The 1031 Exchange Brothers

1031 + IRA + Airbnb + Reverse Exchanges Overview (00:26). Market Changes & New Tax Legislation (02:13). Can You Combine a 1031 Exchange with a Self-Directed IRA? (08:16). Deal Structuring: Ownership, Loans & Key 1031 Rules (10:20). UBIT Explained (13:48). Advanced Strategy: Owning Property in an IRA Long-Term (19:34). Airbnb & Short-Term Rentals: Do They Qualify for 1031? (38:36). IRS Vacation Home Rules (Rental vs Pers...

1:19 — F1 Experience & Japan Sabbatical
7:14 — The Bear Encounter
11:14 — Mentorship & Entrepreneurship
15:30 — From Flipping Houses at 19 → Property Management
18:36 — Oregon Rent Control & Market Reality
24:28 — Investor Strategy & Property Management Insights

Nick Cook started flipping houses at just 19 years old—during the height of the NINJA loan era. Today, he leads one of Oregon’s top prope...

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 Adva...

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 w...

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 wh...

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, Sp...

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://w...

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 ...

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 dr...

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 waitin...

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, w...

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, c...

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 g...

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”
  

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 inve...

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 st...

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 Tra...

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, a...

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 l...