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Long-term Debt | 12 Months Ended
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Dec. 31, 2024
Debt Disclosure [Abstract] |
Long-term Debt | (8) Long-term Debt The net carrying value of the Company’s outstanding debt (in thousands) consisted of the following as of:
|  | December 31, |
|  | 2024 |  |  | 2023 |
2025 Convertible Notes |  | $ | 0 |  |  | $ | 643,931 |
2027 Convertible Notes |  |  | 1,041,352 |  |  |  | 1,037,306 |
2028 Convertible Notes |  |  | 998,543 |  |  |  | 0 |
2029 Convertible Notes |  |  | 2,975,037 |  |  |  | 0 |
2030 Convertible Notes |  |  | 785,172 |  |  |  | 0 |
2031 Convertible Notes |  |  | 594,476 |  |  |  | 0 |
2032 Convertible Notes |  |  | 787,417 |  |  |  | 0 |
2028 Secured Notes |  |  | 0 |  |  |  | 491,193 |
Other long-term secured debt |  |  | 9,678 |  |  |  | 10,161 |
Total |  | $ | 7,191,675 |  |  | $ | 2,182,591 |
Reported as: |  |  |  |  |  |
Current portion of long-term debt, net |  |  | 517 |  |  |  | 483 |
Long-term debt, net |  |  | 7,191,158 |  |  |  | 2,182,108 |
Total |  | $ | 7,191,675 |  |  | $ | 2,182,591 |
Convertible Senior Notes The Company has issued the following convertible notes (collectively, the “Convertible Notes”) in private offerings: • $650.0 million aggregate principal amount of 0.750% Convertible Senior Notes due 2025 (the “2025 Convertible Notes”), all of which were previously redeemed or converted into our class A common stock by July 15, 2024; • $1.050 billion aggregate principal amount of 0% Convertible Senior Notes due 2027 (the “2027 Convertible Notes”); • $1.010 billion aggregate principal amount of 0.625% Convertible Senior Notes due 2028 (the “2028 Convertible Notes”); • $3.000 billion aggregate principal amount of 0% Convertible Senior Notes due 2029 (the “2029 Convertible Notes”); • $800.0 million aggregate principal amount of 0.625% Convertible Senior Notes due 2030 (the “2030 Convertible Notes”); • $603.8 million aggregate principal amount of 0.875% Convertible Senior Notes due 2031 (the “2031 Convertible Notes”); and • $800.0 million aggregate principal amount of 2.25% Convertible Senior Notes due 2032 (the “2032 Convertible Notes”). The outstanding Convertible Notes are senior unsecured obligations of the Company and rank senior in right of payment to any of the Company’s indebtedness that is expressly subordinated in right of payment to the Convertible Notes; equal in right of payment to any of the Company’s unsecured indebtedness that is not so subordinated; effectively junior in right of payment to any of the Company’s secured indebtedness to the extent of the value of the assets securing such indebtedness; and structurally junior to all indebtedness and other liabilities (including trade payables) of the Company’s subsidiaries. The outstanding Convertible Notes also rank senior in right of payment to the Company’s Series A perpetual strike preferred stock issued in the first quarter of 2025. Refer to Note 18, Subsequent Events to the Consolidated Financial Statements for further information on the Company’s Series A perpetual strike preferred stock issuance. The following table summarizes the key terms of each of the Convertible Notes (principal at inception, net proceeds, and issuance costs are each reported in thousands):
| 2025 Convertible Notes |  |  | 2027 Convertible Notes |  |  | 2028 Convertible Notes |  |  | 2029 Convertible Notes |  |  | 2030 Convertible Notes |  |  | 2031 Convertible Notes |  |  | 2032 Convertible Notes |
Issuance Date | December 2020 |  |  | February 2021 |  |  | September 2024 |  |  | November 2024 |  |  | March 2024 |  |  | March 2024 |  |  | June 2024 |
Maturity Date (1) | December 15, 2025 |  |  | February 15, 2027 |  |  | September 15, 2028 |  |  | December 1, 2029 |  |  | March 15, 2030 |  |  | March 15, 2031 |  |  | June 15, 2032 |
Principal at Inception | $ | 650,000 |  |  | $ | 1,050,000 |  |  | $ | 1,010,000 |  |  | $ | 3,000,000 |  |  | $ | 800,000 |  |  | $ | 603,750 |  |  | $ | 800,000 |
