#1Q4 2023 Financial Results February 6, 2024 Copyright © 2024 MicroStrategy Incorporated. All Rights Reserved. m#2MicroStrategy Q4 2023 Earnings Call Safe Harbor Statement FORWARD-LOOKING STATEMENTS Some of the information we provide in this presentation regarding our future expectations, plans, and prospects may constitute forward-looking statements. Actual results may differ materially from these forward-looking statements due to various important factors, including the risk factors discussed in our most recent 10-Q filed with the SEC. We assume no obligation to update these forward-looking statements, which speak only as of today. Also, in this presentation, we will refer to certain non-GAAP financial measures. Reconciliations showing GAAP versus non-GAAP results are available in our earnings release and the appendix of this presentation, which were issued today and are available on our website at www.microstrategy.com. 2 וח#3Operational Results Phong Le, President & Chief Executive Officer Copyright © 2024 MicroStrategy Incorporated. All Rights Reserved. m#42023 Year in Review Bitcoin Holdings 190,000 as of February 5, 2024 Acquired 56,650 bitcoin in 2023 for $1.9B at average price of $33,580 Total market value of bitcoin holdings ~$8.1B Largest corporate holder of bitcoin in the world Subscription Services Revenues $81.2M increase of 34% YoY First to market with Al + BI platform integration Accelerated cloud transition Streamlined, agility-focused organization Healthy corporate liquidity and cash flows A וח#5B "MicroStrategy is the world's first Bitcoin Development Company" MicroStrategy (Nasdaq: MSTR) considers itself the world's first Bitcoin development company. We are a publicly-traded operating company committed to the continued development of the bitcoin network through our activities in the financial markets, advocacy and technology innovation. As an operating business, we are able to use cashflows as well as proceeds from equity and debt financings to accumulate bitcoin, which serves as our primary treasury reserve asset. We also develop and provide industry-leading Al-powered enterprise analytics software that promotes our vision of Intelligence Everywhere and are using our software development capabilities to develop bitcoin applications. We believe that the combination of our operating structure, bitcoin strategy and focus on technology innovation provides a unique opportunity for value creation. 5 ו#6Bitcoin Development Company MicroStrategy's unique value proposition Cash Bitcoin Development Company Bitcoin and Software Bitcoin Holdings Development 1 Equity Excess Cash Debt Increase Bitcoin Holdings and Shareholder Value 1 Includes bitcoin acquisition, bitcoin advocacy initiatives, and software development related to BI, AI, Cloud, Bitcoin, and Lightning. 6 וח#72024 Software Strategic Focus olo Grow Cloud Innovate with Al Increase Profitability 7 וח#8Grow Cloud and Al Multi-cloud | Cloud-native | Marketplace MicroStrategy Cloud Focus on customer migration & new business growth Accelerate subscription services revenues growth in 2024 MicroStrategy Al First to market in Q3 2023 Microsoft Azure OpenAl partnership Embedded, customizable, Al-bot 5 aws O A aws 8 AI MICROSTRATEGY ONE THE AI/BI PLATFORM BI וח#9Operating Profitability 2022A 2023A 2024 Targets $499M $496M Growing Revenue Non-GAAP Operating Income ($1,212M) ($45M) $70-$90M(1) Digital Asset Impairments $1,286M $116M N/A(2) (1) 2024 targeted non-GAAP operating income excludes any digital asset impairment charges for 2024. (2) Digital asset impairments will be at least $29 million on the bitcoin held as of December 31, 2023, based on changes in the market price of bitcoin through February 5, 2024. 