Constitution Foundation

The Constitution Foundation is Michael J. Saylor's personal private foundation, established in 1999 in Annapolis, Maryland. Saylor — founder and executive chairman of Strategy (formerly MicroStrategy), a leading Bitcoin treasury company — serves as its sole trustee, wielding complete discretionary control over all grantmaking decisions. There is no formal public application process; the IRS filing records '__none__' for application instructions, and no grant portal, LOI form, or published deadlines exist.

Giving reflects Saylor's personal philanthropic priorities rather than any institutionalized grant program. Historically, this has meant sustained, multi-year giving to a very short list of causes: performing arts (Wolf Trap for the Performing Arts received $326,420 across four grants), libertarian/Objectivist ideas (Atlas Society received $65,000 across three grants), health research (Breast Cancer Research Foundation, $17,500 across four grants), and online civic education (the constitution.org website is the foundation's primary operating program).

The relational nature of this foundation cannot be overstated. Access flows through personal connections to Saylor or his immediate circle, not through unsolicited proposals. Saylor is a prominent figure in technology and Bitcoin circles who has spoken extensively about the moral importance of free, open-access digital education — a value that permeates his giving. Organizations that can demonstrate genuine alignment with these themes and approach through a warm introduction stand the best chance of success.

First-time applicants should also be aware that the foundation's external grantmaking has declined sharply in recent years — from roughly $148,000 in FY2019 to just $10,050 in FY2023 — as Saylor's attention has shifted primarily to Bitcoin advocacy. Any outreach should be calibrated to this context: this is a foundation in a lower-activity period, not one actively seeking new grantees.

The Constitution Foundation's financial disclosures require careful interpretation. 'Total giving' on IRS Form 990-PF ($1.8M–$3M per year) is dominated by program service expenditures for the constitution.org educational website, not discretionary grants to outside organizations. Actual external grants paid are far smaller and have declined significantly:

• FY2023: $10,050 in grants paid
• FY2022: $102,740
• FY2021: $57,088
• FY2020: $136,352
• FY2019: $148,454
• FY2015: $98,040

The realistic baseline for external grantmaking is approximately $10,000–$150,000/year, with the trend pointing toward the lower end.

From documented grantee records, 12 total grants totaling $408,970 have been recorded (average: $34,081/grant). The distribution is highly concentrated:

• Wolf Trap for the Performing Arts (VA): $326,420 across 4 grants (~$81,600/grant average) — accounts for 80% of documented external giving
• Atlas Society (NY): $65,000 across 3 grants (~$21,667/grant average)
• Breast Cancer Research Foundation: $17,500 across 4 grants (~$4,375/grant average)
• Alzheimer's Association: $50 (single gift, likely nominal)

The grant size range is therefore extreme: from $50 to approximately $110,000+ per individual award. The median grant, excluding the Alzheimer's nominal gift, is roughly $21,000–$22,000.

Geographically, grants cluster in Virginia (4 grants), New York (4), and Texas (3), with one Illinois grant — a footprint consistent with organizations in Saylor's personal network rather than a deliberate geographic strategy.

Total assets peaked at $27.2M in FY2020 after a $19.4M one-time contribution, declining to $17.3M by FY2024. Net investment income ($907K–$2.1M/year) is the primary revenue driver, suggesting a marketable securities portfolio.

The Constitution Foundation sits within the NTEE T20 (Philanthropy & Grantmaking) category alongside similarly-sized personal and family foundations. The following peers share comparable asset levels (~$17.3M) as of the most recently available filings:

All five peer foundations are personal or family foundations in the T20 category with no public application processes. The Constitution Foundation is distinguished from most peers in two important respects: first, it is operated by an extremely prominent technology entrepreneur whose profile creates unique opportunities for relationship-building in specific networks (tech, Bitcoin, classical arts); second, it operates a significant ongoing program (constitution.org) that absorbs the bulk of its expenditures, making its external grantmaking unusually small relative to its total assets and total giving figures. Among the peer set, the Constitution Foundation is the only one with a documented mission statement and active operating program tied directly to its grantmaking philosophy.

No press releases, grant announcements, or program updates specific to the Constitution Foundation were identified in 2025 or 2026 public sources. The foundation maintains an extremely low institutional profile, with no standalone communications strategy, press room, or social media presence separate from Michael Saylor's personal accounts.

The most significant contextual development shaping the foundation's recent trajectory is Saylor's near-total pivot to Bitcoin advocacy following MicroStrategy's (now Strategy) decision in August 2020 to adopt Bitcoin as its primary treasury asset. The company held over 200,000 BTC as of early 2025. This shift in Saylor's focus correlates directly with the foundation's external grantmaking falling from $136,352 (FY2020) to $102,740 (FY2022) to $10,050 (FY2023).

The constitution.org website — the foundation's primary operating program — remains active as a civic education resource covering constitutional law and American founding documents. The site hosts a 'Liberty Library of Constitutional Classics' and produces educational video content.

Historically, the foundation supported major arts organizations (Washington Ballet, Lincoln Center, Kennedy Center, Wolf Trap), education initiatives (Saylor Academy, Fight for Children, Jill's House), and health causes (Elton John AIDS Foundation, amfAR). Recent IRS filings suggest the grantee roster has narrowed sharply to Wolf Trap and the Atlas Society as primary recipients.

Given that the Constitution Foundation has no public application process and all giving is discretionary to Michael J. Saylor as sole trustee, the following tips are grounded in what we know about Saylor's giving history and personal values — not a formal grant program.

1. Do not cold-apply. There is no grant portal, no LOI form, and no published contact for grant inquiries. The IRS filing lists contact '% Thomas Heyer' at the Annapolis address, who is likely a professional fiduciary administrator, not a program officer.

2. Identify genuine mission alignment. Documented giving clusters in four areas: (a) free and open-access digital education, (b) Objectivist/libertarian philosophy and think tanks (Atlas Society is the Ayn Rand Institute's major competitor), (c) classical and fine performing arts, and (d) women's health and cancer research. If your organization does not genuinely fit one of these categories, the Constitution Foundation is not a realistic prospect.

3. Build a pathway to Saylor personally. Saylor is highly accessible in Bitcoin/crypto conferences, technology forums, and online through X, where he is one of the most-followed Bitcoin voices. Meaningful engagement with his public ideas on education and economic freedom — not generic networking — creates the most credible introduction pathway.

4. Use alignment language strategically. Saylor has written extensively on the moral obligation to provide free digital education and on Objectivist economic principles. Proposals should echo his documented values: impact at scale, open access, rational self-reliance, and long-term societal benefit through education.

5. Calibrate ask size appropriately. New grantees should target $5,000–$25,000 for an initial request. Wolf Trap's ~$81,600/grant reflects a decade-long relationship; expect to start much smaller.

6. Expect no formal review cycle. Grants appear made at Saylor's discretion with no seasonal deadline. Relationship cultivation is ongoing, not event-driven.

7. Prioritize organizations in Virginia, New York, or with national reach. Geographic concentration of past grants suggests personal connection to these areas.