor’s and MicroStrategy’s motion to dismiss the amended complaint. The final outcome of this matter is not presently determinable.

Item 1A. Ri sk Factors

You should carefully consider the risks described below before making an investment decision. The risks and uncertainties described below are not the only ones we face. Additional risks and uncertainties not presently known to us or that we currently deem immaterial may also impair our business operations.

If any of the following risks occur, our business, financial condition, or results of operations could be materially adversely affected. In such case, the market price of our class A common stock could decline, and you may lose all or part of your investment.

Risks Related to Our Business in General

Our quarterly operating results, revenues, and expenses may fluctuate significantly, which could have an adverse effect on the market price of our stock

For many reasons, including those described below, our operating results, revenues, and expenses have varied in the past and may vary significantly in the future from quarter to quarter. These fluctuations could have an adverse effect on the market price of our class A common stock.

Fluctuations in Quarterly Operating Results. Our quarterly operating results may fluctuate, in part, as a result of:

•
fluctuations in the price of bitcoin, of which we have significant holdings and with respect to which we expect to continue to make significant future purchases, and potential material impairment charges that may be associated therewith;
•
any sales by us of our bitcoin at prices above their then-current carrying costs, which would result in our recording gains upon sale of our digital assets;
•
regulatory, commercial, and technical developments related to bitcoin or the Bitcoin blockchain, or digital assets more generally;
•
the size, timing, volume, and execution of significant orders and deliveries;
•
the mix of our offerings ordered by customers, including product licenses and cloud subscriptions, which can affect the extent to which revenue is recognized immediately or over future quarterly periods;
•
the timing of the release or delivery of new or enhanced offerings and market acceptance of new and enhanced offerings;

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•
the timing of announcements of new offerings by us or our competitors;
•
changes in our pricing policies or those of our competitors;
•
the length of our sales cycles;
•
seasonal or other buying patterns of our customers;
•
changes in our operating expenses;
•
the impact of war, terrorism, infectious diseases (such as COVID-19 and its variants), natural disasters and other global events, and government responses to such events, on the global economy and on our customers, suppliers, employees, and business;
•
the timing of research and development projects;
•
utilization of our consulting and education services, which can be affected by delays or deferrals of customer implementation of our software;
•
fluctuations in foreign currency exchange rates;
•
bilateral or multilateral trade tensions, which could affect our offerings in particular foreign markets;
•
our profitability and expectations for future profitability and their effect on our deferred tax assets and net income for the period in which any adjustment to our net deferred tax asset valuation allowance may be made;
•
increases or decreases in our liability for unrecognized tax benefits; and
•
changes in customer decision-making processes or customer budgets.

Limited Ability to Adjust Expenses. We base our operating expense budgets on expected revenue trends and strategic objectives. Many of our expenses, such as interest expense on our long-term debt, office leases and certain personnel costs, are relatively fixed. We may be unable to adjust spending quickly enough to offset any unexpected revenue shortfall or impairment losses related to our digital assets. Accordingly, any shortfall in revenue from our enterprise analytics software business or impairment losses related to our digital assets may cause significant variation in operating results in any quarter.

Based on the above factors, we believe quarter-to-quarter comparisons of our operating results are not a good indication of our future performance. It is possible that in one or more future quarters, our operating results may be below the expectations of public market analysts and investors. In that event, the market price of our class A common stock may fall.

We may not be able to maintain or increase profitability in future periods

We generated net income for the six months ended June 30, 2023, due in part to a $513.5 million tax benefit generated primarily from the release of the remaining valuation allowance on our deferred tax asset related to the impairment on our bitcoin holdings (attributable to the increase in market value of bitcoin as of June 30, 2023 compared to December 31, 2022) and a $44.7 million gain on debt extinguishment resulting from the repayment of the 2025 Secured Term Loan, however, we may not be able to maintain or increase profitability in future periods. If our revenues are not sufficient to offset our operating expenses, we are unable to adjust our operating expenses in a timely manner in response to any shortfall in anticipated revenue, or we incur additional significant impairment losses related to our digital assets, we may incur operating losses in future periods, our profitability may decrease, or we may cease to be profitable. As a result, our business, results of operations, and financial condition may be materially adversely affected.

As of June 30, 2023, we had $719.0 million of deferred tax assets, which reflects a $2.6 million valuation allowance. The largest deferred tax asset relates to the impairment on our bitcoin holdings. Changes to the valuation allowance against the deferred tax asset are largely dependent on the change in the market value of bitcoin from the previous reporting date. If the market value of bitcoin at a future reporting date is less than the market value of bitcoin at the previous reporting date, we may be required to record a valuation allowance against the deferred tax asset. Additionally, if we are unable to maintain or increase profitability in the future, we may also be required to increase the valuation allowance against the remaining deferred tax assets. A significant increase in the valuation allowance could result in a charge that would materially adversely affect net income in the period in which the charge is incurred.

We may have exposure to greater than anticipated tax liabilities

We are subject to income taxes and non-income taxes in a variety of domestic and foreign jurisdictions. Our future income tax liability could be materially adversely affected by earnings that are lower than anticipated in jurisdictions where we have lower statutory rates, earnings that are higher than anticipated in jurisdictions where we have higher statutory rates, changes in the valuation of our deferred tax assets and liabilities, changes in the amount of our unrecognized tax benefits, or changes in tax laws, regulations, accounting principles, or interpretations thereof. In addition, if we sold any of our bitcoin at prices greater than the cost basis of the bitcoin sold, we would incur a tax liability with respect to any gain recognized, and such tax liability could be material.

Changes in the tax laws of foreign jurisdictions could arise, including as a result of the project undertaken by the Organisation for Economic Co-operation and Development (“OECD”) to combat base erosion and profit shifting (“BEPS”). The OECD, which represents a coalition of member countries, has issued recommendations that, in some cases, make substantial changes to numerous long-standing

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tax positions and principles. These changes, many of which have been adopted or are under active consideration by OECD members and/or other countries, could increase tax uncertainty and may adversely affect our provision for income taxes.

After enactment of the U.S. Tax Cuts and Jobs Act, most of our income is taxable in the U.S. with a significant portion taxable under the Global Intangible Low-Taxed Income (“GILTI”) regime. Beginning in fiscal year 2027, the deduction allowable under the GILTI regime will decrease from 50% to 37.5%, which will increase the effective tax rate imposed on our income. The U.S. also enacted the Inflation Reduction Act of 2022 (“IRA”) in August 2022. The IRA applies to tax years beginning after December 31, 2022 and introduces a 15% corporate alternative minimum tax for corporations whose average annual adjusted financial statement income for any consecutive three-tax-year period preceding the tax year exceeds $1 billion and a 1% excise tax on certain stock repurchases made by publicly traded U.S. corporations after December 31, 2022. If we are subject to these new taxes under the IRA, it could materially affect our financial results, including our earnings and cash flow.

Our determination of our tax liability is subject to review by applicable domestic and foreign tax authorities. Any adverse outcome of such reviews could have an adverse effect on our operating results and financial condition. The determination of our worldwide provision for income taxes and other tax liabilities requires significant judgment and there are many transactions and calculations, including in respect of transactions involving bitcoin, where the ultimate tax determination is uncertain. Moreover, as a multinational business, we have subsidiaries that engage in many intercompany transactions in a variety of tax jurisdictions where the ultimate tax determination is uncertain.

We also have contingent tax liabilities that, in management’s judgment, are not probable of assertion. If such unasserted contingent liabilities were to be asserted, or become probable of assertion, we may be required to record significant expenses and liabilities in the period in which these liabilities are asserted or become probable of assertion.

As a result of these and other factors, the ultimate amount of tax obligations owed may differ from the amounts recorded in our financial statements and any such difference may materially affect our financial results in future periods in which we change our estimates of our tax obligations or in which the ultimate tax outcome is determined.

Risks Related to Our Bitcoin Acquisition Strategy and Holdings

Our bitcoin acquisition strategy exposes us to various risks associated with bitcoin

Our bitcoin acquisition strategy exposes us to various risks associated with bitcoin, including the following:

Bitcoin is a highly volatile asset. Bitcoin is a highly volatile asset that has traded below $20,000 per bitcoin and above $30,000 per bitcoin on the Coinbase exchange (our principal market for bitcoin) in the 12 months preceding the date of this Quarterly Report.

Bitcoin does not pay interest or dividends. Bitcoin does not pay interest or other returns and so our ability to generate cash from our bitcoin holdings depends on sales or implementing strategies that we may consider to create income streams or otherwise generate cash by using our bitcoin holdings. Even if we pursue any such strategies, we may be unable to create income streams or otherwise generate cash from our bitcoin holdings, and any such strategies may subject us to additional risks.

Our bitcoin holdings significantly impact our financial results. Our bitcoin holdings have significantly affected our financial results and if we continue to increase our overall holdings of bitcoin in the future, they will have an even greater impact on our financial results and the market price of our class A common stock. See “Risks Related to Our Bitcoin Acquisition Strategy and Holdings – Our historical financial statements do not reflect the potential variability in earnings that we may experience in the future relating to our bitcoin holdings.”

Our bitcoin acquisition strategy has not been tested over an extended period of time or under different market conditions. We are continually examining the risks and rewards of our bitcoin acquisition strategy. This strategy has not been tested over an extended period of time or under different market conditions. For example, although we believe bitcoin, due to its limited supply, has the potential to serve as a hedge against inflation in the long term, the short-term price of bitcoin has declined in recent periods during which the inflation rate increased. Some investors and other market participants may disagree with our bitcoin acquisition strategy or actions we undertake to implement it. If bitcoin prices were to decrease or our bitcoin acquisition strategy otherwise proves unsuccessful, our financial condition, results of operations, and the market price of our class A common stock would be materially adversely impacted.

We are subject to counterparty risks, including in particular risks relating to our custodians. Although we have implemented various measures that are designed to mitigate our counterparty risks, including by storing substantially all of the bitcoin we own in custody accounts at U.S.-based, institutional-grade custodians and negotiating contractual arrangements intended to establish that our property interest in custodially-held bitcoin is not subject to claims of the custodian’s creditors, applicable insolvency law is not fully developed

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with respect to the holding of digital assets in custodial accounts. If our custodially-held bitcoin were nevertheless considered to be the property of our custodian’s estate in the event that the custodian enters bankruptcy, receivership or similar insolvency proceedings, we could be treated as a general unsecured creditor of the custodian, inhibiting our ability to exercise ownership rights with respect to such bitcoin and this may ultimately result in the loss of the value related to some or all of such bitcoin. Even if we are able to prevent our bitcoin from being considered the property of the custodian’s bankruptcy estate as part of an insolvency proceeding, it is possible that we would still be delayed or may otherwise experience difficulty in accessing our bitcoin held by the affected custodian during the pendency of the insolvency proceedings. Any such outcome could have a material adverse effect on our financial condition and the market price of our class A common stock.

The broader digital assets industry is subject to counterparty risks, which could adversely impact the adoption rate, price, and use of bitcoin. A series of recent high-profile bankruptcies, closures, liquidations, regulatory enforcement actions and other events relating to companies operating in the digital asset industry, including the filings for bankruptcy protection by Three Arrows Capital, Celsius Network, Voyager Digital, FTX Trading and Genesis Global Capital, the closure or liquidation of certain financial institutions that provided lending and other services to the digital assets industry, including Signature Bank and Silvergate Bank, SEC enforcement actions against Coinbase, Inc. and Binance Holdings Ltd., and the cease-and-desist order issued by Nevada’s Department of Business and Industry to Prime Trust, have highlighted the counterparty risks applicable to owning and transacting in digital assets. Although these bankruptcies, closures, liquidations and other events have not resulted in any loss or misappropriation of our bitcoin, nor have such events materially impacted our access to our bitcoin, they have, in the short-term, likely negatively impacted the adoption rate and use of bitcoin. Additional bankruptcies, closures, liquidations, regulatory enforcement actions or other events involving participants in the digital assets industry in the future may further negatively impact the adoption rate, price, and use of bitcoin.

Changes in our ownership of bitcoin could have accounting, regulatory and other impacts. While our bitcoin is currently owned directly by us or our wholly owned subsidiaries, we may investigate other potential approaches to owning bitcoin, including indirect ownership (for example, through ownership interests in a fund that owns bitcoin). If we were to own all or a portion of our bitcoin indirectly, the accounting treatment for our bitcoin, our ability to use our bitcoin as collateral for additional borrowings, and the regulatory requirements to which we are subject, may correspondingly change.

Changes in the accounting treatment of our bitcoin holdings could have significant accounting impacts, including increasing the volatility of our results. A change in the accounting treatment of our bitcoin holdings could have a material impact on our results of operations in future periods and could increase the volatility of our reported results of operations as well as affect the carrying value of our bitcoin on our balance sheet, which in turn could have a material adverse effect on our financial results and the market price of our class A common stock. For example, on March 23, 2023, the Financial Accounting Standards Board (“FASB”) issued an exposure draft for comment that would cause in-scope crypto assets (such as bitcoin) to be measured at fair value, with fair value changes recorded in current period earnings. The comment letter period for the exposure draft ended on June 6, 2023. If the FASB issues a final ASU substantially similar to the exposure draft, the change in presentation could increase the volatility of our reported results of operations as well as affect the carrying value of our bitcoin on our balance sheet.

The broader digital assets industry, including the technology associated with digital assets, the rate of adoption and development of, and use cases for, digital assets, market perception of digital assets, and the legal, regulatory, and accounting treatment of digital assets are constantly developing and changing, and there may be additional risks in the future that are not possible to predict.

