Bitcoin Taxes, Inheritance & Knowing When You Have Enough | Jessy Gilger

How much Bitcoin is enough—and what is it actually for? Jessy Gilger, CFP® and founder of Verify Wealth, joins Walker to connect Bitcoin conviction with the practical work of taxes, inheritance, cash flow, and making time for the people you love.

We discuss why your legal documents, financial plan, and Bitcoin keys need to agree; how unclear inheritance instructions can burden a grieving family; and how tax planning fits into a life built around Bitcoin. Jessy also explains the idea behind Bitcoin Scholars Fund and why “stay humble, stack Saturdays” matters just as much as stacking sats.

Jessy Gilger

Verify Wealth — Walker landing page: https://verifywealth.com/Walker

I do not receive any commission from this link; it is only a landing-page tracking link.

Jessy on X: https://x.com/idahohodl

Bitcoin Scholars Fund: https://bitcoinscholars.org

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Chapters

00:00 Intro: death, taxes, 21 million

01:11 Jessy Gilger: Cybertruck, self-driving & privacy

10:49 Why Jessy built Verify Wealth

12:22 Sponsor: Ledn

13:36 Sponsor: Blockstream Jade Plus

14:47 Why Bitcoiners need a financial plan

16:57 The problem with percentage-based advisory fees

21:24 Bitcoin taxes, cost basis & planning ahead

25:07 Roth accounts, gifting & tax buckets

28:10 Expats, residency & capital gains

30:14 Tax-loss harvesting & wash-sale discussion

33:15 Bitcoin Scholars Fund & school-choice credits

37:38 Connect your keys to your inheritance plan

42:09 Probate, trusts & family privacy

47:52 Give your spouse confidence, not a puzzle

50:22 Plan B: jurisdiction, custody & optionality

55:20 Death, taxes, 21 million & the money printer

01:00:42 Cash flow, retirement & spending with purpose

01:07:05 Market cycles, goals & when to sell

01:14:08 “I have enough Bitcoin”

01:17:54 Stay humble, stack Saturdays

01:18:59 Verify Wealth & Bitcoin Scholars Fund

Newsletter: https://walkeramerica.substack.com

Editorial Correction

At approximately 1:04:29, the conversation mentions airline pilots retiring at 62. The FAA limit for pilots serving in Part 121 airline operations is 65: https://www.faa.gov/faq/what-maximum-age-pilot-can-fly-airplane