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The Short-Term Shop

Starting from Scratch with Bailey Kramer

Starting from Scratch with Bailey Kramer

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Starting from Scratch with Bailey Kramer

Bailey Kramer, a 21-year-old entrepreneur, shares how he got started in real estate with short-term rentals. He talks about his journey from reading Rich Dad Poor Dad to doing fix and flips, long-term rentals, and eventually landing a $779,000 property that pushed him toward short-term rentals as a more viable option. He explains how he took inspiration from a neighboring Airbnb property to make the decision and his approach to risk and learning in real estate.

Avery: Hey y’all, welcome back to the Short Term Show! Today we have a really cool guest; his name is Bailey Kramer, and he’s our second 21-year-old guest to have on the show in the past little while. So I find that really exciting that the kids—well, I feel so old saying ‘kids’—are doing such cool things. I’m 33, by the way! I’m not that old, but the kids are doing some great things.

Avery: I’m really excited to interview you, Bailey. How’s it going?

Bailey: Yeah, thanks, Avery. Really appreciate you having me on.

Avery: Yeah, no problem! Thanks so much. So tell us a little bit about yourself, who you are, where you come from, and how you got into real estate.

Bailey: Sure! Like you said, my name is Bailey Kramer. Right now, I live in Orlando, Florida, but I grew up in Milwaukee, Wisconsin. I got into short-term rentals as my first foray into real estate. I always knew I wanted to be an entrepreneur. My whole goal was to go to college and build a business. By the time I was ready for graduation, I wanted the business to support me so I wouldn’t have to get a W-2 job. That was the root of it all.

Bailey: When I was 19, a sophomore in college, I read the book Rich Dad Poor Dad, and it totally shifted my mindset. I learned about the concept of real estate investing, and I realized that was the path I wanted to take. My goal became to reach financial independence by the time I graduated, so I got into fix and flips. And when I say I fast-forwarded, it took a year of networking, learning, and meeting the right people.

Bailey: I finally did my first fix and flip, and then did a couple of long-term rentals and another fix and flip. Eventually, I found another property for sale, which we did direct-to-seller marketing for. The owner was really motivated to sell. It was a larger house, but it had health issues and was in rough shape.

Bailey: The houses I’d bought before were between $68,000 and $200,000, but this house in Illinois cost $779,000. That’s a lot of money, especially for one of my first couple of projects. We were initially thinking of doing another long-term rental, but the numbers just weren’t going to work out. We were too afraid to fix and flip it because it felt like a huge gamble. Rehab costs weren’t going to make sense either.

Avery: Yeah, I can see how a $779,000 house would feel like a big leap!

Bailey: Exactly! So we thought, “What else can we do?” We looked up Airbnb to see if short-term rental would be a good option. We knew it was happening in the area because our next-door neighbor had his house listed on Airbnb. Our house was bigger, with a better location and view, and it could accommodate more people. We thought, if our neighbor is making money from his, we could do even better.

Bailey: We ran the numbers, and if we could get $1,000 a night, it would be a solid deal. So that’s how we decided to go the short-term rental route with that property.

Avery Carl

Avery Carl

Avery Carl was named one of Wall Street Journal’s Top 100 and Newsweek’s Top 500 agents in 2020. She and her team at The Short Term Shop focus exclusively on Vacation Rental and Short Term Rental Clients, having closed well over 1 billion dollars in real estate sales. Avery has sold over $300 million in Short Term/Vacation Rentals since 2017. An investor herself, with a portfolio of over 100 Doors, Avery specializes in connecting investors with short term rentals with the highest ROI potential, and then training them to manage their short term rental from their smart phone from anywhere in the world.

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