Long-term Debt | (5) Long-term Debt The net carrying value of the Company’s long-term debt (in thousands) consisted of the following, as of: March 31, 2024 December 31, 2023 2025 Convertible Notes $ 644,698 $ 643,931 2027 Convertible Notes 1,038,316 1,037,306 2030 Convertible Notes 782,248 0 2031 Convertible Notes 592,368 0 2028 Secured Notes 491,622 491,193 Other long-term secured debt 9,549 9,678 Total $ 3,558,801 $ 2,182,108 Convertible Senior Notes Prior Years Issuances of Convertible 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 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, respectively, 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, 2023. Current Year Issuances of Convertible Notes In March 2024, the Company issued $ 800.0 million aggregate principal amount of 0.625 % Convertible Senior Notes due 2030 (the “2030 Convertible Notes”) in a private offering. The 2030 Convertible Notes are senior unsecured obligations of the Company and bear interest at a fixed rate of 0.625% per annum, payable semiannually in arrears on March 15 and September 15 of each year, beginning on September 15, 2024 . Holders of the 2030 Convertible Notes may receive additional interest under specified circumstances as outlined in the indenture relating to the issuance of the 2030 Convertible Notes (the “2030 Convertible Notes Indenture”). The 2030 Convertible Notes will mature on March 15, 2030 , unless earlier converted, redeemed, or repurchased in accordance with their terms. The total net proceeds from the 2030 Convertible Notes offering, after deducting initial purchaser discounts and issuance costs, were approximately $ 782.0 million. In March 2024, the Company also issued $ 603.8 million aggregate principal amount of 0.875 % Convertible Senior Notes due 2031 (the “2031 Convertible Notes”) in a private offering. The 2031 Convertible Notes are senior unsecured obligations of the Company and bear interest at a fixed rate of 0.875% per annum, payable semiannually in arrears on March 15 and September 15 of each year, beginning on September 15, 2024 . Holders of the 2031 Convertible Notes may receive additional interest under specified circumstances as outlined in the indenture relating to the issuance of the 2031 Convertible Notes (the “2031 Convertible Notes Indenture”). The 2031 Convertible Notes will mature on March 15, 2031 , unless earlier converted, redeemed, or repurchased in accordance with their terms. The total net proceeds from the 2031 Convertible Notes offering, after deducting initial purchaser discounts and issuance costs, were approximately $ 592.3 million. The 2030 Convertible Notes and 2031 Convertible Notes are convertible into shares of the Company’s class A common stock at initial conversion rates of 0.6677 shares per $ 1,000 principal amount (equivalent to an initial conversion price of approximately $ 1,497.68 per share of class A common stock) for the 2030 Convertible Notes and 0.4297 shares per $ 1,000 principal amount (equivalent to an initial conversion price of approximately $ 2,327.21 per share of class A common stock) for the 2031 Convertible Notes. 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 2030 Convertible Notes or 2031 Convertible Notes, respectively, in connection with such corporate event or notice of redemption, as the case may be, in certain circumstances as provided in the 2030 Convertible Notes Indenture or 2031 Convertible Notes Indenture, respectively. Prior to September 15, 2029 and September 15, 2030 for the 2030 Convertible Notes and 2031 Convertible Notes, respectively, the 2030 Convertible Notes and 2031 Convertible Notes are convertible only under the following circumstances: (1) during any calendar quarter commencing after the calendar quarter ending on June 30, 2024 (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 2030 Convertible Notes or 2031 Convertible Notes, respectively, on each applicable trading day; (2) during the five business day period after any five consecutive trading day period (the “measurement period”) in which the “trading price” (as defined in the 2030 Convertible Notes Indenture or 2031 Convertible Notes Indenture, respectively) per $ 1,000 principal amount of the 2030 Convertible Notes or 2031 Convertible Notes, respectively, 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; (3) if the Company calls any or all of the 2030 Convertible Notes or 2031 Convertible Notes, respectively, for redemption, at any time prior to the close of business on the second scheduled trading day immediately preceding the redemption date; and (4) upon occurrence of specified corporate events as described in the 2030 Convertible Notes Indenture or 2031 Convertible Notes Indenture, respectively . On or after September 15, 2029 or September 15, 2030 for the 2030 Convertible Notes and 2031 Convertible Notes, respectively, until the close of business on the second scheduled trading day immediately preceding the maturity dates of the 2030 Convertible Notes or 2031 Convertible Notes, respectively, holders may convert the 2030 Convertible Notes or 2031 Convertible Notes, respectively, at any time. Upon conversion of the 2030 Convertible Notes or 2031 Convertible Notes, respectively, 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. Prior