Episode 20: The Future of STR Investing: Mitigating Risk and Finding New Opportunities

Host: Casey Silveria

Guest: Rob Bergeron


Casey is joined by Rob Bergeron, a real estate investor specializing in helping out-of-state investors invest in Kentucky. They discuss Rob’s background and how he got into real estate investing. They also discuss the benefits of investing in Airbnb and how it can generate compounding returns. Additionally, Rob pitches a real estate deal involving a horse farm near the Noah’s Ark theme park in Kentucky that could be turned into an Airbnb and wedding venue. Rob discusses their strategy for investing in real estate, focusing on Airbnb rentals. They explain that they only take on projects allowing them to force appreciation, ensuring their mortgages remain low. They also avoid buying properties in HOAs or gated communities and prefer to buy commercially easy or zone properties, as they don’t have to worry about getting permits. They believe that small Airbnbs cannibalize each other and that going big is better for creating a memorable experience. The speaker shares a recent example of how they converted a one-bedroom property to a three-bedroom one, which will likely sell for $350-360K, and discusses the benefits of tapping into equity for other deals. Rob is excited about the opportunities presented by AI and other tools but also recognizes the potential risks and challenges. He emphasizes the importance of staying aware of new developments and taking advantage of them as quickly as possible while also being mindful of the potential downsides. He advocates for an optimistic, abundant mindset regarding technology and business. When asked about his advice for the future, Rob suggests that people should be thinking about how to mitigate risk and be creative in finding new opportunities, given the current economic climate.

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Key Points: Real-Estate Investing, Renting

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