Chess Foundation

## How to Approach the CHESS Foundation

The CHESS Foundation, managed by trustees Scott and Caroline Wallach from Purchase, NY, operates with a clear philanthropic philosophy: promoting access to opportunity and reducing obstacles to a healthy and fulfilling life. With over $10 million in assets and no paid staff, this is a lean, donor-directed family foundation.

Key alignment signals: - Youth focus: The YES (Youth Empowerment through Sports) program is the foundation's flagship initiative, targeting ages 11-18 through mentoring combined with sports and outdoor instruction. - Low-income communities: The foundation explicitly prioritizes organizations serving low-income youth. Demonstrating measurable impact on underserved populations is essential. - Regional presence: Strong preference for New England and Mid-Atlantic organizations. Local roots and community ties matter. - Multi-sector interests: While youth sports is the primary vehicle, the foundation also funds health (Memorial Sloan Kettering), gun violence prevention (Everytown, Sandy Hook Promise), historic preservation (Jay Heritage Center), and higher education (Trinity College).

Theory of change: The Wallachs believe that structured mentorship through physical activity and outdoor access creates lasting positive outcomes for disadvantaged youth. Proposals should connect programmatic activities to long-term youth development outcomes.

What to avoid: The foundation states it "only makes contributions to preselected charitable organizations" — cold outreach without a prior relationship or open RFP is unlikely to succeed. Watch for periodic RFPs (YES program, Access to Nature) as the primary entry point.

## Funding Patterns

The CHESS Foundation has demonstrated steady growth in both assets and grantmaking over the past decade.

Financial trajectory: - 2013: $3.4M in assets (founding year) - 2020: $6.9M in assets, $440K distributed across 19 grants - 2023: ~$8.0M in assets, $527K distributed across 35 grants - 2024: $10.2M in assets, $622K in charitable disbursements

Grant distribution: - Typical range: $1,000 to $78,000 per grant - Median grant: $10,000 - Total annual giving: $500K-$620K - Number of grants: 19-35 per year, trending upward

Revenue model: The foundation generates income primarily from investment returns — asset sales (89.8%), dividends (6.6%), and interest (3.6%). With $0 in officer compensation and $0 in liabilities, virtually all revenue flows to grantmaking after minimal administrative expenses.

Sector allocation (2023): - Education and youth development: ~35% - Health and wellness: ~20% - Gun violence prevention/safety: ~15% - Historic preservation and arts: ~15% - Human services and community: ~15%

Geographic distribution: Grants flow to organizations across multiple states including New York, Connecticut, Maine, Arizona, Georgia, Kansas, and Massachusetts, with concentration in the Northeast corridor.

## Peer Comparison

The CHESS Foundation operates in the family foundation space focused on youth development and community welfare. Here is how it compares to peers in a similar asset range and focus area:

Key differentiators: - The CHESS Foundation is notably more diversified than chess-specific foundations — its name appears to be an acronym rather than a reference to the board game. - At $10.2M in assets, it sits in the mid-range for family foundations but punches above its weight in grant volume (35 grants on $10M vs. typical 15-20 for this asset class). - The foundation's zero-compensation model means a higher percentage of assets flow to charitable purposes compared to staffed foundations of similar size. - Unlike many preselected-only foundations, CHESS periodically opens competitive RFPs (YES, Access to Nature), creating genuine access points for new grantees.

## Recent Activity

2024 Financial Growth: The CHESS Foundation saw significant asset growth in 2024, reaching $10.18 million — up from approximately $8 million in 2023. Total revenue of $3.05 million was driven primarily by $2.74 million in asset sales, suggesting active portfolio management. Charitable disbursements increased to $622,750 in 2024, the foundation's highest level of giving to date.

Expanding Grant Programs: The foundation has been broadening its grantmaking scope. In addition to the established Youth Empowerment through Sports (YES) program, the CHESS Foundation launched an Access to Nature grants initiative with an RFP deadline of September 19, 2025, and awards expected by December 31, 2025. This represents a strategic expansion into environmental access and outdoor education.

Growing Grantee Portfolio: The number of grants has increased from 19 in 2020 to 35 in 2023, indicating the Wallachs are diversifying their grantee base. Major 2023 recipients included Jay Heritage Center ($70,000), Memorial Sloan Kettering Cancer Center ($50,000), and Everytown for Gun Safety ($50,000), alongside multiple $25,000 grants to organizations like Feeding Westchester, Sandy Hook Promise Foundation, and Habitat for Humanity.

Consistent Leadership: Scott and Caroline Wallach continue to serve as the sole trustees, each dedicating approximately one hour per week to foundation management without compensation. This lean governance structure has remained unchanged since the foundation's inception in 2013.

## Application Tips

1. Watch for open RFPs — they are your primary entry point. The CHESS Foundation periodically issues competitive Requests for Proposals for specific programs (YES and Access to Nature). Monitor Philanthropy News Digest, GrantStation, and the chessfdn@gmail.com address for announcements. When an RFP opens, act quickly — windows are typically 2-3 months.

2. Keep proposals concise and data-driven. The YES program requires submissions of no more than 3 pages. This signals that the Wallachs value brevity and clarity. Lead with outcomes data, not narrative. Include specific numbers: youth served, demographics, retention rates, and measurable impact metrics.

3. Demonstrate mentoring integration. The foundation is not just funding sports programs — it specifically requires mentoring alongside athletic instruction. Proposals must clearly articulate how adult mentors are recruited, trained, and matched with youth participants. A sports-only program without structured mentoring will not be competitive.

4. Show financial stability. The YES program requires a minimum $250,000 annual operating budget. The foundation wants to fund programs within established organizations, not startup ventures. Demonstrate financial health, diverse funding sources, and organizational capacity.

5. Emphasize geographic and demographic fit. New England and Mid-Atlantic organizations have a clear advantage. If your organization serves low-income youth ages 11-18 in this region, lead with that alignment. Include demographic data showing the populations you serve.

6. Build a relationship before the next RFP. While the foundation is primarily preselected, the Wallachs clearly expand their grantee network over time (from 19 to 35 grants in three years). Attend regional philanthropic events, connect through mutual grantee organizations (Jay Heritage Center, Feeding Westchester), and establish awareness before the next competitive cycle.

7. For health and safety organizations: The foundation's support for Memorial Sloan Kettering and gun violence prevention organizations (Everytown, Sandy Hook Promise) shows that health and public safety are within scope even outside the youth sports focus. Proposals in these areas should emphasize measurable harm reduction and prevention outcomes.