Gregg Winiarski
StrategyAbout Gregg Winiarski
Independent director at MicroStrategy (MSTR), age 54, serving since December 2024; currently a member of the Audit Committee. Background: Chief Legal Officer at Fanatics Holdings since February 2023 (senior advisor Aug 2021–Feb 2023); previously EVP & General Counsel at IAC, Inc. (Feb 2005–Jun 2021). Education: B.S. (Fordham University); J.D. (Columbia Law School). The Board cites his legal and governance expertise and public company board experience in complex corporate structures as qualifications .
Past Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| IAC, Inc. | EVP & General Counsel | Feb 2005 – Jun 2021 | Senior legal leadership across diversified public holding company |
| Fanatics Holdings, Inc. | Senior Advisor | Aug 2021 – Feb 2023 | Advisory to privately held digital sports platform |
External Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| Fanatics Holdings, Inc. | Chief Legal Officer | Feb 2023 – Present | Corporate legal leadership |
| ANGI Homeservices, Inc. | Director | Sep 2017 – May 2022 | Board service (prior public company) |
| Match Group, Inc. | Director | Nov 2015 – Jun 2020 | Board service (prior public company) |
Board Governance
- Committee assignments: Audit Committee member; current Audit Committee comprised of Graham (Chair), Patten, Winiarski, and Dietze; all members independent for audit purposes. Audit met five times in 2024; all then-current members attended all meetings .
- Board attendance and engagement: The Board met 14 times in 2024 and acted by unanimous written consent six times; all then-current directors attended all Board meetings in 2024 .
- Independence: Board determined all non-employee directors (including Winiarski) are independent under Nasdaq Rule 5605(a)(2). Board considered two disclosed transactions tied to Fanatics and a related person; both were arm’s-length, immaterial, and neither Winiarski nor any related person had a material interest or received compensation .
- Nominating process: Winiarski was recommended by a third-party that provided professional services to a Company executive officer; background checks were performed; no search firm engaged in 2024 .
- Board structure: No lead independent director; independent directors meet in executive sessions. Company ceased “controlled company” status in Nov 2024 and established a Nominating Committee (sole member Rickertsen) with charter; majority independent board and fully independent Compensation Committee now in place .
Fixed Compensation
| Component | Amount | Notes |
|---|---|---|
| Fees earned or paid in bitcoin (2024) | $25,000 | Paid quarterly in bitcoin via payment processor; Director compensation is denominated in USD, paid in BTC. For 2024, Winiarski’s reported fees totaled $25,000 . |
| Annual outside director retainer (policy) | $100,000 per year | $25,000 per quarter; not contingent on meeting attendance . |
| Audit Committee fee (policy) | $10,000 per quarter (member); $15,000 (Chair) | Payable only if serving on last day of quarter . |
| Compensation Committee fee (policy) | $5,000 per quarter (member); $7,500 (Chair) | Payable only if serving on last day of quarter . |
| Nominating Committee fee (policy) | No fees paid | Committee established in Nov 2024; no fees . |
Performance Compensation
| Award Type | Grant Size | Aggregate Fair Value | Grant/Effective Date | Vesting |
|---|---|---|---|---|
| Initial new director RSUs | 2,745 RSUs | $1,000,000 | Granted Dec 2024; effective upon stockholder approval Jan 21, 2025 | Equal annual installments over four years . |
| Initial new director stock options | Options to purchase 3,709 shares | $1,000,000 | Granted Dec 2024; effective upon stockholder approval Jan 21, 2025 | Equal annual installments over four years . |
- Annual director equity policy: On May 31 each year, non-employee directors automatically receive awards with aggregate grant-date fair value of $300,000, split $150,000 options / $150,000 RSUs, vesting on first anniversary .
Other Directorships & Interlocks
| Company | Type | Overlap/Interlock Considerations |
|---|---|---|
| ANGI Homeservices, Inc. (prior) | Public company board | Prior IAC portfolio company; historical interlock via IAC. No current MSTR conflict disclosed . |
| Match Group, Inc. (prior) | Public company board | Prior IAC asset; historical interlock via IAC. No current MSTR conflict disclosed . |
Expertise & Qualifications
- Experienced attorney and executive leader with deep expertise in complex corporate structures; prior GC of IAC, board experience at Match and ANGI .
- Education: B.S. (Accounting & Business/Management) Fordham University; J.D. Columbia Law School .
- Board qualification: Independent; service on Audit Committee; Board designated Graham (not Winiarski) as audit committee financial expert .
Equity Ownership
| As of Date | Class A Shares | Outstanding Options | Unvested RSUs |
|---|---|---|---|
| December 31, 2024 | 0 | 0 | 0 |
| Notes | |||
| As disclosed, newly appointed director grants to Winiarski (3,709 options; 2,745 RSUs; $2,000,000 aggregate fair value) were subject to stockholder approval and became effective Jan 21, 2025; thus not reflected in the Dec 31, 2024 holdings table . |
Governance Assessment
- Independence and conflicts: The Board explicitly reviewed and upheld Winiarski’s independence after considering ordinary-course sales by MSTR to a Fanatics subsidiary (where he is CLO) and a separate entity employing a related person. Both transactions were arm’s-length, immaterial, and without personal interest or compensation to Winiarski—mitigating conflict concerns .
- Committee effectiveness: Addition to the Audit Committee aligns with his legal and governance background; Audit Committee oversight includes financial reporting and cybersecurity/data privacy risks; all Audit meetings in 2024 had full attendance, supporting engagement .
- Compensation alignment: New director equity grant structure ($2,000,000 split evenly between options and RSUs, four-year vesting) promotes multi-year alignment; fees paid in bitcoin signal cultural alignment with the Company’s digital asset strategy but may introduce volatility optics for director pay value realization .
- Board process and independence: Board majority independent, independent Compensation Committee, Nominating Committee chartered post cessation of “controlled company” status—positive governance trajectory. No lead independent director, but regular executive sessions of independent directors provide counterbalance .
- RED FLAGS (monitored):
- Related-party proximity: Ongoing Fanatics role requires continued monitoring; Board’s arm’s-length assessment and immateriality mitigate risk, but continued disclosure is prudent .
- D&O coverage history: Company relied on indemnification agreements personally provided by Executive Chairman due to inability to secure acceptable D&O insurance terms; Board concluded such arrangements do not impair independent judgment of non-employee directors, but reliance on an insider for coverage is an optics risk worth monitoring .
- Crypto-denominated fees: Director fees paid in bitcoin could raise volatility and perception issues; policy is clearly disclosed and applied uniformly to outside directors .
Overall signal: Strong independence determinations, full attendance, and long-vesting equity for new directors support investor confidence; continued scrutiny of Fanatics-related transactions and insurance coverage arrangements is warranted .