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

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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