Episode #243 - Jon Hilley – The 1031 Playbook episode artwork

EPISODE · Sep 12, 2025 · 22 MIN

Episode #243 - Jon Hilley – The 1031 Playbook

from Real Estate Investor Podcast · host Gary Lipsky

1031 exchanges are incredibly valuable for investors and are often underutilized and ignored. Today on the Real Estate Investor Podcast, co-founder and CEO of 1031 Specialists, Jon Hilley, joins us to share a play-by-play of 1031 deals. Tuning in, you’ll hear all about Jon’s career and what his company does, the structure of a 1031 deal, a definition of a few 1031 terms, and so much more! We delve into Jon’s thoughts on Delaware Statutory trusts before he stresses the importance of hiring a qualified intermediary for 1031 exchanges. He even discusses the fee structures and reminds us why proper planning is key in these kinds of deals. Finally, our guest touches on some common mistakes he sees being made in 1031 exchanges. Thanks for listening in! Key Points From This Episode:A warm welcome to today’s guest, Jon Hilley. What Jon and his company, 1031 Specialists, do.The structure of a 1031 deal and why it’s important. Jon explains basis, equity, and net investment goal. His thoughts on DSTs (Delaware Statutory Trusts). The importance of hiring a qualified intermediary. Jon explains his fee structures for 1031 deals. The importance of proper planning in 1031 exchanges. Common mistakes investors make in 1031 deals. Links Mentioned in Today’s Episode:Jon Hilley on LinkedIn1031 Specialists Call 1031 Specialists on 631-438-1031National Association of REALTORSAsset Management Mastery Facebook Group Invest SmartBreak of Day Capital Break of Day Capital InstagramBreak of Day Capital YouTubeGary Lipsky on LinkedIn🙏 Special thanks to our sponsor, Bromley Palamountain of Northwestern Mutual — helping professionals and business owners build financial plans that support long-term freedom. To book your complimentary consultation, click the link.

Episode metadata supplied by the publisher feed · Published Sep 12, 2025

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1031 exchanges are incredibly valuable for investors and are often underutilized and ignored. Today on the Real Estate Investor Podcast, co-founder and CEO of 1031 Specialists, Jon Hilley, joins us to share a play-by-play of 1031 deals. Tuning in, you’ll hear all about Jon’s career and what his company does, the structure of a 1031 deal, a definition of a few 1031 terms, and so much more! We delve into Jon’s thoughts on Delaware Statutory trusts before he stresses the importance of hiring a q...

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Episode #243 - Jon Hilley – The 1031 Playbook

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