Season 2 Premiere • Overall Episode 26

A quick paperwork review can save you from a prohibited transaction.

In this episode, David and Tom explain the DST/IRA documentation mistakes that catch people off guard, why your retirement account is “not you,” and how checkbook IRA control can backfire if you don’t understand the rules.

They also cover 1031 exchange pitfalls after divorce, intent rules, and when the opportunity cost of waiting makes an exchange less attractive.

00:00 Nobody Wants to Call… And That’s the Problem
01:15 ROBS Explained: The Retirement Strategy People Misuse
06:40 The IRA Structure That Gets Deals Rejected
12:20 “$10,000 Later…” The Document That Was Useless
20:15 The Paperwork Mistake That Slows Everything Down
27:00 Checkbook IRA: The Best Feature… And the Worst Risk
29:10 DST Paperwork Red Flag (Qualified Funds Warning)
36:25 Divorce + 1031: Where People Get Tripped Up
44:00 The Hidden Cost of Waiting (Opportunity Cost)

Have you ever been told, “just assign it to the IRA” or had an attorney/custodian reject your operating agreement?

Drop your story in the comments — we’ll cover the best questions in a future episode!

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Self-directed IRAs give investors the ability to move beyond Wall Street and invest in real assets like real estate, private notes, and alternative investments—but that control comes with important rules and risks.

In this episode, we break down what investors need to understand before using retirement funds outside traditional brokerage accounts, including how Required Minimum Distributions (RMDs) work, when they should be taken, when an IRA holds illiquid assets, how valuations are handled, and why certain mistakes inside an IRA cannot be undone.

01:00 – 2026 IRA Contribution Limits Explained
02:00 – Required Minimum Distributions (RMDs): What Triggers Them
03:00 – Valuing Real Estate & Alternative Assets Inside an IRA
05:15 – What Happens When Your IRA Has No Cash for an RMD
05:40 – In-Kind Distributions: Taking Assets Instead of Cash
06:10 – What Is a Checkbook IRA (IRA LLC)?
09:10 – Annual Valuations vs. RMD Valuations
12:45 – IRS Scrutiny, In-Kind Distributions & Audit Risk
16:25 – DIY IRA LLCs, Prohibited Transactions & Costly Mistakes 

This conversation is for investors who want flexibility and control in their retirement strategy, while staying compliant and avoiding unnecessary taxes and penalties.

If you’re considering real estate or alternative investments inside an IRA, this episode provides practical insight to help you make informed decisions before moving forward.

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In this episode, David and Tom of the Exchange Bros discuss year-end planning for 1031 exchanges, focusing on deadlines, tax reporting, and strategies to manage multi-year tax exposure.

They break down boot, debt relief, partial exchanges, installment sales, seller financing, and refinancing strategies, and explain how timing and intent can impact tax outcomes. The conversation also covers combining Section 121 and 1031 exchanges, converting investment properties into future primary residences, and why thoughtful planning matters more than automated solutions.

The episode closes with a reminder that in real estate tax planning, tax exposure is not the same as taxes owed.

01:10 Year-end 1031 Exchange Deadlines, Extensions & Tax reporting
03:58 Understanding boot, debt relief & when 1031 taxes are triggered
07:09 Installment sales, seller carry & common tax misconceptions
09:26 Full vs partial 1031 exchanges: value, equity & mortgage rules
14:27 Tax exposure vs taxes owed: portfolio planning & ROI strategy
19:27 Cash-out refinancing before vs after a 1031 exchange
28:42 Using Section 121 with 1031 exchanges (primary residence strategies)
40:03 Why experience matters: planning vs AI & automated exchanges
47:53 Seller financing in 1031 exchanges: notes, deferral & pitfalls

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In our latest episode of the Exchange Brothers, David and Tom dive into Appreciation Homes and the Direct Title Security (DTS) model, a new approach that gives investors direct ownership of real property with the passive benefits of a triple-net lease. 

Tune in as Derek Vogel and Forrest James of Appreciation Homes cover how the DTS works, how it could solve major pain points of the traditional DST, and how investors can use it to gain control, liquidity, and flexibility, without sacrificing passivity. The DTS also gives investors the ability to cash-out refinance post-acquisition, a feature many want, but often can’t access in traditional deals.

01:28 – What Are Appreciation Homes?
04:30 – How the DTS Model Was Created
07:20 – DTS vs. DST Explained Simply
08:18 – How DTS Works (Ownership + Long-Term Lease)
10:29 – Property Types, Markets & Inventory
11:31 – Key Benefits: Control, Liquidity & Risk Reduction
18:07 – Debt, Leverage & Cash-Out Refi Options
23:03 – Returns & Who This Is Best For
58:56 – Closing Thoughts & Next Steps 

Have questions? Drop them in the comments, we’re planning a follow-up episode! 

