Four Winds Foundation

Four Winds Foundation is a sole-trustee private foundation established in Boxford, Massachusetts, in 2014 with a $30 million founding endowment. The entire operation is controlled by a single individual, trustee Diana D. Merriam, who receives no compensation and has no support staff — making this a personal philanthropy vehicle rather than an institutional grantmaker in the conventional sense.

The foundation's giving philosophy is entirely relationship-driven and preselective. There is no public RFP, no online application portal, no formal grant cycle, and no documented LOI process. All grantees have been preselected by the trustee, which means the pathway to funding runs exclusively through cultivating a direct relationship with Diana D. Merriam. Organizations that have received grants — Eagle Hill School, Esperanza Academy, and Alzheimer's Research — almost certainly came to the trustee's attention through personal networks, existing philanthropic relationships, or board-level introductions.

A notable complexity: the foundation's formal mission statement references "Indigenous crisis counselling and support services" in Victoria, Australia, and its web-enrichment data lists an Australian geographic focus. Applicants should disregard this language when assessing fit. The actual grant record is entirely US-based, focused on Connecticut, Massachusetts, and California, and concentrated in specialized education and health research. The stated mission appears to reflect language from a connected but distinct Australian entity; the US foundation's revealed priorities diverge significantly.

For first-time applicants, the practical entry path is a brief, personalized cold introduction via fourwindsfoundationlimited@gmail.com — the only confirmed contact. Keep the message to 3-4 sentences: who you are, what specific program you want funded, the dollar amount, and an explicit link to one of her documented grantees or cause areas. No attachments. The goal of the first contact is not to submit a proposal but to open a conversation.

Organizations should expect no formal review timeline. In a sole-trustee structure, decisions happen on the trustee's personal schedule. A follow-up after 60 days is appropriate, but patience is essential. Multi-year relationships appear to be the norm — Eagle Hill School's consecutive $1M grants over at least three years demonstrate that the trustee values sustained commitments to partners she trusts.

The foundation's grant history reveals a concentrated, high-value model with very few grantees receiving very large awards.

From 2015 through 2023, total annual giving ranged between $241K (2015, earliest active year) and $3.43M (2020, a COVID-period spike). For the five-year span from 2019 to 2023, annual giving settled into a consistent $1.31M–$2.19M band, with grants-paid specifically tracking at $1M per year in each of those years — all to a single grantee, Eagle Hill School.

Fiscal 2024 represents a dramatic departure. Total charitable disbursements reached approximately $6.5M across three grantees: - Eagle Hill School (Greenwich, CT): $1,000,000 (repeat grantee) - Esperanza Academy (Lawrence, MA): $2,500,000 (new grantee) - Alzheimers Research (Novato, CA): $2,950,000 (new grantee)

The average grant in 2024 was approximately $2.17M, with a range of $1M–$2.95M. This represents a material shift from the prior five-year baseline average of ~$1M per grant.

By sector, the cumulative grant record breaks down roughly as: ~45% to specialized/independent K-12 education (Eagle Hill School, Esperanza Academy), ~45% to Alzheimer's and health research (new in 2024), and ~10% to earlier, smaller disbursements in the foundation's early years (2015–2018).

Geographically, Connecticut has historically dominated (Eagle Hill School is the anchor), with Massachusetts added in 2024 (Esperanza Academy) and California emerging as a new geography (Alzheimers Research, Novato).

Asset trajectory signals spend-down: Assets fell from ~$30M at founding (2014) to $26.7M (2023) and then sharply to $22.5M (2024), a decline of ~$4.2M in a single year while net investment income of ~$1.1M cannot offset $6.5M in disbursements. If this pace continues, the foundation may exhaust its endowment within 4–6 years, making the current window especially important for organizations seeking to establish a relationship.

The foundation operates within a cohort of similarly-sized private grantmaking foundations (NTEE code T20, Philanthropy & Grantmaking) with assets clustered in the $22–$23M range as of the most recent fiscal year.

