How it all started...Jennings' First Deal

Episode 1: Jennings' First Deal

Intro
The very first deal is always the toughest to close—but it’s also the deal that can change your life. That’s what this podcast is all about. We’re interviewing people on their very first deal: what it took to close it, the emotions before and after, the setbacks, the obstacles, and how it played out full cycle.

Not just the glamor stories of closing a deal and running it into the ground—we’re talking full-cycle deals. We want to give you confidence, belief, and hope for closing your first deal.

So, welcome to My First Deal podcast with my co-host, Yeadon Smith.

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Jennings

Glad to be here, brother. I’m excited for the launch of this series. I remember back—what, seven years ago now?—we were doing property management. Then you said, “Yeadon, you should check out this course I bought on buying apartments.”

Yeadon

How long had you had that course at that time?

Jennings

About two years. I bought Michael Blank’s Ultimate Apartment Syndicator spreadsheet—just the analyzer for $150. I didn’t want to buy the full $1,100 course at first. But once I bought the spreadsheet, one of those ClickFunnel upsells popped up: “Apply what you’ve paid toward the full course.”

I thought I was probably getting scammed, but I went for it anyway. Turned out to be a solid course, and that analyzer was well-built. It gave me confidence the rest of the content would be good too.

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Yeadon

I remember thinking that was the dumbest thing ever. Like—you really bought a course online on how to become a gazillionaire?

Jennings

(laughs) Exactly. Back then, I had never bought anything online besides shoes from Amazon. Online courses were new to me. I thought, no way I’m falling for this.

But I dove in, and pretty quickly realized: you can’t just learn from YouTube or a book. You need mentors and people ahead of you who can help you through the unseen obstacles, especially when you’re analyzing real deals.

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Yeadon

So you’re going through the course, getting excited, but struggling to find anything that penciled.

Jennings

Right. I saw deals online, but none of them made sense. Then I found one listed at $750,000 in the upstate. To me, that was massive. I thought I’d need $200–300K down and a $500K loan. Way too big. My brain went straight to worst-case scenarios—bankruptcy, losing my house, my wife leaving me.

So instead, I looked for something smaller.

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Yeadon

And that’s when you found the 12-unit in Williamston, North Carolina?

Jennings

Yep. It was listed for $250,000—about $20K a door. Even back in 2019, that was cheap. I figured something had to be wrong. But I thought, I can handle this. If it goes sideways, I’ll figure it out.

I called the broker. Turns out the seller was a wealthy guy with bigger properties elsewhere. This little 12-unit was neglected. The management company wasn’t giving it any attention. Rents were way below market—$350–$400. And the expenses were out of control: he was paying for water, gas for a giant water heater, and even double-paying for trash service.

That’s when I realized: this is a value-add deal.

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Yeadon

How did you figure out management? Small towns usually have limited options.

Jennings

I found a local realtor/property manager—an older lady named Georgie—who managed about 50 units in town. She knew the market and had a great reputation. She offered to manage it for 8%, way better than the 27% the big company was charging.

That sealed it for me. I offered $240K and asked for seller financing. He agreed: 30% down, 70% financed over five years at 5%.

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Yeadon

That’s a bold ask—what did it feel like?

Jennings

Honestly, I wasn’t nervous. I approached it from strength: I’m solving your problem. If you’d run this properly, it would be bank-financeable. Since it’s not, here’s how we can structure it. He agreed without much pushback.

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Yeadon

So now you needed $75K for the down payment.

Jennings

Right. I pitched a couple investors, but they didn’t want to bet on someone with no multifamily track record. Finally, I went to the “Bank of Dad.” He grilled me hard—especially on why I wanted 60/40 in my favor when he was bringing all the money.

But I told him: Money is a commodity. I’ve got the deal. If you don’t do it, someone else will. He agreed, and we closed.

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Operations

We fired the expensive manager, switched to Georgie, cut the trash bill, implemented a utility bill-back, and stabilized the property. Within months, it was cash flowing.

Eighteen months later, I sold it for $415K. Bought at $240K, sold at $415K. After paying my dad his $90K back plus $70K profit, I still cleared $105K tax-free thanks to depreciation.

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Yeadon

That’s life-changing money.

Jennings

Exactly. One deal, one time, can change your life forever. That first six-figure check gave me the confidence and the fuel to go full-time. Since then, we’ve built a $60M portfolio.

But it all started with that first deal—and pushing through the nos, the fears, the awkward conversations, and the “valley of embarrassment.”

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Outro
That’s why we started this podcast: to share the real stories behind people’s first deals. The obstacles, the lessons, and the wins. Because the first deal is not only the hardest—it’s also the most life-changing.

If you’re inspired, connect with us at myfirstmillioninmultifamily.com. Check out Unlock Your Life for more content, and don’t forget to like, subscribe, and rate the show.

Until next time...