Stated Interest Rate (2) |  | 0.750 | % |  |  | 0.000 | % |  |  | 0.625 | % |  |  | 0.000 | % |  |  | 0.625 | % |  |  | 0.875 | % |  |  | 2.250 | %
Interest Payment Dates (3) | June 15 & December 15 |  |  | February 15 & August 15 |  |  | March 15 & September 15 |  |  | June 1 & December 1 |  |  | March 15 & September 15 |  |  | March 15 & September 15 |  |  | June 15 & December 15 |
Net Proceeds | $ | 634,749 |  |  | $ | 1,025,830 |  |  | $ | 997,375 |  |  | $ | 2,974,250 |  |  | $ | 782,000 |  |  | $ | 592,567 |  |  | $ | 786,000 |
Issuance Costs (4) | $ | 15,251 |  |  | $ | 24,170 |  |  | $ | 12,625 |  |  | $ | 25,750 |  |  | $ | 18,000 |  |  | $ | 11,183 |  |  | $ | 14,000 |
Effective Interest Rate (4) |  | 1.23 | % |  |  | 0.39 | % |  |  | 1.05 | % |  |  | 0.24 | % |  |  | 1.14 | % |  |  | 1.30 | % |  |  | 2.63 | %
Date of Holder Put Option (5) | n/a |  |  | n/a |  |  | September 15, 2027 |  |  | June 1, 2028 |  |  | September 15, 2028 |  |  | September 15, 2028 |  |  | June 15, 2029 |
Initial Conversion Rate (6) |  | 25.126 |  |  |  | 6.981 |  |  |  | 5.4589 |  |  |  | 1.4872 |  |  |  | 6.677 |  |  |  | 4.297 |  |  |  | 4.894 |
Initial Conversion Price (7) | $ | 39.80 |  |  | $ | 143.25 |  |  | $ | 183.19 |  |  | $ | 672.40 |  |  | $ | 149.77 |  |  | $ | 232.72 |  |  | $ | 204.33 |
Convertible at any time after the following date (8) (9) | June 13, 2024 |  |  | January 24, 2025 |  |  | March 15, 2028 |  |  | June 1, 2029 |  |  | September 15, 2029 |  |  | September 15, 2030 |  |  | December 15, 2031 |
Not redeemable by the Company prior to the following date (10) | December 20, 2023 |  |  | February 20, 2024 |  |  | December 20, 2027 |  |  | December 4, 2026 |  |  | March 22, 2027 |  |  | March 22, 2028 |  |  | June 20, 2029 |
Redemption Date (11) | July 15, 2024 |  |  | February 24, 2025 |  |  | n/a |  |  | n/a |  |  | n/a |  |  | n/a |  |  | n/a |
(1) “Maturity Date” is the stated maturity date under each applicable indenture governing such notes, unless earlier converted, redeemed, or repurchased in accordance with their terms. (2) Holders may receive additional or special interest under specified circumstances as outlined under each applicable indenture governing the Convertible Notes. (3) For the Convertible Notes issued in 2024, interest payments begin on (a) September 15, 2024 for each of the 2030 Convertible Notes and the 2031 Convertible Notes, (b) December 15, 2024 for the 2032 Convertible Notes, (c) March 15, 2025 for the 2028 Convertible Notes, and (d) June 1, 2025 (special interest only, if any) for the 2029 Convertible Notes. (4) “Issuance Costs” reflect the customary offering expenses associated with each of the Convertible Notes. The Company accounts for these issuance costs as a reduction to the principal amount of the respective Convertible Notes and amortizes the issuance costs to interest expense from the respective debt issuance dates through the earlier of the “Maturity Date” or the “Date of Holder Put Option,” if applicable, at the “Effective Interest Rates” stated in the table. (5) “Date of Holder Put Option” represents the respective dates upon which holders of the 2028 Convertible Notes, 2029 Convertible Notes, 2030 Convertible Notes, 2031 Convertible Notes, and 2032 Convertible Notes each have a noncontingent right to require the Company to repurchase for cash all or any portion of their respective notes at a repurchase price equal to 100% of the principal amount of such notes to be repurchased, plus any accrued and unpaid interest to, but excluding the repurchase date. (6) The “Initial Conversion Rate” is stated in shares of the Company’s class A common stock per $1,000 principal amount. The conversion rates are subject to customary anti-dilution adjustments. In addition, following certain events that may occur prior to the respective maturity dates or if the Company delivers a notice of redemption, the Company will increase the conversion rate for a holder who elects to convert its respective Convertible Notes in connection with such corporate event or notice of redemption, as