The 1031 Exchange Brothers

00:00 Intro: Flipping Properties with an IRA
01:03 Prohibited Transactions & IRS Risks
02:13 UBIT Tax: Why Flips Get Taxed
03:24 Investor vs Dealer Status Explained
05:22 Sweat Equity & Legal Ways to Flip (ROBS Option)

Thinking a Roth IRA flip means zero taxes? Not so fast. Most investors get this wrong… and the IRS has no sense of humor when they do.

In this episode, Dave and Tom Moore from IRA Advantage break down exactly what happens when you try to flip properties inside a self-directed IRA or 401K, including the rules that can blow up your en...

00:00 – The BIG Myth: Do You Have to Replace Debt in a 1031?
04:24 – How to Pull Cash Out Without Triggering Taxes
04:43 – Cash-Out Refi Timing: What Triggers IRS Problems
05:09 – The “Step Transaction” Rule (What Can Get You Audited)
09:40 – Costly Mistake: Over-Financing & Unexpected Taxes

Many investors are told they have to replace debt in a 1031 exchange, but that’s not always the case. In this episode, we walk through how debt can be offset, when taking cash can trigger taxes, and how to structure transactions the right way.

We also dive into one of the biggest risk are...

In this episode, we break down one of the most misunderstood parts of a 1031 exchange: the identification rules.

Many investors know about the 45-day identification deadline, but far fewer understand how the three identification rules actually work or how mistakes during identification can jeopardize an exchange.

We discuss the fundamentals of identifying replacement property, common misunderstandings, and how identification works when investors are acquiring multiple properties, DST investments, or partial ownership interests.

If you're planning a 1031 exchange, understanding the identification process can help you avoid costly mistakes...

00:00 – Reddit Question: 1031 Exchange into a DST. 02:32 – DST vs 721 (UPREIT) Explained. 05:51 – 45-Day Rule Warning: DON'T LET IT CLOSE. 07:53 – Sponsor Risk & Why Experience Matters. 09:56 – How 721 Lets You Sell Through Basis. 14:43 – DST Identification Rules & Common Mistakes. 20:02 – Final Thoughts: “What Good Is Tax Deferral If What You Buy Goes Away?”

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. For more, visit https://www.1031exchange.com/podcasts/

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We answer the top 1031 exchange questions pulled from Reddit — including AI tax advice gone wrong (00:00–04:00), whether a partial 1031 exchange is worth it (07:38–14:08), the S-Corp mistake that eliminated future planning flexibility (14:08–19:42), and how to decide if a 1031 exchange actually makes financial sense (20:17–end). 

You can find every episode of this show on Apple Podcasts, Spotify or YouTube. For more, visit https://www.1031exchange.com/podcasts/

Send us Fan Mail

Thanks for listening! Subscribe to get all of the latest tax news and information. 

1. Student housing market overview (0:00)
2. Why governments misunderstand 1031 exchanges (2:45)
3. Insurance carriers, drones & deal-killing inspections (5:00)
4. Seller carry strategies inside a 1031 exchange (7:00)
5. Wrap notes, risk, and lender realities (12:30)
6. Rent control vs student housing (15:30)
7. Renovations, displacement & aggressive rent projections (19:30)
8. Insurance premium shocks and forced upgrades (23:00)
9. Why investors are exiting multifamily (31:00)
10. Replacing income with smarter 1031 strategies (36:00)
11. Why many exchange companies won’t answer real questions (41:30)

Student housing owners and multifamily investors are facing a new set of challenges heading into 2025–2027. Rising insurance premiums, tightening rent control regulations, and last-minute financing failures are chan...

The student housing game has changed, and if you’re waiting until spring to lease, you’re already behind.

In this market update, David Moore (Equity Advantage) and student housing expert Rene Nelson (Park West Commercial) break down the massive "Supply Shock" hitting college towns like Eugene, Oregon. With mega-developments like "The Hub" adding thousands of beds, the pre-leasing timeline has shifted dramatically.

If you own older student housing stock or small multifamily units near campus, this new luxury inventory is your direct competition. We discuss exactly what the "Pre-Leasing Signal" is for the 2026-2027 scho...

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 Th...

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 Distri...

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...

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 w...

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 prop...

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, lo...

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 smar...

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 R...

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
1:3...

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 costsCapital improvements before saleHandling “boot” and avoiding unexpected tax consequencesCreating liens to recover funds legallyWorking 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...

In this special edition of the Exchange Bros, David and Tom dive deep into the world of self-directed IRAs — what they are, how they work, and how you can take control of your retirement dollars to invest in real estate, private loans, and beyond.

They break down:

Why Wall Street IRAs are limiting your optionsThe difference between “true” self-direction vs. what your broker saysHow to structure an IRA LLC (aka Checkbook IRA)Common pitfalls, prohibited transactions & disqualified partiesReal-world examples and war stories from years in the business

Whether you're new to retire...

In this episode, David Moore of Equity Advantage sits down with CPA and tax strategist Jonathan McGuire of Aldrich Advisors to unpack the sweeping real estate tax changes brought about by Trump's One Big Beautiful Bill. From the latest on Opportunity Zones and 1031 exchanges to new rules around bonus depreciation, cost segregation, Section 179, and the permanent Qualified Business Income Deduction, this conversation covers everything investors and developers need to know.

