Mr. Galloway grew up in Los Angeles to immigrant mother and father. His father, a captivating gross sales government raised in Depression-era Scotland, had a “terrible relationship with money,” he mentioned. His mother and father divorced when he was 9, and he lived along with his mom, who labored as a secretary.
“It was an enormous source of stress that we didn’t have money,” he mentioned. “It was also very emasculating.” Mr. Galloway turned obsessive about cash, and purchased his first inventory (Columbia Pictures) as an eighth grader. He wasn’t in style. “I looked like Ichabod Crane with bad skin,” he mentioned. In highschool, he ran for sophistication president three years in a row, and misplaced every time. He additionally developed physique dysmorphia, he mentioned.
He went to varsity at U.C.L.A. and described his time there, in a not-entirely-convincing tone of remorse, as a “missed opportunity to be responsible.” He joined a fraternity, rowed crew and gained 20 kilos of muscle. “Quite frankly, my life changed,” he mentioned. “All of a sudden women were very interested in me.”
During enterprise faculty at the University of California, Berkeley, he and a classmate began a agency known as Prophet Brand Strategy, advising corporations on find out how to construct their manufacturers. This being the early Nineteen Nineties, their recommendation usually amounted to: Use the web. They attracted large purchasers, together with Williams-Sonoma, Levi Strauss and Apple. In the dot-com growth, they began a collection of corporations, together with an e-commerce web site known as RedEnvelope, the place individuals might purchase and ship last-minute items.
RedEnvelope acquired an inflow of money from enterprise capital corporations, together with Sequoia Capital, however Mr. Galloway thought the new financiers have been steering the firm in a horrible path. His battle to exchange the board failed, however did entice the consideration of hedge funds. “They said, ‘We like the cut of your crazy jib,’” he mentioned.