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Loophole

Appreciated Crypto / Stock to DAF

Avoid capital-gains tax AND deduct full fair-market value.

Overview

Donate long-term-held appreciated assets (crypto, stock, private equity) directly to a DAF — the donor deducts full FMV at contribution AND avoids capital-gains tax on the appreciation. On $1M of appreciated Bitcoin (basis $50K), donor saves $190K cap-gains tax AND deducts $1M against ordinary income. Never sell first — always transfer in kind.

Best fit
Crypto holders with large gainsConcentrated stock holdersPre-IPO liquidity events
Estimated impact
23.8% cap-gains avoidance + 30–37% deduction

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