to March 22, 2027 or March 22, 2028 for the 2030 Convertible Notes and 2031 Convertible Notes, respectively, the Company may not redeem the 2030 Convertible Notes or 2031 Convertible Notes, respectively. The Company may redeem for cash all or a portion of the 2030 Convertible Notes or 2031 Convertible Notes, at its option, on or after March 22, 2027 or March 22, 2028 , respectively, 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 2030 Convertible Notes or 2031 Convertible Notes, respectively, 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 2030 Convertible Notes or 2031 Convertible Notes, respectively, to be redeemed, plus accrued and unpaid interest to, but excluding, the redemption date. Holders of the 2030 Convertible Notes and 2031 Convertible Notes each have the right to require the Company to repurchase for cash all or any portion of their 2030 Convertible Notes or 2031 Convertible Notes, respectively, on September 15, 2028 at a repurchase price equal to 100 % of the principal amount of the 2030 Convertible Notes or 2031 Convertible Notes, respectively, to be repurchased, plus any accrued and unpaid interest to, but excluding the repurchase date. If the Company undergoes a “fundamental change,” as defined in the 2030 Convertible Notes Indenture or 2031 Convertible Notes Indenture, respectively, prior to maturity, subject to certain conditions, holders may require the Company to repurchase for cash all or any portion of their 2030 Convertible Notes or 2031 Convertible Notes, respectively, at a fundamental change repurchase price equal to 100 % of the principal amount of the 2030 Convertible Notes or 2031 Convertible Notes, respectively, to be repurchased, plus any accrued and unpaid interest to, but excluding, the fundamental change repurchase date. The 2030 Convertible Notes Indenture and 2031 Convertible Notes Indenture 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 of the outstanding 2030 Convertible Notes or 2031 Convertible Notes, respectively, may declare 100 % of the principal of, and accrued and unpaid interest, if any, on, all the 2030 Convertible Notes or 2031 Convertible Notes, respectively, to be due and payable. The Company incurred approximately $ 18.0 million and $ 11.5 million in customary offering expenses associated with the 2030 Convertible Notes and 2031 Convertible Notes, respectively (“issuance costs”). The Company accounts for these issuance costs as a reduction to the principal amount of the 2030 Convertible Notes and 2031 Convertible Notes, respectively, and amortizes the issuance costs to interest expense from the respective debt issuance dates through September 15, 2028 (the date upon which holders of each of the 2030 Convertible Notes and 2031 Convertible Notes have noncontingent rights to exercise their respective put option) at an effective interest rate of 1.14 % for the 2030 Convertible Notes and 1.31 % for the 2031 Convertible Notes. Although the 2030 Convertible Notes and 2031 Convertible Notes, respectively, contain embedded conversion features, the Company accounts for the 2030 Convertible Notes and 2031 Convertible Notes, respectively, 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. Collective Convertible Notes Disclosures The 2025 Convertible Notes, 2027 Convertible Notes, 2030 Convertible Notes, and 2031 Convertible Notes (collectively, the “Convertible Notes”) are senior unsecured obligations 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. There have been no adjustments to the initial conversion rates for any of the Convertible Notes as of March 31, 2024. As of March 31, 2024 , the maximum number of shares into which the Convertible Notes could be potentially converted if the conversion features are triggered are 1,633,190 shares, 733,005 shares, 534,160 shares, and 259,431 shares for the 2025 Convertible Notes, 2027 Convertible Notes, 2030 Convertible Notes, and 2031 Convertible Notes, respectively. The following summarizes which periods, if any, that each of the Convertible Notes were convertible at the option of the holders during the three months ended March 31, 2024 and 2023: Three Months Ended March 31, 2024 2023 2025 Convertible Notes Convertible Not convertible at any time 2027 Convertible Notes Not convertible at any time Not convertible at any time 2030 Convertible Notes Not convertible at any time n/a 2031 Convertible Notes Not convertible at any time n/a During the three months ended March 31, 2024, the Company received from certain holders of the 2025 Convertible Notes requests to convert an immaterial principal amount of the 2025 Convertible Notes, which the Company expects to settle during the quarter ending June 30, 2024, in accordance with the terms and provisions of the indenture governing the 2025 Convertible Notes. The Company did no t settle any conversions of the Convertible Notes during the three months ended March 31, 2024 or 2023. 