From deep dish debates to dream destinations, Jay and Jessica head to the Windy City to chat with Matt Taylor, the opening General Manager of the new Sports Illustrated Resort Chicago. Matt shares his journey from aspiring professor to hospitality leader, his Disney roots, and what it’s like to launch an entirely new resort brand in one of America’s most iconic cities.

Along the way, we talk leadership lessons, Chicago favorites, and his wandering win—a day spent among redwoods and vineyards that proves the best trips mix a little nature and a little Napa.