Mr. Galloway grew up in Los Angeles to immigrant dad and mom. His father, a captivating gross sales govt raised in Melancholy-era Scotland, had a “horrible relationship with cash,” he mentioned. His dad and mom divorced when he was 9, and he lived along with his mom, who labored as a secretary.
“It was an infinite supply of stress that we didn’t have cash,” he mentioned. “It was additionally very emasculating.” Mr. Galloway grew to become obsessive about cash, and acquired his first inventory (Columbia Photos) as an eighth grader. He wasn’t well-liked. “I appeared like Ichabod Crane with dangerous pores and 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 school at U.C.L.A. and described his time there, in a not-entirely-convincing tone of remorse, as a “missed alternative to be accountable.” He joined a fraternity, rowed crew and gained 20 kilos of muscle. “Fairly frankly, my life modified,” he mentioned. “Unexpectedly ladies had been very desirous about me.”
Throughout enterprise faculty on the College of California, Berkeley, he and a classmate began a agency known as Prophet Model Technique, advising corporations on how you can construct their manufacturers. This being the early Nineteen Nineties, their recommendation usually amounted to: Use the web. They attracted large shoppers, together with Williams-Sonoma, Levi Strauss and Apple. Within the dot-com increase, they began a collection of corporations, together with an e-commerce web site known as RedEnvelope, the place folks may purchase and ship last-minute items.
RedEnvelope obtained an inflow of money from enterprise capital companies, together with Sequoia Capital, however Mr. Galloway thought the brand new financiers had been steering the corporate in a horrible route. His battle to interchange the board failed, however did appeal to the eye of hedge funds. “They mentioned, ‘We just like the lower of your loopy jib,’” he mentioned.