Building Financial and Time Freedom: Chad Phillis's Checkmate Rentals Story | The YEN Podcast Ep.2

The YEN Podcast

In this episode of The YEN Podcast, host Matt Chute sits down with Chad Phillis, the visionary founder of Checkmate Rentals, to discuss his journey in entrepreneurship. Chad shares how he navigated the challenges of launching a rental property business during the peak of COVID, his motivation for achieving financial and time freedom, and the invaluable lessons he learned along the way. With a unique background that includes multiple side hustles and a key role in scaling a startup’s operations, Chad’s story is a testament to resilience, adaptability, and the power of strategic thinking.

Tune in to learn how Chad built Checkmate Rentals from the ground up, the strategies he used to expand operations nationwide, and his insights on achieving true independence in business. Whether you’re an aspiring entrepreneur or simply curious about the world of short-term rentals, this episode offers inspiration and practical advice for carving out your own path to success.