Lillie Family Foundation

Lillie Family Foundation is a small, closely-held family trust run entirely by its two namesake trustees, James E. Lillie and Lisa Marie Sheffield, both of whom report roughly two hours a week and take no compensation. There is no program staff, no grants portal, and — despite a listed website (lilliefamily.org) in public records — no live public web presence to consult; that domain now resolves to an unrelated nonprofit. This is a hallmark of a relationship-driven, closely-held giving vehicle rather than an institutional grantmaker with published guidelines. Organizations with the best odds fall into two buckets drawn directly from the grantee list: those serving the trustees' home communities of Block Island, RI (Block Island Health Services, $415,000 across 4 grants; Block Island Conservancy; Block Island Fire and Rescue; The Nature Conservancy's Block Island effort) and Aspen, CO (JAS Jazz Aspen Snowmass; Round Up River Ranch; Aspen Valley Hospital Foundation; Mountain Rescue Aspen; Independence Pass Foundation; Aspen Fire Protection District), and those connected to the trustees' professional or personal network in Miami Beach, where James Lillie serves as Vice Chairman of Mariposa Capital and formerly led APi Group Corporation (the foundation's largest 2025 grant, $250,000, went to APi Group's own corporate foundation). The single largest historical grantee overall, Health In The Hood ($625,000 across 4 grants, roughly 48% of the foundation's tracked cumulative giving), is a Miami-based urban agriculture and health nonprofit — reinforcing that a home-turf or personal connection matters more than a formal thematic fit. First-time applicants with no existing tie to Block Island, Aspen, Miami Beach, or the trustees' professional circle should treat this as a long shot; a cold written letter is the only documented path in, but the concentration of dollars in a handful of repeat, multi-year relationships (nearly every top grantee received 2-4 separate grants) suggests the foundation renews rather than seeks out new partners. Given the FY2025 capital infusion that more than doubled assets to $10.4M, there is realistic upside for expanded giving in coming cycles, but nothing in the record indicates the foundation plans to formalize an open application process.

Across the tracked grant history (40 grants, $1,312,183 cumulative, average $32,805 per grant), giving is heavily concentrated: the top two recipients — Health In The Hood ($625,000) and Block Island Health Services ($415,000) — together account for 79% of all dollars tracked, while the remaining 14 grantees split about $272,000 in gifts mostly ranging from $1,000 to $20,000. The foundation's own reported typical grant size (most recent full cycle) shows a median of $8,900 and mean of $24,756 on a range of $5,000 to $105,000 — meaning a handful of large, repeat commitments coexist with many small, one-off community gifts. Annual payout has grown steadily off a small base: $264,450 (FY2019) to $325,680 (FY2020) to $285,265 (FY2021) to $272,459 (FY2022) to $504,575 (FY2023) to an estimated $363,980-$501,300 in the most recent filings (sources diverge slightly on fiscal-year labeling, but all cluster in the $360K-$500K range). Assets, by contrast, jumped sharply: from $3.55M (2019) to a peak near $5.9M (2020, on a $2.66M contribution) to $4.5M (2022-2023) to $10.37M in the most recent filing, driven by a roughly $6.1M capital contribution in the fiscal year ending June 2025 — the trustees are actively growing the corpus faster than they are increasing payout. Geographically, Colorado (13 of 40 tracked grants) and Rhode Island (10 of 40) dominate by count, with Connecticut (7), Florida (4), Maryland (3), New York (2), and New Hampshire (1) rounding out the map — a footprint that tracks the trustees' known residences (Aspen, Block Island, Miami Beach) plus a Connecticut-based grantee (Family & Children's Agency, $85,025) that may reflect an earlier personal tie, since the foundation's contact listing traces to a Connecticut area code (203). Nearly all grants (100% of the top-50 list) carry an 'UNRESTRICTED' purpose designation — this foundation funds general operations, not restricted projects.

All five peer foundations sit within roughly $10,000 of Lillie Family Foundation's asset base and share its NTEE classification of Philanthropy & Grantmaking, but only Hilaron Foundation maintains a public website — the rest, like Lillie, appear to be closely-held family vehicles with no public grant guidelines. This is a structural pattern at the ~$10M asset tier: foundations here typically lack program staff and operate on personal referral rather than open competition, which means Lillie Family Foundation's written-letter approach is actually more transparent than most of its immediate size peers, four of which offer no discoverable entry point at all.

The most consequential recent development is financial rather than programmatic: the foundation's fiscal year ending June 2025 filing shows total assets rising to $10,372,280 from $4,533,910 the prior year, driven by a contribution of approximately $6.1M from the trustees (contributions made up 98.6% of that year's $6.2M in revenue per CauseIQ's summary of the filing). This more than doubled the foundation's corpus in a single year — the largest capital event since its 2018 IRS ruling. On the grantmaking side, FY2025 data aggregated by Instrumentl and Grantable show 10 grants totaling $363,980-$364,000, with the single largest gift ($250,000) going to API Group Foundation — the corporate foundation of APi Group Corporation, where trustee James E. Lillie served as Co-Chairman and CEO following the company's 2019 acquisition and NYSE listing. Other confirmed FY2025 recipients include Round Up River Ranch ($35,000) and JAS Jazz Aspen Snowmass ($26,350), both continuing the foundation's long-standing Aspen-area giving pattern seen in the multi-year grantee list. No independent news coverage, press releases, or leadership changes were identified for the foundation itself — it has no communications presence, and searches for 'Lillie Family Foundation' news are dominated by unrelated organizations (Lilly Endowment Inc., Eli Lilly and Company Foundation, various unrelated 'Lillie'-named charities). The most reliable forward-looking signal is the asset growth itself: a foundation that just added $6M+ in capital typically increases its 5%-minimum-payout requirement in subsequent filing years, which could mean materially larger checks are possible in FY2026-2027 even without any change in stated priorities.

Because Lillie Family Foundation publishes no grant guidelines, portal, or deadline, the only documented instruction — straight from its IRS filing — is to 'apply in writing and include the purpose of the grant.' Treat this literally: a one- to two-page letter, not a full proposal narrative, addressed to the trustees (James E. Lillie and Lisa Marie Sheffield) at the foundation's Miami Beach address (3651 Collins Avenue, Unit 300, Miami Beach, FL 33140), is the appropriate format — lengthy applications built for institutional funders will likely be a mismatch for a two-person, no-staff operation that spends roughly two hours a week on foundation business. Because 100% of the top-50 tracked grants are coded 'UNRESTRICTED,' frame the ask as general operating support tied to organizational mission and impact rather than a itemized project budget — this foundation has shown no pattern of restricted, deliverable-based giving. Geographic and relational alignment matters more than thematic fit: organizations based in or directly serving Block Island, RI or Aspen, CO have historically received the largest share of grant count (23 of 40 tracked grants between the two), and the FY2025 addition of API Group Foundation as a top recipient confirms that professional and personal ties to the trustees (Mariposa Capital, APi Group Corporation) also open doors. A common mistake would be treating this as an open, competitive grant program — the concentration of repeat, multi-year gifts to the same ~16 organizations (many receiving 2-4 separate grants over the tracked period) indicates the foundation renews existing relationships far more often than it originates new ones. There is no visible LOI-to-full-proposal pipeline, no site-visit process documented, and no application_deadline on file, so there is no 'optimal season' to identify from the data — cold outreach should focus on building a warm introduction (a board member, an Aspen or Block Island community connection, or a Mariposa Capital/APi Group relationship) before submitting a written request, since that is the only channel with any evidence of working.