Is Scott Galloway the Howard Stern of business?

Mr. Galloway grew up in Los Angeles to immigrant parents. His father, a charming sales manager raised in Depression-era Scotland, had a “terrible relationship with money”, he said. His parents divorced when he was 9 and he lived with his mother, who worked as a secretary.

“It was a huge source of stress that we didn’t have any money,” he said. “It was also very emasculating.” Mr. Galloway became obsessed with money and bought his first stock (Columbia Pictures) in eighth grade. He was not popular. “I looked like Ichabod Crane with bad skin,” he said. In high school, he ran for class president three years in a row and lost each time. He also developed body dysmorphia, he said.

He went to college at UCLA and described his time there, in a not-quite-convincing tone of regret, as a “missed opportunity to be responsible.” He joined a fraternity, rowed, and gained 20 pounds of muscle. “Quite frankly, my life has changed,” he said. “All of a sudden, women became very interested in me.”

While studying business at the University of California, Berkeley, he and a classmate started a company called Prophet Brand Strategy, advising companies on how to grow their brands. In the early 1990s, their advice often boiled down to: Use the Internet. They attracted big customers, including Williams-Sonoma, Levi Strauss and Apple. In the dot-com boom, they launched a series of businesses, including an e-commerce site called RedEnvelope, where people could shop and send last-minute gifts.

RedEnvelope received an influx of cash from venture capitalists, including Sequoia Capital, but Mr Galloway believed the new financiers were steering the company in a terrible direction. His battle to replace the board failed, but caught the attention of hedge funds. “They said, ‘We like the cut of your crazy jib,'” he said.

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