In this episode, Scott hops on Zoom with entrepreneur and family man, Rande Gerber. The two discuss similar childhoods and random connections, having grown up together on Long Island. Scott talks to Rande about his incredible journey starting as a model to his career in commercial real estate. Along the way they reminisce on stories with Ian Schrager, Studio 54, and the genesis of his nightlife empire.

The duo discuss the story of how Rande met his supermodel wife, Cindy Crawford, and how eventually he set out with his best friend, George Clooney, to launch Casamigos. The brand story is explained from the foundation to the billion-dollar sale. They touch base on the lifestyle and culture of the tequila brand and Rande shares a great story on the first Casamigos video with George Clooney. Last but not least they touch upon his new boot collaboration with Thursdays Boots and what's next for Rande.