Stewart Brand was by Ken Kesey's side when things got freaky. Then he stepped off the bus and brought the hippies and the computer geeks together. That's when he really changed the world.
Credit: Photograph by Jake Stangel

Stewart Brand, techno guru, counterculture impresario, inspects my ragtag clothes, spots the cotton long-underwear shirt I've layered beneath a fleece.

"Cotton is the stupidest thing you can wear on the mountain," he says matter-of-factly. We're hiking Mount Tamalpais, Marin County's highest peak, just north of the Golden Gate Bridge and not far from where Brand lives. Luckily, it's 45 degrees out, with little chance of hypothermia. "You could die," he tells me.

We break for water sometime later, at a clearing overlooking the San Francisco Bay, which this morning is enveloped in a mossy blue fog. The 74-year-old Brand, who has long, angular features and in his safari hat resembles a craggier Crocodile Dundee, demonstrates in a blur of motion how fast he can shed his GoLite pack and draw a knife from a sheath on his right hip. Other hikers sometimes don't follow the rules, he explains, and let their dogs run off-leash.

"Have you ever, you know, had to put one down?" I ask, curious to plumb the depths of Brand's practicality. It is no great shock that the editor and publisher of the Whole Earth Catalog – the atlas-size compendium of "tools" that Brand started in 1968, a publication Steve Jobs once called a "Google in paperback" and "one of the bibles of my generation" – would outfit himself with an array of useful instruments. But I didn't anticipate his wielding one with such martial purpose.

Brand says a dog did charge him once, and – knees bent, his left arm crooked into a shield – he had reached with his right hand for the blade. But it came up empty. He had left the knife on his dresser.

"The aggressive act was enough to show him who was alpha," he says. The dog slunk away, tail tucked.

Brand first came to national attention in his twenties, promoting – and enjoying – the liberating powers of LSD as one of Ken Kesey's Merry Pranksters. Over the next half-century, Brand proved to be an endless purveyor of information and invention, a constant catalyst of activity and surprising assemblies. A Sixties icon, he has also shaped our culture in each successive decade.

With the Whole Earth Catalog, which was filled with thousands of short appraisals covering everything from hydroponic farming practices to electronic music, stretching techniques, windmills, and even early personal computers, Brand defined a countercultural ethos that became what is now, essentially, the mainstream. Today, practically all the items covered in the Catalog are available at the click of a mouse; back then, it was an invaluable resource for the country's growing ranks of environmentalists, do-it-yourselfers, and back-to-the-landers. Maybe more revolutionary was that the Catalog combined ecological mindfulness with a belief in the transformative power of technology. In its pages, Brand showed that entrepreneurship and consumerism could also bring power to the people. After all, the kind of activities for which the Catalog provided in-depth instruction – building your own cabin or starting a commune – might just require the purchase of a few products, and that was going to take cash. "Whether you survive in those circumstances," Brand says, explaining his view of self-reliance, "very much depends on your understanding of money." The Catalog didn't simply ground the era's "turn on, tune in, drop out" ideals in the real world – it provided the millions whose minds had been blown open the practical tools to make that world anew. "What we were really was counter-counterculture," Brand says as we continue our ascent.

There were always computer guys hanging out at the epochal Bay Area parties, drawn, no doubt, to the psychedelics but also to Brand. "That Stewart was so at home in the world of computers baffled us," says Brand's friend Gurney Norman, a former Merry Prankster as well as the 2010 Kentucky Poet Laureate. "The rest of us sat around trashing IBM and big business, believing computers symbolized something evil," he adds. "We were so dumb."

Kevin Kelly, a founding editor of 'Wired' magazine, credits Brand with finally turning hippies on to the computer, showing it to be another human-scale tool, a better means than drugs to human augmentation and expanded consciousness. "Stewart brought together personal enlightenment and the personal computer," Kelly says. "Today, the Bay Area is all about the fusion of those two things. What seemed so contradictory in the Sixties is now so obviously complementary."

In the 1990s, Brand helped create the Long Now Foundation, a think tank that adopts a 10,000-year outlook to foster responsible future behavior. The group continues to hold seminars each month, with talks by Silicon Valley executives, academics, futurists, and historians; the foundation is also developing an online archive of the world's 7,000 known human languages. Jeff Bezos, founder of Amazon.com, is letting Brand build, on his West Texas estate, the "Clock of the Long Now" – which is, well, an actual 200-foot clock that will keep time and sound a unique chime in a different sequence each day for the next 10 millennia as a physical incarnation of the group's ideals. Brand believes that the 10,000-year time frame holds, perhaps, an unlikely appeal to the captains of dot-com industry. "These are the people surfing Moore's Law," he explains, citing the notion that computer processing power doubles every two years. "They're intensely convinced that things are moving faster and faster. So they feel the need to balance their lives and thoughts with something large-scale and long-frame."