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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.