The price of bitcoin can fluctuate for a variety of reasons, and fluctuations in the price of bitcoin have in the past influenced and are likely to continue to influence our financial results and the market price of our class A common stock

Fluctuations in the price of bitcoin have in the past influenced and are likely to continue to influence our financial results and the market price of our class A common stock. Our financial results and the market price of our class A common stock would be adversely affected, and our business and financial condition would be negatively impacted, if the price of bitcoin decreased substantially (as it has in the past), including as a result of:

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decreased user and investor confidence in bitcoin, including due to the various factors described herein;
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investment and trading activities of highly active retail and institutional users, speculators, miners and investors, including actual or perceived manipulation of the market for bitcoin;
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negative publicity, media or social media coverage, or sentiment due to events in or relating to, or perception of, bitcoin or the broader digital assets industry, for example, (i) public perception that bitcoin can be used as a vehicle to circumvent sanctions, including sanctions imposed on Russia or certain regions related to the ongoing conflict between Russia and Ukraine; (ii) expected or pending civil, criminal, regulatory enforcement or other high profile actions against major participants in the bitcoin ecosystem, including the SEC’s enforcement actions against Coinbase, Inc. and Binance Holdings Ltd.; (iii) additional filings for bankruptcy protection or bankruptcy proceedings of major digital asset industry participants, such as the bankruptcy proceeding of FTX Trading and its affiliates; and (iv) the actual or perceived environmental impact of bitcoin and related

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activities, including environmental concerns raised by private individuals, governmental and non-governmental organizations, and other actors related to the energy resources consumed in the bitcoin mining process;
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changes in consumer preferences and the perceived value or prospects of bitcoin;
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competition from other digital assets that exhibit better speed, security, scalability, or energy efficiency, that feature other more favored characteristics, that are backed by governments, including the U.S. government, or reserves of fiat currencies, or that represent ownership or security interests in physical assets;
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a decrease in the price of other digital assets, including stablecoins, or the crash or unavailability of stablecoins that are used as a medium of exchange for bitcoin purchase and sale transactions, such as the crash of the stablecoin Terra USD in 2022, to the extent the decrease in the price of such other digital assets or the unavailability of such stablecoins may cause a decrease in the price of bitcoin or adversely affect investor confidence in digital assets generally;
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the identification of Satoshi Nakamoto, the pseudonymous person or persons who developed bitcoin, or the transfer of substantial amounts of bitcoin from bitcoin wallets attributed to Mr. Nakamoto;
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disruptions, failures, unavailability, or interruptions in service of trading venues for bitcoin, such as, for example, the announcement by the digital asset exchange FTX Trading that it would freeze withdrawals and transfers from its accounts and subsequent filing for bankruptcy protection and the recent SEC enforcement action brought against Binance Holdings Ltd., which initially sought to freeze all of its assets during the pendency of the enforcement action;
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the filing for bankruptcy protection by, liquidation of, or market concerns about the financial viability of digital asset custodians, trading venues, lending platforms, investment funds, or other digital asset industry participants, such as the filing for bankruptcy protection by digital asset trading venues FTX Trading and BlockFi and digital asset lending platforms Celsius Network and Voyager Digital Holdings in 2022, the ordered liquidation of the digital asset investment fund Three Arrows Capital in 2022, the announced liquidation of Silvergate Bank in 2023, the government-mandated closure and sale of Signature Bank in 2023, and the cease-and-desist order issued by the Nevada Department of Business and Industry to Prime Trust, LLC in 2023;
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regulatory, legislative, enforcement and judicial actions that adversely affect the price, ownership, transferability, trading volumes, legality or public perception of bitcoin, or that adversely affect the operations of or otherwise prevent digital asset custodians, trading venues, lending platforms or other digital assets industry participants from operating in a manner that allows them to continue to deliver services to the digital assets industry;
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further reductions in mining rewards of bitcoin, including block reward halving events, which are events that occur after a specific period of time that reduce the block reward earned by “miners” who validate bitcoin transactions, or increases in the costs associated with bitcoin mining, including increases in electricity costs and hardware and software used in mining, that may cause a decline in support for the bitcoin network;
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transaction congestion and fees associated with processing transactions on the bitcoin network;
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macroeconomic changes, such as changes in the level of interest rates and inflation, fiscal and monetary policies of governments, trade restrictions, and fiat currency devaluations;
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developments in mathematics or technology, including in digital computing, algebraic geometry and quantum computing, that could result in the cryptography used by the Bitcoin blockchain becoming insecure or ineffective; and
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changes in national and international economic and political conditions, including, without limitation, the adverse impact attributable to the economic and political instability caused by the current conflict between Russia and Ukraine and the economic sanctions adopted in response to the conflict.

Bitcoin and other digital assets are novel assets, and are subject to significant legal, commercial, regulatory and technical uncertainty

Bitcoin and other digital assets are relatively novel and are subject to significant uncertainty, which could adversely impact their price. The application of securities laws and other laws and regulations to digital assets is unclear in certain respects, and it is possible that regulators in the United States or foreign countries may interpret or apply existing laws and regulations in a manner that adversely affects the price of bitcoin.

The U.S. federal government, states, regulatory agencies, and foreign countries may also enact new laws and regulations, or pursue regulatory, legislative, enforcement or judicial actions, that could materially impact the price of bitcoin or the ability of individuals or institutions such as us to own or transfer bitcoin. For example:

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On March 9, 2022, President Biden signed an executive order relating to cryptocurrencies. While the executive order did not mandate the adoption of any specific regulations, it instructed various federal agencies to consider potential regulatory measures, including the evaluation of the creation of a U.S. central bank digital currency (“CBDC”). On September 16, 2022, the White House released a framework for digital asset development, based on reports from various government agencies, including the U.S. Department of Treasury, the Department of Justice, and the Department of Commerce. Among other things, the framework encourages regulators to pursue enforcement actions, issue guidance and rules to address current and emergent risks, support the development and use of innovative technologies by payment providers to increase access to instant payments, consider creating a federal framework to regulate nonbank payment providers, and evaluate whether to call upon Congress to

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amend the Bank Secrecy Act and laws against unlicensed money transmission to apply explicitly to digital asset service providers.
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On April 4, 2022, SEC Chair Gary Gensler announced that he has asked SEC staff to work (i) to register and regulate digital asset platforms like securities exchanges; (ii) with the Commodity Futures Trading Commission on how to jointly address digital asset platforms that trade both securities and non-securities; (iii) on segregating out digital asset platforms’ custody of customer assets, if appropriate; and (iv) on segregating out the market making functions of digital asset platforms, if appropriate. Similarly, foreign government authorities have recently expanded their efforts to restrict certain activities related to bitcoin and other digital assets.
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On September 8, 2022, the White House Office of Science and Technology Policy issued a report in coordination with other federal agencies relating to the climate and energy implications of digital assets, including bitcoin, in the United States. Among its finding are that digital assets are energy intensive and drive significant environmental impacts, and the report recommends further study of the environmental impact of digital assets and the development of environmental performance regulations for digital asset miners, which may include limiting or eliminating digital assets that use high energy intensity consensus mechanisms, including the proof-of-work consensus mechanisms on which the Bitcoin blockchain is based.
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In the United Kingdom, in February 2023, His Majesty’s Treasury issued its first comprehensive set of rules designed to regulate digital assets. Of note, (i) digital assets firms, including exchanges and custodians, operating in or providing services to the United Kingdom would need a license to operate and would be required to comply with minimum capital and liquidity requirements, and (ii) the proposed rules would impose issuer liability on exchanges that permit the trading of decentralized digital assets, including bitcoin. The current proposed rules are subject to a comment and review period that is open until April 30, 2023, after which the government will consider the feedback and prepare its response.
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On March 1, 2023, the U.S. Under Secretary for Domestic Finance provided an update on the development of a U.S. CBDC, indicating that the U.S. Department of Treasury would be providing an initial set of findings and recommendations regarding the development and adoption of a U.S. CBDC in the coming months.
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In April 2023, the European Parliament approved the Markets in Crypto Assets Regulation (“MiCA”), a comprehensive digital asset regulatory framework for the issuance and use of digital assets, like bitcoin, with the requirements phasing into effect throughout 2023 and 2024. MiCA also requires the European Commission (i) to provide a report on the environmental impact of crypto-assets and (ii) based upon such report, introduce mandatory minimum sustainability standards for consensus mechanisms, including the proof-of-work consensus mechanisms on which the Bitcoin blockchain is based.
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On April 14, 2023, the SEC reopened the comment period for its proposal to amend the definition of “exchange” under Exchange Act Rule 3b-16 to encompass trading and communication protocol systems for digital asset securities and trading systems that use distributed ledger or blockchain technology, including both so-called “centralized” and “decentralized” trading systems. The comment period is now closed. The SEC may determine whether to adopt the revised definition after an evaluation of comments provided during the comment period. If adopted in its proposed form, the new definition would have a sweeping impact on digital asset trading venues and other digital asset industry participants.
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On June 5, 2023, the SEC filed a complaint against Binance Holdings Ltd. and other affiliated entities in federal district court for the District of Columbia, alleging, among other claims related to the operation of the affiliates and their platforms, that: (i) the Binance entities commingled and diverted customer assets; (ii) various affiliates of Binance Holdings Ltd. operated as exchanges, brokers, dealers and clearing agencies without registration under the Exchange Act; (iii) Binance Holdings Ltd. engaged in the unregistered offer and sale of securities; (iv) affiliates of Binance Holdings Ltd. operated in a manner to evade U.S. federal securities laws, and (v) affiliates of Binance Holdings Ltd. misled customers and investors concerning the existence and adequacy of market surveillance and controls to detect and prevent manipulative trading.
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On June 6, 2023, the SEC filed a complaint against Coinbase, Inc. and other affiliated entities in federal district court in the Southern District of New York, alleging, among other claims: (i) that Coinbase, Inc. violated the Exchange Act by failing to register with the SEC as a national securities exchange, broker-dealer, and clearing agency, in connection with activities involving certain identified digital assets that the SEC’s complaint alleges are securities, (ii) that Coinbase, Inc. violated the Securities Act by failing to register with the SEC the offer and sale of securities in connection with its staking program, and (iii) that Coinbase Global Inc. is jointly and severally liable as a control person under the Exchange Act for Coinbase Inc.’s violations of the Exchange Act to the same extent as Coinbase Inc.
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In China, the People’s Bank of China and the National Development and Reform Commission have outlawed cryptocurrency mining and declared all cryptocurrency transactions illegal within the country.

Moreover, the risks of engaging in a bitcoin acquisition strategy are relatively novel and have created, and could continue to create, complications due to the lack of experience that third parties have with companies engaging in such a strategy, such as increased costs of director and officer liability insurance or the potential inability to obtain such coverage on acceptable terms in the future.

The growth of the digital assets industry in general, and the use and acceptance of bitcoin in particular, may also impact the price of bitcoin and is subject to a high degree of uncertainty. The pace of worldwide growth in the adoption and use of bitcoin may depend, for instance, on public familiarity with digital assets, ease of buying and accessing bitcoin, institutional demand for bitcoin as an investment

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asset, the participation of traditional financial institutions in the digital assets industry, consumer demand for bitcoin as a means of payment, and the availability and popularity of alternatives to bitcoin. Even if growth in bitcoin adoption occurs in the near or medium-term, there is no assurance that bitcoin usage will continue to grow over the long-term.

Because bitcoin has no physical existence beyond the record of transactions on the Bitcoin blockchain, a variety of technical factors related to the Bitcoin blockchain could also impact the price of bitcoin. For example, malicious attacks by miners, inadequate mining fees to incentivize validating of bitcoin transactions, hard “forks” of the Bitcoin blockchain into multiple blockchains, and advances in digital computing, algebraic geometry, and quantum computing could undercut the integrity of the Bitcoin blockchain and negatively affect the price of bitcoin. The liquidity of bitcoin may also be reduced and damage to the public perception of bitcoin may occur, if financial institutions were to deny or limit banking services to businesses that hold bitcoin, provide bitcoin-related services or accept bitcoin as payment, which could also decrease the price of bitcoin. Liquidity of bitcoin may also be impacted to the extent that changes in applicable laws and regulatory requirements negatively impact the ability of exchanges and trading venues to provide services for bitcoin and other digital assets.

Our historical financial statements do not reflect the potential variability in earnings that we may experience in the future relating to our bitcoin holdings

Our historical financial statements do not fully reflect the potential variability in earnings that we may experience in the future from holding or selling significant amounts of bitcoin.

The price of bitcoin has historically been subject to dramatic price fluctuations and is highly volatile. As explained more fully in Note 2(g) to the Consolidated Financial Statements of our Annual Report on Form 10-K for the year ended December 31, 2022, we determine the fair value of our bitcoin based on quoted (unadjusted) prices on the Coinbase exchange (our principal market for bitcoin). We perform an analysis each quarter to identify whether events or changes in circumstances, principally decreases in the quoted (unadjusted) prices on the active exchange, indicate that it is more likely than not that any of our bitcoin assets are impaired. In determining if an impairment has occurred, we consider the lowest price of one bitcoin quoted on the active exchange at any time since acquiring the specific bitcoin held. If the carrying value of a bitcoin exceeds that lowest price at any time during the quarter, an impairment loss is deemed to have occurred with respect to that bitcoin in the amount equal to the difference between its carrying value and such lowest price, and subsequent increases in the price of bitcoin will not affect the carrying value of our bitcoin. Gains (if any) are not recorded until realized upon sale, at which point they would be presented net of any impairment losses. In determining the gain to be recognized upon sale, we calculate the difference between the sale price and carrying value of the specific bitcoin sold immediately prior to sale.

As a result, any decrease in the fair value of bitcoin below our carrying value for such assets at any time since their acquisition requires us to incur an impairment charge, and such charge could be material to our financial results for the applicable reporting period, which may create significant volatility in our reported earnings and decrease the carrying value of our digital assets, which in turn could have a material adverse effect on the market price of our class A common stock. Conversely, any sale of bitcoins at prices above our carrying value for such assets creates a gain for financial reporting purposes even if we would otherwise incur an economic or tax loss with respect to such transaction, which also may result in significant volatility in our reported earnings. In addition, on March 23, 2023, the FASB issued an exposure draft for comment that would cause in-scope crypto assets (such as bitcoin) to be measured at fair value, with fair value changes recorded in current period earnings. The comment letter period for the exposure draft ended on June 6, 2023. If the FASB issues a final ASU substantially similar to the exposure draft, the change in presentation could increase the volatility of our reported results of operations as well as affect the carrying value of our bitcoin on our balance sheet.

At June 30, 2023, we carried $2.323 billion of digital assets on our balance sheet, consisting of approximately 152,333 bitcoins and reflecting $2.196 billion in cumulative impairment losses attributable to bitcoin trading price fluctuations, and held $66.0 million in cash and cash equivalents, compared to a carrying value of $1.988 billion of digital assets, consisting of approximately 129,699 bitcoins, and $69.4 million in cash and cash equivalents at June 30, 2022. Digital asset impairment losses of $43.1 million incurred during the six months ended June 30, 2023 represented 18.4% of our operating expenses and were included in our net income of $483.4 million for the six months ended June 30, 2023, compared to $1.088 billion in digital asset impairment losses incurred during the six months ended June 30, 2022 which represented 85.1% of our operating expenses and contributed to our net loss of $1.193 billion for the six months ended June 30, 2022.

Because we intend to purchase additional bitcoin in future periods and increase our overall holdings of bitcoin, we expect that the proportion of our total assets represented by our bitcoin holdings will increase in the future. As a result, volatility in our earnings in future periods may be significantly more than what we experienced in prior periods.

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Changes in securities regulations, or the adoption of new laws or regulations, relating to digital assets generally or bitcoin specifically could adversely affect the price of bitcoin or our ability to transact in or own bitcoin, which may adversely impact the market price of our class A common stock

Although bitcoin and other digital assets have experienced a surge of investor attention since bitcoin was invented in 2008, investors in the United States currently have limited means to gain direct exposure to bitcoin through traditional investment channels, and instead generally must hold bitcoin through “hosted” wallets provided by digital asset service providers or through “unhosted” wallets that expose the investor to risks associated with loss or hacking of their private keys. Given the relative novelty of digital assets, general lack of familiarity with the processes needed to hold bitcoin directly, as well as the potential reluctance of financial planners and advisers to recommend direct bitcoin holdings to their retail customers because of the manner in which such holdings are custodied, some investors have sought exposure to bitcoin through investment vehicles that hold bitcoin and issue shares representing fractional undivided interests in their underlying bitcoin holdings. Although a number of investment vehicles currently offer this exposure to bitcoin, none of these investment vehicles currently offers its shares directly to the public in the United States, and such shares are offered only to “accredited investors” on a private placement basis. Investors who are not eligible to participate in these private placements may nevertheless purchase shares of these investment vehicles in the over-the-counter market, where such shares have in the past traded at a premium to the net asset value (“NAV”) of the underlying bitcoin. These premiums have at times been substantial, although such vehicles have recently traded at a discount to NAV.

One reason that such vehicles have in the past traded at a substantial premium to NAV may be because of the relative scarcity of traditional investment vehicles providing investment exposure to bitcoin. To the extent investors view our class A common stock as providing such exposure, it is possible that the value of our class A common stock may also include a premium over the value of our bitcoin. Any such premium may increase or decrease in different market conditions and our class A common stock could also trade at a discount relative to the value of our bitcoin, including if one or more alternative investment vehicles that provide spot market exposure to bitcoin are approved to list their shares on a U.S. national securities exchange.