📞 Connect with our guests: 
Forrest James – [email protected]  
Derek Vogel – [email protected] 

🎙️ Hosted by David & Tom Moore, The Exchange Brothers | Equity Advantage 1031Exchange.com

1031 Risk Disclosure: 

There is no guarantee that any strategy will be successful or achieve investment objectives; 
Potential for property value loss – All real estate investments have the potential to lose value during the life of the investments; 
Change of tax status – The income stream and depreciation schedule for any investment property may affect the property owner’s income bracket and/or tax status. An unfavorable tax ruling may cancel deferral of capital gains and result in immediate tax liabilities; 
Potential for foreclosure – All financed real estate investments have potential for foreclosure; 
Illiquidity – Because 1031 exchanges are commonly offered through private placement offerings and are illiquid securities. There is no secondary market for these investments. 
Reduction or Elimination of Monthly Cash Flow Distributions – Like any investment in real estate, if a property unexpectedly loses tenants or sustains substantial damage, there is potential for suspension of cash flow distributions; 
Impact of fees/expenses – Costs associated with the transaction may impact investors’ returns and may outweigh the tax benefits

For more information on Emerson Equity, please visit FINRA’s BrokerCheck website. You can also download a copy of Emerson Equity’s Customer Relationship Summary to learn more about their role and services. 

General Disclosure: 

Not an offer to buy, nor a solicitation to sell securities. All investing involves risk of loss of some or all principal invested. Past performance is not indicative of future results. Speak to your finance and/or tax professional prior to investing. Any information provided is for informational purposes only.

Securities through Emerson Equity LLC Member: FINRA/SIPC. Only available in states where Emerson Equity LLC is registered. Emerson Equity LLC is not affiliated with any other entities identified in this communication.

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In this episode, David Moore (Equity Advantage) sits down with Robert Smith of Peregrine Private Capital to unpack the evolving world of 1031 exchanges, DSTs (Delaware Statutory Trusts), and 721 UPREITs in today’s unpredictable real estate market.

📈 Key Topics:

• The recent interest rate changes and how they’re reshaping investor behavior
  
  
• Why 721 UPREITs have become Wall Street’s favorite “exit strategy”
  
  
• The risks and misconceptions around liquidity in DSTs and UPREITs
  
  
• Tax strategies every real estate investor should know in 2025
  
  
• The impact of policy changes, rent control, and state taxes on property owners
  
  
• How investors can protect wealth and plan smarter for generational real estate transitions

00:00 – Disclaimer & Investment Risk Overview
00:47 – Welcome: David Moore & Robert Smith on Today’s Market
02:57 – Interest Rates, Uncertainty & the 2025 Real Estate Landscape
05:05 – When Tax Deferral Doesn’t Make Sense
08:11 – DSTs & 721 UPREITs Explained: How They Work
12:20 – DST vs. 721: Key Differences and Hidden Risks
17:25 – The Endgame Strategy: When a 721 Exchange Fits
23:47 – Liquidity, Tax Benefits & Wall Street’s Real Estate Agenda
43:00 – Taxes, Policy & Why Investors Are Leaving Blue States
55:36 – The Future of Real Estate Ownership in America

🎧 Subscribe for more deep dives into real estate investing, tax strategy, and wealth management from The Exchange Bros. 

Important note: This podcast is not an offer to buy or a solicitation to sell a security. The podcast is a discussion pertaining to one or more investment strategies and/or asset class(es), and is not a discussion of any specific offering, past or present, of securities. As a reminder, there is no guarantee that any investment or strategy will perform as targeted, past performance is no guarantee of future performance, and any investment involves risk of the loss of some or all principal invested. The podcast contains statements intended for educational and hypothetical purposes only, and is not to be construed as a promise of performance. Information presented herein reflects the opinions of the speakers and is from sources believed to be reliable, but all information is subject to change. You should always speak to your finance and/or tax professional prior to investing. 

Securities offered through Emerson Equity LLC Member: FINRA/SIPC. Only available in states where Emerson Equity LLC is registered. Emerson Equity LLC is not affiliated with any other entities identified in this communication. 

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In this episode, we are catching up with Paul Locatelli, a Santa Cruz real estate veteran and old friend, with stories you won’t hear anywhere else! From Versace to navigating tricky appraisals, Paul’s seen it all — and yes, Tom’s swim record is still standing.

In this chat, we break down:

- How rent control is reshaping the Santa Cruz housing market
- Current market changes affecting buyers, sellers, and investors
- Paul’s personal journey in real estate, including wild stories and lessons learned

Whether you’re local, looking to invest, or just love a good Santa Cruz story, this interview is packed with real estate insights, laughs, and behind-the-scenes tales.

