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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