Illustration by Tim Robinson.

Stewart Brand is not a scientist. He’s not an artist, an engineer, or a programmer. Nor is he much of a writer or editor, though as the creator of the Whole Earth Catalog, that’s what he’s best known for. Brand, 83, is a huckster—one of the great hucksters in a time and place full of them. Over the course of his long life, Brand’s salesmanship has been so outstanding that scholars of the American 20th century have secured his place as a historical figure, picking out the blond son of Stanford from among his peers and seating him with inventors, activists, and politicians at the table of men to be remembered. But remembered for what, exactly?

Whole Earth: The Many Lives of Stewart Brand is the first full biographical consideration of a man who has already provided useful fodder for writers seeking to characterize the various social and intellectual movements that came out of California in the final third of the 20th century. The author, the longtime tech journalist John Markoff, has covered Brand at length before, in What the Dormouse Said: How the Sixties Counterculture Shaped the Personal Computer Industry. But his new book puts Brand, the man—rather than his role as an exemplary connector of others—at the center of its story. An authorized project, Markoff’s biography draws primarily from Brand’s own words in contemporary interviews and in his detailed journals, to which the author had access. If, in the historical light of 2022, it were possible to make Stewart Brand look good, I’m sure Markoff would have managed it, which makes it all the more remarkable that he does not.

In works ranging from Tom Wolfe’s The Electric Kool-Aid Acid Test—the book opens with Brand driving the famous Merry Prankster bus—to Fred Turner’s 2004 study From Counterculture to Cyberculture, Brand found a way to put himself behind the wheel, most often by buying the car. He pops up repeatedly in what has become the standard prehistory of Silicon Valley: organizing the San Francisco Trips Festivals, which kick-started the hippie movement, helping show off the first personal computer prototype, supplying those newly minted hippies with “back to the land” fantasies, advising the Zen governor of California Jerry Brown, telling America about early computer games, cofounding one of the first successful experiments in Internet community, and coining the phrase “Information wants to be free.” As an overlapping member of so many relevant milieus, Brand is like a transitional fossil, revealing changes and continuities. In him, academics and reporters have found a useful tool for narrating the period, helping readers ride smoothly from the 1960s to the 1980s and linking together the ostensibly disparate cultures in Turner’s title.

Unlike Forrest Gump, who jogged through the same period blissfully ignorant and unseduced by any particular line, Brand fervently believed in almost everything—at least for a little while. Born into an ownership-class family in Rockford, Ill., he was the youngest of four children. His father was a partner at an advertising agency, but the family money traced to the Midwestern timber boom. Stewart attended prep schools, boarding at Exeter Academy in New Hampshire, where despite his intellectual disposition, he was an unexceptional student, especially compared with a standout older brother. It was here, Markoff writes, that Brand developed a “coping mechanism” that became an “operating manual” for him throughout his life: “Brand figured out that the best way to compete was not to follow the crowd but to instead chart his own iconoclastic path.” For an underachieving elitist, better to be incomparably strange than second-rate.

As a young man, Brand struggled to find a balance between his conventional thinking and his need for open fields where he could succeed. Looking at colleges in the West, where the level of competition was lower, he considered Reed but was disturbed to hear that the school was left-wing. The prospective student sent a letter inquiring about Reed’s “pink” reputation and its students, who seemed “a shade odd.” He ended up at Stanford.

Stanford was, at the time, a small, rural, middling private college best known as the alma mater of Herbert Hoover. It was also a conservative place; the first thing Brand did when he got to town was hit the Brooks Brothers outlet in San Francisco. But thanks to the maneuverings of its provost, Fred Terman, Stanford was in the early stages of an exciting new trajectory. Palo Alto was the launchpad for the West Coast postwar electronics industry, and though Brand was not particularly technologically inclined, his MIT-trained father and his brother Mike—a Stanford alum and an early employee at the Oregon electronics company Tektronix—were, and they introduced him to the scene, connecting Stewart with family friends.

Brand felt at home in Palo Alto, and he assumed that with his Exeter training he’d cruise to the top of his class; but despite his enthusiasm for the coursework, he made the same, lackluster grades that he did in boarding school. And though on paper he was the perfect Stanford Man—athletic and sporting but no jock, excited about ideas but no egghead, outdoorsy but no loner, and rich—he had trouble making friends and fitting into a crowd. Markoff writes that classmates remember him as a straitlaced “square” who wore his ROTC uniform around campus. Rejected by his brother Mike’s fraternity, Stewart hung out with the school’s foreign students, fretted about overpopulation, and dove into the hyper-individualist writings of Ayn Rand.

Here the reader starts to sense the contours of a black hole at the center of Markoff’s narrative. Throughout the book, people who meet Stewart Brand often disappear from his life so fast that it’s as if they were repelled by an unseen force. He had his own car and off-campus spot, but aside from a pay-to-play adventure on a summer trip to Paris, Brand remained sexually frustrated into his 20s, sending his sole female friend of note a letter calling her a “bitch” when she declined a romantic relationship. His male friendships faded about as fast. In a place where similarly bright-eyed young men of all sorts formed ambitious lifelong partnerships with their chums, Stewart—who had access to plenty of resources and could have used the disciplined focus of a contrasting partner—didn’t. I couldn’t help but wonder: Was this guy an asshole?

