Do it like the Dossmans and strive to own multiple properties

Corie Murray’s ‘Black Men Sundays’ podcast focuses on business, finance and building generational wealth

Caleb and Sherese Dossman (Copyright 2023 by WKMG ClickOrlando - All rights reserved.)

ORLANDO, Fla. – Not everyone who sets out on a real estate journey can say they’re as successful as this couple, so how is it that the Dossmans came to own five properties?

Well, they had six, but we’re told Caleb sold one so he could quit his job, too.

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This week on “Black Men Sundays,” it’s a throwback classic to March 2022 when host Corie Murray interviewed Caleb Dossman and Sherese Dossman, a realtor husband and finance pro wife who work together to invest in real estate.

“Some remember in 2008, that was a recession. During the recession... that’s when we started,” Caleb said. “...Together, we invested in our first property, first property in 2008. I think we paid like $175,000 for it, but that’s where we started, didn’t feel like we knew everything about real estate at the time but we just love looking at houses, love looking around, you know, being nosy, looking at everybody’s model home, even looking at the rich million-dollar homes.”

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Before even buying blinds for their first house, the couple said they fell in love with another.

“We’re just like that. We’re like, ‘How do we get it?’ So we talked to the lender and they were like, ‘You own the property, why don’t you find tenants for your first property and then we can put you under contract over here?’ So what we did was, we had to figure it out: How to get a property management contract. How do we find — you know, and at this time I wasn’t a real estate agent — how do we find the contracts and how do we get this going? And basically, we got it going and we found tenants, got a contract, built the three story home ... it was the one that we sold,” Caleb said. “I think the recession was still going on. That’s what they said on TV, they said ‘Recession,’ but we were doing fine and basically, we sold that house, the money I made from that house — we made a little over 100 grand — and I was like, ‘That’s the money I’m gonna use to put aside so I could quit my job so I can do what I want to do full time.’”

According to Sherese, they had to figure out the entire process on their own, though the couple added it saved them money in the long run. A good thing, too, as she learned she was pregnant when the third house came into focus.

“That was just crazy that we got a contract on our house at the same time that I found out that I was pregnant with our second child, and so we we basically took the money, we moved to an apartment, waited for this house to finish building. And so we finally moved into that property, and then that was about five years ago. We stayed there and we kind of talked through, like, ‘OK, what are we going to do next?’ And we we stayed the house for about a little over a year and we were like, ‘Well, maybe we should rent this out at some point.’ And it just so happened that God lined it up just correctly to where I just happened to be at a dentist’s appointment and it just took way too long, I was like, ‘Let me just reschedule.’ I went over to the model home and I just happened to be talking to a lady that was there and the actual realtor that was in the office, and she said, ‘Yeah, there’s a lady in here. And she’s looking to rent.’”

Hear the full interview and more in Season 2, Episode 25 of “Black Men Sundays.”

Black Men Sundays talks about building generational wealth. Check out every episode in the media player below.


About the Authors

Brandon, a UCF grad, joined the ClickOrlando team in November 2021. Before joining News 6, Brandon worked at WDBO.

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