Circle Square Foundation

Circle Square Foundation is an IRS-designated private operating foundation (subsection 03), meaning it exists to operate its own charitable programs rather than to distribute grants to external organizations. This distinction is the single most important fact any grant seeker must internalize before investing time in a funding approach.

Founded in 2019 through a transformational $124.9 million endowment contribution from the Colen family of Ocala, FL, the foundation's entire charitable purpose is the development, construction, and operation of two facilities at Circle Square Commons in southwest Ocala: the Florida Aquatics Swimming & Training center (FAST) and a Joint Worship Facility. FAST opened to serve the Ocala community after the closure of the Newton A. Perry Aquatic Complex at the College of Central Florida, featuring a 10-lane 50-meter indoor competition pool, an outdoor 8-lane 50-meter pool, a splash pad, and drown-prevention programming.

Kenneth D. Colen serves as the sole Trustee, devoting 20 hours per week without compensation — a strong signal that this is a family-directed operating foundation, not an institutional philanthropy with staff program officers reviewing proposals. Executive Director Rebecca Rogers ($80,000–$97,000 annually) manages operations, supported by General Manager Kevin Milak ($131,226), Director of Facilities Stephen Coy ($97,521), and Head Swim Coach Christopher George ($83,972). The roughly 10-person staff reflects a facility operations culture, not a philanthropic grants culture.

External community giving is minimal and relationship-driven. The Community Foundation for Ocala Marion County has received $75,500 across 3 grants (average $25,167), representing the only consistent external beneficiary outside of the Colen Family Charitable Trust. Token grants of $120 each to Trinity Catholic High School, Blessed Trinity, and Happy Hearts Preschool in FY2024 reflect the Colen family's personal ties to southwest Ocala's residential and faith community, not a competitive grant program.

For the rare external organization that does receive funding consideration, the relationship almost certainly begins with a personal introduction to Kenneth Colen or Rebecca Rogers through Ocala's civic, faith, or aquatics community networks — not through a formal application process.

Circle Square Foundation's giving history falls into three distinct phases since its 2019 founding:

Phase 1 — Pre-operational (FY2019–FY2020): No external grants were paid in either year ($0 grants paid), despite assets of $126.5M–$134.1M. The $124.9M founding endowment arrived in FY2019 via contributions, and the foundation focused entirely on planning and permitting FAST. Total giving was just $806,956 (FY2019) and $906,307 (FY2020), reflecting early pre-construction costs only.

Phase 2 — Capital and launch (FY2021–FY2023): Grantmaking spiked to $17.19M (FY2021) and $11.98M (FY2022), with total giving at $18.97M and $17.49M respectively. The dominant flow was to the Colen Family Charitable Trust: $46.27M across 3 grants, representing 99.8% of all identifiable grantee disbursements. These are best understood as inter-entity capital transfers for facility construction financing, not community philanthropy. External giving remained negligible.

Phase 3 — Operational steady-state (FY2024–FY2025): Grantmaking collapsed to approximately $2.0M in FY2024 (Colen Family Trust: $1.99M; Community Foundation for Ocala: $25,500; local schools: $120 each). FY2025 reports $5.02M in charitable disbursements but these primarily represent FAST operating program expenses — facility management ($6.26M expense line), construction/development ($12.20M program expense in prior filings), and worship facility operations ($40,579) — not external grant distributions.

External community grantmaking summary (all years): - Community Foundation for Ocala Marion County: $75,500 total (3 grants, avg $25,167) - Trinity Catholic High School: $120 (FY2024) - Blessed Trinity: $120 (FY2024) - Happy Hearts Preschool: $120 (FY2024) - Veterans Helping Veterans: $100 (1 grant)

Total external community grantmaking: approximately $76,000 across 7 grants. Median external grant: $120. The only grant of meaningful scale to a community organization was the Community Foundation for Ocala, and even there, individual grants averaged under $26,000.

The foundation's revenue model relies on investment income ($821K interest, $739K dividends in FY2025), aquatic center user fees and memberships (~$2.21M in other income), and minimal outside contributions ($102,500 in FY2025). With operating expenses of $8.7M against revenue of $4.68M in FY2025, the foundation is intentionally drawing down its $105.1M endowment to subsidize FAST's community mission.