Another reason for the substantial premium to NAV exhibited in the past by the trading prices of shares of some bitcoin investment vehicles is that such vehicles operate in a manner similar to closed-end investment funds as opposed to exchange-traded funds (“ETFs”) and therefore do not continuously offer to create and redeem their shares at NAV in exchange for bitcoin. Although several bitcoin investment vehicles have attempted to list their shares on a U.S. national securities exchange to permit them to function in the manner of an ETF with continuous share creation and redemption at NAV, the SEC has generally declined to approve any such listing, citing concerns over the surveillance of trading in markets for the underlying bitcoin as well as concerns about fraud and manipulation in bitcoin trading markets. For example, in June 2022 the SEC denied proposals from NYSE Arca, Inc. to convert Grayscale Bitcoin Trust into a spot bitcoin exchange-traded product (“ETP”) and to list and trade shares of the Bitwise Bitcoin ETP. However, in October 2021, the SEC permitted the listing of ETFs that invest primarily in bitcoin futures contracts, and on June 23, 2023, the SEC approved the first leveraged bitcoin futures ETF, 2x Bitcoin Strategy (BITX). It is unclear as to whether or to what extent the existence of ETFs that invest in bitcoin futures contracts will have on any premium over the value of our bitcoin holdings that may be included in the value of our class A common stock.

If the SEC were to further resolve its concerns regarding surveillance of and the existence of fraud and manipulation in the bitcoin trading markets, it is possible that the SEC would permit the listing of ETPs specializing in the direct acquisition and holding of bitcoin, allowing these funds to offer their shares directly to the public. In addition to greatly simplifying the task of gaining investment exposure to bitcoin, the listing of a bitcoin ETP with continuous share creation and redemption at NAV would be expected to eliminate the NAV premiums currently exhibited by shares of investment vehicles that trade in the over-the-counter market. To the extent that our class A common stock is viewed as an alternative-to-bitcoin investment vehicle and trades at a premium to the value of our bitcoin holdings, that premium may also be eliminated, causing the price of our class A common stock to decline.

In addition, the introduction of the bitcoin-futures-focused ETFs and any future bitcoin-focused ETPs on U.S. national securities exchanges may be viewed by investors as offering “pure play” exposure to bitcoin that would generally not be subject to federal income tax at the entity level as we are, or the other risk factors applicable to an operating business, such as ours.

As a result of the foregoing factors, to the extent investors view our class A common stock as linked to the value of our bitcoin holdings, the expansion of avenues for investing in bitcoin, including the listing of bitcoin ETFs and ETPs on U.S. national securities exchanges, could have a material adverse effect on the market price of our class A common stock.

Our bitcoin acquisition strategy subjects us to enhanced regulatory oversight

As noted above, several bitcoin investment vehicles have attempted to list their shares on a U.S. national securities exchange to permit them to function in the manner of an ETF with continuous share creation and redemption at NAV. To date the SEC has declined to approve any such listing, citing concerns over the surveillance of trading in markets for the underlying bitcoin as well as concerns about

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fraud and manipulation in bitcoin trading markets. Even though we do not function in the manner of an ETF and do not offer continuous share creation and redemption at NAV, it is possible that we nevertheless could face regulatory scrutiny from the SEC due to our bitcoin holdings.

In addition, there has been increasing focus on the extent to which digital assets can be used to launder the proceeds of illegal activities, fund criminal or terrorist activities, or circumvent sanctions regimes, including those sanctions imposed in response to the ongoing conflict between Russia and Ukraine. While we have implemented and maintain policies and procedures reasonably designed to promote compliance with applicable anti-money laundering and sanctions laws and regulations and take care to only acquire our bitcoin through entities subject to anti-money laundering regulation and related compliance rules in the United States, if we are found to have purchased any of our bitcoin from bad actors that have used bitcoin to launder money or persons subject to sanctions, we may be subject to regulatory proceedings and any further transactions or dealings in bitcoin by us may be restricted or prohibited.

As of July 31, 2023, approximately 15,731 bitcoins serve as part of the collateral securing our 2028 Secured Notes and we may consider issuing additional debt or other financial instruments that may be collateralized by our bitcoin holdings. We may also consider pursuing strategies to create income streams or otherwise generate funds using our bitcoin holdings. These types of bitcoin-related transactions are the subject of enhanced regulatory oversight. These and any other bitcoin-related transactions we may enter into, beyond simply acquiring and holding bitcoin, may subject us to additional regulatory compliance requirements and scrutiny, including under federal and state money services regulations, money transmitter licensing requirements and various commodity and securities laws and regulations.

Additional laws, guidance and policies may be issued by domestic and foreign regulators following the filing for Chapter 11 bankruptcy protection by FTX, one of the world’s largest cryptocurrency exchanges, in November 2022. While the financial and regulatory fallout from FTX’s collapse did not directly impact our business, financial condition or corporate assets, the FTX collapse may have increased regulatory focus on the digital assets industry. For example, the SEC has recently proposed a number of rules with implications for digital assets. Notably, on April 14, 2023, the SEC reopened the comment period for its proposal to significantly expand the definition of “exchange” under Exchange Act Rule 3b-16 to encompass trading and communication protocol systems for digital asset securities and trading systems that use distributed ledger or blockchain technology, including both so-called “centralized” and “decentralized” trading systems. If adopted in its proposed form, the proposed rule would have a sweeping impact on digital asset trading venues and other digital asset industry participants. U.S. and foreign regulators have also increased, and are highly likely to continue to increase, enforcement activity, and are likely to adopt new regulatory requirements in response to FTX’s collapse. Increased enforcement activity and changes in the regulatory environment, including changing interpretations and the implementation of new or varying regulatory requirements by the government or any new legislation affecting bitcoin, as well as enforcement actions involving or impacting our trading venues, counterparties and custodians, may impose significant costs or significantly limit our ability to hold and transact in bitcoin.

In addition, private actors that are wary of bitcoin or the regulatory concerns associated with bitcoin have in the past taken and may in the future take further actions that may have an adverse effect on our business or the market price of our class A common stock. For example, an affiliate of HSBC Holdings has prohibited customers of its HSBC InvestDirect retail investment platform from buying shares of our class A common stock after determining that the value of our stock is related to the performance of bitcoin, indicating that it did not want to facilitate exposure to virtual currencies.

Due to the unregulated nature and lack of transparency surrounding the operations of many bitcoin trading venues, bitcoin trading venues may experience greater fraud, security failures or regulatory or operational problems than trading venues for more established asset classes, which may result in a loss of confidence in bitcoin trading venues and adversely affect the value of our bitcoin

Bitcoin trading venues are relatively new and, in many cases, unregulated. Furthermore, there are many bitcoin trading venues which do not provide the public with significant information regarding their ownership structure, management teams, corporate practices and regulatory compliance. As a result, the marketplace may lose confidence in bitcoin trading venues, including prominent exchanges that handle a significant volume of bitcoin trading and/or are subject to regulatory oversight, in the event one or more bitcoin trading venues cease or pause for a prolonged period the trading of bitcoin or other digital assets, or experience fraud, significant volumes of withdrawal, security failures or operational problems.

In 2019 there were reports claiming that 80-95% of bitcoin trading volume on trading venues was false or non-economic in nature, with specific focus on unregulated exchanges located outside of the United States. The SEC also alleged as part of its June 5, 2023, complaint that Binance Holdings Ltd. committed strategic and targeted “wash trading” through its affiliates to artificially inflate the volume of certain digital assets traded on its exchange. Such reports and allegations may indicate that the bitcoin market is significantly smaller than expected and that the United States makes up a significantly larger percentage of the bitcoin market than is commonly understood. Any actual or perceived false trading in the bitcoin market, and any other fraudulent or manipulative acts and practices, could adversely

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affect the value of our bitcoin. Negative perception, a lack of stability in the broader bitcoin markets and the closure, temporary shutdown or operational disruption of bitcoin trading venues, lending institutions, institutional investors, institutional miners, custodians, or other major participants in the bitcoin ecosystem, due to fraud, business failure, cybersecurity events, government-mandated regulation, bankruptcy, or for any other reason, may result in a decline in confidence in bitcoin and the broader bitcoin ecosystem and greater volatility in the price of bitcoin. For example, in 2022, each of Celsius Networks, Voyager Digital Holdings, Three Arrows Capital, FTX, and BlockFi filed for bankruptcy, following which the market prices of bitcoin and other digital assets significantly declined. In addition, in June 2023, the SEC announced enforcement actions against Coinbase, Inc., and Binance Holdings Ltd., two providers of large trading venues for digital assets, which similarly was followed by a decrease in the market price of bitcoin and other digital assets. To the extent investors view our class A common stock as linked to the value of our bitcoin holdings, the failure of a major participant in the bitcoin ecosystem could have a material adverse effect on the market price of our class A common stock.

The concentration of our bitcoin holdings enhances the risks inherent in our bitcoin acquisition strategy

As of July 31, 2023, we held approximately 152,800 bitcoins that were acquired at an aggregate purchase price of $4.534 billion and we intend to purchase additional bitcoin and increase our overall holdings of bitcoin in the future. The concentration of our bitcoin holdings limits the risk mitigation that we could take advantage of by purchasing a more diversified portfolio of treasury assets, and the absence of diversification enhances the risks inherent in our bitcoin acquisition strategy. The price of bitcoin experienced a significant decline in 2022, and this has had, and any future significant declines in the price of bitcoin would have, a more pronounced impact on our financial condition than if we used our cash to purchase a more diverse portfolio of assets.

The emergence or growth of other digital assets, including those with significant private or public sector backing, could have a negative impact on the price of Bitcoin and adversely affect our business

As a result of our bitcoin acquisition strategy, the majority of our assets are concentrated in our bitcoin holdings. Accordingly, the emergence or growth of digital assets other than bitcoin may have a material adverse effect on our financial condition. As of June 30, 2023, bitcoin was the largest digital asset by market capitalization. However, there are numerous alternative digital assets and many entities, including consortiums and financial institutions, are researching and investing resources into private or permissioned blockchain platforms or digital assets that do not use proof-of-work mining like the bitcoin network. For example, in late 2022, the Ethereum network transitioned to a “proof-of-stake” mechanism for validating transactions that requires significantly less computing power than proof-of-work mining. The Ethereum network has completed another major upgrade since then, and may undertake additional upgrades in the future. If the mechanisms for validating transactions in Ethereum and other alternative digital assets are perceived as superior to proof-of-work mining, those digital assets could gain market share relative to bitcoin.

Other alternative digital assets that compete with bitcoin in certain ways include “stablecoins,” which are designed to maintain a constant price because of, for instance, their issuers’ promise to hold high-quality liquid assets (such as U.S. dollar deposits and short-term U.S. treasury securities) equal to the total value of stablecoins in circulation. Stablecoins have grown rapidly as an alternative to bitcoin and other digital assets as a medium of exchange and store of value, particularly on cryptocurrency trading platforms. As of June 30, 2023, two of the five largest digital assets by market capitalization are U.S. dollar-backed stablecoins.

Additionally, central banks in some countries have started to introduce digital forms of legal tender. For example, China’s CBDC project was made available to consumers in January 2022, and governments including the United States, the European Union, and Israel have been discussing the potential creation of new CBDCs. Whether or not they incorporate blockchain or similar technology, CBDCs, as legal tender in the issuing jurisdiction, could also compete with, or replace, bitcoin and other digital assets as a medium of exchange or store of value. As a result, the emergence or growth of these or other digital assets could cause the market price of bitcoin to decrease, which could have a material adverse effect on our business, prospects, financial condition, and operating results.

Our bitcoin holdings are less liquid than our existing cash and cash equivalents and may not be able to serve as a source of liquidity for us to the same extent as cash and cash equivalents

In September 2020, we adopted bitcoin as our primary treasury reserve asset. Historically, the bitcoin markets have been characterized by significant volatility in price, limited liquidity and trading volumes compared to sovereign currencies markets, relative anonymity, a developing regulatory landscape, potential susceptibility to market abuse and manipulation, compliance and internal control failures at exchanges, and various other risks inherent in its entirely electronic, virtual form and decentralized network. During times of market instability, we may not be able to sell our bitcoin at reasonable prices or at all. For example, a number of bitcoin trading venues recently have temporarily halted deposits and withdrawals, although the Coinbase exchange (our principal market for bitcoin) has, to date, not done so. As a result, our bitcoin holdings may not be able to serve as a source of liquidity for us to the same extent as cash and cash equivalents. Further, our custodians, trade execution partners and trading venues (including Coinbase) are not banking institutions or otherwise members of the Federal Deposit Insurance Corporation (“FDIC”) or the Securities Investor Protection Corporation (“SIPC”) and, therefore, digital asset deposits held with such entities are not subject to the protections enjoyed by depositors with FDIC or SIPC

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member institutions. Additionally, we may be unable to enter into term loans or other capital raising transactions collateralized by our unencumbered bitcoin or otherwise generate funds using our bitcoin holdings, including in particular during times of market instability or when the price of bitcoin has declined significantly. If we are unable to sell our bitcoin, enter into additional capital raising transactions using bitcoin as collateral, or otherwise generate funds using our bitcoin holdings, or if we are forced to sell our bitcoin at a significant loss, in order to meet our working capital requirements, our business and financial condition could be negatively impacted.

If we or our third-party service providers experience a security breach or cyberattack and unauthorized parties obtain access to our bitcoin, or if our private keys are lost or destroyed, or other similar circumstances or events occur, we may lose some or all of our bitcoin and our financial condition and results of operations could be materially adversely affected

Substantially all of the bitcoin we own is held in custody accounts at institutional-grade digital asset custodians. Security breaches and cyberattacks are of particular concern with respect to our bitcoin. Bitcoin and other blockchain-based cryptocurrencies and the entities that provide services to participants in the bitcoin ecosystem have been, and may in the future be, subject to security breaches, cyberattacks, or other malicious activities. For example, in October 2021 it was reported that hackers exploited a flaw in the account recovery process and stole from the accounts of at least 6,000 customers of the Coinbase exchange (our principal market for bitcoin), although the flaw was subsequently fixed and Coinbase reimbursed affected customers. Similarly, in November 2022, hackers exploited weaknesses in the security architecture of the FTX Trading digital asset exchange and reportedly stole over $400 million in digital assets from customers. A successful security breach or cyberattack could result in:

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a partial or total loss of our bitcoin in a manner that may not be covered by insurance or the liability provisions of the custody agreements with the custodians who hold our bitcoin;
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harm to our reputation and brand;
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improper disclosure of data and violations of applicable data privacy and other laws; or
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significant regulatory scrutiny, investigations, fines, penalties, and other legal, regulatory, contractual and financial exposure.

Further, any actual or perceived data security breach or cybersecurity attack directed at other companies with digital assets or companies that operate digital asset networks, regardless of whether we are directly impacted, could lead to a general loss of confidence in the broader Bitcoin blockchain ecosystem or in the use of bitcoin networks to conduct financial transactions, which could negatively impact us.