The answer to this question only peeks through Markoff’s authorized prose, but against Brand’s gray account of himself, the occasional glimpse of other people’s perceptions reveals a lot. What else do you need to know about a man who habitually induced his Whole Earth Catalog coworkers to play a game with padded swords just so he, with his experience and size, could beat the crap out of them? Arrogant, lazy, pretentious, and mean: Between the lines, it sure sounds like this guy sucks. This admittedly uncharitable lens brings Whole Earth into sharper focus.

Brand spent his early 20s moving in two directions at once. For a class assignment on the “anomic personality,” he checked out the burgeoning Beat scene in San Francisco’s North Beach and was relieved to find the whole thing much straighter than it was depicted in the media. Brand chilled with ex-surrealists and future hippies, house-sitting a luxurious three-bedroom rent-free. But then, with seeming incongruity, he shipped off to Fort Benning in Georgia to start Army Ranger training. ROTC was one of Brand’s favorite parts of Stanford—an uncommon sentiment—and the idea of joining an elite corps appealed to him, so after deciding that three years was too long to become a Marine, he signed up for two years in the Army. He completed his basic officer training but lasted only two weeks in Ranger School.

Markoff’s stenographic style makes for easy reading, but if you ask a proud guy why he dropped out of Ranger School, you’re not likely to get the authoritative answer. Whole Earth, the author notes, is intended not as a scholarly work but as an authorized biography, which leaves it to Brand to make himself look bad, and he does so constantly. “With no war, it wouldn’t do for a book,” he wrote, reevaluating his choice to enlist on egomaniacal grounds. “I am a character in search of an author, situation, plot, and other characters.” Instead of becoming a lowly grunt, he haggled with bureaucrats and used his connections—including his sister’s husband, a fast-rising commandant educated at West Point—to get better assignments, including a sinecure at New Jersey’s Fort Dix, where he spent the weekends as an art scenester in Greenwich Village and got into trouble for falling asleep on duty. Still, Stewart’s dreams of military glory weren’t finally over until he was told that he couldn’t apply to become a Green Beret until he had 18 months of training. Instead, less than a year into his two-year commitment, Brand got permission (“magically,” Markoff writes) to leave early and study art in San Francisco, where he rented a houseboat.

If becoming a flea-bitten trust-funder tooling around the Bay on his new sailboat, driving to the woods in his new red VW bus (imported from Germany), and trailing Jack Kerouac sounds like the worst road Brand could have taken, it’s worth keeping the alternative in mind. Had he possessed the endurance or patience to join an elite military unit, he likely would have been among the first boots on the ground in Vietnam, where the US Special Forces began the war with a murderous counterinsurgency campaign. Say what you will about rich-kid beatniks, but at least they were not war criminals.

The catalyst that turned beatniks into hippies was LSD, and Brand was there almost from the start. Like a new boat or car, an LSD trip was available as a luxury purchase, and he paid $500 to the International Foundation for Advanced Study for a supervised set of experimental trips, which sound nightmarish even to a reader who enjoys the drug. Though he’d forever be associated with acid culture, Brand preferred the inhalant that the experimenters gave him as a warm-up, and he huffed his way through the ’60s, eventually developing a tank-a-week nitrous habit.

Brand styled himself a photographer—he’d used a camera to stand out during his short military career—and envisioned a career as a freelance reporter and author who would illustrate his own work. But his pitches to national outlets yielded no assignments, and a series of projects on American Indians went unfinished as Brand jumped from one thing to the next. He made experimental sound works that were devoid of musicality, and not in a good way. “What he had,” Markoff writes, “just as he had had as a child, was an unending stream of notions.” It’s not a flattering thing to say about a man.

Brand did have the luck, however, to be fishing in a well-stocked pond with the luxuries of time and good equipment. The Trips Festival wasn’t Brand’s idea—he got it from the Merry Pranksters, who wanted to do a concert-size Acid Test—but he had $300 for a venue deposit as well as connections to concert professionals in San Francisco, including the young promoter Bill Graham. As a vehicle for Brand’s experimental art, the festival was a total bust, but as a Grateful Dead concert it was a success, and Brand reassured his father not only that he had no interest in becoming a socialist but that there was good money to be made as a beatnik.