the case may be, in certain circumstances as provided in each indenture governing the respective Convertible Notes. (7) The “Initial Conversion Price” is stated in dollars per share of the Company’s class A common stock. (8) On or after the stated dates until the close of business on the second scheduled trading day immediately preceding the respective maturity dates, holders may convert the Convertible Notes at any time. Upon conversion of the Convertible Notes, the Company will pay or deliver, as the case may be, cash, shares of the Company’s class A common stock, or a combination of cash and shares of class A common stock, at the Company’s election. For the 2025 Convertible Notes, the date presented is the date on which the Company delivered its notice of full redemption of the 2025 Convertible Notes, which resulted in the 2025 Convertible Notes being convertible at any time thereafter until 5:00 p.m., New York City time, on July 11, 2024. See below under “Conversions and Redemption of 2025 Convertible Notes” for further information. For the 2027 Convertible Notes, the date presented is the date on which the Company delivered its notice of full redemption of the 2027 Convertible Notes, which resulted in the 2027 Convertible Notes being convertible at any time thereafter until 5:00pm New York City time, on February 20, 2025. See Note 18, Subsequent Events, to the Consolidated Financial Statements for further information. (9) Prior to the respective dates, the Convertible Notes are convertible only under the following circumstances: (a) during any calendar quarter commencing after the calendar quarter ending on March 31, 2021 for the 2025 Convertible Notes (of which all then outstanding notes were redeemed on July 15, 2024), on June 30, 2021 for the 2027 Convertible Notes, on June 30, 2024 for the 2030 Convertible Notes and 2031 Convertible Notes, on September 30, 2024 for the 2032 Convertible Notes, on December 31, 2024 for the 2028 Convertible Notes, or on March 31, 2025 for the 2029 Convertible Notes (and only during such calendar quarter), if the last reported sale price of the Company’s class A common stock for at least 20 trading days (whether or not consecutive) during the period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding calendar quarter is greater than or equal to 130% of the conversion price of the respective Convertible Notes on each applicable trading day; (b) during the five business day period after any five consecutive trading day period (the “measurement period”) in which the “trading price” (as defined under each applicable indenture governing the respective Convertible Notes) per $1,000 principal amount of the respective Convertible Notes for each trading day of the measurement period was less than 98% of the product of the last reported sale price of the Company’s class A common stock and the applicable conversion rate on each such trading day; (c) if the Company calls any or all of the respective Convertible Notes for redemption, at any time prior to the close of business on the second scheduled trading day immediately preceding the redemption date; and (d) upon occurrence of specified corporate events as described in each applicable indenture governing the respective Convertible Notes. (10) The Company may redeem for cash all or a portion of the Convertible Notes at its option, on or after the stated dates, if the last reported sale price of the Company’s class A common stock has been at least 130% of the conversion price of the respective Convertible Notes then in effect for at least 20 trading days (whether or not consecutive), including the trading day immediately preceding the date on which the Company provides a notice of redemption, during any 30 consecutive trading day period ending on, and including, the trading day immediately preceding the date on which the Company provides notice of redemption. The redemption price will be equal to 100% of the principal amount of the Convertible Notes to be redeemed, plus accrued and unpaid interest to, but