The database identifies five peer foundations in the Human Services NTEE category with comparable asset profiles. Annual giving data for peers is not publicly reported in the available database records; asset figures are drawn from the most recent available IRS filings.

Circle Square Foundation sits near the median of its peer group by asset size at $105.1M, closely comparable to Paul Simons Foundation ($109.3M) and Aspire Foundation ($101.7M). However, it diverges fundamentally in structure: as a private operating foundation, Circle Square consumes its resources running its own programs, while traditional grant-making foundations in this peer group distribute assets to external nonprofits. The Linda Pace Foundation (San Antonio, TX) is perhaps the most instructive peer — a family art foundation that operates its own cultural facilities and gives by invitation only. Bella Mente Quantum Racing Association presents a similarly unusual categorization under Human Services, suggesting that NTEE coding in this peer set reflects recreational and community programming rather than traditional social services delivery. Organizations seeking grant opportunities from similarly-sized foundations should look beyond this peer group to foundations with published open application cycles.

The foundation's most significant public milestone was the October 27, 2020 groundbreaking for FAST (Florida Aquatics Swimming & Training) in Ocala, FL, at which Trustee Kenneth Colen articulated the facility's community mission: to fill the gap left by the closure of the Newton A. Perry Aquatic Complex at the College of Central Florida and to provide Ocala's high school swim teams and recreational swimmers with world-class facilities.

No public news releases, grant announcements, or leadership changes were identified for 2025 or 2026. The most recent Form 990-PF, filed February 14, 2026 for the fiscal year ending March 2025, provides the clearest window into current activity. That filing shows expanded operational leadership — Kevin Milak added as General Manager at $131,226, alongside Stephen Coy (Director of Facilities, $97,521) and Christopher George (Head Swim Coach, $83,972) — confirming FAST is now in full operational mode with a mature management team.

Assets declined to $105.1M in FY2025 from $109.1M in FY2024, continuing a multi-year draw-down trend. The Colen Family Charitable Trust received $1.99M in FY2024, the Community Foundation for Ocala Marion County received $25,500, and three local Ocala schools received token $120 grants each. No major new program areas, community grant competitions, or strategic pivots have been publicly announced. The Circle Square Cultural Center at Circle Square Commons (8395 SW 80th St, Ocala) continues to operate as an adjacent entertainment and performing arts venue, further establishing the Colen family's integrated vision for the SW Ocala community.

The foundational reality is that Circle Square Foundation does not operate a grants program. Its IRS Form 990-PF records application instructions as 'none,' and grant databases flag it as 'preselected only.' No unsolicited proposal, letter of inquiry, or grant application submitted to this foundation will be considered through a formal process. The advice below is therefore oriented toward the realistic paths by which an organization might eventually benefit from Circle Square resources:

Route 1 — Community Foundation for Ocala Marion County (CFOM). CFOM is the only consistently funded external community beneficiary, receiving $75,500 across three grants from Circle Square Foundation. Ocala-area nonprofits with strong CFOM relationships are far better positioned to access Colen family philanthropy indirectly than through any direct approach. Build CFOM relationships, apply to CFOM's regular grant cycles, and note shared priorities with FAST and the southwest Ocala community in your CFOM applications.

Route 2 — Programmatic partnership with FAST. The aquatic center is a living, operational facility hosting swim teams, recreational programs, and drown-prevention classes. Nonprofits offering complementary programming — adaptive aquatics for people with disabilities, youth development through swimming, water safety education for underserved populations — have a legitimate basis to approach FAST's operational leadership for program partnerships. Contact Rebecca Rogers, Executive Director, at (352) 387-7492. Lead with programming alignment, not funding asks.

Route 3 — Local civic and faith-community presence. The $120 grants to Blessed Trinity, Trinity Catholic High School, and Happy Hearts Preschool reveal that the Colen family maintains personal ties to Ocala's Catholic and preschool communities near Circle Square Commons. Faith-based and early childhood organizations in southwest Ocala's 34481 ZIP code should prioritize authentic community relationship-building with the Colen family over grant-writing.

Critical caution on outreach: Do NOT send correspondence or emails to www.circlesquare.org — that website belongs to Circle in the Square Theatre School in New York City. Use the correct mailing address: 8435 SW 80th St Unit 2, Ocala, FL 34481-9127, phone (352) 387-7492. The foundation's fiscal year ends March 31, so any relationship-building targeting year-end generosity should be timed for January–March.