Avoid Capital Gains: 1031 Exchange & DST Secrets for Wealth Transfer | Jon Taylor

If you’ve built real estate wealth and are now wondering how to unlock that equity without triggering massive tax bills—or how to simplify life as you approach retirement—this episode is for you.

In this deep-dive conversation, Matt Templeton is joined by Jon Taylor of JRW Investments to explore how investors can use advanced tools like 1031 exchanges, Delaware Statutory Trusts (DSTs), and even 721 exchanges into REITs to reduce management headaches, defer taxes, and pass on wealth more effectively.

From minimizing capital gains and avoiding probate, to helping heirs receive clean, easy-to-distribute assets, Jon breaks down the strategies his team uses to help clients exit real estate with confidence. If you're a property owner, financial advisor, estate attorney, or family trustee, you’ll walk away with clear insight on how to navigate these tools—and when they’re the right fit.

 Show Notes:

Guest: Jon Taylor, Real Estate Investment Advisor at JRW Investments Host: Matt Templeton, Real Estate Planner | Templeton Real Estate Group

Key Topics Covered:

• [00:01:00] Why real estate investors are exploring 1031 exchanges in today’s market

• [00:04:00] Jon’s due diligence process: stress-testing deals across 25+ variables

• [00:09:00] What qualifies for a 1031 exchange—and how “like-kind” rules really work

• [00:12:00] DSTs vs. syndications: key differences in tax treatment and ownership

• [00:15:00] Why the typical DST investor is 75 years old—and how these tools simplify life

• [00:17:00] Using DSTs to handle partial exchanges and leftover “boot”

• [00:21:00] Understanding the real return on appreciated properties—especially in high-cost markets

• [00:26:00] Advanced strategy: what is a 721 exchange, and how does it tie into REITs?

• [00:30:00] Why DSTs are powerful estate planning tools—even without a REIT exit

• [00:36:00] The #1 wealth transfer mistake Jon sees: adding children to title too early

• [00:38:00] How JRW collaborates with CPAs, financial advisors, and estate attorneys

 Key Takeaways:

• A DST offers fractional ownership of large-scale, professionally managed properties while preserving 1031 eligibility.

• For many older investors, the greatest value isn’t tax savings—it’s freedom from management and simplifying the estate.

• REIT exits via 721 exchanges can provide posthumous liquidity and clean distribution to heirs, but not all DSTs offer this option.

• Never put your children on title prematurely—it could eliminate the step-up in basis and cost them dearly in capital gains.

• Advisors should coordinate early with clients to structure real estate exits in a way that aligns with the estate plan.

 Connect with Jon Taylor & JRW Investments:  Email: [e-mail]  Phone: [phone]  Website: https://www.jrw.com

 

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