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The Short-Term Shop

How She Built a $555k/year Short Term Rental Empire

How She Built a $555k/year Short Term Rental Empire

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How She Built a $555k/year Short Term Rental Empire

In this episode, Avery interviews Jen Dickson, a repeat Short Term Shop client and seasoned short term rental investor who built a wildly profitable Airbnb business, and reached financial independence, in just a few years. Jen emphasizes her approach in choosing to buy real estate in vacation markets where her family likes to go, and how she was able to build her rental property portfolio during Covid. See Jen’s property walk through here:

Jen: My husband and I are partners in this; we kind of started this journey together, and it was really kind of by accident. Um, we were living and working in Chicago, and we decided to move to Los Angeles right before COVID hit. Oh gosh, two months before. Um, we moved in January of 2020, COVID hit in about March of 2020, and so we were on lockdown. We were really missing our friends and family in Chicago, and we thought, ‘Wouldn’t it be cool if we could just buy some sort of house that we can use to go back and visit friends and family, and then rent it out when we’re not there?’ Um, so we saved up just enough money; I mean, we like scraped together, I think, the down payment of it, and we decided to go for it. Um, we found this lake house in Fox Lake, Illinois; it’s about an hour north of Chicago. We had been frequenting that area, sort of kind of like on weekends, going boating and such, and um, we knew that you could do short-term rentals in Fox Lake. So, we found this great lake house, and we just like took the plunge and bought it. We started freaking out after we bought it because we were so worried that we had just made the worst decision of our lives. In fact, it was like the best decision. So, uh, we bought it, um, did some renovations to it, um, and then we went live, like, in the middle of winter. Um, at a lake; it doesn’t sound very promising, but we started getting bookings, and we had like this crazy busy summer with guests coming through. After we got through the busy season, we thought, ‘Oh my God, this is so lucrative; I cannot believe how much money we’re pulling in with this house.’ We were able to use it as well. It was just like the perfect scenario. So, that was when we started to realize, like, this is actually a thing; people actually make this a business. And so, we started doing research— a lot of research. We went on Bigger Pockets, um, just trying to understand, like, where are the markets that people are doing this because we want to keep doing it. I think that was the time where I read your book too, so I started to get a really good idea of how to operate a short-term rental. Because when we bought the lake house, we didn’t know anything about anything. We didn’t know what a pro forma was or like, we were certainly not calculating any sort of cash-on-return; like, we just went in with it totally blindly. .

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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