excluding, the redemption date. See below “Conversions and Redemption of 2025 Convertible Notes” subsection for information regarding the Company’s notice of redemption of the 2025 Convertible Notes. (11) “Redemption Date” for the 2025 Convertible Notes is the date on which the Company redeemed all outstanding 2025 Convertible Notes. See discussion further below under “Conversions and Redemption of 2025 Convertible Notes” pertaining to redemption of the 2025 Convertible Notes. “Redemption Date” for the 2027 Convertible Notes is the date on which the Company will redeem all outstanding 2027 Convertible Notes, as discussed under Note 18, Subsequent Events, to the Consolidated Financial Statements. If the Company undergoes a “fundamental change,” as defined in the respective indentures governing the Convertible Notes prior to maturity, subject to certain conditions, holders may require the Company to repurchase for cash all or any portion of their respective Convertible Notes at a fundamental change repurchase price equal to 100% of the principal amount of the respective Convertible Notes to be repurchased, plus any accrued and unpaid interest to, but excluding, the fundamental change repurchase date. The respective indentures governing the Convertible Notes contain customary terms and covenants, including that upon certain events of default occurring and continuing, either the Trustee or the holders of at least 25% in principal amount outstanding of the respective Convertible Notes may declare 100% of the principal of, and accrued and unpaid interest, if any, on, all the respective Convertible Notes to be due and payable. Although the Convertible Notes contain embedded conversion features, the Company accounts for the Convertible Notes in their entirety as a liability because the conversion features are indexed to the Company’s class A common stock and meet the criteria for classification in stockholders’ equity and therefore do not qualify for separate derivative accounting. Conversions and Redemption of 2025 Convertible Notes On June 13, 2024, the Company announced that it delivered a notice of redemption (the “Redemption Notice”) to the trustee of the 2025 Convertible Notes for redemption of all $650.0 million in aggregate principal amount of the 2025 Convertible Notes then outstanding on July 15, 2024 (the “Redemption Date”). Due to the Company’s issuance of the Redemption Notice, the 2025 Convertible Notes became convertible at the option of the holders of such notes from the delivery of the Redemption Notice until 5:00 p.m., New York City time, on July 11, 2024. The Company elected to satisfy its conversion obligation with respect to the 2025 Convertible Notes by delivering solely shares of its class A common stock, together with cash in lieu of any fractional shares. Holders of the 2025 Convertible Notes requested to convert $649.7 million in principal amount of the 2025 Convertible Notes prior to the Redemption Date, for which the Company issued 16,323,050 shares of the Company’s class A common stock and paid a nominal amount of cash in lieu of fraction shares upon settlement of such conversion requests, in accordance with the terms and provisions of the indenture governing the 2025 Convertible Notes. On the Redemption Date, the Company redeemed $0.3 million aggregate principal amount of 2025 Convertible Notes, constituting all of the 2025 Convertible Notes then outstanding, at an aggregate redemption price of $0.3 million in cash, equal to 100% of the principal amount of the 2025 Convertible Notes redeemed, plus accrued and unpaid interest, to but excluding the Redemption Date. Collective Convertible Notes Disclosures As of December 31, 2024, the maximum number of shares into which the Convertible Notes could have been potentially converted if the conversion features were triggered at the conversion rates then in effect based on the Convertible Notes then outstanding on such date was 7,330,050 shares, 5,513,489 shares, 4,461,600 shares, 5,341,600 shares, 2,594,314 shares, and 3,915,200 