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Cash and Cash Equivalents, and Investments and Fair Value Measurements | 12 Months Ended
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Dec. 31, 2022
Cash and Cash Equivalents [Abstract] |
Cash and Cash Equivalents, and Investments and Fair Value Measurements | Cash and Cash Equivalents, and Investments and Fair Value Measurements The following tables show our cash and cash equivalents, and investments’ fair value level classification, adjusted cost, unrealized gain, unrealized loss and fair value as of December 31, 2022 and 2021 (in thousands):
| December 31, 2022
| Fair Value Level |  | Adjusted Cost |  | Unrealized Gain |  | Unrealized Loss |  | Fair Value
Cash and cash equivalents: |  |  |  |  |  |  |  |  |
Cash |  |  | $ | 33,532 |  |  | $ | — |  |  | $ | — |  |  | $ | 33,532 |
Money market funds | Level 1 |  | 440,145 |  |  | — |  |  | — |  |  | 440,145 |
Total cash and cash equivalents |  |  | $ | 473,677 |  |  | $ | — |  |  | $ | — |  |  | $ | 473,677 |
Short-term investments: |  |  |  |  |  |  |  |  |
Commercial paper | Level 2 |  | $ | 11,744 |  |  | $ | — |  |  | $ | (29) |  |  | $ | 11,715 |
Corporate debt securities | Level 2 |  | 491,459 |  |  | — |  |  | (4,130) |  |  | 487,329 |
U.S. treasury securities | Level 1 |  | 85,271 |  |  | — |  |  | (342) |  |  | 84,929 |
Total short-term investments |  |  | $ | 588,474 |  |  | $ | — |  |  | $ | (4,501) |  |  | $ | 583,973 |
Long-term investments: |  |  |  |  |  |  |  |  |
Corporate debt securities | Level 2 |  | $ | 125,735 |  |  | $ | 158 |  |  | $ | (909) |  |  | $ | 124,984 |
Agency bonds | Level 2 |  | 60,635 |  |  | — |  |  | (141) |  |  | 60,494 |
U.S. treasury securities | Level 1 |  | 30,633 |  |  | 122 |  |  | — |  |  | 30,755 |
Total long-term investments |  |  | $ | 217,003 |  |  | $ | 280 |  |  | $ | (1,050) |  |  | $ | 216,233 |
| December 31, 2021
| Fair Value Level |  | Adjusted Cost |  | Unrealized Gain |  | Unrealized Loss |  | Fair Value
Cash and cash equivalents: |  |  |  |  |  |  |  |  |
Cash |  |  | $ | 30,324 |  |  | $ | — |  |  | $ | — |  |  | $ | 30,324 |
Money market funds | Level 1 |  | 823,754 |  |  | — |  |  | — |  |  | 823,754 |
Total cash and cash equivalents |  |  | $ | 854,078 |  |  | $ | — |  |  | $ | — |  |  | $ | 854,078 |
Short-term investments: |  |  |  |  |  |  |  |  |
Commercial paper | Level 2 |  | $ | 124,211 |  |  | $ | 2 |  |  | $ | (33) |  |  | $ | 124,180 |
Corporate debt securities | Level 2 |  | 552,609 |  |  | 36 |  |  | (546) |  |  | 552,099 |
Agency bonds | Level 2 |  | 15,500 |  |  | 2 |  |  | — |  |  | 15,502 |
Total short-term investments |  |  | $ | 692,320 |  |  | $ | 40 |  |  | $ | (579) |  |  | $ | 691,781 |
Long-term investments: |  |  |  |  |  |  |  |  |
Corporate debt securities | Level 2 |  | $ | 724,517 |  |  | $ | — |  |  | $ | (3,277) |  |  | $ | 721,240 |
U.S. treasury securities | Level 1 |  | $ | 24,860 |  |  | $ | — |  |  | $ | (107) |  |  | $ | 24,753 |
Total long-term investments |  |  | $ | 749,377 |  |  | $ | — |  |  | $ | (3,384) |  |  | $ | 745,993 |
As of December 31, 2022, we determined that the declines in the market value of our investment portfolio were not driven by credit related factors. During the years ended December 31, 2022, 2021 and 2020, we did not recognize any losses on our investments due to credit related factors. The following table presents the gross realized gain and loss related to our investments (in thousands):
|  |  | Years Ended December 31,
|  |  |  |  | 2022 |  | 2021 |  | 2020
Realized gain |  |  |  |  | $ | 64 |  |  | $ | 84 |  |  | $ | 308 |
Realized loss |  |  |  |  | (9,739) |  |  | (262) |  |  | — |
Realized (loss)/gain on sale of investments |  |  |  |  | $ | (9,675) |  |  | $ | (178) |  |  | $ | 308 |
The following table shows our cash equivalents and investments' adjusted cost and fair value by contractual maturity as of December 31, 2022 (in thousands):
| December 31, 2022
| Cost |  | Fair Value
Due within one year | $ | 588,474 |  |  | $ | 583,973 |
Due after one year through three years | 217,003 |  |  | 216,233 |
Investments not due at a single maturity date | 440,145 |  |  | 440,145 |
Total | $ | 1,245,622 |  |  | $ | 1,240,351 |
Investments not due at a single maturity date in the preceding table consisted of money market funds. Strategic Investments In July 2022, we completed an investment of $6.0 million in Knack Technologies, Inc. (Knack), a privately held U.S. based peer-to-peer tutoring platform for higher education institutions. We do not have the ability to exercise significant influence over Knack's operating and financial policies and have elected to account for our investment at cost as it does not have a readily determinable fair value. We previously invested $2.0 million in TAPD, Inc., also known as Frank; a U.S.-based service that helps students access financial aid and $3.0 million in a foreign entity to explore expanding our reach internationally. In 2021, we sold our investments for total consideration of $17.5 million, resulting in a $12.5 million gain included within other income (expense), net on our consolidated statements of operations. We received cash payments of $16.1 million included within cash flows from investing activities on our consolidated statements of cash flows. We did not record any impairment charges on our strategic investments, other than a $10.0 million impairment charge previously recorded in 2020 on our strategic investment in WayUp, Inc. During the years ended December 31, 2022, 2021 and 2020, there were no significant identified events or changes in circumstances that would be considered an indicator for impairment. There were no observable price changes in orderly transactions for the identical or similar investments of the same issuers during the years ended December 31, 2022, 2021 and 2020. Financial Instruments Not Recorded at Fair Value on a Recurring Basis We report our financial instruments at fair value with the exception of the notes. The estimated fair value of the notes was determined based on the trading price of the notes as of the last day of trading for the period. We consider the fair value of the notes to be a Level 2 measurement due to the limited trading activity. The estimated fair value of the 2026 notes as of December 31, 2022 and 2021 was $385.0 million and $840.0 million, respectively. The estimated fair value of the 2025 notes as of December 31, 2022 and 2021 was $640.5 million and $682.2 million, respectively. For further information on the notes refer to Note 11, “Convertible Senior Notes.”

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