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.
Halligan didn’t know it yet, but that first show would turn him from a curious listener into a full-blown superfan of the Grateful Dead. And throughout his professional life—he became a cofounder and CEO of HubSpot, which at its peak valuation in late 2024 had a market capitalization of about $38 billion; a partner at Sequoia Capital working with hot AI startups; and a senior lecturer at MIT—he has carried the Dead’s ethos with him.
On Tuesday, he’s releasing a new edition of his book, Marketing Lessons From the Grateful Dead. The book folds together his dual life, Deadhead kid hitchhiking to a concert and the scale-up CEO advising founders burning through growth curves never before seen in tech.