9 וח#10Intelligent Leverage MicroStrategy is unique in acquiring bitcoin using excess cash on balance sheet and proceeds from issuances of equity and corporate debt Cash $726M total cash on balance sheet invested Equity ~$3.1B of equity issued Increase Bitcoin Holdings and Shareholder Value 10 Debt $2.2B in senior secured and convertible debt outstanding וח#11Financial Results Andrew Kang, Senior Executive VP & Chief Financial Officer Copyright © 2024 MicroStrategy Incorporated. All Rights Reserved. m#12Revenue and Billings Q4 2023 ($ in Millions) Total Revenues $124.5M Q4 2023 Total Revenues 6% YoY decrease $496.3M FY 2023 Total Revenues 1% YoY decrease Subscription Services Revenues Q4 2023 +23% YOY increase Current Subscription Billings Q4 2023 +33% YOY increase $21.0 $21.5 $41.3 $19.9 $18.8 $17.5 $31.1 $23.1 $16.8 $13.7 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 12 וח#13Disciplined Cost Structure • Total Non-GAAP expenses for Q4 down 52% year over year • Headcount 10% lower YoY • Non-GAAP operating loss for Q4 of $23 million, which includes $39 million of non-cash bitcoin impairment charges Non-GAAP Expenses By Type ($M) Total: $309M Total: $148M Headcount $198 2,152 1,934 $37 $39 $35 $26 $28 $27 $26 $21 $20 Q4 2022 Cost of Revenues ■Research & Development ■ Digital Asset Impairment Charges Q4 2023 ■Sales & Marketing General & Administrative 13 12/31/2022 12/31/2023 Total Headcount וח#14Growth in Bitcoin Holdings MicroStrategy has acquired additional bitcoin in every quarter since Q3 2020 • In Q4 2023 30,555 bitcoins purchased for $1.2 billion using proceeds from capital markets activities (Macro) • 350 bitcoins purchased for $13.4 million using excess cash (Micro) • In Q1 2024 850 bitcoins purchased for $37.2 million using excess cash (Micro) 190,000 bitcoins(1) held on balance sheet, acquired for a total cost of $5.93 billion, or $31,224 per bitcoin Bitcoin Holdings 38,250 158,245 152,333 140,000 124,391 129,218 129,699 130,000 132,500 114,042 105,085 91,326 70,469 189,150 190,000 173,069 173,069 137,069 142,514 110,942 115,110 115,110 115,110 117,610 125,110 100,593 92,079 13,005 13,449 13,449 14,108 14,589 14,890 14,890 14,890 15,264 15,731 16,081 16,931 Q3 20 Q4 20 Q1 21 Q2 21 Q3 21 Q4 21 Q1 22 Q2 22 Q3 22 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 2/5/24 ■MicroStrategy (Restricted) (2) ■MacroStrategy (Unrestricted) (1) As of February 5, 2024. (2) All bitcoin holdings were unrestricted prior to Q2 2021. 14 וח#15Bitcoin Holdings Carrying Value vs. Market Value Aggregate cost of $5.9 billion and current market value of $8.1 billion Carrying value of $3.7 billion, net of ~$2.3 billion in cumulative impairment charges ($ in Billions) $9.0 ■Carrying Value ■Market Value $8.0 $8.1 $8.0 $7.0 $6.0 $5.0 $4.6 $4.3 $4.0 $3.7 $4.0 $3.6 $3.0 $2.2 $2.0 $2.3 $2.5 $1.8 $2.0 $1.0 $0.0 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 (1) 2/5/24 Note: Calculations are based on prices as of 4pm Eastern Time on the last day of the respective quarter or date noted. (1) The carrying value presented for 2/5/24 equals the 12/31/23 carrying value of our bitcoin plus the cost of bitcoin purchases during 2024 and does not reflect any impairment charges incurred after 12/31/23. 15 In#16Use of Excess Cash to Acquire More Bitcoin Incremental bitcoin accretion per share through purchases using excess cash -$726M ($ in Millions) Historical accumulated cash $490 Total Excess Cash Invested Operations $120 ~48K Bitcoins Purchased with Excess Cash $41 $38 $37 2020 2021 2022 2023 2024 YTD ~41.4k BTC ~2.6k BTC ~1.4k BTC ~1.2k BTC ~850 BTC 16 וח#17Capital Markets Activities to Acquire More Bitcoin Strong track record of accretive capital allocation strategy ~$2.2B Net Proceeds from Debt Capital Markets Activity ~$3.1B Net Proceeds from Equity ~142K Bitcoins Purchased with Debt & Equity Capital Raised for Bitcoin Purchases (Gross Proceeds in $M) Equity Financing ■Debt Financing $1,000 $1,550 $1,869 $47 $650 $205 2020 2021 ~50.6k BTC 2022 2023 (1) ~7.4k BTC ~55.5k BTC ~29.0k BTC (1) Does not include $160M of incremental equity issued in 2023 to repay $205M of bitcoin-backed loan raised in 2022. 