AMID THE SEA OF SILK TIES, charcoal suits, and glinting cuff links at the Museum of American Finance’s annual gala, PayPal president and CEO Dan Schulman is an easy mark. He’s wearing jeans, for one thing. His shoulders are slouched. And his wavy brown hair could use a trim. Those who know him—or those who have benefited from the nearly 200% rise in PayPal’s stock price since the 2015 spinout from eBay that Schulman led—dodge trays of hors d’oeuvres and watermelon- pink champagne cocktails to shake his hand. Those who don’t, raise their eyebrows. “Why is he wearing those jeans?” a woman seated at a table of Citi employees whisper-hisses to a companion.
Schulman’s work uniform hasn’t always been light-wash denim and beat-up cowboy boots (he owns three pairs, all made of ostrich). For his first job after college, an entry-level role at one of AT&T’s regional Ma Bells in 1981, he was told to buy a suit—and dutifully returned to work the next day sporting one made of brown polyester. Gradually, as he built a career as a telecom salesman, he developed a C-suite wardrobe to match, including the shimmering gold tie he wore to the New York Stock Exchange in 2007 to ring in Virgin Mobile USA’s IPO. But by the time Schulman arrived at American Express, in 2010, he’d had enough, and fully embraced jeans as a signal of his counter (corporate) culture tendencies.
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