Retail Rebel Tristan Walker Rethinks Everything

Everyone wants a piece of Tristan Walker. He’s in demand at conferences. Reporters call him constantly. His fans treat him as an inspiration. But after years in the limelight, he’s leaning more into this realization: All that means nothing if he isn’t a great CEO first.

- J.J. McCorvey

The 40 or so students sitting before him nod. They’re assembled here at the Stanford Graduate School of Business for a class called Entrepreneurship from Diverse Perspectives, where female and minority entrepreneurs and investors are invited to speak. The hope is to cultivate an appreciation for the value of diversity among the country’s next business leaders.

If you’ve ever heard Tristan Walker speak, diversity was almost certainly the topic. A Stanford grad himself, he keynotes conferences on the subject. He’s been a fixture at SXSW. Almost any newspaper article, radio segment, or magazine story about diversity in business (including, full disclosure, a few written by me) will quote Walker, if not focus on him almost exclusively. And it makes sense that he’d find himself in this position. After all, he’s the black man who rocked his way through some of tech’s hottest companies, raised $33.3 million to launch a startup of his own, and then, like an action-movie hero who just leaped across a chasm, immediately started pulling other people across with him. “You gotta succeed,” he implores the students. “If you’re not succeeding, you’re not recruiting anybody.” He’s good at this: natural, earnest, and yet never lecturing. He makes people want to succeed. And in turn, they want him to succeed. Because his success is their success. His success makes more success possible.

But later, during a one-on-one conversation, Walker confesses that this role has been weighing heavily on him. “I have this kind of internal conflict, where it’s like, Tristan, you can’t mess this up,” he says. Every entrepreneur feels that at some point, of course. Most feel it damn near all the time. But he has the unique challenge of feeling many other people’s hopes on his shoulders. If his success is their success, then is his failure their failure?