17 וח#182023 Value Creation from Bitcoin Activities BTC Count BTC Price ($ in Millions) $2,194 $3,442 Unique to MSTR $507 $8,045 $1,902 12/31/2022 BTC Holdings Market Value 132,500 $16,556 BTC Price Appreciation (Prior Holdings) Capital Raised + Excess Cash (2023 Purchases) Additions: 56,650 Avg Price: $33,580 BTC Price Appreciation (2023 Purchases) 12/31/2023 BTC Holdings Market Value 189,150 $42,531 18 ו#19MicroStrategy Bitcoin Net Asset Value Hypothetical scenarios in which bitcoin price increases – Illustrative Bitcoin Forward Price Spot Bitcoin Price MSTR (Current Leverage) MSTR (Incremental $0.5B Leverage) MSTR (Incremental $1.0B Leverage) $43,000 $69,000 $100,000 $250,000 60% 135% 480% I I 85% 180% 660% 90% 190% 700% 95% 205% 740% Note: Assumptions: Rounded to the nearest 5% up or down. Leverage levels set forth above are provided for illustrative purposes only and do not reflect any current plans of the Company. Percentage amounts above refer to the mathematical outputs only based solely on the underlying assumptions and are not a projection or prediction of future bitcoin prices or underlying bitcoin net asset values. Scenarios in which the bitcoin forward price is less than $43,000 would result in a proportionate decrease in bitcoin net asset value. Bitcoin Net Asset Value = Bitcoin Holdings Market Value less Total Outstanding Debt. No change to MSTR share count, no conversion of outstanding convertible debt, ignores interest on debt for simplification of mathematical exercise, no indication on the time frame for the forward bitcoin price or debt maturity, excludes software business. Incremental leverage scenarios assume that MSTR is able to issue the additional debt and invest the proceeds in bitcoin at market prices as of February 5, 2024. 19 ו#20Strategy & Bitcoin Michael Saylor, Executive Chairman Copyright © 2024 MicroStrategy Incorporated. All Rights Reserved. m#21MicroStrategy Outperformance Since Adoption of Bitcoin Strategy Key Assets and Indices Big Tech Stocks Enterprise Software Stocks 305% 260% II.. 48% 42% 1% -18% -19% Bitcoin S&P 500 Nasdaq Gold Silver Bonds 97% 92% 81% 65% 17% 9% MSFT GOOG META AAPL NFLX AMZN 111% 53% 45% 11% ORCL IBM CRM SAP Stock performance since August 10, 2020, when MicroStrategy adopted its bitcoin strategy. Source: FactSet as of 4pm Eastern Time on February 2, 2024. 21 MSTR וח#22MicroStrategy – Bitcoin Development Company Unique value proposition versus Spot Bitcoin ETPs 1 Company Structure 2 Ability to Develop Software MicroStrategy Operating company Active control over capital structure No management fee Ability to innovate to create incremental value Spot Bitcoin ETPs Trust company Limited control over capital structure Non-zero management fee None 3 Ability to Generate Cash from Operations Reinvest cash from software business None ($726M to date; ~$40M per year in 2022/23) 4 Ability to Leverage Capital Markets Note: Debt - Secured or Unsecured Convertible or Structured Notes Equity, Preferred Equity $2.2B debt and $3.1B equity capital invested) Limited Based on the Company's own view of the relative positioning of the various categories shown. MicroStrategy is not an exchange traded product ("ETP") or an exchange-traded fund (“ETF”) registered under the Investment Company Act of 1940, as amended, is not subject to the same rules and regulations as an ETP or an ETF and does not operate as an ETP or ETF. See Appendix slide 30 for additional information. 