How did the deal with Walmart materialize?

An old business school friend suggested I talk to Walmart executive Marc Lore, who had been a mentor. We mind-melded on the future of e-commerce. Then we went out to dinner with the CEO, Doug McMillon, where I learned how he was transforming Walmart. After that, I was literally praying that the deal would happen. The price discussion was easy. The harder part was, "Do they want to do it?"

What was the biggest lesson you learned from your time at Walmart?

How to do leadership at scale. Internally, 2.4 million people are watching what Doug says. I observed how thoughtful his communication was. If you're a leader invested with real power, you don't need to talk to have authority. In staff meetings, it's smarter to just ask a lot of questions and speak only when needed.

How well did the two companies' cultures mix?

I feel like it worked out. Early-stage venture-backed companies operate in a move-fast-
­and-break-things way, so when you bring them into the environment of a large profitable company, there's a lot of stuff that happens. I can't picture how you change each other organizationally without conflict.

Did that conflict influence your decision to leave?

Entrepreneurs are rebels, so being inside a large enterprise is a challenge. At some point, you have a craving to build something new. Everyone tells you to get out after six to 12 months, though I don't think that's always the right answer. Once we'd done what I came into Walmart to do, that's when I felt like, "Mission accomplished."

What are you doing now?

I'm playing a lot of chess. I'm also writing a book, and working on a nonretail project in the dating space. At night, I dream about having no inventory and no stores.