Attacks upon systems across a variety of industries, including industries related to bitcoin, are increasing in frequency, persistence, and sophistication, and, in many cases, are being conducted by sophisticated, well-funded and organized groups and individuals, including state actors. The techniques used to obtain unauthorized, improper or illegal access to systems and information (including personal data and digital assets), disable or degrade services, or sabotage systems are constantly evolving, may be difficult to detect quickly, and often are not recognized or detected until after they have been launched against a target. These attacks may occur on our systems or those of our third-party service providers or partners. We may experience breaches of our security measures due to human error, malfeasance, insider threats, system errors or vulnerabilities or other irregularities. In particular, unauthorized parties have attempted, and we expect that they will continue to attempt, to gain access to our systems and facilities, as well as those of our partners and third-party service providers, through various means, such as hacking, social engineering, phishing and fraud. In the past, hackers have successfully employed a social engineering attack against one of our service providers and misappropriated our digital assets, although, to date, such events have not been material to our financial condition or operating results. Threats can come from a variety of sources, including criminal hackers, hacktivists, state-sponsored intrusions, industrial espionage, and insiders. In addition, certain types of attacks could harm us even if our systems are left undisturbed. For example, certain threats are designed to remain dormant or undetectable, sometimes for extended periods of time, or until launched against a target and we may not be able to implement adequate preventative measures. Further, there has been an increase in such activities since the beginning of the COVID-19 pandemic. The risk of cyberattacks could also be increased by cyberwarfare in connection with the ongoing conflict between Russia and Ukraine or other future conflicts, including potential proliferation of malware into systems unrelated to such conflicts. Any future breach of our operations or those of others in the bitcoin industry, including third-party services on which we rely, could materially and adversely affect our business.

We face risks relating to the custody of our bitcoin, including the loss or destruction of private keys required to access our bitcoin and cyberattacks or other data loss relating to our bitcoin

We hold our bitcoin with regulated custodians that have duties to safeguard our private keys. Although as of the date of this Quarterly Report we hold a substantial portion of our bitcoin with a single custodian, our custodial agreements do not restrict us from reallocating our bitcoin holdings among our custodians. In light of the significant amount of bitcoin we hold, we are continuing to seek a greater degree of diversification in the use of custodial services as the extent of potential risk of loss is dependent, in part, on the degree of diversification. If there is a decrease in the availability of digital asset custodians that we believe can safely custody our bitcoin, for example, due to regulatory developments or enforcement actions that cause custodians to discontinue or limit their services in the United

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States, we may need to enter into agreements that are less favorable than our current agreements or take other measures to custody our bitcoin, and our ability to seek a greater degree of diversification in the use of custodial services would be materially adversely affected.

As of June 30, 2023, the insurance that covers losses of our bitcoin holdings covers only a small fraction of the value of the entirety of our bitcoin holdings, and there can be no guarantee that such insurance will be maintained as part of the custodial services we have or that such coverage will cover losses with respect to our bitcoin. Moreover, the use of custodians to hold our bitcoin exposes us to the risk that the bitcoin custodially-held on our behalf could be subject to insolvency proceedings and we could be treated as a general unsecured creditor of the custodian, inhibiting our ability to exercise ownership rights with respect to such bitcoin. Any loss associated with such insolvency proceedings is unlikely to be covered by any insurance coverage we maintain related to our bitcoin.

Bitcoin is controllable only by the possessor of both the unique public key and private key(s) relating to the local or online digital wallet in which the bitcoin is held. While the Bitcoin blockchain ledger requires a public key relating to a digital wallet to be published when used in a transaction, private keys must be safeguarded and kept private in order to prevent a third party from accessing the bitcoin held in such wallet. To the extent the private key(s) for a digital wallet are lost, destroyed, or otherwise compromised and no backup of the private key(s) is accessible, neither we nor our custodians will be able to access the bitcoin held in the related digital wallet. Furthermore, we cannot provide assurance that our digital wallets, nor the digital wallets of our custodians held on our behalf, will not be compromised as a result of a cyberattack. The bitcoin and blockchain ledger, as well as other digital assets and blockchain technologies, have been, and may in the future be, subject to security breaches, cyberattacks, or other malicious activities.

Regulatory change reclassifying bitcoin as a security could lead to our classification as an “investment company” under the Investment Company Act of 1940 and could adversely affect the market price of bitcoin and the market price of our class A common stock

While senior SEC officials have stated their view that bitcoin is not a “security” for purposes of the federal securities laws, the SEC has so far refused to permit the listing of any bitcoin spot-market-based ETPs, citing, among other things, concerns regarding bitcoin market integrity and custodial protections. It is possible that the SEC could take a contrary position to the one taken by its senior officials or a federal court could conclude that bitcoin is a security. Such a determination could lead to our classification as an “investment company” under the Investment Company Act of 1940, which would subject us to significant additional regulatory controls that could have a material adverse effect on our business and operations and may also require us to substantially change the manner in which we conduct our business.

In addition, if bitcoin is determined to constitute a security for purposes of the federal securities laws, the additional regulatory restrictions imposed by such a determination could adversely affect the market price of bitcoin and in turn adversely affect the market price of our class A common stock.

A significant decrease in the market value of our bitcoin holdings could adversely affect our ability to service our indebtedness

As a result of our bitcoin acquisition strategy and our Treasury Reserve Policy, the majority of our assets are concentrated in our bitcoin holdings. The concentration of our assets in bitcoin limits our ability to mitigate risk that could otherwise be achieved by purchasing a more diversified portfolio of treasury assets. Accordingly, a significant decline in the market value of bitcoin could have a material adverse effect on our financial condition. Any material adverse effect on our financial condition caused by a significant decline in the market value of our bitcoin holdings may create liquidity and credit risks for our business operations, as we would have limited means to obtain cash beyond the revenues generated by our enterprise analytics software business. To the extent that the cash generated by our enterprise analytics software business is insufficient to satisfy our debt service obligations, and to the extent that the liquidation of our bitcoin holdings would be insufficient to satisfy our debt service obligations, we may be unable to make scheduled payments on our current or future indebtedness, which could cause us to default on our debt obligations. Any default on our current or future indebtedness may have a material adverse effect on our financial condition. See “Risks Related to Our Outstanding and Potential Future Indebtedness” for additional details about the risks which may impact us if we are unable to service our indebtedness.

Our bitcoin acquisition strategy exposes us to risk of non-performance by counterparties

Our bitcoin acquisition strategy exposes us to the risk of non-performance by counterparties, whether contractual or otherwise. Risk of non-performance includes inability or refusal of a counterparty to perform because of a deterioration in the counterparty’s financial condition and liquidity or for any other reason. For example, our execution partners, custodians, or other counterparties might fail to perform in accordance with the terms of our agreement with them, which could result in a loss of bitcoin, a loss of the opportunity to generate funds, or other losses.

Our primary counterparty risk with respect to our bitcoin is custodian performance obligations under the various custody arrangements we have entered into. A series of recent high-profile filings for bankruptcy protection by companies operating in the digital asset industry

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and certain of their affiliates, including Three Arrows Capital, Celsius Network, Voyager Digital, FTX Trading and Genesis Global Capital, has highlighted the perceived and actual counterparty risk applicable to digital asset ownership and trading. Legal precedent created in these bankruptcy proceedings may increase the risk of future rulings adverse to our interests in the event one or more of our custodians becomes a debtor in a bankruptcy case or is the subject of other liquidation, insolvency or similar proceedings.

On January 23, 2023, the NYDFS released “Guidance on Custodial Structures for Customer Protection in the Event of Insolvency” with the stated purpose of helping to protect customers in the event that a custodian enters bankruptcy, receivership or similar insolvency proceedings. While all of our custodians are NYDFS-regulated custodians, no assurance can be provided that the stated guidance from the NYDFS will be followed or will not be changed or that custodially-held bitcoin will not become part of the custodian’s insolvency estate in the event one or more of our custodians enters bankruptcy, receivership or similar insolvency proceedings. Additionally, if we pursue any strategies to create income streams or otherwise generate funds using our bitcoin holdings, we would become subject to additional counterparty risks. Any significant non-performance by counterparties, including in particular the custodians with which we custody substantially all of our bitcoin, could have a material adverse effect on our business, prospects, financial condition, and operating results.

Risks Related to Our Enterprise Analytics Software Business Strategy

We depend on revenue from a single software platform and related services as well as revenue from our installed customer base

Our revenue is derived from sales of our analytics software platform and related services. Although demand for analytics software has continued to grow, the market for analytics offerings continues to evolve. Resistance from consumer and privacy groups to commercial collection, use, and sharing of personal data has grown in recent years and our customers, potential customers, or the general public may perceive that use of our analytics software could violate individual privacy rights. In addition, increasing government restrictions on the collection, use, and transfer of personal data could impair the further growth of the market for analytics software, especially in foreign markets. Because we depend on revenue from a single software platform and related services, our business could be harmed by a decline in demand for, or in the adoption or prices of, our platform and related services as a result of, among other factors, any change in our pricing or packaging model, increased competition, maturation in the markets for our platform, or other risks described in this Quarterly Report. In addition, the adoption of our bitcoin acquisition strategy and the increase in our indebtedness has caused and may in the future cause certain of our existing or prospective customers to form negative perceptions regarding our corporate risk profile or our financial viability as a commercial counterparty, and such negative perceptions could negatively impact sales of our analytics software platform and related services to current or prospective customers. Such risks can also be exacerbated if the price of bitcoin declines or due to adverse developments in the digital assets industry including, for example, the high-profile filings for bankruptcy protection by companies operating in that industry, such as the recent bankruptcy filings by Three Arrows Capital, Voyager Digital, BlockFi and FTX Trading, and the SEC enforcement actions against Coinbase, Inc. and Binance Holdings Ltd. We also depend on our installed customer base for a substantial portion of our revenue. If our existing customers cancel or fail to renew their service contracts or fail to make additional purchases from us for any reason, including due to the risks inherent in our bitcoin acquisition strategy, our revenue could decrease and our operating results could be materially adversely affected.

As our customers increasingly shift from a product license model to a cloud subscription model, we could face higher future rates of attrition, and such a shift could continue to affect the timing of revenue recognition or reduce product licenses and product support revenues, which could materially adversely affect our operating results

We offer our analytics platform in the form of a product license or a cloud subscription. Given that it is relatively easy for customers to migrate on and off our cloud subscription platform, as we continue to shift our customers toward our cloud platform, we could face higher future rates of attrition among our customers. In addition, the payment streams and revenue recognition timing for our product licenses are different from those for our cloud subscriptions. For product licenses, customers typically pay us a lump sum soon after entering into a license agreement, and we typically recognize product licenses revenue when control of the license is transferred to the customer. For cloud subscriptions, customers typically make periodic payments over the subscription period and we recognize subscription services revenues ratably over the subscription period. As a result, as our customers increasingly shift to, or new customers purchase, cloud subscriptions instead of product licenses, the resulting change in payment terms and revenue recognition may result in our recognizing less revenue in the reporting period in which the sale transactions are consummated than has been the case in prior periods, with more revenue being recognized in future periods. This change in the timing of revenue recognition could materially adversely affect our operating results and cash flows for the periods during which such a shift or change in purchasing occurs. Accordingly, in any particular reporting period, cloud subscription sales could negatively impact product license sales to our existing and prospective customers, which could reduce product licenses and product support revenues. Additionally, our ability to accelerate our cloud strategy could be negatively impacted by any inability to provide necessary sales and sales engineering support, including the support of channel partners, our internal sales team, and digital marketing. Finally, if we are not able to successfully grow sales of our cloud subscription platform, we may not be able to achieve the scale necessary to achieve increased operating margins.

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We use channel partners and if we are unable to maintain successful relationships with them, our business, operating results, and financial condition could be materially adversely affected

In addition to our direct sales force, we use channel partners, such as system integrators, consulting firms, resellers, solution providers, managed service providers, OEMs, and technology companies, to license and support our offerings. For the six months ended June 30, 2023, transactions by channel partners for which we recognized revenue accounted for 33.9% of our total product licenses revenues, and our ability to achieve revenue growth in the future will depend in part on our ability to maintain these relationships. Our channel partners may offer customers the products and services of several different companies, including competing offerings, and we cannot be certain that they will prioritize or devote adequate resources to selling our offerings. If we are unable to maintain our relationships with our channel partners, or if we experience a reduction in sales by our channel partners, our business, operating results, and financial condition could be materially adversely affected.

In addition, we rely on our channel partners to operate in accordance with applicable laws and regulatory requirements. If they fail to do so, we may need to incur significant costs in responding to investigations or enforcement actions or paying penalties assessed by the applicable authorities. We also rely on our channel partners to operate in accordance with the terms of their contractual agreements with us. For example, some of our agreements with our channel partners prescribe the terms and conditions pursuant to which they are authorized to resell or distribute our software and offer technical support and related services. If our channel partners do not comply with their contractual obligations to us, our business, operating results, and financial condition may be materially adversely affected.

Our recognition of deferred revenue and advance payments is subject to future performance obligations and may not be representative of revenues for succeeding periods

Our deferred revenue and advance payments totaled $207.1 million as of June 30, 2023. The timing and ultimate recognition of our deferred revenue and advance payments depend on various factors, including our performance of various service obligations.

Because of the possibility of customer changes or delays in customer development or implementation schedules or budgets, and the need for us to satisfactorily perform product support and other services, deferred revenue and advance payments at any particular date may not be representative of actual revenue for any succeeding period.

In addition, we had $87.2 million of other remaining performance obligations as of June 30, 2023, consisting of the portions of multi-year contracts that will be invoiced in the future that are not reflected on our balance sheet. As with deferred revenue and advance payments, these other remaining performance obligations at any particular date may not be representative of actual revenue for any succeeding period.

We may lose sales, or sales may be delayed, due to the long sales and implementation cycles of certain of our offerings, which could materially adversely affect our revenues and operating results

The decision to purchase our offerings typically requires our customers to invest substantial time, money, personnel, and other resources, which can result in long sales cycles that can exceed nine months. These long sales cycles increase the risk that intervening events, such as the introduction of new offerings and changes in customer budgets and purchasing priorities, will affect the size, timing, and completion of an order. Even if an order is completed, the time and resources required to implement and integrate our offerings vary widely depending on customer needs and the complexity of deployment. If we lose sales or sales are delayed due to these long sales and implementation cycles, our revenues and operating results for that period may be materially adversely affected.

Our results in any particular period may depend on the number and volume of large transactions in that period and these transactions may involve lengthier, more complex, and more unpredictable sales cycles than other transactions

Larger, enterprise-level transactions often require considerably more resources, are often more complex to implement, and typically require additional management approval, which may result in a lengthier, more complex, and less predictable sales cycle and may increase the risk that an order is delayed or not brought to completion. We may also encounter greater competition and pricing pressure on these larger transactions, and our sales and delivery efforts may be more costly. The presence or absence of one or more large transactions in a particular period may have a material effect on our revenues and operating results for that period and may result in lower estimated revenues and earnings in future periods. For the six months ended June 30, 2023, our top three product licenses transactions with recognized revenue totaled $4.4 million, or 13.3% of total product licenses revenues, compared to $8.6 million, or 23.4% of total product licenses revenues, for the six months ended June 30, 2022.

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Our offerings face intense competition, which may lead to lower prices for our offerings, reduced gross margins, loss of market share, and reduced revenue

The analytics market is highly competitive and subject to rapidly changing technology. Within the analytics space, we compete with many different software vendors, including IBM, Microsoft, Oracle, Qlik, Salesforce, and SAP. Our future success depends on our ability to differentiate our offerings and successfully compete across analytics implementation projects of varying sizes. Our ability to compete successfully depends on a number of factors, both within and outside of our control. Some of these factors include software deployment options; analytical, mobility, data discovery, visualization, artificial intelligence (“AI”), and machine learning capabilities; performance and scalability; the quality and reliability of our customer service and support; and brand recognition. Failure to compete successfully in any one of these or other areas may reduce the demand for our offerings and materially adversely affect our revenue from both existing and prospective customers.

