Episode 550: How One Expired Listing Turned Into an $80K Subject-To Deal with Richard Whitman

March 11, 2026•2 min read

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In this family-cast episode of the Smart Real Estate Coach Podcast, I sit down with our High 6 Associate Richard Whitman to walk through his 20-year journey from mechanic and accountant to creative real estate investor building three-payday deals. Rich bought his first flip back in 2005, was actively buying foreclosures through the 2008 crash, and today holds 13 properties, 20 units, and an Airbnb—plus he’s now stacking terms deals on top of that portfolio.

We break down how he turned an expired listing from a veteran on the brink of giving the house back to the bank into a subject-to, three-payday deal worth roughly $80,000 in total profit, with $30,000 down, strong monthly cash flow, and a solid back-end. You’ll hear how the bootcamp “light bulbs” helped him stop over-rehabbing, how our buyer-side systems and Wednesday Q&A calls fast-tracked his confidence, and why his mission now is to help families avoid foreclosure while hitting his goal of two creative finance deals a month.

If you’re a W-2 earner, a seasoned flipper, or a buy-and-hold investor who knows there’s more leverage in terms, this conversation will show you how to plug into the three-payday system and move from baby steps to “jogging” toward financial freedom.

Key Talking Points of the Episode

00:00 Introduction

02:03 How Rich got the real estate itch

03:01 Buying foreclosures through the 2008 crash

04:10 Passion for foreclosures and helping people

05:26 From bootcamp light-bulb moments to joining the community

06:50 Why the three-payday structure clicked

07:25 Building a family business with his daughter

08:12 Deal breakdown: expired listing, veteran, and sub-to

09:10 Learning subject-to on the fly and educating the seller

10:02 Support from the Smart Real Estate Coach team

11:21 Why weekly buyer Q&A calls matter

15:02 The numbers: $30K down and ~80K total profit

16:04 Gratitude and impact: serving both sides of the table

17:55 Deal timelines: from lead to contract to funded buyer

18:37 Balancing helping family, flips, and three-payday goals

20:21 Leveraging coaches and a deep bench of experience

22:01 Mindset shift: from loss and fear to baby steps and jogging

Quotables

“I bought my first flip, cost me ten grand, put about twelve in it and sold it for fifty. So that gave me a good itch to start doing more.”

“I’m just thankful for anything. I’m thankful I could help somebody out… I’m thankful I got somebody in a house that weren’t able to get qualified through banks.”

“Even if you just start out at the bottom level, get in there, put your foot in there and start taking the baby steps, and sooner or later you’ll be jogging.”

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