Among this asset-size peer group, Four Winds Foundation stands out for its sole-trustee governance and spend-down trajectory. Most foundations at this scale maintain at least a part-time program officer or advisory board and distribute a conventional 5% of assets annually (~$1.1M–$1.6M). Four Winds' 2024 payout of $6.5M was roughly four times the peer-group norm, suggesting an atypical operating posture — either deliberate spend-down or a one-time acceleration.

The Elaine P. Wynn & Family Foundation is the most strategically comparable peer: a family foundation of similar asset scale with a documented interest in education and children's welfare, also operating primarily through invited grantmaking rather than open applications. Grant seekers who have navigated invite-only family foundations of Wynn's type will find the dynamics at Four Winds familiar.

The most significant development at Four Winds Foundation is the dramatic expansion of grantmaking in fiscal year 2024. After at least five consecutive years of single-grantee, $1M disbursements exclusively to Eagle Hill School, the foundation awarded three grants totaling approximately $6.5M — the largest annual disbursement in its documented history.

The addition of Alzheimers Research (Novato, CA) as a $2.95M grantee represents the foundation's first known grant to a health or research organization, and its first grant to a California recipient. The exact recipient organization could not be independently confirmed from public filings, but Novato-area Alzheimer's organizations include research and care entities in the greater San Francisco Bay Area.

Esperanza Academy (Lawrence, MA), a tuition-free Catholic school for girls in one of Massachusetts' most economically distressed cities, received $2.5M — the foundation's largest single-year educational grant to a new institution and its first Massachusetts grant. This gift signals a possible interest in faith-based, equity-focused education alongside the specialized learning-differences model represented by Eagle Hill.

No press releases, public announcements, or leadership changes were found through web research for 2025 or 2026. The foundation's website (fourwindsfoundation.com) appears inactive or minimal. Diana D. Merriam has remained the sole trustee throughout the foundation's life. The complete absence of social media presence, press coverage, or public communications is consistent with a deliberately private philanthropic posture — a pattern that is unlikely to change.

Because Four Winds Foundation operates as an invite-only grantmaker with no public application process, conventional grant-writing strategy does not apply. Success depends entirely on relationship access to trustee Diana D. Merriam. The following tips are specific to this funder:

1. Confirm alignment with the three demonstrated priority areas before any outreach. The foundation has funded: (a) specialized or independent K-12 schools serving students with learning, language, or social differences (Eagle Hill School model); (b) tuition-free Catholic or faith-based K-12 education in underserved urban communities (Esperanza Academy model); and (c) Alzheimer's disease research or care (new in 2024). Only organizations genuinely fitting one of these areas should invest time pursuing this funder.

2. Ignore the stated mission language. The foundation's formal mission references Indigenous crisis counseling in Australia. This does not reflect actual US grantmaking and should not be used to frame your alignment pitch.

3. Send a brief, targeted cold email to fourwindsfoundationlimited@gmail.com. Three to four sentences maximum: (1) who your organization is and what it does; (2) the specific program you need funded; (3) the dollar amount; and (4) an explicit connection to her prior grantees. No attachments.

4. Anchor your pitch to known grantees. Eagle Hill School and Esperanza Academy are the strongest reference points. If your organization shares board members, serves similar students, uses a comparable model, or has been formally affiliated with either school, say so.

5. Request no more than $1M in a first conversation. Eagle Hill's consistent $1M floor is the clearest signal of the entry-level grant size for a new relationship. Larger asks ($2-3M) appear reserved for established partners.

6. Operate at organizational scale. The foundation does not make sub-$1M grants in recent years. Organizations with operating budgets under $2–3M may lack the capacity infrastructure that a grantee of this size requires.

7. Act with some urgency. The foundation's rapidly declining asset base and 2024 spend-up suggest a possible wind-down horizon. Organizations that delay outreach risk missing the window entirely.

8. Follow up once, at 60 days. There is no program staff to track inquiries. A single polite follow-up is appropriate; beyond that, redirect your energy elsewhere until circumstances change.