22 m#23Appendix Copyright © 2024 MicroStrategy Incorporated. All Rights Reserved. m#24Current Bitcoin Holdings • 91% of our total bitcoin holdings are unencumbered as of February 5, 2024 158,400 90% 142,514 10% 15,886 As of October 31, 2023 ■MicroStrategy: Restricted 24 190,000 173,069 91% 16,931 As of February 5, 2024 ■MacroStrategy: Unrestricted } 9% וח#25$500M ATM Equity Program and Principal Debt Maturities(1) Received $1.2B net proceeds from issuances under the at-the-market ("ATM") equity offering program in Q4; remaining ~$138M capacity Total $2.2B debt outstanding at weighted average annual fixed interest rate 1.6%, ~$36M annualized fixed interest expense $1,050M I $650M I I Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 2024 2025 2026 2027 0.000% Senior Instrument Convertible 2028 6.125% Senior Secured Notes Maturity Annualized Interest Expense 0.750% Senior Convertible Notes Dec 2025 $4.9M (1) Excludes $10.5M principal amount of other long-term secured debt. Please refer to the Q3 2023 10-Q for further detail. Notes Feb 2027 Jun 2028(3) $0.0M $30.6M (2) Bitcoin "halving", which is expected to next occur in April 2024, refers to the decrease in the block reward from 6.25 to 3.125 bitcoins per block, resulting in fewer bitcoins generated per block. (3) Please refer to the Q3 2023 10-Q for the springing maturity provisions that may accelerate the maturity date of the senior secured notes. 25 Expected Bitcoin Halving (Q2 2024)(2) I וח#26Non-GAAP Reconciliations ($ in Millions) Q4 2023 Reconciliation of GAAP to non-GAAP income (loss) from operations Revenues Cost of Revenues Q1 22 $119.3 Q2 22 Q3 22 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 $122.1 $125.4 $132.6 $121.9 $120.4 $129.5 $124.5 $25.7 $25.2 $25.4 $26.7 $27.9 $27.1 $26.7 $28.2 Operating Expenses $263.6 $1,015.0 $93.9 $299.5 $114.3 $120.0 $128.0 $139.0 GAAP Income (Loss) from Operations $(170.0) $(918.1) $6.1 $(193.7) $(20.3) $(26.7) $(25.2) $(42.8) GAAP Operating Margin % -142% -752% 5% -146% -17% -22% -20% -34% Share-Based Compensation $14.4 $15.3 $16.9 $17.0 $17.6 $15.5 $16.8 $19.7 Non-GAAP Income (Loss) from Operations ($155.6) ($902.8) $23.0 ($176.7) ($2.8) ($11.2) ($8.4) ($23.1) Non-GAAP Operating Margin % -130% -740% 18% -133% -2% -9% -7% -19% Digital Asset Impairment Losses, Net of Gains on Sale $170.1 $917.8 $0.7 $197.6 $18.9 $24.1 $33.6 $39.2 Reconciliation of subscription services revenues to non-GAAP current subscription billings Q1 22 Q2 22 Q3 22 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 Current Deferred Subscription Services Revenues $34.2 $40.3 $38.3 $51.9 $46.7 $49.9 $45.7 $65.5 Subscription Services Revenues $12.8 $14.0 $16.4 $17.5 $18.8 $19.9 $21.0 $21.5 Change in Current Deferred Subscription Services Revenues $(1.4) $6.1 $(2.0) $13.6 $(5.1) $3.2 $(4.2) $19.8 Non-GAAP Current Subscription Billings $11.4 $20.1 $14.4 $31.1 $13.7 $23.1 $16.8 $41.3 Reconciliation of subscription services revenues to annual subscription billings FY 2022 FY 2023 Current Deferred Subscription Services Revenues $51.9 $65.5 Subscription Services Revenues $60.7 $81.2 Change in Current Deferred Subscription Services Revenues $16.3 $13.7 Non-GAAP Annual Subscription Billings $77.0 $94.8 26 וח#27Non-GAAP Reconciliations ($ in Millions) Q4 2023 Reconciliation of non-GAAP operating expenses Q1 22 Q2 22 Q3 22 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 GAAP Operating Expenses $263.6 $1,015.0 $93.9 $299.5 $114.3 $120.0 $128.0 $139.0 Share-Based Compensation (1) $13.4 $14.2 $15.8 $15.9 $16.5 $14.4 $15.6 $18.5 Non-GAAP Operating Expenses $250.2 $1,000.7 $78.1 $283.6 $97.8 $105.6 $112.5 $120.5 Digital Asset Impairment Losses, Net of Gains on Sale $170.1 $917.8 $0.7 $197.6 $18.9 $24.1 $33.6 $39.2 Reconciliation of total non-GAAP