Michael Saylor
StrategyAbout Michael Saylor
Michael J. Saylor (age 60) is Executive Chairman and Chairman of the Board at MicroStrategy Inc. d/b/a Strategy (MSTR). He founded the company in 1989, served as CEO until August 2022, and currently chairs the Investments Committee overseeing bitcoin strategy. He holds SB degrees in Aeronautics & Astronautics and in Science, Technology & Society from MIT . Since adoption of the bitcoin strategy in August 2020, the stock price increased by 2,232% versus bitcoin and major indices, evidencing extraordinary TSR performance during his leadership pivot . Pay-versus-performance data show Strategy’s $100 investment grew to $2,029 by 2024 versus $301 for peer group, reflecting significant shareholder value creation .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Strategy (MicroStrategy) | Founder; Chairman & Executive Chairman | 1989–present | Founder; chairs Investments Committee; oversight of bitcoin treasury strategy |
| Strategy (MicroStrategy) | Chief Executive Officer | 1989–Aug 2022 | Led company for 30+ years; pivotal transition to bitcoin strategy |
| Strategy (MicroStrategy) | President | 1989–2000; 2005–2012; 2016–2020 | Multiple stints leading operations and product strategy |
| E.I. du Pont de Nemours & Co. | Venture Manager | 1988–1989 | Venture management experience pre-MicroStrategy |
| Federal Group, Inc. | Consultant | 1987–1988 | Early consulting experience |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| — | — | — | No public company directorships or external board roles disclosed in proxy . |
Fixed Compensation
Multi-year compensation (all amounts USD):
| Metric | 2022 | 2023 | 2024 |
|---|---|---|---|
| Salary ($) | $1 | $1 | $1 |
| Bonus ($) | $0 | $0 | $0 |
| Stock Awards ($) | $0 | $0 | $0 |
| Option Awards ($) | $0 | $0 | $0 |
| All Other Compensation ($) | $670,811 | $799,669 | $791,911 |
| Total ($) | $670,812 | $799,670 | $791,912 |
2024 perquisites detail:
| Perquisite | 2024 Amount ($) |
|---|---|
| Security Program | $299,834 |
| Personal use of Company Aircraft | $356,533 |
| Tax gross-ups | $124,605 |
| Personal website use (Michael.com) | $6,000 |
| Supplemental Disability Insurance | $4,939 |
Policy parameters for perquisites and caps include security program capped at $1.4M (including tax gross-ups), car services cap $100k (ex tax gross-ups), entertainment events cap $75k, President’s Club perquisite cap $30k (ex tax gross-ups), and Company Aircraft and other corporate programs permitted under policies .
Performance Compensation
| Component | Metric | Weighting | Target | Actual/Payout | Vesting |
|---|---|---|---|---|---|
| Cash bonus | — | — | Eliminated since Sept 2014 | None; no bonus established for 2024 or 2025 (at Saylor’s request) | |
| Equity awards | — | — | No new awards in 2024 | None; compensation tied to legacy options exercised in 2024; no RSUs/PSUs outstanding |
Notes:
- Base salary set at $1 since 2014 to align compensation with stock performance; no discretionary cash bonus arrangement for Saylor .
- Saylor exercised legacy options in 2024 prior to expiration (see Vesting/Selling section below) .
Equity Ownership & Alignment
Beneficial ownership as of April 22, 2025:
| Class | Shares | % of Class | Total Voting Power % |
|---|---|---|---|
| Class A | 378,500 (held by charitable foundation; Saylor disclaims beneficial ownership) | <1% (*) | — |
| Class B | 19,616,680 (owned by Alcantara LLC, wholly owned by Saylor) | 99.9% | — |
| Combined Voting Equity (A+B) | 19,995,180 equivalent votes | — | 44.1% |
(*) Less than 1.0% of Class A outstanding; beneficial ownership of Class A (including as-converted Class B) is 7.4% .
Vested vs unvested as of 12/31/2024:
| Instrument | Exercisable | Unexercisable | Unvested RSUs | Unvested PSUs |
|---|---|---|---|---|
| Options/RSUs/PSUs | 0 | 0 | 0 | 0 |
Vesting/selling pressure indicators:
- In 2024, Saylor exercised 4,000,000 options, realizing $363,497,489; no stock awards vested for him in 2024 .
- No pledging of shares disclosed; insider trading policy prohibits hedging transactions .
Ownership guidelines:
- Company deems equity ownership guidelines not meaningful for Saylor given significant stake; prohibition on hedging applies .
Employment Terms
| Term | Disclosure |
|---|---|
| Employment agreement | None; Saylor serves at will of the Board |
| Severance | None disclosed for Saylor |
| Change-in-control | Equity awards generally feature double-trigger vesting (termination without cause or for good reason within 12 months post-CoC, or non-assumption by acquirer); Saylor had no outstanding awards at 12/31/2024 |
| Clawback | Dodd-Frank compliant compensation recovery policy effective Oct 2, 2023 (applies to Covered Officers) |
| Insider trading | Policy prohibits illegal trading and hedging; pre-clearance required for certain persons |
| Non-compete / non-solicit | Not disclosed |
Related arrangements and transactions:
- D&O indemnification: Saylor personally provided indemnity coverage in 2021–2023 (Original/Renewed/Excess/Tail agreements); Company later bound commercial D&O policies and extended a tail indemnification agreement with Saylor (payments and refunds disclosed) .