Some of our competitors have longer operating histories, more focused business strategies and significantly greater financial, technical, and marketing resources than we do. As a result, they may be able to respond more quickly to new or emerging technologies and changes in customer requirements or devote greater resources to the development, promotion, sale, and marketing of their offerings than we can, such as offering certain analytics products free of charge when bundled with other products. In addition, many of our competitors have strong relationships with current and potential customers, extensive industry and specialized business knowledge, and corresponding proprietary technologies that they can leverage. As a result, they may be able to prevent us from penetrating new accounts or expanding existing accounts.

Increased competition may lead to price cuts, reduced gross margins, and loss of market share. The failure to compete successfully and meet the competitive pressures we face may have a material adverse effect on our business, operating results, and financial condition.

Current and future competitors may also make strategic acquisitions or establish cooperative relationships among themselves or with others. By doing so, these competitors may increase their ability to meet the needs of our potential customers by their expanded offerings and rapidly gain significant market share, which could limit our ability to obtain revenues from new customers and to sustain software maintenance revenues from our installed customer base. In addition, basic office productivity software suites, such as Microsoft Office, could evolve to offer advanced analysis and reporting capabilities that may reduce the demand for our analytics offerings.

Integration of artificial intelligence into our enterprise analytics product offerings and our use of artificial intelligence in our operations could result in reputational or competitive harm, legal liability, and other adverse effects on our business

We have integrated, and plan to further integrate, AI capabilities into certain components of our enterprise analytics product offerings and we expect to use AI in our operations. Such integration and use of AI may become more important in our product offerings and operations over time. These AI-related initiatives, whether successful or not, could cause us to incur substantial costs and could result in delays in our software release cadence. Our competitors or other third parties may incorporate AI into their products or operations more quickly or more successfully than we do, which could impair our ability to compete effectively. Additionally, AI algorithms may be flawed and datasets underlying AI algorithms may be insufficient or contain biased information. If the AI tools integrated into our products or that we use in our operations produce analyses or recommendations that are or are alleged to be deficient, inaccurate, or biased, our reputation, business, financial condition, and results of operations may be adversely affected.

Other companies have experienced cybersecurity incidents that implicate confidential and proprietary company data and/or the personal data of end users of AI applications integrated into their software offerings or used in their operations. If we were to experience a cybersecurity incident, whether related to the integration of AI capabilities into our product offerings or our use of AI applications in our operations, our business and results of operations could be adversely affected. AI also presents various emerging legal, regulatory and ethical issues, and the incorporation of AI into our product offerings and our use of AI applications in our operations could require us to expend significant resources in developing, testing and maintaining our product offerings and may cause us to experience brand, reputational, or competitive harm, or incur legal liability.

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Risks Related to Our Technology and Intellectual Property

If we are unable to develop and release new offerings and software enhancements to respond to rapid technological change, new customer requirements, or evolving industry standards in a timely and cost-effective manner, our business, operating results, and financial condition could be materially adversely affected

The market for our offerings is characterized by frequent new offerings and software enhancements in response to rapid technological change, new customer requirements, and evolving industry standards. The introduction of new or enhanced offerings can quickly make existing ones obsolete. We believe our future success depends largely on our ability to continue to support popular operating systems and databases, maintain and improve our current offerings, rapidly develop new offerings and software enhancements that achieve market acceptance, maintain technological competitiveness, and meet an expanding range of customer requirements.

Analytics applications are inherently complex, and research and development can be costly and time consuming. In addition, customers may delay their purchasing decisions because they anticipate that new or enhanced versions of our offerings will soon become available or because of concerns regarding the complexity of migration or performance issues related to new offerings. We cannot be sure that we will succeed in developing, marketing, and delivering, on a timely and cost-effective basis, new or enhanced offerings that will achieve market acceptance. Moreover, even if our new offerings achieve market acceptance, we may experience a decline in revenues of our existing offerings that is not fully matched by the new offering’s revenue. This could result in a temporary or permanent revenue shortfall and materially adversely affect our business, operating results, and financial condition.

We depend on technology licensed to us by third parties, and changes in or discontinuances of such licenses could impair our software, delay implementation of our offerings, or force us to pay higher license fees

We license third-party technologies that are incorporated into or utilized by our existing offerings. These licenses may be terminated, or we may be unable to license third-party technologies for future offerings. In addition, we may be unable to renegotiate acceptable third-party license terms, or we may be subject to infringement liability if third-party technologies that we license are found to infringe intellectual property rights of others. Changes in or discontinuance of third-party licenses could lead to a material increase in our costs or to our offerings becoming inoperable or their performance being materially reduced. As a result, we may need to incur additional development costs to help ensure continued performance of our offerings, and we may experience a decreased demand for our offerings.

Changes in third-party software or systems or the emergence of new industry standards could materially adversely affect the operation of and demand for our existing software

The functionalities of our software depend in part on the ability of our software to interface with our customers’ information technology (“IT”) infrastructure and cloud environments, including software applications, network infrastructure, and end user devices, which are supplied to our customers by various other vendors. When new or updated versions of these third-party software or systems are introduced, or new industry standards in related fields emerge, we may be required to develop updated versions of or enhancements to our software to help ensure that it continues to effectively interoperate with our customers’ IT infrastructure and cloud environments. If new or modified operating systems are introduced or new web standards and technologies or new standards in the field of database access technology emerge that are incompatible with our software, development efforts to maintain the interoperability of our software with our customers’ IT infrastructure and cloud environments could require substantial capital investment and employee resources. If we are unable to update our software in a timely manner, cost-effectively, or at all, the ability of our software to perform key functions could be impaired, which may impact our customers’ satisfaction with our software, potentially result in breach of warranty or other claims, and materially adversely affect demand for our software.

The nature of our software makes it particularly susceptible to undetected errors, bugs, or security vulnerabilities, which could cause problems with how the software performs and, in turn, reduce demand for our software, reduce our revenue, and lead to litigation claims against us

Despite extensive testing by us and our current and potential customers, we have in the past discovered software errors, bugs, or security vulnerabilities (including the log4j and SpringShell vulnerabilities which surfaced in December 2021 and March 2022, respectively, and affected companies worldwide) in our offerings after commercial shipments began and they may be found in future offerings or releases. This could result in lost revenue, damage to our reputation, or delays in market acceptance, which could have a material adverse effect on our business, operating results, and financial condition. We may also need to expend resources and capital to correct these defects if they occur.

Our customer agreements typically contain provisions designed to limit our exposure to product liability, warranty, and other claims. It is possible these provisions are unenforceable in certain domestic or international jurisdictions, and we may be exposed to such claims. A successful claim against us could have a material adverse effect on our business, operating results, and financial condition.

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Our intellectual property is valuable, and any inability to protect it could reduce the value of our offerings and brand

Unauthorized third parties may try to copy or reverse engineer portions of our software or otherwise obtain and use our intellectual property. Copyrights, patents, trademarks, trade secrets, confidentiality procedures, and contractual commitments can only provide limited protection. Any intellectual property owned by us may be invalidated, circumvented, or challenged. Any of our pending or future intellectual property applications, whether or not currently being challenged, may not be issued with the scope we seek, if at all. Moreover, amendments to and developing jurisprudence regarding U.S. and international law may affect our ability to protect our intellectual property and defend against claims of infringement. In addition, although we generally enter into confidentiality agreements with our employees and contractors, the confidential nature of our intellectual property may not be maintained. Furthermore, the laws of some countries do not provide the same level of protection of our intellectual property as do the laws of the United States. If we cannot protect our intellectual property against unauthorized copying or use, we may not remain competitive.

Third parties may claim we infringe their intellectual property rights

We periodically receive notices from third parties claiming we are infringing their intellectual property rights. The frequency of such claims may increase as we expand our offerings and branding, the number of offerings and level of competition in our industry grow, the functionality of offerings overlaps, and the volume of issued patents, patent applications, and copyright and trademark registrations continues to increase. Responding to any infringement claim, regardless of its validity, could:

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be time-consuming, costly, and/or result in litigation;
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divert management’s time and attention from developing our business;
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require us to pay monetary damages or enter into royalty or licensing agreements that we would normally find unacceptable;
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require us to stop selling certain of our offerings;
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require us to redesign certain of our offerings using alternative non-infringing technology or practices, which could require significant effort and expense;
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require us to rename certain of our offerings or entities; or
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require us to satisfy indemnification obligations to our customers or channel partners.

Additionally, while we monitor our use of third-party software, including open-source software, our processes for controlling such use in our offerings may not be effective. If we fail to comply with the terms or conditions associated with third-party software that we use, if we inadvertently embed certain types of third-party software into one or more of our offerings, or if third-party software that we license is found to infringe the intellectual property rights of others, we could become subject to infringement liability and be required to re-engineer our offerings, discontinue the sale of our offerings, or make available to certain third parties or generally available, in source code form, our proprietary code, any of which could materially adversely affect our business, operating results, and financial condition.

If a successful infringement claim is made against us and we fail to develop or license a substitute technology or brand name, as applicable, our business, results of operations, financial condition, or cash flows could be materially adversely affected.

Risks Related to Our Operations

Business disruptions, including interruptions, delays, or failures of our systems, third-party data center hosting facility, or other third-party services, as a result of geopolitical tensions, acts of terrorism, natural disasters, pandemics (like the COVID-19 pandemic), and similar events, could materially adversely affect our operating results or result in a material weakness in our internal controls that could adversely affect the market price of our stock

A significant portion of our research and development activities or certain other critical business operations are concentrated in facilities in Northern Virginia, China, Argentina, and Poland. In addition, we serve our customers and manage certain critical internal processes using a third-party data center hosting facility located in the United States and other third-party services, including AWS, Azure, and other cloud services. Any disruptions or failures of our systems or the third-party hosting facility or other services that we use, including as a result of a natural disaster, fire, cyberattack (including the potential increase in risk for such attacks due to cyberwarfare in connection with the ongoing conflict between Russia and Ukraine), act of terrorism, geopolitical conflict (including due to the ongoing conflict between Russia and Ukraine and any potential conflict involving China and Taiwan), pandemic (including the COVID-19 pandemic), the effects of climate change, or other catastrophic event, as well as power outages, telecommunications infrastructure outages, a decision by one of our third-party service providers to close facilities that we use without adequate notice or to materially change the pricing or terms of their services, host country restrictions on the conduct of our business operations or the availability of our offerings, or other unanticipated problems with our systems or the third-party services that we use, such as a failure to meet service standards, could severely impact our ability to conduct our business operations or to attract new customers or maintain existing customers, or result in a material weakness in our internal control over financial reporting, any of which could materially adversely affect our future operating results.

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Our international operations are complex and expose us to risks that could have a material adverse effect on our business, operating results, and financial condition

We receive a significant portion of our total revenues from international sales and conduct our business activities in various foreign countries, including some emerging markets where we have limited experience, where the challenges of conducting our business can be significantly different from those we have faced in more developed markets, and where business practices may create internal control risks. International revenues accounted for 40.7% and 39.2% of our total revenues for the three months ended June 30, 2023 and 2022, respectively, and 41.8% and 41.3% of our total revenues for the six months ended June 30, 2023 and 2022, respectively. Our international operations require significant management attention and financial resources and expose us to additional risks, including:

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fluctuations in foreign currency exchange rates;
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new, or changes in, regulatory requirements;
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tariffs, export and import restrictions, restrictions on foreign investments, tax laws, sanctions, laws and policies that favor local competitors (such as mandatory technology transfers), and other trade barriers or protection measures;
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compliance with a wide variety of laws, including those relating to labor matters, antitrust, procurement and contracting, consumer and data protection, privacy, data localization, governmental access to data, network security, and encryption;
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costs of localizing offerings and lack of acceptance of localized offerings;
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difficulties in and costs of staffing, managing, and operating our international operations;
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economic weakness or currency-related crises;
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generally longer payment cycles and greater difficulty in collecting accounts receivable;
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weaker intellectual property protection;
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increased risk of corporate espionage or misappropriation, theft, or misuse of intellectual property, particularly in foreign countries where we have significant software development operations that have access to product source code, such as China;
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our ability to adapt to sales practices and customer requirements in different cultures;
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natural disasters, acts of war (including risks relating to the ongoing conflict between Russia and Ukraine and any potential conflict involving China and Taiwan), terrorism, or pandemics (including the COVID-19 pandemic); and
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political instability and security risks in the countries where we are doing business, including, without limitation, political and economic instability caused by the current conflict between Russia and Ukraine and economic sanctions adopted in response to the conflict.

Disruptions to trade, weakening of economic conditions, economic and legal uncertainties, or changes in currency rates may adversely affect our business, financial condition, operating results, and cash flows. The United States has put in place higher tariffs and other restrictions on trade with China, the European Union, Canada, and Mexico, among other countries, including limiting trade and/or imposing tariffs on imports from such countries. In addition, China, the European Union, Canada, and Mexico, among others, have either threatened or put into place retaliatory tariffs of their own. These tariffs and any further escalation of protectionist trade measures could adversely affect the markets in which we sell our offerings and, in turn, our business, financial condition, operating results, and cash flows. It is unclear whether and to what extent such measures will be reversed in the future or whether the Biden administration will make additional changes to U.S. trade policy that may result in further impacts on our business.

Changes to the U.S. taxation of our international income, or changes in foreign tax laws, could have a material effect on our future operating results. For example, the Tax Act led to corporate income tax rate changes, the modification or elimination of certain tax incentives, changes to the existing regime for taxing overseas earnings, and measures to prevent BEPS, and the United Kingdom adopted legislation imposing a tax related to offshore receipts in respect of intangible property held in low tax jurisdictions.

Moreover, compliance with foreign and U.S. laws and regulations that are applicable to our international operations is complex and may increase our cost of doing business in international jurisdictions. Our failure to comply with these laws and regulations has exposed, and may in the future expose, us to fines and penalties. These laws and regulations include anti-bribery laws, such as the U.S. Foreign Corrupt Practices Act, the UK Bribery Act, local laws prohibiting corrupt payments to government officials, and local laws relating to procurement, contracting, and antitrust. These laws and regulations also include import and export requirements and economic and trade sanctions administered by the Office of Foreign Assets Control and the U.S. Department of Commerce based on U.S. foreign policy and national security goals against targeted foreign states, organizations, and individuals. Although we have implemented policies and procedures designed to help ensure compliance with these laws, our employees, channel partners, and other persons with whom we do business may take actions in violation of our policies or these laws. For example, following an internal review initiated in 2018, we believe our Brazilian subsidiary failed or likely failed to comply with local procurement regulations in conducting business with certain Brazilian government entities and these matters are the subject of investigation by Brazilian authorities. Any violation of these laws could subject us to civil or administrative penalties, including substantial fines, prohibitions, or other limitations on our ability to sell our offerings to one or more countries, and could also materially damage our reputation and our brand.

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These factors may have a material adverse effect on our future sales, business, operating results, and financial condition.

We face a variety of risks in doing business with U.S. and foreign federal, state, and local governments and government agencies, including risks related to the procurement process, budget constraints and cycles, termination of contracts, and compliance with government contracting requirements

Our customers include the U.S. government, state and local governments and government agencies. There are a variety of risks in doing business with government entities, including:

Procurement. Contracting with public sector customers is highly competitive and can be time-consuming and expensive, requiring us to incur significant up-front time and expense without any assurance that we will win a contract.

Budgetary Constraints and Cycles. Public sector funding reductions or delays adversely impact demand and payment for our offerings.

Termination of Contracts. Public sector customers often have contractual or other legal rights to terminate contracts for convenience or due to a default. If a contract is terminated for convenience, we may only be able to collect fees for software or services delivered prior to termination and settlement expenses. If a contract is terminated due to a default, we may not recover even those amounts, and we may be liable for excess costs incurred by the customer for procuring alternative software or services.

