Diapers.com & Jet.com: Marc Lore
Around 2003, after forays into banking, baseball cards, and—believe it or not—bobsledding, Marc Lore landed on an idea for an e-commerce business: a website to make it simple for parents to order diapers. The only problem, as he quickly discovered, was that it's impossible to make money selling diapers on the internet. But Marc and his co-founder had a strategy: they'd lose money on diapers, but make it up by selling other baby products. By 2010, Diapers.com was such a competitive threat that Amazon acquired the company for over $500 million. In 2015, Marc launched another e-commerce venture and Amazon competitor called Jet.com. Walmart bought Jet.com less than a year later in a deal valued at $3.3 billion.
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