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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, Jack Walker reveals his journey from a 19-year-old rookie agent to running a multimillion-dollar luxury vacation rental company. He breaks down the brutal reality of today’s Airbnb market, why most sub-$1M rentals are collapsing, and what hosts must do to survive. Jack shares the operational mistakes that nearly broke his business, the challenges of scaling, and the mindset shifts that finally allowed him to grow. We also dive into taxes, hiring, delegation, and why delaying gratification is the key to long-term success. This episode is a must-listen for anyone in real estate, entrepreneurship, or the short-term rental world.
83 episodes
