Blog

Avery interviews Mark Simpson about the benefits of direct booking websites for short-term rental hosts. They discuss why it’s important, even for small operators, to own their booking process and avoid reliance on platforms like Airbnb and Vrbo, which can make them dependent on third-party rules.

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.

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.

In this conversation, Kent Ritter, CEO of Hudson Investing, shares his entrepreneurial journey from consulting to launching his own firm, then transitioning into real estate. He details how he used his experiences to diversify investments, focusing on real estate syndication after successfully exiting his previous ventures.

In this interview with Rod Khleif, he shares his inspiring story of immigrating to the U.S., struggling financially, and rising to become a successful real estate investor and podcast host. He talks about mindset, how he got into real estate at 18, and the importance of psychology in achieving success, particularly in the uncertain real estate market.

In this episode of the Short-Term Show, Avery talks with Tim Grillot, who shares his real estate journey. Starting at 17 by flipping an old tavern and railroad depot, Tim worked his way up to owning multiple long-term and short-term rentals. He recently sold his house to live in an RV, using the profits to invest further in short-term rentals. Tim also highlights his learning curve with Bigger Pockets and his evolving strategy with short-term rentals.