shares for the 2027 Convertible Notes, 2028 Convertible Notes, 2029 Convertible Notes, 2030 Convertible Notes, 2031 Convertible Notes, and 2032 Convertible Notes, respectively. Other than the 2025 Convertible Notes (which were convertible during the first quarter of 2022, the first and second quarters of 2024, and upon the Company’s issuance of the Redemption Notice in June 2024 as discussed above under the “Conversions and Redemption of 2025 Convertible Notes” subsection), the Convertible Notes were not convertible at the option of the holders during the years ended December 31, 2024, 2023, and 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 December 31, 2024, the last reported sale price of the Company’s class A common stock for at least 20 trading days during the 30 consecutive trading days ending on, and including, December 31, 2024 was greater than or equal to 130% of the conversion price of each of the 2027 Convertible Notes, 2028 Convertible Notes, 2030 Convertible Notes, 2031 Convertible Notes, and 2032 Convertible Notes on each applicable trading day. Therefore, the 2027 Convertible Notes, 2028 Convertible Notes, 2030 Convertible Notes, 2031 Convertible Notes, and 2032 Convertible Notes are convertible at the option of the holders of the respective Convertible Notes during the first quarter of 2025. As a result of the notice of redemption delivered January 24, 2025 to holders of the 2027 Convertible Notes, the 2027 Convertible Notes are convertible at any time thereafter until 5:00pm New York City time, on February 20, 2025. See Note 18, Subsequent Events, to the Consolidated Financial Statements for further information. No conversions of the Convertible Notes occurred during the years ended December 31, 2024, 2023, and 2022, except for the 2025 Convertible Notes as discussed above under the “Conversions and Redemption of 2025 Convertible Notes” subsection. Other than the Company’s redemption of the 2025 Convertible Notes, the Company had not redeemed any of the Convertible Notes as of December 31, 2024. As of December 31, 2024 and 2023, 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 December 31, 2024 (in thousands):
|  | December 31, 2024
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2027 Convertible Notes |  | $ | 1,050,000 |  |  | $ | (8,648 | ) |  | $ | 1,041,352 |  |  | $ | 2,134,125 |  |  | Level 2
2028 Convertible Notes |  |  | 1,010,000 |  |  |  | (11,457 | ) |  |  | 998,543 |  |  |  | 1,927,828 |  |  | Level 2
2029 Convertible Notes |  |  | 3,000,000 |  |  |  | (24,963 | ) |  |  | 2,975,037 |  |  |  | 2,447,682 |  |  | Level 2
2030 Convertible Notes |  |  | 800,000 |  |  |  | (14,828 | ) |  |  | 785,172 |  |  |  | 1,657,323 |  |  | Level 2
2031 Convertible Notes |  |  | 603,750 |  |  |  | (9,274 | ) |  |  | 594,476 |  |  |  | 877,559 |  |  | Level 2
2032 Convertible Notes |  |  | 800,000 |  |  |  | (12,583 | ) |  |  | 787,417 |  |  |  | 1,324,602 |  |  | Level 2
Total |  | $ | 7,263,750 |  |  | $ | (81,753 | ) |  | $ | 7,181,997 |  |  | $ | 10,369,119 |  |  |
The following is a summary of the Company’s convertible debt instruments as of December 31, 2023 (in thousands):
|  | December 31, 2023
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2025 Convertible Notes |  | $ | 650,000 |  |  | $ | (6,069 | ) |  | $ | 643,931 |  |  | $ | 1,074,713 |  |  | Level 2
2027 Convertible Notes |  |  | 1,050,000 |  |  |  | (12,694 | ) |  |  | 1,037,306 |  |  |  | 913,808 |  |  | Level 2
Total |  | $ | 1,700,000 |  |  | $ | (18,763 | ) |  | $ | 1,681,237 |  |  | $ | 1,988,521 |  |  |
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 years ended December 31, 2024, 2023 and 2022, interest expense related to the Convertible Notes was as follows (in thousands):
|  | Year Ended December 31, 2024 |  |  | Year Ended December 31, 2023 |  |  | Year Ended December 31, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2025 Convertible Notes |  | $ | 2,371 |  |  | $ | 1,494 |  |  | $ | 3,865 |  |  | $ | 4,875 |  |  | $ | 3,043 |  |  | $ | 7,918 |  |  | $ | 4,875 |  |  | $ | 3,006 |  |  | $ | 7,881 |