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 March 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, March 31, 2024 was greater than or equal to 130 % of the conversion price of the 2025 Convertible Notes on each applicable trading day. Therefore, the 2025 Convertible Notes are convertible at the option of the holders of the 2025 Convertible Notes during the second quarter of 2024. The Company has no t redeemed any of the Convertible Notes as of March 31, 2024. As of March 31, 2024 and December 31, 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 March 31, 2024 (in thousands): March 31, 2024 Outstanding Unamortized Net Carrying Fair Value Principal Amount Issuance Costs Value Amount Leveling 2025 Convertible Notes $ 650,000 $ ( 5,302 ) $ 644,698 $ 2,847,274 Level 2 2027 Convertible Notes 1,050,000 ( 11,684 ) 1,038,316 1,437,616 Level 2 2030 Convertible Notes 800,000 ( 17,752 ) 782,248 1,064,727 Level 2 2031 Convertible Notes 603,750 ( 11,382 ) 592,368 638,466 Level 2 Total $ 3,103,750 $ ( 46,120 ) $ 3,057,630 $ 5,988,083 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 three months ended March 31, 2024 and 2023, interest expense related to the Convertible Notes was as follows (in thousands): Three Months Ended March 31, 2024 Three Months Ended March 31, 2023 Contractual Amortization of Contractual Amortization of Interest Expense Issuance Costs Total Interest Expense Issuance Costs Total 2025 Convertible Notes $ 1,219 $ 767 $ 1,986 $ 1,219 $ 757 $ 1,976 2027 Convertible Notes 0 1,010 1,010 0 1,006 1,006 2030 Convertible Notes 319 248 567 0 0 0 2031 Convertible Notes 191 89 280 0 0 0 Total $ 1,729 $ 2,114 $ 3,843 $ 1,219 $ 1,763 $ 2,982 The Company did no t pay any interest related to the Convertible Notes during the three months ended March 31, 2024 and 2023 . The Company has no t 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 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 Company has no t redeemed any of the 2028 Secured Notes as of March 31, 2024. 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. “Liquidity” is defined in the 2028 Secured Notes Indenture and includes the Digital Asset Market Value (as defined in the 2028 Secured Notes Indenture) of the bitcoin owned by the Company and its Restricted Subsidiaries (as defined in the 2028 Secured Notes Indenture) immediately prior to the issuance of the 2028 Secured Notes (which are referred to as “Existing Digital Assets”). As of March 31, 2024 , for purposes of calculating Liquidity, the Company and its Restricted Subsidiaries owned approximately 92,079 Existing Digital Assets, all of which were unencumbered. 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, 2023. 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 March 31, 2024. As of March 31, 2024 and 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 Sheets. The following is a summary of the 2028 Secured Notes as of March 31, 2024 (in thousands): March 31, 2024 Outstanding Unamortized Net Carrying Fair Value Principal Amount Issuance Costs Value Amount Leveling 2028 Secured Notes $ 500,000 $ ( 8,378 ) $ 491,622 $ 483,125 Level 2 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 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 March 31, 2024 and 2023, interest expense related to the 2028 Secured Notes was as follows (in thousands): Three Months Ended March 31, 2024 Three Months Ended March 31, 2023 Contractual Amortization of Contractual Amortization of Interest Expense Issuance Costs Total Interest Expense Issuance Costs Total 2028 Secured Notes $ 7,656 $ 429 $ 8,085 $ 7,656 $ 401 $ 8,057 The Company did no t pay any interest related to the 2028 Secured Notes during the three months ended March 31, 2024 and 2023. Secured Term Loan On March 23, 2022, MacroStrategy 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, 2023. 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. 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 three months ended March 31, 2023, interest expense related to the 2025 Secured Term Loan was as follows (in thousands): Three Months Ended March 31, 2023 Contractual Amortization of Interest Expense Issuance Costs Total 2025 Secured Term Loan $ 3,781 $ 31 $ 3,812 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. 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 $ 10.0 million and $ 10.2 million as of March 31, 2024 and December 31, 2023, respectively, and an outstanding principal balance of $ 10.2 million and $ 10.3 million as of March 31, 2024 and December 31, 2023, respectively. As of March 31, 2024 and December 31, 2023 , $ 0.5 million and $ 0.5 million of the respective net carrying values were short-term and were 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 March 31, 2024 (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 March 31, 2024, 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. The principal payments related to the 2030 Convertible Notes and 2031 Convertible Notes, respectively, are included in the table below as if the holders exercised their right to require the Company to repurchase all of the 2030 Convertible Notes and 2031 Convertible Notes on September 15, 2028. Payments due by period ended March 31, 2025 Convertible Notes 2027 Convertible Notes 2030 Convertible Notes 2031 Convertible Notes 2028 Secured Notes Other long-term secured debt Total 2025 $ 0 $ 0 $ 0 $ 0 $ 0 $ 547 $ 547 2026 650,000 0 0 0 500,000 577 1,150,577 2027 0 1,050,000 0 0 0 608 1,050,608 2028 0 0 0 0 0 8,477 8,477 2029 0 0 800,000 603,750 0 0 1,403,750 Thereafter 0 0 0 0 0 0 0 Total $ 650,000 $ 1,050,000 $ 800,000 $ 603,750 $ 500,000 $ 10,209 $ 3,613,959 |