413: How Shipt Founder Bill Smith is Serving a New Generation of Renters

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Bill Smith asked for a briefcase on his 5th birthday, and it’s been all business since. After dropping out of school at age 16, Bill started, built, and sold 3 companies over the past 15 years. His last business, grocery delivery service Shipt, sold to Target in 2019 for half a billion dollars. But Bill didn’t rest on his success. The same year he exited Shipt, he started Landing, a flexible and furnished rental apartment service. So what’s next for this wunderkind turned startup mogul?

Listen to Nathan and Bill discuss

  • Dropping out of school without his parents knowing
  • Figuring out the prepaid technology business
  • Exiting his first company to Green Dot Corporation
  • His step-by-step process for proving a business idea
  • Why he never takes breaks between businesses
  • Proving demand in the early days of Shipt
  • Selling Shipt to Target for half a billion dollars
  • Why selling Shipt changed his philosophy of business
  • His goal to build Landing into an enduring company
  • And much more business scaling advice…

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