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What happens when a certified financial planner sells two homes to buy bitcoin? In this episode, we sit down with Jessy Gilger, Senior Advisor at Sound Advisory, to explore the radical shift happening inside the financial advisory industry. Jessy shares how he went from flipping houses to building multi-generational wealth on a bitcoin standard, and why more clients—and even advisors—are quietly making the leap. We cover how ETFs are changing incentives, how to navigate capital allocation between real estate and bitcoin, and the risks of high bitcoin exposure in retirement. Jessy explains why volatility planning matters, how to survive bitcoin drawdowns, and how to protect your family with proper inheritance planning. We also get into his take on the national bitcoin reserve and potential tax changes.
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TIMESTAMPS:
00:00 - Intro
01:18 - Why Jessy sold two houses for bitcoin
02:35 - Jessy’s thesis for bitcoin as internet-native money
04:13 - How financial advisors react to buying bitcoin
05:34 - Why ETFs changed the game for advisors
07:26 - When to buy a house vs. buy more bitcoin
09:17 - Using long-term mortgages as low-cost leverage
12:03 - How Jessy thinks about portfolio allocation
13:15 - What 90% bitcoin portfolios look like in real life
15:09 - Why retirees need a bitcoin bear market survival plan
20:01 - Bitcoin’s volatility and the four-year cash barbell
24:37 - Could the next 80% bitcoin drawdown be the last?
27:06 - The return of austerity and why it matters for bitcoiners
30:04 - Tax changes coming in 2025 and what to do now
43:37 - When it’s time to fire your financial advisor
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