2027 Convertible Notes |  |  | 0 |  |  |  | 4,046 |  |  |  | 4,046 |  |  |  | 0 |  |  |  | 4,029 |  |  |  | 4,029 |  |  |  | 0 |  |  |  | 4,014 |  |  |  | 4,014 |
2028 Convertible Notes |  |  | 1,771 |  |  |  | 1,168 |  |  |  | 2,939 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
2029 Convertible Notes |  |  | 0 |  |  |  | 787 |  |  |  | 787 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
2030 Convertible Notes |  |  | 4,069 |  |  |  | 3,172 |  |  |  | 7,241 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
2031 Convertible Notes |  |  | 4,154 |  |  |  | 1,909 |  |  |  | 6,063 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
2032 Convertible Notes |  |  | 9,650 |  |  |  | 1,417 |  |  |  | 11,067 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Total |  | $ | 22,015 |  |  | $ | 13,993 |  |  | $ | 36,008 |  |  | $ | 4,875 |  |  | $ | 7,072 |  |  | $ | 11,947 |  |  | $ | 4,875 |  |  | $ | 7,020 |  |  | $ | 11,895 |
The Company paid $16.5 million, $4.9 million and $4.9 million, respectively, in interest related to the Convertible Notes during the years ended December 31, 2024, 2023, and 2022. The Company has not paid any additional interest or special interest related to the Convertible Notes to date. Senior Secured Notes On June 14, 2021, the Company issued $500.0 million aggregate principal amount of 2028 Secured Notes. The 2028 Secured Notes were sold under a purchase agreement, dated as of June 8, 2021, entered into by and among the Company, MicroStrategy Services Corporation, a wholly owned subsidiary of the Company (the “Guarantor”), and Jefferies LLC, for resale to qualified institutional buyers. The terms of the 2028 Secured Notes were governed by an indenture, dated as of June 14, 2021 (the “2028 Secured Notes Indenture”), among the Company, the Guarantor, and U.S. Bank National Association, as trustee and collateral agent. The 2028 Secured Notes were unconditionally guaranteed, jointly and severally, on a senior secured basis by the Guarantor and certain subsidiaries of the Company (excluding MacroStrategy) (collectively, the “Subsidiary Guarantors”). The 2028 Secured Notes bore 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 had 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 under certain conditions outlined in the 2028 Secured Notes Indenture. The springing maturity feature was not triggered while the 2028 Secured Notes were outstanding. The Company redeemed all of the 2028 Secured Notes on September 26, 2024 at a redemption price equal to 103.063% of the principal amount of the 2028 Secured Notes, plus accrued and unpaid interest to, but excluding, September 26, 2024 (the “Redemption Price”). The Redemption Price consisted of a $515.3 million payment to redeem the full $500.0 million outstanding principal amount of the 2028 Secured Notes as of September 26, 2024 and an $8.6 million payment for accrued unpaid interest on the 2028 Secured Notes to but excluding September 26, 2024. The Company also incurred $0.1 million in third party fees in connection with the redemption of the 2028 Secured Notes. The net carrying value of the 2028 Secured Notes as of September 26, 2024, immediately prior to their redemption, was $492.5 million, which resulted in a $22.9 million loss on debt extinguishment recognized in the Company’s Consolidated Statement of Operations in the third quarter of 2024. While outstanding, the 2028 Secured Notes were secured, on a senior secured basis with the Company’s existing and future senior indebtedness, by a first priority security interest in substantially all of the Company’s and the Subsidiary Guarantors’ assets (the “Collateral”). The Collateral included any bitcoins or other digital assets acquired by the Company or a Subsidiary Guarantor on or after June 14, 2021. As of December 31, 2023, approximately 16,081 of the bitcoins held by the Company served as part of the Collateral. Upon the redemption of the 2028 Secured Notes in September 2024, all collateral securing the 2028 Secured Notes was