Compliance with Government Contracting Requirements. Government contractors are required to comply with a variety of complex laws, regulations, and contractual provisions relating to the formation, administration, or performance of government contracts that give public sector customers substantial rights and remedies, many of which are not typical for commercial contracts. These may include rights regarding price protection, the accuracy of information provided to the government, contractor compliance with socio-economic policies, and other terms unique to government contracts. Governments and government agencies routinely investigate and audit contractors for compliance with these requirements. If, as a result of an audit or review, it is determined that we have failed to comply with these requirements, we may be subject to civil and criminal penalties or administrative sanctions, including contract termination, forfeiture of profits, fines, and suspensions or debarment from future government business and we may suffer harm to our reputation.

Our customers also include foreign governments and government agencies. Similar procurement, budgetary, contract, and audit risks also apply to these entities. In addition, compliance with complex regulations and contracting provisions in a variety of jurisdictions can be expensive and consume significant management resources. In certain jurisdictions, our ability to win business may be constrained by political and other factors unrelated to our competitive position in the market. Each of these difficulties could materially adversely affect our business and results of operations.

If we are unable to recruit or retain skilled personnel, or if we lose the services of Michael J. Saylor, our business, operating results, and financial condition could be materially adversely affected

Our future success depends on our continuing ability to attract, train, assimilate, and retain highly skilled personnel. There has historically been significant competition for qualified employees in the technology industry, and such competition may be further amplified by evolving restrictions on immigration, travel, or availability of visas for skilled technology workers. We may not be able to retain our current key employees or attract, train, assimilate, and retain other highly skilled personnel in the future. Our future success also depends in large part on the continued service of Michael J. Saylor, our Chairman of the Board of Directors and Executive Chairman. If we lose the services of Mr. Saylor, or if we are unable to attract, train, assimilate, and retain the highly skilled personnel we need, our business, operating results, and financial condition could be materially adversely affected.

Changes in laws or regulations relating to privacy or the collection, processing, disclosure, storage, localization, or transmission of personal data, or any actual or perceived failure by us or our third-party service providers to comply with such laws and regulations, contractual obligations, or applicable privacy policies, could materially adversely affect our business

Aspects of our business involve collecting, processing, disclosing, storing, and transmitting personal data, which are subject to certain privacy policies, contractual obligations, and U.S. and foreign laws, regulations, and directives relating to privacy and data protection. We store a substantial amount of customer and employee data, including personal data, on our networks and other systems and the cloud environments we manage. In addition, the types of data subject to protection as personal data in the European Union, China, the United States, and elsewhere have been expanding. In recent years, the collection and use of personal data by companies have come under increased regulatory and public scrutiny, especially in relation to the collection and processing of sensitive data, such as healthcare, biometric, genetic, financial services, and children’s data, precise location data, and data regarding a person’s race or ethnic origins, political opinions, or religious beliefs. For example, in the United States, protected health information is subject to the Health Insurance Portability and Accountability Act of 1996 (“HIPAA”), which can provide for civil and criminal penalties for noncompliance. Entities (such as us) that engage in creating, receiving, maintaining, or transmitting protected health information provided by covered entities

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and other business associates are subject to enforcement under HIPAA. Our access to protected health information triggers obligations to comply with certain privacy rules and data security requirements under HIPAA.

In addition to potential enforcement by the United States Department of Health and Human Services for potential HIPAA violations, we are also potentially subject to privacy enforcement from the Federal Trade Commission (“FTC”). The FTC has been particularly focused on certain activities related to the processing of sensitive data, including the unpermitted processing of health and genetic data through its recent enforcement actions and is expanding the types of privacy violations that it interprets to be “unfair” under Section 5 of the FTC Act, as well as the types of activities it views to trigger the Health Breach Notification Rule (which the FTC also has the authority to enforce). The agency is also in the process of developing rules related to commercial surveillance and data security that may impact our business. We will need to account for the FTC’s evolving rules and guidance for proper privacy and data security practices in order to mitigate our risk for a potential enforcement action, which may be costly. If we are subject to a potential FTC enforcement action, we may be subject to a settlement order that requires us to adhere to very specific privacy and data security practices, which may impact our business. We may also be required to pay fines as part of a settlement (depending on the nature of the alleged violations). If we violate any consent order that we reach with the FTC, we may be subject to additional fines and compliance requirements. We face risks of similar enforcement from State Attorneys General and, potentially, other regulatory agencies.

Any systems failure or security breach that results in the release of, or unauthorized access to, personal data, or any failure or perceived failure by us or our third-party service providers to comply with applicable privacy policies, contractual obligations, or any applicable laws or regulations relating to privacy or data protection, could result in proceedings against us by domestic or foreign government entities or others, including private plaintiffs in litigation. Such proceedings could result in the imposition of sanctions, fines, penalties, liabilities, government orders, and/or orders requiring that we change our data practices, any of which could have a material adverse effect on our business, operating results, reputation, and financial condition.

Various U.S. and foreign government bodies may enact new or additional laws or regulations, or issue rulings that invalidate prior laws or regulations, concerning privacy, data storage, data protection, and cross-border transfer of data that could materially adversely impact our business. In the European Union, the General Data Protection Regulation (“GDPR”) took effect in May 2018. GDPR establishes requirements regarding the handling and security of personal data, requires disclosure of data breaches to individuals, customers, and data protection authorities in certain circumstances, requires companies to honor data subjects’ requests relating to their personal data, permits regulators to impose fines of up to €20,000,000 or 4% of global annual revenue, whichever is higher, and establishes a private right of action. Furthermore, a new ePrivacy Regulation, regulating electronic communications, was proposed in 2017 and is under consideration by the European Commission, the European Parliament, and the European Council. In July 2020, the Court of Justice of the European Union (“CJEU”) invalidated the U.S.-EU Privacy Shield, which provided a mechanism to lawfully transfer personal data from the European Union to the United States and certain other countries. In the wake of the invalidation of the U.S.-EU Privacy Shield, we transitioned to reliance on the EU Standard Contractual Clauses (“SCCs”) to lawfully transfer certain personal data from the European Union to the United States. The CJEU decision also drew into question the long-term viability of the SCCs for transfers of personal data from the EU and European Economic Area to the U.S. As a result, in October 2022, President Biden signed an executive order to implement the EU-U.S. Data Privacy Framework, which would serve as a replacement to the EU-U.S. Privacy Shield. The European Union initiated the process to adopt an adequacy decision for the EU-U.S. Data Privacy Framework in December 2022 and the European Commission adopted the adequacy decision on July 10, 2023. The adequacy decision will permit U.S. companies who self-certify to the EU-U.S. Data Privacy Framework to rely on it as a valid data transfer mechanism for data transfers from the EU to the U.S. and will also provide support for the use of standard contractual clauses. However, some privacy advocacy groups have already suggested that they will be challenging the EU-U.S. Data Privacy Framework. If these challenges are successful, they may not only impact the EU-U.S. Data Privacy Framework, but they may also further limit the viability of the standard contractual clauses and other data transfer mechanisms. The uncertainty around this issue has the potential to impact our business internationally. Because the rules involving this data transfer mechanism are also undergoing revision and this transfer mechanism may also be declared invalid (or require us to change our business practices) in the future, these developments may require us to provide an alternative means of data transfer. In addition, the required terms for contracts containing SCCs along with recommended supplemental provisions are changing and may require us to assume additional obligations, otherwise inhibit or restrict our ability to undertake certain activities, or incur additional costs related to data protection.

In addition, in June 2021, the European Data Protection Board (“EDPB”) issued a new set of SCCs and formal recommendations on measures to ensure compliance with the EU data protection requirements when transferring personal data outside of the European Economic Area (the “EDPB Recommendations”). The new SCCs were required to be in place for new transfers of personal data as of September 27, 2021 and to replace those being used for existing transfers of personal data by December 27, 2022. The new SCCs place obligations on us in relation to government authorities’ access requests in respect of personal data transferred under the SCCs, and other obligations to bring the SCCs in line with the requirements of the GDPR. The EDPB Recommendations are designed to be read in tandem with the new SCCs and set out new requirements for organizations to assess third countries and identify appropriate supplementary data protection and security measures to be implemented on a case-by-case basis where needed.

Moreover, due to Brexit, the SCCs issued by the European Commission are no longer automatically adopted in the United Kingdom post-Brexit. In response, the UK’s Information Commissioner’s Office (“ICO”) published a template Addendum to the new EU SCCS which adapts the new EU SCCs for UK use. In the alternative, the ICO also published the international data transfer agreement (“IDTA”).

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The IDTA replaces the current set of SCCs being used in the UK. The UK SCCs Addendum and IDTA, after having been put before UK parliament, have been in force as of March 2022 and UK-based organizations were required to start using the UK IDTA or Addendum for new data transfer arrangements starting in September 2022. The UK and the US are also in discussions to develop a US-UK “data bridge,” which would function similarly to the EU-US Data Privacy Framework and provide an additional legal mechanism for companies to transfer data from the UK to the US.

The rules involving these alternative SCC data transfer options are continually undergoing revision and these transfer mechanisms may also be declared invalid (or require us to change our business practices) in the future, requiring us to provide an alternative means of data transfer or implement significant changes in our data security and protection practices. In addition, the required terms for contracts containing SCCs along with recommended supplemental provisions are changing and may require us to assume additional obligations, otherwise inhibit or restrict our ability to undertake certain activities, or incur additional costs related to data protection.

Similar requirements are also coming into force in other countries. Brazil enacted the Lei Geral de Proteção de Dados (the “Brazilian General Data Protection Law”), which became effective in August 2020 and imposes requirements largely similar to GDPR on products and services offered to users in Brazil. In China, we may also be subject to the Cybersecurity Law that went into effect in June 2017 and the revision of the Personal Information Security Specification that went into effect in October 2020, which have broad but uncertain application and impose a number of new privacy and data security obligations. China also adopted new legislation on the protection of privacy and personal data in November 2021, including the Personal Information Protection Law (“PIPL”) and Data Security Law that impose new data processing obligations on us. Under these new regulations, if an entity operating in China violates the law, regulators may order it to take corrective actions, issue warnings, confiscate illegal income, suspend services, revoke operating permits or business licenses, or issue a fine. The fine can be up to ¥50 million or 5 percent of an organization’s annual revenue for the prior financial year.

Further, in connection with cross-border transfer of personal information under the PIPL in China, China regulators published the Draft Rules on Standard Contracts Regarding Export of Personal Information and, under the PIPL, the adoption of standard contractual clauses between the data controller (the entity which transfers personal information to a location outside the PRC) and the offshore recipient is required to lawfully facilitate the offshore transfer of personal information from China. These requirements apply to companies operating in China and seeking to transfer personal data outside of China and organizations which do not satisfy these conditions may be required to satisfy additional regulatory requirements and/or be subject to penalties or fines.

Other countries are considering new or expanded laws governing privacy and data security that may impact our business practices. These developments, including in Brazil and China, may impact our activities with our customers, other MicroStrategy entities and vendors, and require us to take additional and appropriate steps in light of data transfers between the U.S. and the EU (and the UK), as well as transfers and onward transfers of personal data from the EU to other non-EU countries.

State privacy laws in the United States also may impact our business operations. The state of California has adopted a comprehensive privacy law, the California Consumer Privacy Act (“CCPA”), which took effect in January 2020 and became enforceable in July 2020. We have been required to devote substantial resources to implement and maintain compliance with the CCPA, and noncompliance could result in regulatory investigations and fines or private litigation. Moreover, in November 2020, California voters approved a privacy law, the California Privacy Rights Act (“CPRA”), which amends the CCPA to create additional privacy rights and obligations in California, and went into effect on January 1, 2023. Numerous other states have passed laws similar to the CCPA, which will go into effect in 2023 and beyond. More states may follow. These laws may impose additional costs and obligations on us. Similarly, in March 2022, the U.S. federal government also passed the Cyber Incident Reporting for Critical Infrastructure Act of 2022, which will require companies deemed to be part of U.S. critical infrastructure to report any substantial cybersecurity incidents or ransom payments to the federal government within 72 and 24 hours, respectively. The implementing regulations are not expected for another two-to-three years.

Furthermore, the U.S. Congress is considering comprehensive privacy legislation. At this time, it is unclear whether Congress will pass such a law and if so, when and what it will require and prohibit. Moreover, it is not clear whether any such legislation would give the Federal Trade Commission (“FTC”) any new authority to impose civil penalties for violations of the Federal Trade Commission Act in the first instance, whether Congress will grant the FTC rulemaking authority over privacy and information security, or whether Congress will vest some or all privacy and data security regulatory authority and enforcement power in a new agency, akin to EU data protection authorities.

Complying with these and other changing requirements could cause us or our customers to incur substantial costs or pay substantial fines or penalties, require us to change our business practices, require us to take on more onerous obligations in our contracts, or limit our ability to provide certain offerings in certain jurisdictions, any of which could materially adversely affect our business and operating results. New laws or regulations restricting or limiting the collection or use of mobile data could also reduce demand for certain of our offerings or require changes to our business practices, which could materially adversely affect our business and operating results.

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If we or our third-party service providers experience a disruption due to a cybersecurity attack or security breach and unauthorized parties obtain access to our customers’, prospects’, vendors’, or channel partners’ data, our data, our networks or other systems, or the cloud environments we manage, our offerings may be perceived as not being secure, our reputation may be harmed, demand for our offerings may be reduced, our operations may be disrupted, we may incur significant legal and financial liabilities, and our business could be materially adversely affected

As part of our business, we process, store, and transmit our customers’, prospects’, vendors’, and channel partners’ data as well as our own, including in our networks and other systems and the cloud environments we manage. Security breaches may occur due to technological error, computer viruses, or third-party action, including intentional misconduct by computer hackers or state actors, physical break-ins, industrial espionage, fraudulent inducement of employees, customers, or channel partners to disclose sensitive information such as usernames or passwords, and employee, customer, or channel partner error or malfeasance. A security breach could result in unauthorized access to or disclosure, modification, misuse, loss, or destruction of our customers’, prospects’, vendors’, or channel partners’ data, our data (including our proprietary information, intellectual property, or trade secrets), our networks or other systems, or the cloud environments we manage. Third parties may also conduct attacks designed to prevent access to critical data or systems through ransomware or temporarily deny customers access to our cloud environments.

We, and our service providers, may experience and have experienced attempts by third parties to identify and exploit software and service vulnerabilities, penetrate or bypass our security measures, and gain unauthorized access to our or our customers’ or service providers’ cloud environments, networks, and other systems. Security measures that we or our third-party service providers have implemented may not be effective against all current or future security threats, including any potential threats from the exploitation of the log4j or SpringShell vulnerabilities. Because there are many different security breach techniques and such techniques continue to evolve, we may be unable to anticipate, detect, or mitigate attempted security breaches and implement adequate preventative measures.

Any security breach, ransomware attack, or successful denial of service attack could result in a loss of customer confidence in the security of our offerings and damage to our brand, reduce the demand for our offerings, disrupt our normal business operations, require us to spend material resources to investigate or correct the breach, require us to notify affected customers or individuals and/or applicable regulators and others, provide identity theft protection services to individuals, expose us to legal liabilities, including litigation, regulatory enforcement actions, and indemnity obligations, and materially adversely affect our revenues and operating results. Our software operates in conjunction with and is dependent on third-party products and components across a broad ecosystem. If there is a security vulnerability in one of these products or components, and if there is a security exploit targeting it, we could face increased costs, liability claims, customer dissatisfaction, reduced revenue, or harm to our reputation or competitive position.