expenses Q1 22 Q2 22 Q3 22 Q4 22 Q1 23 Q2 23 Q3 23 Q4 23 Cost of Revenues Operating Expenses $25.7 $25.2 $25.4 $26.7 $27.9 $27.1 $26.7 $28.2 $263.6 $1,015.0 $93.9 $299.5 $114.3 $120.0 $128.0 $139.0 Total GAAP Expenses $289.2 $1,040.2 $119.3 $326.3 $142.2 $147.1 $154.7 $167.3 Share-Based Compensation $14.4 $15.3 $16.9 $17.0 $17.6 $15.5 $16.8 $19.7 Total Non-GAAP Expenses $274.8 $1,024.9 $102.4 $309.2 $124.7 $131.6 $137.9 $147.6 Digital Asset Impairment Losses, Net of Gains on Sale $170.1 $917.8 $0.7 $197.6 $18.9 $24.1 $33.6 $39.2 (1) Share-Based Compensation shown reflects the amounts recorded to Sales & Marketing, Research & Development, and General & Administrative only. 27 וח#28Non-GAAP Reconciliations ($ in Millions) Q4 2023 Reconciliation of total non-GAAP expenses Q4 22 Q4 23 GAAP Expenses Cost of Revenues Sales & Marketing $26.7 $28.2 $41.4 $40.3 Research & Development $31.6 $30.2 General & Administrative $28.9 $29.4 Digital Asset Impairment Losses, Net of Gains on Sale $197.6 $39.2 Total GAAP Expenses $326.3 $167.3 Share-Based Compensation Cost of Revenues Sales & Marketing Research & Development General & Administrative Total Share-Based Compensation Non-GAAP Expenses Cost of Revenues Sales & Marketing $1.1 $1.2 $4.6 $5.5 $3.7 $4.1 $7.6 $8.9 $17.0 $19.7 $25.6 $27.0 $36.8 $34.8 Research & Development $28.0 $26.0 General & Administrative $21.3 $20.5 Digital Asset Impairment Losses, Net of Gains on Sale $197.6 $39.2 Total Non-GAAP Expenses $309.2 $147.6 28 וח#29Basic and Adjusted Diluted Shares Outstanding Calculation Total Bitcoin Holdings 6/30/2020 12/31/2020 70,470 12/31/2021 124,391 12/31/2022 132,500 12/31/2023 189,150 Shares Outstanding (in '000s) Class A 7,651 7,623 9,322 9,585 14,904 Class B 2,035 1,964 1,964 1,964 1,964 Basic Shares Outstanding (1) 9,686 9,587 11,286 11,549 16,868 2025 Convert Shares @$398 1,633 1,633 1,633 1,633 2027 Convert Shares @$1,432 733 733 733 Options Outstanding 1,481 1,157 1,167 1,577 1,294 RSU/PSU Unvested 74 105 120 235 Adj. Diluted Shares Outstanding (2) 11,167 12,451 14,924 15,612 20,763 (1) Basic Shares Outstanding reflects the actual Class A and Class B common stock outstanding as of the dates presented. (2) Adjusted Diluted Shares Outstanding reflects the maximum potential impact from conversion of our 2025 and 2027 Convertible Notes at conversion prices of $398 and $1,432, respectively, outstanding stock option awards at average exercise price of $287, outstanding restricted stock units and performance stock units as of the dates presented. 29 וח#30Additional Information MicroStrategy is not an exchange traded product ("ETP") or an exchange-traded fund ("ETF") registered under the Investment Company Act of 1940, as amended, is not subject to the same rules and regulations as an ETP or an ETF, and does not operate as an ETP or ETF. In particular, unlike spot bitcoin ETPs, we (i) do not seek for our shares of Class A common stock to track the value of the underlying bitcoin we hold before payment of expenses and liabilities, (ii) do not benefit from various exemptions and relief under the Securities Exchange Act of 1934, as amended, including Regulation M, and other securities laws, which enable spot bitcoin ETPs to continuously align the value of their shares to the price of the underlying bitcoin they hold through share creation and redemption, (iii) are a Delaware corporation rather than a statutory trust, and do not operate pursuant to a trust agreement that would require us to pursue one or more stated investment objectives, (iv) are subject to federal income tax at the entity level and the other risk factors applicable to an operating business, such as ours, and (v) are not required to provide daily transparency as to our bitcoin holdings or our daily NAV. 30 וח