released. The 2028 Secured Notes Indenture contained certain covenants with which the Company was required to 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 December 31, 2023 and through to the redemption of the 2028 Secured Notes in September 2024. The Company incurred approximately $12.8 million in customary offering expenses associated with the 2028 Secured Notes. The Company accounted for these issuance costs as a reduction to the principal amount of the 2028 Secured Notes and amortized the issuance costs to interest expense over the contractual term of the 2028 Secured Notes at an effective interest rate of 6.58%. As of December 31, 2023, 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 Sheet. The following is a summary of the 2028 Secured Notes as of December 31, 2023 (in thousands):
|  | December 31, 2023
|  | Outstanding |  |  | Unamortized |  |  | Net Carrying |  |  | Fair Value
|  | Principal Amount |  |  | Issuance Costs |  |  | Value |  |  | Amount |  |  | Leveling
2028 Secured Notes |  | $ | 500,000 |  |  | $ | (8,807 | ) |  | $ | 491,193 |  |  | $ | 485,070 |  |  | Level 2
The fair value of the 2028 Secured Notes was 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 years ended December 31, 2024, 2023, and 2022, interest expense related to the 2028 Secured Notes was as follows (in thousands):
|  | Year Ended December 31, 2024 |  |  | Year Ended December 31, 2023 |  |  | Year Ended December 31, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2028 Secured Notes |  | $ | 22,628 |  |  | $ | 1,287 |  |  | $ | 23,915 |  |  | $ | 30,625 |  |  | $ | 1,646 |  |  | $ | 32,271 |  |  | $ | 30,625 |  |  | $ | 1,541 |  |  | $ | 32,166 |
The Company paid $23.9 million, $30.6 million, and $30.6 million, respectively, in interest related to the 2028 Secured Notes during the years ended December 31, 2024, 2023, and 2022. 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. 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. Prior to the prepayment, the 2025 Secured Term Loan was a senior secured obligation of MacroStrategy that bore interest at a floating rate equal to the Secured Overnight Financing Rate 30 Day Average, as published by the Federal Reserve Bank of New York’s website, plus 3.70%, with a floor of 3.75%, with interest payable monthly in arrears beginning May 2022. The 2025 Secured Term Loan was scheduled to mature on March 23, 2025, unless earlier prepaid or repaid in accordance with the terms of the Credit and Security Agreement. The total net proceeds from the 2025 Secured Term Loan, after deducting lender fees and third-party costs, were approximately $204.6 million. In accordance with the terms of the Credit and Security Agreement, the 2025 Secured Term Loan was initially collateralized at closing by bitcoin with a value of approximately $820.0 million placed in a collateral account (the “Bitcoin Collateral Account”) with a custodian mutually authorized by Silvergate and MacroStrategy. While the 2025 Secured Term Loan was outstanding, MacroStrategy was required to maintain a loan to collateral value ratio (“LTV Ratio”) of less than 50%. As a result, MacroStrategy was required to maintain more than $410.0 million of bitcoin in the Bitcoin Collateral Account, assuming the full $205.0 million of 2025 Secured Term Loan principal remained outstanding. The Company incurred approximately $0.4 million in lender fees and third-party costs (“issuance costs”) associated with the 2025 Secured Term Loan. The Company accounted for these issuance costs as a reduction to the principal amount of the 2025 Secured Term Loan and amortized the issuance costs to interest expense over the contractual term of the 2025 Secured Term Loan at an effective interest rate of 3.87% until the 2025 Secured Term Loan's prepayment in March 2023. 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 years ended December 31, 2023 and 2022, interest expense related to the 2025 Secured Term Loan was as follows (in thousands):
|  | Year Ended December 31, 2023 |  |  | Year Ended December 31, 2022 |
