Windward Foundation

Windward Foundation is a closed, relationship-driven family foundation run entirely by the Perry family of Virginia Beach — President J Christopher Perry (who succeeded founding president Joseph C Perry in the 2024 tax year) and Secretary Cathryn T Perry, both unpaid, with no program staff. The IRS filing lists no application form, no deadline, no funding cycle, and no grants portal (application_instructions field is explicitly blank), and the foundation's own database record flags it as 'preselected only' — meaning the overwhelming pattern in its giving is renewal of existing relationships, not response to open solicitations. Grant seekers should not expect a cold LOI or online application to work here; there is no mechanism for one.

The grantee roster confirms this: across 56 tracked grants totaling $1,489,333, just three organizations — Norfolk Academy ($501,000 across 5 grants), JDRF ($225,000/4 grants), and YMCA of South Hampton Roads ($200,000/4 grants) — absorb 62% of all dollars. These read as anchor relationships (a private school likely tied to family or board ties, a national health charity, a hometown YMCA) that get funded repeatedly, year after year, rather than a rotating cast of new grantees. A second tier of Hampton Roads and Outer Banks community organizations (An Achievable Dream, Dare County Boat Builders Foundation, Foodbank of Southeastern Virginia, Elizabeth River Project, Virginia Beach Billfish Tournament, Hatteras Marlin Club) suggests the Perrys' personal and recreational interests — sport fishing and boating on the Outer Banks, Chesapeake/coastal environmental causes — shape a meaningful share of discretionary giving.

For a first-time applicant, the realistic path is not a proposal but an introduction: a board member, staff, or community contact with a genuine tie to the Perry family or to one of the anchor grantees (Norfolk Academy, YMCA of South Hampton Roads, JDRF's local chapter) is far more likely to get a hearing than any written application. Organizations based outside Hampton Roads, VA, or the Outer Banks, NC corridor face long odds: 45 of the 56 tracked grants (80%) went to Virginia recipients, with the remainder scattered across NC, NY, NH, and LA in ones and twos.

Windward Foundation's giving has contracted sharply from its high-water mark. Total giving peaked at $800,747 in FY2019, then declined to $576,644 (2020), $507,401 (2021), $291,903 (2022), and $331,583 in FY2023 (grants paid: $311,000) — a 59% drop from peak to the most recent fully reported year. FY2024 shows charitable disbursements of roughly $328,696 against total revenue of just $192,071, meaning the foundation is distributing more than it earns and drawing down principal; total assets fell from $5,421,388 (FY2023) to $5,261,720 (FY2024), continuing a slide from $5.9-6.2M in 2019-2020.

Per-grant sizing (typical_grant_size field): median $10,000, average $36,194, range $5,000-$266,000 — the wide gap between median and average reflects a small number of large, recurring checks pulling the mean up. Looking at the full 56-grant history, most individual disbursements cluster between $1,000 and $40,000, while the three anchor relationships (Norfolk Academy $501,000, JDRF $225,000, YMCA of South Hampton Roads $200,000) account for $926,000 — 62% of the $1,489,333 cumulative total captured in the data.

By rough program area: education/youth development takes roughly 40% of tracked dollars (Norfolk Academy $501,000, An Achievable Dream $85,000, First Tee of Hampton Roads $20,000); health and human services roughly 25% (JDRF $225,000, Foodbank of Southeastern Virginia $70,000, Salvation Army $40,000, Mercy Chefs $10,000, Meals on Wheels VB $10,000, Samaritan House $10,000); community/recreation roughly 22% (YMCA $200,000, Virginia Beach Billfish Tournament $35,000, Dare County Boat Builders Foundation $75,000, Hatteras Marlin Club $33,333); and environment a small remainder (Elizabeth River Project $40,000, Virginia Aquarium $2,000). Geographically, 45 of 56 grants (80%) stayed in Virginia, concentrated in the Virginia Beach/Norfolk/Hampton Roads area, with secondary clusters in coastal North Carolina (Outer Banks) and scattered single grants to New York, New Hampshire, and Louisiana.

