Discover a framework for bitcoin based philanthropy that enhance tax efficiency and support lasting impact.
What Bitcoin-Based Philanthropy Solves for HODLers
For bitcoiners who acquired their coins early, the numbers involved can be staggering — and so can the tax bill on selling them. In our latest whitepaper, A Framework for Bitcoin-Based Philanthropy, Bespoke Founder & Senior Managing Director Jonathan A. Mintz lays out how strategic philanthropy lets bitcoin holders give meaningfully without giving up their upside.
Charitable Remainder Trusts: Cash Flow Without Selling Your Stack
The paper walks through how a Charitable Remainder Trust (CRT) lets a donor contribute low-basis bitcoin, defer capital gains tax, and receive an income stream for life or a set term — with the remainder passing to charity. Mintz illustrates this with a $10 million bitcoin contribution that can generate over $20 million in after-tax cash flow over 20 years, while still leaving more than $17 million for charity.
Pairing a CRT with Tax-Free Growth Through PPLI
The paper then shows how pairing a CRT with Private Placement Life Insurance (PPLI) can extend the benefit further, generating tax-free growth and potentially tens of millions more in family wealth alongside the charitable outcome.
Donor-Advised Funds and the Bitcoin-Based Philanthropy Trap
Finally, the paper covers Donor-Advised Funds (DAFs) — including why most DAF sponsors force an immediate bitcoin sale, and how working with a sponsor that allows continued bitcoin holding can meaningfully increase what ultimately reaches charity.
Bespoke’s Approach to BTC Treasury Management
Identifying “strategic” times to sell bitcoin within a CRT or DAF is the goal of Bespoke’s rules-based BTC Treasury Management strategy — designed to concentrate liquidations when bitcoin is overbought and avoid them when it’s oversold, maximizing the long-term value of both the fund and the giving it enables.
The upshot: bitcoin holders who plan strategically don’t have to choose between liquidity, legacy, and giving — the right structure can deliver all three.
Is Bitcoin-Based Philanthropy Right for You? Download the Full Framework
Download the full whitepaper to see the complete calculations, distribution schedules, and strategy comparison.
