Brett Swarts on Outsmarting Capital Gains Taxes
In this episode of Hosting Bitcoin, we sit down with Brett Swarts —capital gains tax strategist, real estate investor, and founder of Capital Gains Tax Solutions to unpack how Bitcoiners and entrepreneurs can build real wealth without being crushed by the tax code. Brett’s journey spans commercial real estate, the 2008 financial crisis, and now a specialty in helping high-net-worth investors legally defer capital gains, design intentional exits, and preserve more of what they’ve earned. With thousands of transactions, a spotless audit record, and decades of track record behind him, Brett has become the go-to guide for those who want to keep and compound their wealth rather than hand half of it to the IRS. This conversation goes far beyond spreadsheets. We dig into the psychological traps of “never sell” strategies, why borrowing against Bitcoin can backfire, and how aligning tax flow, cash flow, and debt flow creates true financial freedom. Brett shares client stories, the mechanics of the Deferred Sales Trust, and why building a family mission, vision, and set of values around wealth is just as critical as the technical strategy.
Hosting Bitcoin · Brett Swarts, Beau Turner
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Show Notes
We cover:
🔹 The three biggest mistakes of “never sell” Bitcoiners
🔹 Deferred Sales Trusts vs. 1031 exchanges — why timing is everything
🔹 Why deferral beats relocation (no Puerto Rico move required)
🔹 Real-world client stories: turning $50K into $50M in BTC and exiting without liquidation risk
🔹 The importance of family mission, vision, and values in wealth planning
🔹 How to avoid trading what’s priceless for what’s merely profitable
🔹 Estate tax traps, generational wealth, and the $100T transfer on the horizon
🔹 Why “truly passive income” is the foundation of impact and freedom
🎙 Guest: Brett Swarts
https://capitalgainstaxsolutions.com/
https://www.youtube.com/channel/UCAykQNmIWZ0KARBeVWcQxUA
https://www.instagram.com/capitalgainstaxsolutions1/
https://www.youtube.com/@BuildItToBillions
https://www.facebook.com/buildittobillions/
https://brettswarts.com/
https://www.linkedin.com/in/brett-swarts/
https://www.instagram.com/brett_swarts/
https://www.facebook.com/brett.swarts
00:00 – Intro & Welcome
01:05 – Brett’s Journey from Real Estate to Tax Strategy
07:18 – Lessons from the 2008 Crash & Broken Systems
14:12 – “Never Sell” Bitcoin Strategy & Its Risks
20:27 – Client Story: $50K to $50M in Bitcoin
28:44 – Building Truly Passive Income & Family Mission
37:10 – Deferred Sales Trust Explained
47:22 – Audit Track Record & Compliance Confidence
56:48 – Legacy, Impact & Parting Advice
Disclaimer: The information shared in this episode is for informational and entertainment purposes only. Nothing discussed should be considered financial, legal, or tax advice. Always do your own research and consult with a qualified professional before making any investment or financial decisions
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