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Cash and Cash Equivalents, and Investments and Fair Value Measurements
12 Months Ended
Dec. 31, 2021
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, 2021 and 2020 (in thousands, except for fair value level):

 December 31, 2021
 Fair Value LevelAdjusted CostUnrealized GainUnrealized LossFair Value
Cash and cash equivalents:   
Cash$30,324 $— $— $30,324 
Money market fundsLevel 1823,754 — — 823,754 
Total cash and cash equivalents$854,078 $— $— $854,078 
Short-term investments:   
Commercial paperLevel 2$124,211 $$(33)$124,180 
Corporate debt securitiesLevel 2552,609 36 (546)552,099 
Agency bondsLevel 215,500 — 15,502 
Total short-term investments$692,320 $40 $(579)$691,781 
Long-term investments:
Corporate debt securitiesLevel 2$724,517 $— $(3,277)$721,240 
U.S. treasury securitiesLevel 124,860 — (107)24,753 
Total long-term investments$749,377 $— $(3,384)$745,993 

 December 31, 2020
 Fair Value LevelAdjusted CostUnrealized GainUnrealized LossFair Value
Cash and cash equivalents:   
Cash$15,054 $— $— $15,054 
Money market fundsLevel 1464,799 — — 464,799 
Total cash and cash equivalents$479,853 $— $— $479,853 
Short-term investments:   
Commercial paperLevel 2$204,152 $24 $(6)$204,170 
Corporate debt securitiesLevel 2459,967 1,478 (48)461,397 
Total short-term investments$664,119 $1,502 $(54)$665,567 
Long-term investments:
Corporate debt securitiesLevel 2$484,275 $605 $(283)$484,597 
Agency bondsLevel 238,995 36 — 39,031 
Total long-term investments$523,270 $641 $(283)$523,628 

As of December 31, 2021, 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, 2021 and 2020 we did not recognize any losses on our investments due to credit related factors. During the years ended December 31, 2021, 2020 and 2019, our gross realized gains and losses on investments were not significant.
The following table shows our cash equivalents and investments' adjusted cost and fair value by contractual maturity as of December 31, 2021 (in thousands):
December 31, 2021
 CostFair Value
Due in 1 year or less$692,320 $691,781 
Due in 1-2 years749,377 745,993 
Investments not due at a single maturity date823,754 823,754 
Total$2,265,451 $2,261,528 

Investments not due at a single maturity date in the preceding table consisted of money market funds.

Strategic Investments

We previously invested $2.0 million in TAPD, Inc., also known as Frank; a U.S.-based service that helps students access financial aid. In September 2021, we sold our investment in Frank for total consideration of $9.2 million, resulting in a $7.2 million gain included within other (expense) income, net on our consolidated statements of operations. We received a cash payment of $9.0 million included within cash flows from investing activities on our consolidated statements of cash flows.

We also previously invested $3.0 million in a foreign entity to explore expanding our reach internationally. In March 2021, we sold our investment in that foreign entity for total consideration of $8.3 million, resulting in a $5.3 million gain included within other (expense) income, net on our consolidated statements of operations. We received a cash payment, net of taxes withheld, of $7.1 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, 2021, 2020 and 2019, as there were no significant identified events or changes in circumstances that would be considered an indicator for impairment. We considered general market conditions as a result of the COVID-19 pandemic in our impairment analysis. 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, 2021, 2020 and 2019. As of December 31, 2021, we had no amounts related to strategic investments recorded on our consolidated balance sheet.

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. For further information on the notes refer to Note 10, “Convertible Senior Notes.”

The carrying amounts and estimated fair values of the notes as of December 31, 2021 and 2020 are as follows (in thousands):
December 31, 2021
December 31, 2020 (1)
 Carrying AmountEstimated Fair ValueCarrying AmountEstimated Fair Value
2026 notes$987,691 $840,000 $761,930 $1,129,370 
2025 notes690,464 682,202 640,614 1,456,800 
2023 notes— — 104,378 376,949 
Convertible senior notes, net$1,678,155 $1,522,202 $1,506,922 $2,963,119 
(1) Prior period amounts have not been adjusted due to the adoption of ASU 2020-06 under the modified retrospective method. Refer to Note 10, “Convertible Senior Notes” for more information.

The carrying amount of the 2026 notes and 2025 notes as of December 31, 2021 was net of unamortized issuance costs of $12.3 million and $9.5 million, respectively, and there is no carrying amount of the 2023 notes as we settled the principal amount of the 2023 notes during the year ended December 31, 2021. The carrying amount of the 2026 notes, 2025 notes and
2023 notes as of December 31, 2020 was net of unamortized debt discount of $226.7 million, $149.1 million and $10.0 million, respectively, and unamortized issuance costs of $11.3 million, $10.2 million and $1.2 million, respectively.