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Fortune
Fortune
Eva Roytburg

The Deadhead who became a $38 billion CEO: What HubSpot cofounder Brian Halligan learned from Jerry Garcia and passed on to his MIT students

Brian Halligan, chief executive officer and co-founder of Hubspot Inc., speaks during the Silicon Slopes Tech Summit in Salt Lake City, Utah, U.S., on Friday, Jan. 31, 2020.

On one hot June day in 1985, a 17-year-old Brian Halligan walked out to a Cape Cod road, scrawled “Saratoga Springs” on a piece of wood, and stuck out his thumb. 

He and Eric Olson, a fellow high-school student and his partner in a painting company, had decided to follow a certain band on tour. Their car, a battered Subaru Brat with a broken starter, wasn’t exactly road-trip-proof. So they thumbed rides from the eastern tip of Massachusetts to the Adirondack foothills, camped for a couple of nights near the venue, took in the tunes, and then hitchhiked home.

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