Windward Foundation sits in a tight cluster of small, single-family, asset-matched private foundations classified under Philanthropy & Grantmaking — all holding roughly $5.26M in assets, which is more a database-matching artifact (identical asset bands) than evidence of similar giving style. None of the peers below have a public website on file, and none disclose annual giving or application processes in the available data, underscoring how opaque this entire tier of foundation is to outside applicants.

Windward is the only foundation in this peer set with enough public grant-level detail (via 990-PF disclosures) to show a clear giving pattern — three anchor relationships absorbing 62% of dollars — which is likely typical of this entire tier of sub-$6M family foundations even where the underlying data isn't visible. Applicants should assume every foundation in this comparison operates the same way: family-run, unstaffed, and driven by personal relationships rather than open competitions.

The most concrete recent development is a leadership transition visible in tax-filing data: the foundation's 2024-tax-year Form 990-PF lists J Christopher Perry as President, replacing founding president Joseph C Perry, who had led the foundation since its 2013 IRS ruling date. Cathryn T Perry continues as Secretary. No press release, news article, or foundation announcement accompanied this change — it surfaced only in aggregator filing data (ProPublica Nonprofit Explorer), consistent with a foundation that has essentially zero public communications presence.

Financially, FY2024 shows the foundation drawing down assets: $192,071 in revenue (90.9% from dividends) against roughly $328,696-$351,739 in disbursements/expenses, continuing a multi-year pattern where distributions have exceeded investment income. Total assets fell from $5,421,388 (FY2023) to $5,261,720 (FY2024).

No new program announcements, no changes to funding focus, and no new major grantees could be identified — the same core relationships (Norfolk Academy, JDRF, YMCA of South Hampton Roads) that anchored giving in the years captured by the underlying data appear to remain intact into 2024, based on the consistent multi-year grant counts (4-5 grants each) tied to those names. One historical data point worth flagging for compliance-minded applicants: a 2022-corrected filing note shows a $33,333 grant to the Hatteras Marlin Club was later determined to have been 'paid in error to non-charitable organization,' with excise tax paid on Form 4720 — a reminder that this foundation's diligence process, while informal, does eventually catch and self-correct grants to non-501(c)(3) recipients.

There is no formal application process to optimize for here — the foundation's own record shows no application form, no deadline, no stated funding cycle, and a 'preselected only' designation, and no dedicated foundation website could be confirmed (the windward.org domain on file belongs to an unrelated land-education nonprofit, not this foundation). Given that, the realistic playbook is relationship-based, not portal-based:

• Timing: With no stated deadline or cycle, disbursements likely follow informal board decisions by the Perry family rather than a competitive review calendar. Don't wait for an RFP that will never be posted; instead build the relationship year-round.
• What they respond to: The grantee list is dominated by long-running, repeat relationships (Norfolk Academy funded in 5 separate years, JDRF and YMCA of South Hampton Roads each funded 4 times). This is a foundation that renews, not one that samples widely — a single strong ask is far less likely to land than a multi-year relationship building toward it.
• Geography matters: 80% of tracked grants went to Virginia organizations, heavily Hampton Roads/Virginia Beach/Norfolk. Groups outside that footprint (or the secondary Outer Banks, NC cluster) should not expect a warm reception without an unusually strong personal connection.
• Common mistake: Submitting a cold LOI or general grant inquiry by mail/email to '% Officers' at 3600 Pacific Avenue is unlikely to be reviewed in any structured way — there is no staff to triage it. The listed phone, (757) 671-1700, is the only public contact point; use it to seek an introduction or conversation, not to 'submit' anything.
• Alignment language: Given the visible portfolio, proposals should speak to youth education, Hampton Roads community services (food security, family services), health research/patient support (JDRF-style causes), or coastal/maritime and environmental stewardship (Elizabeth River Project, Virginia Aquarium) — these map directly onto where dollars have actually gone.
• Compliance note: Confirm your organization's 501(c)(3) status is unambiguous and documented before any ask — the foundation has previously had to file an excise-tax correction (Form 4720) after a grant to a non-qualifying recipient (Hatteras Marlin Club, 2022 correction), so they are attentive to (if not infallible on) this point.
• Realistic expectation-setting: With total giving down roughly 59% from its 2019 peak and the foundation now distributing more than it earns in a given year, this is a shrinking pool, not a growing one — new relationships likely compete with an already-committed base of recurring, multi-year grantees.