Philanthropy gets easier when your tools match the way you actually hold wealth, and Giving Tuesday is a perfect moment to zoom out and do that kind of thinking. In this Digital Wealth Frontiers conversation, Marty Bent is joined by Phoenix Hafen (UI Charitable), Alex Gladstein (Human Rights Foundation), and entrepreneur-donor Jason Keil to unpack what it looks like when bitcoin becomes part of a real giving strategy.
A big theme: donor-advised funds (DAFs) can separate the tax moment from the giving moment. Hafen describes a DAF as a charitable account where you contribute assets, take an immediate tax deduction, and then recommend grants to nonprofits over time. He also notes why DAFs have grown in popularity as an alternative to private foundations: they’re typically easier to set up, lower-cost, and, unlike private foundations, generally have no annual distribution requirement. That flexibility matters on Giving Tuesday because it lets you act before the end of the year while still giving yourself time to be thoughtful about where the money goes.
The conversation gets especially practical when it turns to bitcoin as the asset being donated. Hafen frames it in plain terms: if you have highly appreciated bitcoin and you sell it to donate cash, you may reduce both your tax deduction and the amount the charity receives due to capital gains taxes. Contributing the asset directly to a DAF can help preserve value, because the deduction is based on the full fair market value and liquidation (if needed) can happen within the charitable vehicle, without the donor taking on that capital gains liability.
They also explore what it means for charities to receive bitcoin and treat it like treasury, not a hot potato. Gladstein explains that at HRF, bitcoin gifts come in and go directly into their treasury, and he encourages organizations not to sell unless they truly have to. Over time, that approach can change what’s possible: he describes scenarios where HRF has been able to deploy multiple times the original dollar amount of a gift while still retaining significant value, if you’re willing to be patient with it. Keil adds a donor’s perspective on why custody and control matter, highlighting the appeal of retaining a key while building a long-term giving vehicle aligned with the causes you care about.
A few ideas worth considering from the conversation:
- Use a DAF to decouple timing: take the deduction now; decide recipients over time.
- Prefer donating appreciated assets: optimize value with regard to capital gains and preserve more for the mission.
- Treat bitcoin gifts with intention: a bitcoin donation often signals the donor wants bitcoin used thoughtfully, not reflexively sold.
- Adopt a low time preference: for mission-driven orgs, bitcoin held responsibly can become strategic endurance capital.
In 2024, charitable giving in the US grew to nearly $600 billion. If Giving Tuesday is your annual reminder to give, let it also be a reminder to build a repeatable, value-preserving approach that aligns with how you store value and what you want your wealth to do in the world. Watch the full replay above for the complete discussion, including real-world donor stories and what it takes for nonprofits to operationalize bitcoin responsibly. And if you’re evaluating how a bitcoin-focused giving strategy fits into your broader legacy plan, Gannett Trust is building for families who value the same thing in philanthropy as in wealth: clarity, durability, and control.
Interested in how charitable giving can fit into your plans? Request an introduction to our experts.
This article is for informational purposes only and has not been tailored to your specific situation. It does not constitute tax, legal, or investment advice. Please consult with your tax, legal, or investment adviser if you need advice on these matters.
