Inside the restless mind of a serial founder

His marriage suffered, and eventually ended. He gave up on hobbies and new friendships. “I sacrificed everything I felt I could,” Lore (pronounced “LOR-ee”) tells the author, sitting in a conference room at the R&D center of his meal-delivery company, Wonder, in Parsippany, N.J. Scribbled on a dry-erase board is a three-year timeline, building up to an IPO in 2027. “I had nothing else left to sacrifice, because when you do this startup thing, you can’t, like, dial it back or do it less. It just is what it is. You’re eating glass every day, you’re working 100 hours a week, and you’re all in on it. It’s the only way to make it work.”

Lore has made it work on a spectacular scale. His 2010 sale of Quidsi, the parent company of Diapers.com, to Amazon for $545 million netted him tens of millions of dollars. The $3.3 billion sale of another company he cofounded, Jet.com, to Walmart in 2016 resulted in a personal windfall that even his grandkids’ grandkids couldn’t spend. By the age of 45, Lore, raised in a tumultuous home on blue-collar Staten Island, had a CV that would surpass many of the world’s most successful entrepreneurs’ bucket lists.

And at 53—with a net worth estimated by Forbes recently to be $2.8 billion, including his ownership stake in the Minnesota Timberwolves NBA franchise—he’s far from done. In his latest big entrepreneurial bet, Lore has poured over $300 million of his own funds into Wonder, a virtual food hall for the digital generation with ambitions to become so much more. 

Lore’s grand vision is to build the app and business into the platform for all food delivery for your home—whether it’s a meal prepared at a Wonder facility or a Grubhub partner restaurant, a Blue Apron boxed kit, or a bag of groceries left on your doorstep—with an AI agent executing the experience. Eventually, he says, that AI might tell you exactly what to eat based on your tastes, dietary goals, and vital signs—then serve you those meals (as Lore’s personal chef already does for him). There may even be a robot making the food.

According to the author what drove him is to get to the bottom of a different question about the serial entrepreneur: Why is this billionaire, whose insatiable drive has already cost him his marriage of 22 years, still grinding through all those 90-hour workweeks? What more does Marc Lore have to prove? And to whom?

The author began reporting on Lore and his companies more than 10 years ago, and have long been fascinated by Lore’s myriad contradictions: He’s a ruthless corporate competitor, though most employees can’t recall him ever raising his voice to even a seven out of 10. He’s a brilliant mind who brags—often—that he doesn’t read anything beyond what’s directly necessary for the job at hand. And he’s a self-made billionaire who still doesn’t feel he has fully succeeded. He hears the industry whispers doubting whether he can ever build a profitable, long-term, independent business.  What would it take for Lore to rest content? A whopper of a public offering would be a nice start, he tells me: “If it’s an IPO and it’s tens of billions—10, 20, 30 billion—that would be the biggest entrepreneurial achievement of my career.”

In Lore’s telling, his sometimes combustible upbringing is the key to how he became the entrepreneur he is. Those years of loneliness and unhappiness left him with the habit of escaping into mental problem-solving—and perhaps living with uncertainty and risk gave him the “cognitive flexibility” that neuroscientists have observed in habitual entrepreneurs.

Over his career, Lore has raised more than $3 billion in venture funding across 15 fundraising rounds. He has been rejected at approximately 2,800 out of 3,000 pitches, by his own calculation—93% of the time.

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