San Jose mayor Matt Mahan wants to prove he’s not just another ‘Silicon Valley guy.’ Will Californians buy it?

San Jose mayor Matt Mahan had been in The Daily Show hotseat all of 30 seconds when Jon Stewart asked about his startup days. At any other period in recent California history, this question might have been a layup for the California gubernatorial hopeful, a chance to talk about Causes, the app he grew to nearly 200 million users across more than 150 countries, or Brigade, the voter activism platform he subsequently cofounded with Napster’s Sean Parker. But this was March 2026, at a time of apex anti-tech sentiment. So rather than boasting about his business chops, Mahan blinked slowly and attempted his best politician’s pivot. “I was in the startup world,” he said. “Before that though I was a public school teacher.” The crowd applauded, and Mahan shot them a winning smile. He said he taught 7th and 8th grade English and history. “That’s wonderful,” Stewart responded, laying a trap. “And you left there . . . when?” “Teaching? 2008,” Mahan replied, stiffening slightly. “Interesting,” Stewart nodded, feigning naivete. “To do what?” Mahan conceded. “To get into the tech world,” he said laughing. “You got me.” “You son of a bitch,” Stewart chided him, flogging Mahan with his notecards. When I ask Mahan later whether there was a bit of an apology in all his bobbing and weaving, he insists there wasn’t. But he says his backstage conversations with Stewart did make him wary of being typecast. “There was just sort of this pigeonholing of ‘Oh, you Silicon Valley guys,’” Mahan tells me over Zoom, sitting in a freshly pressed button-down in front of a half-wiped whiteboard. “I wanted him and his audience, and everyone who cares and is paying attention to this governor’s race to know that those stereotypes are huge oversimplifications.” That may be. But the fact that a 43-year-old candidate for California’s highest office would sooner tout his post-undergrad Teach for America fellowship than his 11-year career as an entrepreneur says a lot about how toxic Big Tech has beco