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

About this episode

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 PARTNERS & DISCOUNTS: LEDN : Bitcoin-backed lending. Go to ledn.io/walker and unlock liquidity WITHOUT selling your bitcoin. BLOCKSTREAM JADE : BLOCKSTREAM JADE HARDWARE WALLET: Head to https://store.blockstream.com/ and use coupon code WALKER for 10% off! CASA MULTI SIG COLLABORATIVE CUSTODY: Get 3 FREE MONTHS off your membership when you use my referral link to sign up for your Casa membership: https://casa.io/pricing?ref=311d0b0f or use my code at checkout: 311d0b0f MINING: Own Bitcoin Miners. Keep 100% Of The Bitcoin. Get 1st month of free hosting with https://abundantmines.com/walker Buy Bitcoin with River: http://partner.river.com/walker GET FOLD ($10 in bitcoin): https://use.foldapp.com/r/WALKER If you enjoy THE Bitcoin Podcast you can help support the show by doing the following: FOLLOW ME (Walker) on @WalkerAmerica on X | @TitcoinPodcast on X | Nostr Personal (walker) | Nostr Podcast (Titcoin) | Instagram | YouTube | Everywhere else 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