These risks will increase as we continue to grow the number and scale of our cloud subscriptions and process, store, and transmit increasingly large amounts of our customers’, prospects’, vendors’, channel partners’, and our own data. In particular, as remote working conditions have led businesses to increasingly rely on virtual environments and communication systems, there has been an increase in cyberattacks and other malicious activities.

Our having entered into an indemnification agreement with Michael J. Saylor, our Chairman of the Board of Directors and Executive Chairman, that supplements our conventional director and officer liability insurance provided by third-party insurance carriers could negatively affect our business and the market price of our class A common stock

We have entered into an indemnification agreement with Michael J. Saylor, our Chairman of the Board of Directors and Executive Chairman, pursuant to which Mr. Saylor has agreed to personally indemnify our directors and officers with respect to certain claims and expenses excluded from the insurance coverage provided by our commercial director and officer insurance carriers, for which we agreed to pay Mr. Saylor an applicable annual fee. Our having entered into this indemnification agreement with Mr. Saylor could have adverse effects on our business, including making it more difficult to attract and retain qualified directors and officers due to the unconventional nature of the arrangement and potential concerns that the indemnification arrangement might not provide the same level of protection that might otherwise be provided by coverage obtained entirely through conventional director and officer insurance. In addition, our indemnification arrangement with Mr. Saylor may result in some investors perceiving that our independent directors are not sufficiently independent from Mr. Saylor due to their entitlement to personal indemnification from him, which may have an adverse effect on the market price of our class A common stock.

Volatile and significantly weakened global economic conditions have in the past and may in the future adversely affect our industry, business and results of operations

Our overall performance depends in part on worldwide economic and geopolitical conditions. The United States and other key international economies have experienced significant economic and market downturns recently characterized by restricted credit, poor liquidity, reduced corporate profitability, volatility in credit, equity and foreign exchange markets, inflation, bank failures, bankruptcies and overall uncertainty with respect to the economy. In addition, geopolitical and domestic political developments, such as existing and

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potential trade wars and other events beyond our control, such as conflict in the Ukraine, can increase levels of political and economic unpredictability globally and increase the volatility of global financial markets. Moreover, these conditions have affected and may continue to affect the rate of IT spending; could adversely affect our customers’ ability or willingness to attend our events or to purchase our software and service offerings; have delayed and may delay customer purchasing decisions; have reduced and may in the future reduce the value and duration of customer subscription contracts; and we expect these conditions will adversely affect our customer attrition rates. All of these risks and conditions could materially adversely affect our future sales and operating results.

Risks Related to Our Class A Common Stock

The market price of our class A common stock has been and may continue to be volatile

The market price of our class A common stock has historically been volatile and this volatility has been significant in recent periods. Since August 11, 2020, the date on which we announced our initial purchase of bitcoin, the closing price of our class A common stock has increased from $123.62 as of August 10, 2020, the last trading day before our announcement, to $437.88 as of July 31, 2023. The market price of our class A common stock may fluctuate widely in response to various factors, some of which are beyond our control. These factors include, but are not limited to:

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fluctuations in the price of bitcoin, of which we have significant holdings, and in which we expect we will continue to make significant purchases and announcements about our transactions in bitcoin;
•
changes to our bitcoin acquisition strategy;
•
announcement of additional capital raising transactions;
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regulatory, commercial and technical developments related to bitcoin or the Bitcoin blockchain;
•
quarterly variations in our results of operations or those of our competitors;
•
announcements about our earnings that are not in line with analyst expectations, the likelihood of which may be enhanced because it is our policy not to give guidance relating to our anticipated financial performance in future periods;
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announcements by us or our competitors of acquisitions, dispositions, new offerings, significant contracts, commercial relationships, or capital commitments;
•
our ability to develop, market, and deliver new and enhanced offerings on a timely basis;
•
commencement of, or our involvement in, litigation;
•
recommendations by securities analysts or changes in earnings estimates and our ability to meet those estimates;
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investor perception of our Company;
•
announcements by our competitors of their earnings that are not in line with analyst expectations;
•
the volume of shares of our class A common stock available for public sale;
•
sales or purchases of stock by us or by our stockholders and issuances of awards under our equity incentive plan; and
•
general economic conditions and slow or negative growth of related markets, including as a result of war, terrorism, infectious diseases (such as COVID-19 and its variants), natural disasters and other global events, and government responses to such events.

In addition, the stock market and the markets for both bitcoin-influenced and technology companies have experienced extreme price and volume fluctuations that have often been unrelated or disproportionate to the operating performance of companies in those markets. These market and industry factors may seriously harm the market price of our class A common stock, regardless of our actual operating performance.

Because of the rights of our two classes of common stock and because we are controlled by Michael J. Saylor, who beneficially owns the majority of our class B common stock, Mr. Saylor could transfer control of MicroStrategy to a third party without the approval of our Board of Directors or our other stockholders, prevent a third party from acquiring us, or limit the ability of our other stockholders to influence corporate matters

We have two classes of common stock: class A common stock and class B common stock. Holders of our class A common stock generally have the same rights as holders of our class B common stock, except that holders of class A common stock have one vote per share while holders of class B common stock have ten votes per share. As of July 25, 2023, there are 1,964,025 shares of class B common stock outstanding, which accounts for approximately 61.8% of the total voting power of our outstanding common stock. As of July 25, 2023, Mr. Saylor, our Chairman of the Board of Directors and Executive Chairman, beneficially owned 1,961,668 shares of class B common stock, or 61.8% of the total voting power. Accordingly, Mr. Saylor can control MicroStrategy through his ability to determine the outcome of elections of our directors, amend our certificate of incorporation and by-laws, and take other actions requiring the vote or consent of stockholders, including mergers, going-private transactions, and other extraordinary transactions and their terms.

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Our certificate of incorporation allows holders of class B common stock to transfer shares of class B common stock, subject to the approval of stockholders holding a majority of the outstanding class B common stock. Mr. Saylor could, without the approval of our Board of Directors or our other stockholders, transfer voting control of MicroStrategy to a third party. Such a transfer of control could have a material adverse effect on our business, operating results, and financial condition. Mr. Saylor could also prevent a change of control of MicroStrategy, regardless of whether holders of class A common stock might otherwise receive a premium for their shares over the then current market price. In addition, this concentrated control limits stockholders’ ability to influence corporate matters and, as a result, we may take actions that our non-controlling stockholders do not view as beneficial or that conflict with their interests. As a result, the market price of our class A common stock could be materially adversely affected.

Our status as a “controlled company” could make our class A common stock less attractive to some investors or otherwise materially adversely affect our stock price

Because we qualify as a “controlled company” under Nasdaq corporate governance rules, we are not required to have independent directors comprise a majority of our Board of Directors. Additionally, our Board of Directors is not required to have an independent compensation or nominating committee or to have the independent directors exercise the nominating function. We are also not required to have the compensation of our executive officers be determined by a compensation committee of independent directors. In addition, we are not required to empower our Compensation Committee with the authority to engage the services of any compensation consultants, legal counsel, or other advisors, or to have the Compensation Committee assess the independence of compensation consultants, legal counsel, and other advisors that it engages.

In light of our status as a controlled company, our Board of Directors has determined not to establish an independent nominating committee or have its independent directors exercise the nominating function and has elected instead to have the Board of Directors be directly responsible for nominating members of the Board. A majority of our Board of Directors is currently comprised of independent directors, and our Board of Directors has established a Compensation Committee comprised entirely of independent directors. The Compensation Committee determines the compensation of our Chief Executive Officer and Executive Chairman. However, our Board of Directors has authorized our Chief Executive Officer to determine the compensation of executive officers other than himself and the Executive Chairman, except that equity-based compensation is determined by the Compensation Committee. Awards made to directors and officers subject to Section 16 of the Exchange Act under the 2023 Equity Plan are also approved by the Compensation Committee. Additionally, while our Compensation Committee is empowered with the authority to retain and terminate outside counsel, compensation consultants, and other experts or consultants, it is not required to assess their independence.

Although currently a majority of our Board of Directors is comprised of independent directors and the Compensation Committee is comprised entirely of independent directors, we may elect in the future not to have independent directors constitute a majority of the Board of Directors or the Compensation Committee, our Executive Chairman’s and Chief Executive Officer’s compensation determined by a compensation committee of independent directors, or a compensation committee of the Board of Directors at all.

Accordingly, should the interests of our controlling stockholder differ from those of other stockholders, the other stockholders may not have the same protections that are afforded to stockholders of companies that are required to follow all of the Nasdaq corporate governance rules. Our status as a controlled company could make our class A common stock less attractive to some investors or otherwise materially adversely affect our stock price.

Future sales, or the perception of future sales, of our class A common stock, convertible debt instruments or other convertible securities could depress the price of our class A common stock

We may issue and sell additional shares of class A common stock, convertible notes, or other securities in subsequent offerings to raise capital or issue shares for other purposes, including in connection with the acquisition of additional bitcoin. For example, through the date of this report we have sold $335.0 million of shares of class A common stock, and we may sell class A common stock having an aggregate offering price of up to an additional $290.0 million from time to time through the 2023 Sales Agents under the 2023 Sales Agreement. We cannot predict:

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the size of future issuances of equity securities;
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the size and terms of future issuances of convertible debt instruments or other convertible securities; or
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the effect, if any, that future issuances and sales of our securities will have on the market price of our class A common stock.

Transactions involving newly issued class A common stock, convertible debt instruments, or other convertible securities could result in possibly substantial dilution to holders of our class A common stock.

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Our amended and restated by-laws provide that the Court of Chancery of the State of Delaware (or, if the Court of Chancery of the State of Delaware does not have jurisdiction, then any other state court located in the State of Delaware, or if no state court located within the State of Delaware has jurisdiction, the federal district court for the District of Delaware) is the exclusive forum for certain litigation that may be initiated by our stockholders, which could limit our stockholders’ ability to obtain a favorable judicial forum for such disputes with us or our directors, officers or employees

Our amended and restated by-laws provide that, unless we consent in writing to the selection of an alternative forum, the Court of Chancery of the State of Delaware (or, if the Court of Chancery of the State of Delaware does not have jurisdiction, then any other state court located in the State of Delaware, or if no state court located within the State of Delaware has jurisdiction, the federal district court for the District of Delaware) shall, to the fullest extent permitted by law, be the sole and exclusive forum for (i) any derivative action or proceeding brought on behalf of the Company, (ii) any action asserting a claim of breach of a fiduciary duty owed by any director, officer, other employee or stockholder of the Company to the Company or the Company’s stockholders, (iii) any action asserting a claim arising pursuant to any provision of the General Corporation Law of the State of Delaware or the Company’s certificate of incorporation or by-laws (in each case, as they may be amended from time to time), or (iv) any action asserting a claim governed by the internal affairs doctrine. This exclusive forum provision would not apply to suits brought to enforce a duty or liability created by the Exchange Act, which provides for exclusive jurisdiction of the federal courts. It could apply, however, to a suit that falls within one or more of the categories enumerated in the choice of forum provision and asserts claims under the Securities Act, inasmuch as Section 22 of the Securities Act creates concurrent jurisdiction for federal and state courts over all suits brought to enforce any duty or liability created by the Securities Act or the rules and regulations thereunder. There is uncertainty as to whether a court would enforce such provision with respect to claims under the Securities Act, and our stockholders will not be deemed to have waived our compliance with the federal securities laws and the rules and regulations thereunder.

The choice of forum provision may limit a stockholder’s ability to bring a claim in a judicial forum that it finds favorable for disputes with us or our directors, officers or other employees, which may discourage such lawsuits against us and our directors, officers and other employees. Alternatively, if a court were to find the choice of forum provision contained in our amended and restated by-laws to be inapplicable or unenforceable in an action, we may incur additional costs associated with resolving such action in other jurisdictions.

Risks Related to Our Outstanding and Potential Future Indebtedness

Our level and terms of indebtedness could adversely affect our ability to raise additional capital to further execute on our bitcoin acquisition strategy, fund our enterprise analytics software operations, and take advantage of new business opportunities

As of June 30, 2023, we had $2.211 billion aggregate indebtedness, consisting of $650.0 million aggregate principal amount of 2025 Convertible Notes, $1.05 billion aggregate principal amount of 2027 Convertible Notes, $500.0 million aggregate principal amount of 2028 Secured Notes and $10.6 million of other long-term indebtedness.

Our substantial indebtedness and interest expense could have important consequences to us, including:

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limiting our ability to use a substantial portion of our cash flow from operations in other areas of our business, including for acquisition of additional bitcoin, working capital, research and development, expanding our infrastructure, capital expenditures, and other general business activities and investment opportunities in our company, because we must dedicate a substantial portion of these funds to pay interest on and/or service our debt;
•
limiting our ability to obtain additional financing in the future for acquisition of additional bitcoin, working capital, capital expenditures, debt service, acquisitions, execution of our strategy, and other expenses or investments planned by us;
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limiting our flexibility and our ability to capitalize on business opportunities and to react to competitive pressures and adverse changes in government regulation, our business, and our industry;
•
increasing our vulnerability to a downturn in our business and to adverse economic and industry conditions generally;
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placing us at a competitive disadvantage as compared to our competitors that are less leveraged; and
•
limiting our ability, or increasing the costs, to refinance indebtedness.

We may be unable to service our indebtedness, which could cause us to default on our debt obligations and could force us into bankruptcy or liquidation

Our ability to make scheduled payments on and to refinance our indebtedness depends on and is subject to our financial and operating performance, which is influenced, in part, by general economic, financial, competitive, legislative, regulatory, counterparty business, and other risks that are beyond our control, including the availability of financing in the U.S. banking and capital markets. If our cash flows and capital resources are insufficient to fund our debt service obligations, we may be forced to reduce or delay capital expenditures, sell assets, seek additional capital, or restructure or refinance our indebtedness. We cannot assure you that future borrowings will be available to us in an amount sufficient to enable us to service our indebtedness, to refinance our indebtedness, or to fund our other

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liquidity needs. Even if refinancing indebtedness is available, any refinancing of our indebtedness could be at higher interest rates and may require us to comply with more onerous covenants that could further restrict our business operations. In addition, our bitcoin acquisition strategy anticipates that we may issue additional debt in future periods to finance additional purchases of bitcoin, but if we are unable to generate sufficient cash flow to service our debt and make necessary capital expenditures, we may be required to sell bitcoin. These alternative measures may not be successful and may not permit us to meet our scheduled debt service obligations or our financial covenants, which could cause us to default on our debt obligations. In addition, any failure to make payments of interest and principal on our outstanding indebtedness on a timely basis would likely result in a reduction of our credit rating, which could harm our ability to incur additional indebtedness.

Upon the occurrence of an event of default under any of MicroStrategy’s indebtedness, the holders of the defaulted indebtedness could elect to declare all the funds borrowed to be due and payable, together with accrued and unpaid interest and, in the case of our 2028 Secured Notes, enforce their security interests on substantially all of MicroStrategy’s assets and the assets of our subsidiary guarantors, but excluding bitcoins that are currently owned by our MacroStrategy subsidiary or acquired by MacroStrategy in future periods in transactions permitted by the terms of the 2028 Secured Notes. Any of these events could in turn result in cross-defaults under our other indebtedness. We may not have sufficient funds available to pay the amounts due upon any such default, particularly in the event that there has been a decrease in the market value of our bitcoin holdings, and we may not be able to raise additional funds to pay such amounts on a timely basis, on terms we find acceptable, or at all. Any financing that we may undertake under such circumstances could result in substantial dilution of our existing stockholders, and in the absence of being able to obtain such financing, we could be forced into bankruptcy or liquidation.

