The HODLer’s Philanthropy Problem
For bitcoiners who acquired their coins early, the wealth involved can far exceed expectations — and so can the reluctance to sell any of it. In this piece, Bespoke Founder Jonathan A. Mintz addresses a specific tension: most bitcoiners are HODLers who believe their coins will keep appreciating, yet strategic philanthropy requires actually giving some away. The solution isn’t choosing between the two — it’s structuring the gift correctly.
Those with significant bitcoin can use strategic philanthropy to accomplish many objectives, including creating an endowment through a Donor Advised Fund. DAFs an be particularly powerful if the structure can continue to hold bitcoin over the long term.
Why Most Donor Advised Funds Fall Short for Bitcoin
A Donor Advised Fund (DAF) lets a donor make an irrevocable gift to a sponsoring charity, take an upfront tax deduction, and recommend grants to IRS-approved charities over time. The catch: while a small number of DAF sponsors accept bitcoin, most force immediate liquidation upon contribution — meaning the charity (and the donor’s legacy) never benefits from bitcoin’s future upside.
Mintz argues that the fix is working with a sponsoring organization that holds the bitcoin in an advisor-managed fund, selling only when it’s strategically advantageous rather than on the sponsor’s arbitrary timeline.
Bespoke’s Approach to BTC Treasury Management
Because bitcoin is highly volatile (25%+ annual standard deviation), Bespoke uses a rules-based strategy to identify when bitcoin is “overbought” or “oversold” on a monthly basis — concentrating liquidations in stronger price periods and avoiding sales during downturns. The result: a DAF can meet its annual giving targets while liquidating less bitcoin and preserving more upside for the future.
The paper illustrates this with a $25 million bitcoin gift: forced immediate liquidation into a 5% price dip costs the fund $1.25 million instantly, while a discretion-based sale strategy lets the fund wait out the dip and preserve — or grow — that value over time.
The Upshot
Bitcoin holders don’t have to sacrifice long-term upside to give strategically. With the right DAF structure, bitcoin can fund an endowment that grows in value over the years, rather than locking in a sale price the moment it’s donated.
Download the full whitepaper to see the complete example and Bespoke’s approach to BTC Treasury Management.
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