00:00:00 Reconnecting with Old Friends
00:03:15 Santa Cruz Market Snapshot
00:08:40 Rent Control Realities
00:14:20 Career Highlights & Funny Tales
00:20:50 721 DST Investments Explained
00:31:45 Investment Returns & Risk
00:41:30 Educating Investors
00:50:10 Buyer & Seller Trends in Santa Cruz
00:57:37 Portfolio Management Tips
01:07:22 People First, Profits Follow
01:16:14 Lessons from Real-Life Cases
01:23:05 Adding Value Without Selling
01:29:18 Wrapping Up & Next Steps

Our Expert:

Paul Locatelli, Epique Real Estate

https://locatellirealestate.com/

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AI can deliver quick answers, but when it comes to 1031 exchanges, it doesn’t know the right questions to ask — and that can cost you big. 

In this episode, Dave and Tom break down why relying solely on AI can lead to missed opportunities, unnecessary risk, and even failed transactions. They share real-world stories, discuss the nuances of reverse and improvement exchanges, and explain why experience, strategy, and human judgment still matter. Whether you’re an investor, broker, or just curious about AI’s role in real estate, this episode will help you avoid costly mistakes and make smarter decisions.

01:00 AI’s Role in Real Estate
02:00 The Big Issue: Not Knowing the Right Questions to Ask
04:30 AI Can’t Review Your Sales Agreement  
07:30 Safe Harbor vs. Non-Safe Harbor Exchanges  
08:30 Why Cheap Isn’t Always Better  
11:20 Referral Fees, Conflicts of Interest, and Client Trust  
15:00 $100M Deal Example: Security & Risk Management  
28:00 Basis, Depreciation, and Why AI Can’t Calculate It  
46:30 Final Thoughts: AI’s Place & Human Expertise

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From IRAs to 401(k)s to 1031s… what’s really legal, and what’s a tax trap? David and Thomas Moore answer real client questions: Can retirement accounts pay property debt? When is selling smarter than exchanging? And what “tax-free” really means.

00:00 – Retirement Accounts + 1031 Exchanges
00:25 – Client Question: Can You Use Home Sale Proceeds to Pay IRA Debt?
01:59 – Why Paying IRA Debt with Personal Funds = Prohibited Transaction
04:05 – Legal Workaround: Using an LLC to Avoid Prohibited Transactions
07:15 – Asking the Right Tax & Legal Questions
15:22 – What to Do When a Seller Wants a 1031 Exchange
18:11 – Equity ≠ Gain: Understanding Your Real Tax Exposure
25:44 – What a 1031 Exchange Really Does (Tax Deferral, Not Tax-Free)
26:39 – Swap Until You Drop: Passing Properties to Heirs Tax-Free
41:04 – 1031 G6 Rules: When You Can (and Can’t) Access Cash

🔔 Subscribe for more tips on 1031 exchanges, retirement investing, and wealth-building strategies.

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In this episode, David Moore from Equity Advantage and IRA Advantage breaks down how you can use retirement funds, including self-directed IRAs, checkbook IRAs, and 401(k) plans, to purchase a business. Learn the differences between investing passively versus working in the business, how to avoid prohibited transactions, and when a Rollover Business Startup (ROBS) is the right move. 

Perfect for entrepreneurs, investors, and anyone exploring tax-advantaged business purchases.

0:00 – Buying a Business with Your IRA or 401(k)
0:26 – Client Case Study: Using Retirement Funds to Purchase a Business
1:11 – Passive Investments vs. Working in the Business
1:33 – How a Self-Directed IRA or Checkbook IRA Works
2:13 – Combining Multiple IRAs & Understanding Disqualified Parties
3:23 – What You Can and Can’t Buy with an IRA or 401(k)
4:04 – The Checkbook Advantage IRA Structure Explained
5:06 – The Risk of Working in an IRA-Owned Business
5:47 – Rollover Business Startup (ROBS) Using a 401(k) + C Corporation
7:05 – Summary & How to Choose the Right Structure

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In this episode, David Moore of Equity Advantage covers the complexities of 1031 Exchange closing cost deductions, providing a lighthearted reminder that one wrong step can derail your entire transaction.

Learn why timing, documentation, and proper planning are critical when it comes to:

• Deducting closing costs
• Capital improvements before sale
• Handling “boot” and avoiding unexpected tax consequences
• Creating liens to recover funds legally
• Working with tax professionals to mitigate exposure

David shares real-world examples, like a client who spent $50K prepping a property for sale, and discusses the gray areas of what’s deductible or what could come back to bite you.

Whether you're an investor, realtor, or advisor, this episode will help you navigate the fine print and protect your investment.

📞 Got questions? Visit 1031Exchange.com or call Equity Advantage for guidance. 

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