The Metamorphosis of Silicon Valley CEOs: From Big to Boring

Technology chief executives were once admired for their force-of-nature personalities and daring. Now boring is the new black (or is it beige?). Except for Elon Musk, of course.

Farhad Manjoo
6 min readSep 12, 2018
Illustration: Doug Chayka

When Joe Barton, a Republican congressman from Texas, greeted Jack Dorsey at a congressional hearing last week, he sounded flummoxed.

“I don’t know what a Twitter CEO should look like,” Barton said. “But you don’t look like what a CEO of Twitter should look like.”

The congressman had a point. Dorsey — who sported a nose ring, a popped-collar shirt and a craggy Moses beard — looked more like a hipster version of a Civil War officer than a tech icon. Yet more striking than his look was his manner before skeptical lawmakers.

Faced with tough questions, Dorsey did not mount an aggressive defense of his company and his technology, as an earlier generation of tech leader might have. Instead, he demurred, conceded mistakes and generally engaged in a nuanced and seemingly heartfelt colloquy on the difficulties of managing tech in a complex world. Even in response to Barton’s comment about his look, Dorsey was solicitous. “My mom agrees with you,” he said.

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