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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 shares how he started his journey into real estate through short-term rentals, discussing his entrepreneurial mindset, early inspiration from Rich Dad Poor Dad, and his experience in fix and flips before transitioning to Airbnb.

Avery: Hey y’all, welcome back to the Short Term Show. Today we have a really cool guest, Bailey Kramer. He’s our second 21-year-old guest. Bailey, how’s it going?

Bailey: Hey, thanks, Avery. I appreciate you having me on.

Avery: Tell us a little bit about yourself. Where are you from, and how did you get into real estate?

Bailey: Yeah, for sure. So, 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, which was my first step into real estate. I always knew I wanted to be an entrepreneur. My whole goal was to go to college, build a business, and be ready to graduate with something that would support me so I wouldn’t have to get a W-2 job.

Avery: That’s awesome! Did you always know real estate was the path?

Bailey: No, not exactly. When I was 19, a sophomore in college, I read the book Rich Dad Poor Dad, and that’s when I learned about real estate investing. I realized that real estate could be the way to achieve financial independence by the time I graduated.

Avery: So you started with fix and flips?

Bailey: Yeah, after a year of networking and learning, I did my first fix and flip. Then, I did a couple of long-term rentals and another fix and flip. Eventually, we found a motivated seller who wanted to sell his house. It was a larger house than what I had worked with before, in Illinois, priced at $779,000. We were too afraid to do a fix and flip because it was such a big project. So, we got creative and looked into Airbnb.

Avery: Did you find Airbnb was a good option?

Bailey: We did! Our next-door neighbor had their property on Airbnb, so we thought, why not try it? It worked out great, and that’s how I got into the short-term rental game.

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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