What if the way you transfer real estate today could make—or break—your family’s future relationships?

In this episode, Matt Templeton is joined by Dan Ihara, founder of the Real Estate Planner Network and Hawaii’s #1 real estate agent, to unpack how families can protect their assets, prevent estate battles, and avoid unnecessary capital gains taxes through intentional real estate planning.

Dan shares how he created a niche that now serves clients with aging parents, large property portfolios, and complicated estate needs. You’ll hear how his team moved from simply selling homes to solving transitions—offering services like senior move management, 1031 exchanges, asset performance reviews, and real estate wealth transfer consulting.

If you’re a trustee, a parent planning your legacy, or a real estate agent who wants to serve high-net-worth clients better, this conversation is a masterclass in what to do—and what to avoid—when transferring real estate wealth.

Guest: Dan Ihara, CEO of The Ihara Team & Founder of the Real Estate Planner Network Host: Matt Templeton, Real Estate Planner | Templeton Real Estate Group

🧭 Episode Highlights & Timestamps:

• [00:01:00] Dan’s journey from entrepreneur to building a real estate niche around aging clients and estate planning

• [00:04:00] How Dan created senior move management services to help aging homeowners transition out of long-held properties

• [00:06:00] The massive oversight: why most families don’t know they’re sitting on investment properties with capital gains liability

• [00:07:30] Real estate’s role in the $30–$40 trillion wealth transfer happening in the next 20 years

• [00:08:00] Why putting property in a trust doesn’t protect against family conflict—and what does

• [00:09:00] The birth of the “Real Estate Planner” title and why the wealthy need one alongside their attorney, CPA, and financial advisor

• [00:10:00] The real enemy of generational wealth? Capital gains tax.

• [00:11:00] Why traditional real estate agents fail their clients: lack of tax knowledge, lack of planning tools

• [00:13:00] What a real estate plan actually looks like—from tax analysis to family legacy questions

• [00:17:00] Using math and empathy to help clients self-discover their best path forward

• [00:19:00] Why most elderly property owners are philanthropists by accident—and how to unlock higher returns or transfer benefits to heirs

• [00:21:00] DSTs (Delaware Statutory Trusts) as a tool for true passive income and seamless estate transition

• [00:22:00] How to collaborate with CPAs, attorneys, and planners—and why they need real estate planners in their network

• [00:25:00] The #1 mistake in wealth transfer: putting kids on title before death

• [00:26:00] How to write a trust to prevent family disputes (including forced liquidation and right of refusal)

💡 Top Takeaways:

• Putting kids on title too early causes massive tax liabilities—wait for the step-up in basis at death.

• Real estate planners fill the critical gap between CPAs, attorneys, and financial advisors.

• Most investors are making just 1–2% on appreciated real estate. Repositioning can triple returns or bless the next generation.

• DSTs allow for completely passive income and clean asset transfer at death—no management, no conflict.

• Building trust with clients starts with one simple question: “What would you like to get accomplished in our time together today?”

📍 Connect with Dan Ihara & the Real Estate Planner Network: 🌐 https://realestateplannernetwork.com (optional)

📬 Connect with Matt or Get Introduced to an Advisor: 📧 Email: matt@templeton.realestate 📱 DM us anytime for introductions to real estate planners, tax advisors, or estate attorneys in your market

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.

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: jTaylor@jrw.com Phone: (440) 463-0128 Website: https://www.jrw.com (optional to include if applicable)

REACH OUT TO US:

Email: matt@templeton.realestate

YOUTUBE: @WealthTransferPodcast