The indenture governing our 2028 Secured Notes imposes significant operating and financial restrictions on us and certain subsidiaries of ours, which may prevent us from capitalizing on business opportunities

The indenture governing our 2028 Secured Notes imposes significant operating and financial restrictions on us and certain designated Restricted Subsidiaries (as defined in the indenture for the 2028 Secured Notes). These restrictions limit our ability, and the ability of such restricted subsidiaries, to, among other things:

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incur or guarantee additional debt or issue disqualified stock or certain preferred stock;
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create or incur liens;
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pay dividends, redeem stock, or make certain other distributions;
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make certain investments;
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create restrictions on the ability of our Restricted Subsidiaries to pay dividends to us or make other intercompany transfers;
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transfer or sell assets;
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merge or consolidate; and
•
enter into certain transactions with affiliates.

As a result of these restrictions, we are limited as to how we conduct our business and we may be unable to raise additional indebtedness or conduct equity financing to compete effectively or to take advantage of new business opportunities. The terms of any future indebtedness we may incur could include more restrictive covenants. We cannot assure you that we will be able to maintain compliance with these covenants in the future and, if we fail to do so, that we will be able to obtain waivers from the lenders or amend the covenants.

Our failure to comply with the restrictive covenants described above, as well as other terms of our indebtedness or the terms of any future indebtedness from time to time could result in an event of default, which, if not cured or waived, could result in our being required to repay these borrowings before their due date, the liquidation of our assets serving as collateral and/or potential insolvency proceedings. If we are forced to refinance these borrowings on less favorable terms or if we cannot refinance these borrowings, our results of operations and financial condition could be adversely affected.

We may be required to repay the 2028 Secured Notes prior to their stated maturity date, if the springing maturity feature is triggered

The 2028 Secured Notes have a stated maturity date of June 15, 2028, but include a springing maturity feature that will cause the stated maturity date to spring ahead to the date that is (i) 91 days prior to the existing maturity date of the 2025 Convertible Notes (which is September 15, 2025), (ii) 91 days prior to the existing maturity date of the 2027 Convertible Notes (which is November 16, 2026), or (iii) the maturity date of any future convertible debt that we may issue that is then outstanding, unless on such dates we meet specified liquidity requirements or less than $100,000,000 of aggregate principal amount of the 2025 Convertible Notes, the 2027 Convertible Notes, or such future convertible debt, as applicable, remains outstanding. If such springing maturity feature is triggered, we will be required to pay all amounts outstanding under the 2028 Secured Notes sooner than they would otherwise be due, we may not have sufficient funds available to pay such amounts at that time, and we may not be able to raise additional funds to pay such amounts on a timely basis, on terms we find acceptable, or at all.

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We may not be able to finance required repurchases of the 2028 Secured Notes or the Convertible Notes upon a change of control or a fundamental change

Upon a change of control or a fundamental change as defined in the indentures governing the 2028 Secured Notes and the Convertible Notes, the holders of such notes will have the right to require us to offer to purchase all of the applicable notes then outstanding at a price equal to 101% of the principal amount of the 2028 Secured Notes and 100% of the principal amount of the Convertible Notes, respectively, plus, in each case, accrued and unpaid interest, if any, to, but excluding, the repurchase date. In order to obtain sufficient funds to pay the purchase price of such notes, we expect that we would have to refinance the notes and we may not be able to refinance the notes on reasonable terms, if at all. Our failure to offer to purchase all applicable notes or to purchase all validly tendered notes would be an event of default under the indentures governing the 2028 Secured Notes and the Convertible Notes.

If a change of control or a fundamental change occurs, we may not have enough assets to satisfy all obligations under the indentures governing the 2028 Secured Notes and the Convertible Notes. Upon the occurrence of a change of control or a fundamental change we could seek to refinance the indebtedness under the 2028 Secured Notes or the Convertible Notes or obtain a waiver from the applicable note holders. However, we may not be able to obtain a waiver or refinance the applicable notes on commercially reasonable terms, if at all. Moreover, the exercise by holders of the 2028 Secured Notes or the Convertible Notes of their right to require us to repurchase such notes could cause a default under future debt agreements, even if the change of control or fundamental change itself does not, due to the financial effect of such repurchase on us.

We may not have the ability to raise the funds necessary to settle for cash conversions of the Convertible Notes

Upon conversion of the 2025 Convertible Notes or the 2027 Convertible Notes, unless we elect (or have previously irrevocably elected) to deliver solely shares of our class A common stock to settle the conversion of such Convertible Notes (other than paying cash in lieu of delivering any fractional share), we will be required to make cash payments in respect of the applicable Convertible Notes being converted as described in the applicable indenture. However, we may not have enough available cash or be able to obtain financing at the time we are required to pay cash with respect to such notes being converted. In addition, our ability to pay cash upon conversions of the Convertible Notes may be limited by law, regulatory authority, the covenants contained in the indenture governing the 2028 Secured Notes, or agreements governing any future indebtedness. Our failure to pay any cash payable on future conversions of the Convertible Notes as required by the respective indentures would constitute a default under the indenture for that series of Convertible Notes and could also lead to a default under the indenture for the other series of Convertible Notes or the 2028 Secured Notes. A default under any indenture could also lead to a default under agreements governing any future indebtedness. If the repayment of the related indebtedness were to be accelerated after any applicable notice or grace periods, we may not have sufficient funds to repay the indebtedness.

The conditional conversion feature of the Convertible Notes, if triggered, may adversely affect our financial condition and operating results

In the event the conditional conversion feature of either the 2025 Convertible Notes or the 2027 Convertible Notes is triggered, holders of the applicable Convertible Notes will be entitled to convert such notes at any time during specified periods at their option. If one or more holders elect to convert their Convertible Notes, unless we elect to satisfy our conversion obligation by delivering solely shares of our class A common stock (other than paying cash in lieu of delivering any fractional share), we would be required to settle a portion or all of our conversion obligation through the payment of cash, which could adversely affect our liquidity. In addition, even if holders do not elect to convert their Convertible Notes, we could be required under applicable accounting rules to reclassify all or a portion of the outstanding principal of the applicable Convertible Notes as a current rather than long-term liability, which would result in a material reduction of our net working capital.

We rely on the receipt of funds from our subsidiaries in order to meet our cash needs and service our indebtedness, including the 2028 Secured Notes, the Convertible Notes, and our other long-term indebtedness, and certain of our subsidiaries holding digital assets may not provide any dividends, distributions, or other payments to us to fund our obligations and meet our cash needs

We depend on dividends, distributions, and other payments from our subsidiaries to fund our obligations, including those arising under the 2028 Secured Notes, the Convertible Notes, and our other long-term indebtedness, and meet our cash needs. The operating results of our subsidiaries at any given time may not be sufficient to make dividends, distributions, or other payments to us in order to allow us to make payments on the 2028 Secured Notes, the Convertible Notes, and our other long-term indebtedness. Our wholly-owned subsidiary, MacroStrategy, which holds the bitcoin that we owned prior to the issuance of the 2028 Secured Notes, the bitcoin that MacroStrategy acquired using the proceeds from the 2025 Secured Term Loan, and the bitcoin that MacroStrategy acquired from the proceeds of the sale of our class A shares pursuant to the sales agreements with various sales agents, is not obligated to provide and may in the future be prohibited from providing any dividends, distributions, or other payments to us to fund our obligations and meet our cash needs under such indebtedness. MacroStrategy holds approximately 137,069 bitcoins that, as of June 30, 2023, had a carrying value of $2.084 billion on our Consolidated Balance Sheet, representing 62.0% of our consolidated total assets at such date. In addition, dividends, distributions, or other payments, as well as other transfers of assets, between our subsidiaries and from our subsidiaries to us

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may be subject to legal, regulatory, or contractual restrictions, which may materially adversely affect our ability to transfer cash within our consolidated companies and our ability to meet our cash needs and service our indebtedness.

Despite our current level of indebtedness, we may be able to incur substantially more indebtedness and enter into other transactions in the future which could further exacerbate the risks related to our indebtedness

Although the indenture governing our 2028 Secured Notes contains, and future debt instruments may contain, restrictions on the incurrence of additional indebtedness and entering into certain types of other transactions, these restrictions are subject to a number of qualifications and exceptions and we may be able to incur significant additional indebtedness in the future. For example, these restrictions do not prevent us from incurring obligations, such as certain trade payables and operating leases, which do not constitute indebtedness as defined under our debt instruments. To the extent we incur additional indebtedness or other obligations, the risks described herein with respect to our indebtedness may increase significantly.

Item 2. Unregistered Sales of Equi ty Securities and Use of Proceeds

During the three and six months ended June 30, 2023, we did not repurchase any equity securities registered by us pursuant to Section 12 of the Exchange Act. See Note 6, Treasury Stock, to the Consolidated Financial Statements in “Part I. Item 1. Financial Statements” for further information regarding the Share Repurchase Program, which expired on April 29, 2023.

Item 5. Other Information

Earnings Release

On August 1, 2023, we issued a press release announcing the Company’s financial results for the quarter ended June 30, 2023. A copy of this press release is attached as Exhibit 99.1 to this Quarterly Report. The information regarding this press release in this Item 5 (including Exhibit 99.1) shall not be deemed “filed” for purposes of Section 18 of the Exchange Act or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly set forth by specific reference in such a filing.

Rule 10b5-1 Information

None of our directors or officers adopted or terminated a Rule 10b5-1 trading arrangement or a non-Rule 10b5-1 trading arrangement (as defined in Item 408(c) of Regulation S-K) during the quarterly period covered by this report.

Item 6. Exhibits

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INDEX TO EXHIBITS

Exhibit Number |  | Description
3.1 |  | Second Restated Certificate of Incorporation of the registrant (incorporated herein by reference to Exhibit 3.1 to the registrant’s Quarterly Report on Form 10-Q for the fiscal quarter ended March 31, 2003 (File No. 000-24435)).
3.2 |  | Amended and Restated By-Laws of the registrant (incorporated herein by reference to Exhibit 3.1 to the registrant’s Current Report on Form 8-K filed with the SEC on January 30, 2015 (File No. 000-24435)).
4.1 |  | Form of Certificate of Class A Common Stock of the registrant (incorporated herein by reference to Exhibit 4.1 to the registrant’s Quarterly Report on Form 10-Q for the fiscal quarter ended June 30, 2003 (File No. 000-24435)).
4.2 |  | Indenture, dated as of December 11, 2020, by and between the registrant and U.S. Bank National Association, as trustee (incorporated herein by reference to Exhibit 4.1 to the registrant’s Current Report on Form 8-K filed with the SEC on December 11, 2020 (File No. 000-24435)).
4.3 |  | Form of 0.750% Convertible Senior Note due 2025 (included within Exhibit 4.2 incorporated herein by reference to Exhibit 4.1 to the registrant’s Current Report on Form 8-K filed with the SEC on December 11, 2020 (File No. 000-24435)).
4.4 |  | Indenture, dated as of February 19, 2021, by and between the registrant and U.S. Bank National Association, as trustee (incorporated herein by reference to Exhibit 4.1 to the registrant’s Current Report on Form 8-K filed with the SEC on February 19, 2021 (File No. 000-24435)).
4.5 |  | Form of 0% Convertible Senior Note due 2027 (included within Exhibit 4.4 incorporated herein by reference to Exhibit 4.1 to the registrant’s Current Report on Form 8-K filed with the SEC on February 19, 2021 (File No. 000-24435)).
4.6 |  | Indenture, dated as of June 14, 2021, by and among the registrant, as issuer, MicroStrategy Services Corporation, as a guarantor, and U.S. Bank National Association, as trustee and notes collateral agent (incorporated herein by reference to Exhibit 4.1 to the registrant’s Current Report on Form 8-K filed with the SEC on June 14, 2021 (File No. 000-24435)).
4.7 |  | Form of 6.125% Senior Secured Note due 2028 (included within Exhibit 4.6 incorporated herein by reference to Exhibit 4.1 to the registrant’s Current Report on Form 8-K filed with the SEC on June 14, 2021 (File No. 000-24435)).
10.1†* |  | Indemnification Agreement, effective as of June 12, 2023, by and between the registrant and Michael J. Saylor.
10.2† |  | U.S. Form of Nonstatutory Stock Option Agreement (incorporated herein by reference to Exhibit 99.1 to the registrant’s Current Report on Form 8-K filed with the SEC on May 30, 2023 (File No. 000-24435)).
10.3† |  | U.S. Form of RSU Agreement (incorporated herein by reference to Exhibit 99.2 to the registrant’s Current Report on Form 8-K filed with the SEC on May 30, 2023 (File No. 000-24435)).
10.4† |  | UK Form of Nonstatutory Stock Option Agreement.
10.5† |  | UK Form of RSU Agreement.
10.6† |  | China Form of Nonstatutory Stock Option Agreement.
10.7† |  | China Form of RSU Agreement.
10.8† |  | Canada Form of RSU Agreement.
10.9† |  | International Form of Nonstatutory Stock Option Agreement.
10.10† |  | International Form of RSU Agreement.
10.11† |  | UK Sub-Plan.
10.12† |  | U.S. Form of Nonstatutory Stock Option Agreement (Non-Employee Director).
10.13† |  | U.S. Form of RSU Agreement (Non-Employee Director).
10.14† |  | U.S. Form of PSU Agreement (incorporated herein by reference to Exhibit 99.3 to the registrant’s Current Report on Form 8-K filed with the SEC on May 30, 2023 (File No. 000-24435)).
10.15 |  | Sales Agreement, dated as of May 1, 2023, by and among the Company, Cowen and Company, LLC and Canaccord Genuity LLC (incorporated herein by reference to Exhibit 1.1 to the registrant’s Current Report on Form 8-K filed with the SEC on May 1, 2023 (File No. 000-24435)).

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10.16† |  | Agreement dated July 12, 2023 between the Company and Kevin Adkisson.
31.1 |  | Certification pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Principal Executive Officer.
31.2 |  | Certification pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Principal Financial Officer.
32.1 |  | Certification pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
99.1 |  | Press release, dated August 1, 2023, regarding the Company’s financial results for the quarter ended June 30, 2023.
101.INS |  | Inline XBRL Instance Document. The instance document does not appear in the Interactive Data File because its XBRL tags are embedded within the Inline XBRL document.
101.SCH |  | Inline XBRL Taxonomy Extension Schema.
101.CAL |  | Inline XBRL Taxonomy Extension Calculation Linkbase.
101.DEF |  | Inline XBRL Taxonomy Extension Definition Linkbase.
101.LAB |  | Inline XBRL Taxonomy Extension Label Linkbase.
101.PRE |  | Inline XBRL Taxonomy Extension Presentation Linkbase.
104 |  | Cover Page Interactive Data File (formatted as inline XBRL with applicable taxonomy extension information contained in Exhibits 101).

† Management contracts and compensatory plans or arrangements.

* Portions of this exhibit have been omitted pursuant to Item 601(b)(10)(iv) of Regulation S-K.

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SIGNAT URES

Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

|  | MICROSTRATEGY INCORPORATED
|  | By: | /s/ Andrew Kang
|  |  | Andrew Kang
|  |  | Senior Executive Vice President & Chief Financial Officer
|  | By: | /s/ Jeanine Montgomery
|  |  | Jeanine Montgomery
|  |  | Senior Vice President & Chief Accounting Officer

Date: August 1, 2023

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