|  | Contractual |  |  | Amortization of |  |  |  |  |  | Contractual |  |  | Amortization of |  |  |  |
|  | Interest Expense |  |  | Issuance Costs |  |  | Total |  |  | Interest Expense |  |  | Issuance Costs |  |  | Total |
2025 Secured Term Loan |  | $ | 3,781 |  |  | $ | 31 |  |  | $ | 3,812 |  |  | $ | 9,006 |  |  | $ | 103 |  |  | $ | 9,109 |
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 $7.7 million in interest related to the 2025 Secured Term Loan during the year ended December 31, 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. After monthly payments made under the terms of the agreement, the loan had a net carrying value of $9.7 million and $10.2 million as of December 31, 2024 and 2023, respectively, and an outstanding principal balance of $9.8 million and $10.3 million as of December 31, 2024 and 2023, respectively. As of December 31, 2024 and 2023, $0.5 million and $0.5 million of the respective net carrying values were short-term and presented in "Current portion of long-term debt, net" in the Consolidated Balance Sheets. Maturities The following table shows the maturities of the Company’s debt instruments as of December 31, 2024 (in thousands). The principal payments related to the 2028 Convertible Notes, 2029 Convertible Notes, 2030 Convertible Notes, 2031 Convertible Notes, and 2032 Convertible Notes are included in the table below as if the holders exercised their right to require the Company to repurchase all of the respective convertible notes on their respective Date of Holder Put Option.
Payments due by period ended December 31, |  | 2027 Convertible Notes |  |  | 2028 Convertible Notes |  |  | 2029 Convertible Notes |  |  | 2030 Convertible Notes |  |  | 2031 Convertible Notes |  |  | 2032 Convertible Notes |  |  | Other long-term secured debt |  |  | Total |
2025 |  | $ | 0 |  |  | $ | 0 |  |  | $ | 0 |  |  | $ | 0 |  |  | $ | 0 |  |  | $ | 0 |  |  | $ | 569 |  |  | $ | 569 |
2026 |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 600 |  |  |  | 600 |
2027 |  |  | 1,050,000 |  |  |  | 1,010,000 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 8,634 |  |  |  | 2,068,634 |
2028 |  |  | 0 |  |  |  | 0 |  |  |  | 3,000,000 |  |  |  | 800,000 |  |  |  | 603,750 |  |  |  | 0 |  |  |  | 0 |  |  |  | 4,403,750 |
2029 |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 800,000 |  |  |  | 0 |  |  |  | 800,000 |
Thereafter |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |  |  |  | 0 |
Total |  | $ | 1,050,000 |  |  | $ | 1,010,000 |  |  | $ | 3,000,000 |  |  | $ | 800,000 |  |  | $ | 603,750 |  |  | $ | 800,000 |  |  | $ | 9,803 |  |  | $ | 7,273,553 |
As part of the Company’s bitcoin strategy, the Company expects to incur or continue to incur additional indebtedness and other fixed charges for the purposes of acquiring additional bitcoin and to satisfy its financial and other obligations. The Company’s ability to obtain equity and debt financing is subject to market conditions and other factors outside of its control, and the Company may not be able to secure equity or debt financing in a timely manner, on favorable terms, or at all. If the Company is unable to obtain equity or debt financing, the Company could seek to use proceeds from the sale of its bitcoin to meet its obligations. Historically, the bitcoin market 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 inherent in its entirely electronic, virtual form and decentralized network. During times of market instability, the Company may not be able to sell its bitcoin at favorable prices or at all. As a result, the Company’s bitcoin holdings may not be able to serve as a source of liquidity for the Company to the same extent as cash and cash equivalents. Further, the Company’s bitcoin holdings do not enjoy the same protections as are available to cash or securities deposited with or transacted by institutions subject to regulation by the Federal Deposit Insurance Corporation or the Securities Investor Protection Corporation.

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