How to Test a Hypothesis with Bill Smith of Shipt

For Starters with Alexa von Tobel

When serial entrepreneur Bill Smith relocated his family across the country to build his third startup, the seedling of an idea for his next startup was born. In 2019, Bill founded Landing, the first membership-based leasing model for flexible living. He has since scaled the business to cities around the country with a network of thousands of apartments. Along the way, he’s amassed $255M in funding and been named Forbes Next Billion Dollar Startup, all while making renting your next apartment as easy as ordering takeout. Prior to Landing, Bill founded, scaled, and exited three companies, including the online grocery delivery marketplace, Shipt, which sold to Target for $550M. Bill shares his advice on navigating negotiations, how he discovered product-market fit by asking customers to pay before his product was even built, and why true partnership is critical for a successful acquisition.