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

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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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