They also explore how the 2025 tax reform impacts individuals, high-net-worth investors, and small businesses, offering practical tax planning advice that could save you thousands. Whether you’re a...

The new One Big Beautiful Bill Act (OBBBA) just passed, and it's set to transform the real estate landscape. From permanent Opportunity Zones to critical updates on 1031 exchanges, bonus depreciation, and SALT deductions, this legislation could have major implications for investors, agents, and property owners.

In this in-depth conversation, David Moore of Equity Advantage and guest, Dan Wagner of Inland Private Capital, break down:

What’s really in the OBBBA bill

How rural and urban communities will be affected

Why 1031 exchanges remain essential for market liquidity

What happens if OZ in...

Tired of government overreach, rent control chaos, and the Terrible T’s (tenants, toilets, trash)? You’re not alone, and you do have options.

In this episode, David Moore and Robert Smith sit down with DST veteran Scott Dixon of Inspired Healthcare Capital to break down how Delaware Statutory Trusts (DSTs),  especially in the senior living space — are helping investors escape high-maintenance real estate, preserve wealth, and capitalize on one of the most powerful demographic shifts of our lifetime.

With over $1B in assets and a full-cycle track record, Scott shares what every real es...

What happens when your sale gets delayed, your replacement property is ready to close, and your financing falls through? In this episode, David and Tom Moore from Equity Advantage dive into the complex world of reverse 1031 Exchanges and the creative financing strategies that can keep your deal alive.

This episode covers: 

What a reverse exchange is and why you can’t own both properties at onceHow seller financing can be a game-changerWhy cash-out refis before a sale might land you in hot water Why calling your 1031 facilitator early can save you time, mone...

In this episode of The Exchange Brothers, David and Tom delve into a crucial topic for real estate investors: determining dealer status and its impact on completing a 1031 exchange.

Using the Klarkowski Court Case, they walk through the 9 IRS factors that help identify whether a property is held for investment or resale, and what that means for your tax strategy.

Common misconceptions about holding periodsWhy intention matters more than timeReal-world scenarios of investors getting tripped up by dealer statusThe risk...

Thinking of exiting real estate but dreading the capital gains tax? In this episode of the Equity Advantage podcast, we sit down with charitable planning expert Lon Dufek (CFP®, CPA) to explore how a Charitable Remainder Trust (CRT) can be a powerful exit strategy — especially for those tired of managing property or not interested in a 1031 exchange.

Topics Covered:

What is a Charitable Remainder Trust (CRT)?

CRT vs. 1031 Exchange: Key Differences

How CRTs help you avoid capital gains tax

Real-life case study: Turning $500K into $2M in benefits

Usi...

Real estate pros David Moore, Steve Mark (Emerson Equity), and Bob Smith (Peregrine Private Capital) break down the best DST and 1031 exchange strategies for 2025. Learn how to preserve wealth, defer taxes, and diversify your investment portfolio with real stories, expert insight, and decades of experience.

Topics include:

DST vs. TIC structuresRisks of 721 UPREITsWhy preservation beats ROIRed state vs. blue state investingHow to vet a DST sponsor

Perfect for real estate investors, brokers, and anyone looking to unlock smarter, tax-efficient strategies this year! 

Reach out to our Experts:

Join David and Tom Moore — The Exchange Brothers — as they unpack everything from their recent trip to Southern California to the complex world of 1031 exchanges and Delaware Statutory Trusts (DSTs). In this episode, they explore how DSTs can be used for tax deferral, common misconceptions about debt replacement, and real-world scenarios involving estate planning, reverse exchanges, and improvement strategies.

Whether you're a broker, investor, or just curious about how to legally defer taxes through real estate, this episode delivers clear advice, real-life examples, and a whole lot of experience.

Topics Covered:

What qual...

Discover the truth about the 1031 exchange holding period requirement! Many real estate investors are misinformed about this crucial aspect of tax-deferred exchanges. Join David and Tom Moore, the Exchange Brothers, as they break down the myths—like the 5-year holding period—and dive into IRS rules and regulations to uncover the real requirements for a successful 1031 exchange.

From exchange timelines and related parties to partnerships and the consolidation of ownership, this podcast delivers expert insights with real-world applications. Whether you're a seasoned investor or just getting started, this essential information will help you avoid costly mistakes and maxi...

Want to keep more of your hard-earned real estate profits? In this episode, we’re diving into powerful tax-saving strategies that savvy investors use to build and preserve wealth. Join us as Rene Nelson of Pacwest Commercial Real Estate breaks down 1031 Exchanges, Section 121 exclusions, and Delaware Statutory Trusts (DSTs)—what they are, how they work, and how you can leverage them to defer taxes, maximize gains, and grow your real estate portfolio.

Whether you're a seasoned investor or just getting started, this episode is packed with must-know insights to help you make smarter financial moves.

🔹 How can...

In this episode, David and Tom Moore, better known as The Exchange Brothers from 1031exchange.com, tackle the most pressing topics in real estate and tax planning.

We’ll break down:

C Corps vs. S Corps: Which structure is right for you?HELOCs: How they fit into your financial strategy.Improvement Exchanges: When are they worth it?IRS Disaster Extensions: What California fire victims need to know.Drop and Swap vs. Swap and Drop: Partnership dissolutions explained.What Happens When Both Parties Can’t Agree on a...