- District of Columbia False Claims Act case: On May 31, 2024, Consent Order resolved case; Saylor paid $40,000,000 to the District and also paid relator’s fees; Company had no obligation to contribute .
Board Governance
- Board service: Director since 1989; Chairman & Executive Chairman; Investments Committee Chair (provides oversight of bitcoin strategy execution) .
- Committee memberships: Investments (Chair); not on Audit or Compensation .
- Independence: Not independent (as Executive Chairman); Board majority independent (per Nasdaq rules) .
- Attendance: Board met 14 times in 2024 and acted by written consent six times; all directors attended all meetings (100% attendance) .
- Leadership structure: CEO and Chair roles separated since Aug 2022; no Lead Independent Director; independent directors meet regularly in executive sessions .
- Governance evolution: Company ceased “controlled company” status on Nov 12, 2024; Compensation and Nominating Committees consist solely of independent directors .
- Nominating Committee: Established Nov 2024; currently chaired by independent director Carl Rickertsen .
Performance & Track Record
Pay vs Performance (Value of $100 investment) and profitability:
| Measure | 2020 | 2021 | 2022 | 2023 | 2024 |
|---|---|---|---|---|---|
| Strategy TSR ($) | 272 | 382 | 99 | 443 | 2,029 |
| Peer Group TSR ($) | 150 | 207 | 133 | 221 | 301 |
| Net Income (Loss) ($000s) | (7,524) | (535,480) | (1,469,797) | 429,121 | (1,166,661) |
| Non-GAAP Adjusted Income from Operations ($000s) | 68,226 | 90,220 | 74,163 | 70,375 | 14,008 |
Recent operating performance (Q3 2025):
- Operating income $3.9B; Net income $2.8B; Diluted EPS $8.42; software revenues $128.7M (+10.9% YoY), subscription services $46.0M (+65.4% YoY); gross margin 70.5% .
- Bitcoin holdings 640,808 BTC as of Oct 26, 2025 (cost $47.44B; average cost $74,032); BTC Yield YTD 26.0%; BTC $ Gain YTD $12.9B .
- FY2025 guidance: Operating income ~$34B; Net income ~$24B; Diluted EPS ~$80 (sensitivity to year-end BTC price assumption of $150k) .
Compensation Peer Group (used for benchmarking)
- 2022 peer group (enterprise software comparables) informed 2024 comp decisions; WTW served as independent compensation consultant. Names include Altair Engineering, Enfusion, Five9, Progress Software, Alteryx*, Everbridge*, Guidewire, SPS Commerce, Coupa Software*, EverCommerce, New Relic*, Teradata, DOMO, EVO Payments*, Pegasystems, Verint (*acquired; no longer public) .
Say-on-Pay & Shareholder Feedback
- Compensation Committee considered shareholder support for the 2023 say-on-pay proposal when setting 2024 compensation; specific approval percentages not disclosed .
Equity Incentive Architecture (Company-wide, context)
- 2023 Equity Plan with options/RSUs/PSUs; executive allocation targeted ~40% options / 40% PSUs / 20% RSUs; PSUs tied to 3-year relative TSR versus Nasdaq Composite (payout 0–200%; cliff vesting) .
Risk Indicators & Red Flags
- Tax gross-ups for perquisites (including security program and entertainment events) are shareholder-unfriendly for many governance frameworks .
- Prior period reliance on Saylor for D&O coverage (now largely replaced with commercial policies) is atypical; tail indemnification continues under agreements .
- DC AG tax case settlement paid personally by Saylor ($40M) resolved the matter; reputational/legal risk event now settled .
- No pledging disclosures identified; hedging prohibited by policy .
Equity Ownership & Alignment Commentary
- Saylor’s voting control remains substantial (44.1%), though the company ceased “controlled company” status in Nov 2024, improving committee independence .
- $1 salary and no cash bonus since 2014 reduce misalignment risk from guaranteed cash; however, significant perquisites and tax gross-ups persist .
- No outstanding unvested equity reduces near-term forced selling risk from vesting; 2024 option exercise created potential liquidity, but subsequent sales are not disclosed in the proxy .
Board Service History & Committee Roles
- Director since 1989; Chair of Investments Committee; not a member of Audit or Compensation Committees; not independent; 2024 Board and Audit/Compensation Committees had full attendance .
Investment Implications
- Alignment: $1 salary and no bonus tie Saylor’s compensation largely to equity performance, aligning interests with shareholders; sustained perquisites and tax gross-ups are governance drawbacks .
- Control & Governance: Large voting power (44.1%) with post-2024 committee independence reduces controlled-company concerns while Saylor retains strategic influence as Investments Chair .
- Execution Signal: Option exercise of 4M shares in 2024 realized substantial value; absence of unvested awards lowers near-term selling pressure; continued leadership in bitcoin strategy and capital markets (as evidenced by 2025 KPIs and guidance) supports momentum but increases sensitivity to BTC price .
- Legal/Insurance: Resolution of DC case removes a legal overhang; historical D&O arrangements reflect unique risk management; now largely normalized with commercial policies .