Can your retirement account buy real estate? Startups? Alpaca farms?! Yes. And in this episode, Dana Udumulla from Madison Trust breaks down how self-directed IRAs actually work, what they can (and can’t) invest in, and why more commercial real estate investors should be using them to raise capital.
Whether you're an accredited investor or a confused podcast co-host (cough Timmy), this conversation is packed with practical takeaways, tax strategies, and jaw-dropping scenarios (like turning $7K/year into $4.75M tax-free).
We also get into:
Don’t invest another dollar until you listen. Your future self will thank you.
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Resources Mentioned In This Episode
00:00:00 – Welcome to Commercially Speaking (and IRR is NOT a pirate noise)00:00:42 – Meet Dana Kudumula: IRA Whisperer & Queen of Custodians00:02:51 – Legal Disclaimer: No Financial Advice, Just Vibes00:04:42 – What Even Is a Self-Directed IRA?00:06:45 – Dana’s Origin Story: $200, Wall Street, and Finding Her Passion00:08:11 – “You Can Invest in WHAT?!” – Real IRA Examples00:10:05 – Roth vs Traditional IRAs Explained00:14:33 – A $400K Tax-Free Growth Scenario00:16:01 – Can You Use Bonus Depreciation in an IRA?00:19:27 – Can a Fund Accept Self-Directed IRA Capital?00:21:48 – What Happens to “Wasted” Depreciation?00:24:42 – The Real Estate Pro Tax Strategy Breakdown00:26:26 – Can You Roll Over Any Retirement Account?00:29:15 – Setting Up a Self-Directed IRA (Step-by-Step)00:32:54 – Who Legally Owns the Asset? It’s Not You!00:33:46 – What Happens to Rental Income?00:34:42 – The Checkbook Control Model00:36:07 – Reminder: It’s Still a Retirement Account00:37:13 – When Can You Take Distributions?00:38:41 – How Much Can You Contribute? (And For Your Kids Too!)00:41:00 – How $7K/Yr Becomes $4.75M – Compound Interest 10100:44:22 – Roth vs Traditional: The Contribution Tradeoff00:45:21 – Yes, Kids Can Have Self-Directed IRAs Too00:46:45 – What Can’t You Do With a Self-Directed IRA?00:48:09 – Creative Legal Loopholes (But Don’t Try These at Home)00:50:22 – Lending to Family: Who’s Disqualified?00:52:13 – Mistakes That Kill Your IRA (Seriously)00:56:05 – The Biggest Scam Red Flags (And How to Vet Deals)00:58:52 – Know Your Risk Profile: Don’t YOLO Retirement Funds01:00:42 – Capital Raising From IRAs: A Hidden Superpower01:03:28 – The $44 Trillion Opportunity01:04:52 – Timmy’s Misconception: “Isn’t There a Menu of Investments?”01:07:16 – Why Financial Advisors Don’t Talk About This01:08:40 – Timmy & Dana Bond Over February Birthdays01:09:10 – Most Common IRA Scams (And the Power of Pause)01:12:02 – The Importance of Trusted Communities01:13:30 – Final Takeaway: Research, Pause, and Diversify