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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode, I talk with Jessie Dillon—a beauty salon owner turned real estate investor who’s on track to hit financial freedom just four years after buying her first rental. Jessie shares how she scaled to nearly 50 units using creative financing, house hacking, and capital partnerships—all while working part-time in her salon. We dive into mindset, money management, and her specialty: value-add multifamily deals in long-distance markets. Whether you’re just starting out or looking to scale with partners, this episode is full of wisdom, strategy, and real-life stories that will inspire and equip you. Let’s get into it!
32 episodes
