Stifler Family Foundation

The Stifler Family Foundation (Brookline, MA; EIN 10-6001398; $48.3M in assets as of FY2024) was established in 2001 by Larry Stifler and Mary McFadden. Larry is the founder of Health Management Resources (HMR), a medical lifestyle-change company he led from 1983–2013; Mary is an attorney and former Executive Director of the Massachusetts Commission on Judicial Conduct. Both have extensive personal and professional backgrounds tied to scholarship support (Larry received scholarships at Calvert, Gilman, Dartmouth, and BU) and to land conservation (the family co-founded the Wareham Land Trust in 2001 and, in 2021, placed a conservation easement on ~12,000 acres in Western Maine called "Northern Retreat"). The Foundation's stated guiding principles are "gratitude, humility and impact," and it publicly identifies five priority areas: land conservation / environment, education, science, social justice, and the arts, with a separately named sub-bucket for grassroots organizations. The Foundation is a family-principal-led, trust-based grantmaker with deliberate second-generation involvement: daughter Molly Stifler became the Foundation's first Director in 2021; daughter Haley serves as an advisor (she founded MassVaccineHelp during COVID). The Foundation emphasizes listening to grantees and tailoring support to each partner's financial and organizational needs — classic trust-based philanthropy language.

The Foundation self-reports "over one thousand grants" awarded since inception in 2001 — a high grant-count indicator of broad, relationship-driven grantmaking rather than a few large institutional commitments. Per ProPublica Nonprofit Explorer, annual expense history shows: FY2024 $1.52M; FY2023 $1.45M; FY2022 $4.41M; FY2021 $3.33M; FY2020 $2.51M; FY2019 $1.33M; FY2015 $1.93M; FY2014 $0.84M. Total assets have grown steadily from ~$9M in 2011 to $48.3M in 2024, suggesting the family has continued to capitalize the Foundation while maintaining a lumpy but typically $1.5M–$4M/year outflow. With >1,000 grants over ~24 years, average grant size is likely in the $5K–$50K range, consistent with a foundation that supports many community and grassroots partners alongside larger anchor commitments. Given the family's own co-founding of the Wareham Land Trust and Maine Mineral & Gem Museum, expect a meaningful share of conservation grants to concentrate on land trusts and place-based stewardship in Massachusetts and Maine. The science portfolio likely ties to biomedical and natural-history organizations reflecting Larry's PhD training and HMR background. No public grants database is published; the most recent Form 990-PF (EIN 10-6001398) is the authoritative source for grantee identity and grant sizes.

Stifler sits in the mid-tier of Massachusetts family foundations. It is closer in posture to Island Foundation or Cabot (relationship-oriented, invitation-leaning) than to the open-RFP Kendall or Boston Foundation. Its distinctive combination — Maine land conservation + Massachusetts-based family with multi-generation involvement — differentiates it from peers with purely regional or purely thematic lenses.

The Foundation's website (stiflerfamily.org, WordPress on the Avada/Fusion theme) confirms active operations with continued emphasis on its five priority areas and grassroots sub-bucket. Notable recent-era milestones: Molly Stifler became the Foundation's first Director in 2021 — a structural signal of professionalization and possible increase in grantmaking capacity; the 2021 conservation easement on ~12,000 acres of Western Maine ("Northern Retreat") is a major family-level commitment with ongoing stewardship implications visible on the About page. FY2024 ProPublica financials show $48.3M in assets (up from $46.6M in 2023 and $43M in 2019) and $1.52M in expenses, consistent with the lower end of the Foundation's historical range. The Foundation's website footer shows a 2022 copyright (not 2026), which may indicate the site content has not been refreshed recently even though grantmaking continues. No public announcements of new programs, RFPs, or strategic shifts were discoverable through open web search. The 990-PF for fiscal year ending 2024 should be consulted directly for the most current grantee list.

1. Do not submit unsolicited grant applications. The Foundation states explicitly: "the Stifler Family Foundation does not accept unsolicited grant applications." Cold submissions are a non-starter. 2. Build a relationship-based pathway. The About page invites the Foundation to "learn about organizations working to improve their communities." The practical implication is that outreach should be introductory and informational (short email introducing your work, board/leadership bios, one-page overview), not a formal ask. 3. Strong geographic fit: Massachusetts and Maine. The family has deep MA roots (Brookline HQ) and major conservation presence in Western Maine (~12,000-acre Northern Retreat). Organizations outside New England have a lower probability of fit. 4. Align to one of five explicit buckets: (a) land conservation / environment, (b) education — especially scholarship and access for first-generation students (Larry's personal story), (c) science and research, (d) social justice, (e) arts. The "grassroots organizations" sub-bucket is a clear opening for small, community-driven nonprofits that larger foundations pass over. 5. Look for warm intros through: Wareham Land Trust board, Dartmouth College alumni philanthropy networks, Maine Mineral & Gem Museum, Massachusetts conservation coalitions (Mass Land Trust Coalition, Mass Audubon), or educational scholarship program leaders in Boston-area independent schools. 6. Expect grants in the $5K–$50K range for new relationships. The Foundation has made over 1,000 grants since 2001 — this is a high-count, many-partner funder, not a write-very-large-checks one. Large commitments are reserved for proven multi-year grantees.