THERE’S SOMETHING SILICON
VALLEY’S MOST INDISPENSABLE CEO COACH MUST GET OFF HIS CHEST. “AT TIMES,” SAYS MATT MOCHARY, “I REALIZE THAT I’M A FRAUD.”
IN THE LAST DECADE, MOCHARY has built a career on guiding a good percentage of the tech industry’s youngest and most prominent CEOs toward being better managers, feeling more comfortable in the role, and even achieving professional joy. He’s not only the guy who teaches young CEOs how to do the job while they’re doing it; what sets him apart is his recognition of the psychological distress his clients are under, and the emphasis he places on off-loading the drudgery and releasing the pressure. His past and present client list is a who’s who of leaders from the go-go 2010s, including Vlad Tenev of Robinhood, which had a market cap that peaked at almost $60 billion; Sam Altman of OpenAI, which has raised more than $1 billion; and Brian Armstrong of crypto exchange Coinbase, which had its market cap exceed $76 billion last year. Even though Mochary, 53, moved to Hawaii two years ago and works exclusively via Zoom with his “coachees,” as he calls them, he continues to exert more influence in Silicon Valley management culture than any other coaching professional.
And he still feels he’s faking it? “That doesn’t make me not a fraud,” Mochary says. “Because when I’m coaching, my goal is to show people how to build massively successful companies—companies that are worth $100 billion or more. I haven’t built a company that’s worth $100 billion or more. So again, I’m a fraud.”
Mochary did once cofound a startup, at the height of the late-’90s dotcom boom: Totality, which provided server maintenance and repair for online retailers. He even sold some shares at the company’s zenith, when it was valued at $500 million, before it took a dive when the bubble burst. The venture survived, ultimately becoming Verizon Business, but Mochary persists.
He describes his time at Totality as one big ball of misery. “I gained lots of weight, and I looked terrible,” he says, wearing a striped polo shirt and shapeless shorts from Costco, where the entirety of his wardrobe is sourced (except for his underwear, which he says he buys from Amazon). “Not that I
