Hold Bitcoin 10 Years, Take the Gains Out Tax-Free

Answering the two most important questions for every long-term Bitcoin holder

Author

Bitcoin Treasuries
June 23, 2026

Tim Enneking and Alec Beckman Break Down The Best-Kept Tax Secret In Bitcoin with Brian Phillips

Two questions underlie any long-term Bitcoin position, and most holders never address either deliberately. The first: what the tax picture looks like if they sell some. The second: assuming self-custody anchors most of the position, where the rest sits.

In the latest episode of the Psalion series, Managing Partner Tim Enneking and VP of Growth Alec Beckman sit down with Brian Phillips of the Pearl Bitcoin Fund. The conversation applies the Opportunity Zone tax code, made permanent under the One Big Beautiful Bill Act in 2025, to a long-term Bitcoin position.

Enneking ran his own Opportunity Zone fund at a near ten-digit family office and has been in Bitcoin for 13 years. As he puts it: "I know a lot about these two things separately. It never occurred to me to put them together."

The conversation is built for treasury managers, family offices, and finance leaders managing or considering a 10-plus-year position who want the planning architecture before they need it.

What it covers

  • The OZ structure, with a timing detail. The program, now permanent under OBBBA, lets long-term gains come out free of capital gains tax after a 10-year hold. The new rolling 5-year deferral applies only to investments made after December 31, 2026, which matters for capital deployed today.

  • The property classification and the wash-sale window. Bitcoin's treatment as property rather than a security keeps it outside the wash-sale rule, with planning consequences for holders sitting on unrealized losses. Legislation to close the window has been proposed and has not passed.

  • Where the rest of the allocation sits. For most allocations, self-custody is and should remain the default. The harder conversation is whether any portion sits elsewhere, and on what terms.

Psalion is a yield business serving institutional Bitcoin holders through segregated managed accounts. The firm's starting position is that self-custody anchors serious allocations, and the roadmap behind the “hodl” is the most important part of the journey.

Listen and share

Watch on YouTube, Spotify, or Apple Podcasts.

Onward,

Visit Psalion.com or contact Tim's team to learn how Psalion generates yield on institutional Bitcoin holdings through segregated managed accounts.

Psalion - Capital multipliers across the blockchain asset class

Psalion provides unique instituional-level investment products tailored to private clients, family offices, and professional investors.

Psalion

Sponsored content. Produced in partnership with Psalion.

This email is informational and educational only. It is not investment, legal, tax, or accounting advice, and it is not an offer or solicitation to buy or sell any asset. Consult qualified advisors before acting.