#110 - What a 1031 Exchange Is — And How It Can Save You Thousands in Taxes with Jonathan Hilley

Path To Passive: Real Estate Investing For Technology Professionals

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What if you could legally keep up to 40% of your profits when you sell real estate, and most people don’t even know it’s possible? In this episode, Steven chats with Jon Hilley, aka “Mr. 1031,” to talk about one of the biggest tax-saving moves in real estate: the 1031 exchange. Jon explains what it is, how it works, and why more investors should be using it. He also shares his own story, from working at Goldman Sachs to running cannabis companies to now leading one of the top 1031 exchange firms in the country. You’ll also hear how he’s using AI to make the process easier and more accessible for everyone. If you own or plan to sell investment property, this episode could save you a lot of money.
Jonathan Hilley is the co-founder and CEO of 1031 Specialists, a fast-growing, tech-forward Qualified Intermediary (QI) firm focused on improving the 1031 exchange experience for real estate investors. Originally from Jupiter, Florida, Jonathan graduated with highest honors from the University of Florida. He began his career as a financial analyst at Goldman Sachs, then moved into hedge fund and private investment roles, later becoming an executive in operating companies. Drawing on that experience, he launched 1031 Specialists to bring better technology, service, and national reach to a niche industry. Under his leadership, the company has expanded rapidly and continues to reshape how investors approach tax-deferral strategies.
Connect with Jonathan:
Website: https://www.1031specialists.com/
LinkedIn: https://www.linkedin.com/in/jonathanhilley/
IG: https://www.instagram.com/1031specialists/
Episode highlights:
(0:00) Intro
(2:59) Meet Jon Hilley: From Goldman Sachs to Mr. 1031
(6:22) Discovering Qualified Intermediaries and a niche ripe for change
(12:32) What a 1031 exchange actually is (and isn’t)
(15:14) How 1031 compounding builds serious long-term wealth
(18:27) 222 QIs in the U.S., but only 10 with real scale
(25:42) The downside of not doing 1031
(30:06) Why 1031 exchanges should be your default strategy
(32:22) How the NAR incubator is helping push 1031 education
(38:45) Solving $500 legal bills with AI: Building a 1031 GPT
(48:28) Advice from Jon: Life will teach you more than books ever will
(55:02) Outro
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