Nov. 5, 2025

EP186: Defer, Defer, Die: The Power of 1031 Exchanges - Jon Hilley

EP186: Defer, Defer, Die: The Power of 1031 Exchanges - Jon Hilley
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Keep more of your profits and build wealth tax-deferred as Jon Hilley reveals how the 1031 exchange helps investors legally defer taxes while compounding their wealth. He shares insights from the cannabis industry and explains how Delaware Statutory Trusts (DSTs) are changing the game for passive investors. Dial in as he breaks down complex tax strategies into simple, actionable steps for long-term financial growth.

Key Takeaways To Listen For

  • Why betting on regulatory reform is risky
  • The rise of Delaware Statutory Trusts
  • How to defer up to 40% of your taxes legally
  • Rules every investor must know to complete an exchange
  • A generational wealth strategy: “Defer, defer, defer, die”

Resources/Links Mentioned In This Episode


About Jon Hilley
Jon Hilley is the Founder of 1031 Specialists, a tech-forward qualified intermediary platform revolutionizing how investors complete 1031 exchanges. A former financial analyst at Goldman Sachs and hedge fund associate at H.I.G. Capital, Jon brings deep financial expertise to the real estate space. He has held executive roles at multiple startups, including Mile High Labs and Firefly Vapor, and currently contributes to ventures like Silver Horn Capital and Silver Horn Ranch. With a focus on innovation, integrity, and investor success, Jon is building a modern solution for tax-deferred wealth building through real estate.

Connect with Jon

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If you’re looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

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