Brand’s next big idea combined his receding interest in photography with his increasing interest in “systems thinking,” a shift from his Randianism to the faddish work of architectural theorist Buckminster Fuller. On one 1966 acid trip, Brand was struck by an idea: Why hadn’t NASA released a satellite picture of the entire planet yet? It was a puzzling question, and with its conspiratorial overtones and hippie implications, Brand recognized what we might call a “good meme.” Lacking social media, he shared his meme by hand, crafting buttons that read “Why haven’t we seen a photograph of the whole Earth yet?” and mailing them to important people in science and politics. Then he donned a costume—a new trademark top hat made him nearly six and a half feet tall—strapped on a plywood sandwich board, and distributed the buttons at some of the country’s top colleges: Berkeley, Stanford, Columbia, Harvard, and MIT. Like the acid advocate Timothy Leary, Brand had a top-down approach to social enlightenment, an elitism that, more than any ideology, position, or interest, has guided his whole life.

NASA did release such a photo the next year, and Brand recycled it for another notion, as the name of his catalog. Why a catalog? One strand that runs through Markoff’s book unremarked is the fact that Brand loved shopping. He was the prototypical early adopter, prepared to pay sticker price for the latest gadgets, a habit linked to his father’s love for mail-order catalogs and even further back to a family hardware supply business. He took the same shopping approach to ideas and identities, always on the lookout for something new. Many of his peers were the same way, and for them he dreamed up the Whole Earth Catalog, a thick brochure for the reverse-engineered store of Stewart.

The form was brilliant, in its way: With no critical or creative agenda to speak of, the Whole Earth Catalog could play fast and loose with copyright, raiding the latest books for their coolest pictures and diagrams. In it, the reader found all sorts of stuff, from walkie-talkies to tepees, calculators to kerosene lamps, as well as a whole lot of what we might now call ’60s books. Brand took the large format from Steve Baer’s newsprint instructional zine Dome Cookbook, the typeface from L.L. Bean, and his famous intro (“We are as gods and might as well get good at it”) from a British anthropologist. Reviewers got $10 apiece, and Brand paid for the latest in bespoke publishing technology. His $25,000 investment ($200,000 or so today) did not break his bank. The 64-page Catalog had a cover price of $5, roughly 10 times the price of a paperback. The hardest-working member of Brand’s staff was his new wife, Lois, who toiled alongside him all day and then did the cooking, cleaning, and laundry at night while her husband watched TV for inspiration. The relationship did not last long. One wonders when Stewart did all the reading his bibliophile image required.

As for politics, Markoff notes that leftists who met Brand assumed he was working with the CIA, an accusation that could be rated as indirectly to literally true, depending on the circumstances (later in life Brand would work alongside the CIA doing scenario planning). When he did take an unusual shine to someone political, as he did later in life with the environmentalist Wendell Berry and the cartoonist R. Crumb, Brand quickly turned them off. At a time when revolution gripped the country, the Whole Earth Catalog reflected his right-wing thought by omission. After one young staffer suggested ways to make the catalog more political, Stewart vetoed the notion with a surprising set of rules: “No politics, no religion, and no art.” What was left? Computers and shopping. As a futurist, he had that much right.

The Whole Earth Catalog was an underground hit, and with the help of John Brockman—Markoff describes him as the East Coast Jewish equivalent of Brand’s West Coast WASP, another individualist huckster hovering around collectivist art scenes—the catalog went mainstream. Though it didn’t actually sell many of the featured items, and though Brand (along with almost everyone else) later denounced the whole back-to-the-land hippie commune movement that served as its ostensible customer base, the Whole Earth Catalog made his reputation. It allowed him to put more than $1 million in profits into a short-lived foundation that awarded small, arbitrary grants to the kinds of projects he liked—Brand, still getting family checks, didn’t need the money. When Stewart and Lois divorced, she got only $10,000 and the TV. He kept the catalog’s National Book Award and the credit, which meant he got the seven-figure advance that Brockman negotiated for a Whole Earth–branded guide to software in the early ’80s, which flopped.

Though, unlike nearly everyone else in his milieu, Brand never programmed a computer, he did find a niche near California’s tech ecosystem. As a transitional figure between the ’70s and the ’80s, he is unparalleled; for Brand, the leap from hippie to yuppie was no more than a step. After the catalog’s success, he committed himself to realizing a new ideal: the “Zen playboy.” In 1986, while he vacationed on a colonial ranch in Kenya and dreamed of a book called Sleeping With Lions, the remainder of the Whole Earth team sent him a letter saying the project was broke and they would have to cut him off. Well into his 40s, Brand could still count on a check from Mom. But how to spend his time? What role could history offer him?

Before he knew it, Brand was on a Shell oil platform, helping the company’s managers find an innovative way to restructure the workforce, despite the labor union’s objections. In the second half of his life, Brand betrayed everything he’d ever embraced in the first half, with the notable exception of capitalism, of which he’s remained in favor. Soon he and several others who worked for Shell began their own consultancy firm. From the mind that created the Whole Earth Catalog came the Global Business Network. Brand charged more than $100,000 a year to show up at the occasional meeting, where he was known for falling asleep. As a consultant, he took to shilling the fashionable theories of the day, from cybernetics to space colonization to Y2K to geo-engineering and resurrecting the woolly mammoth. Brand no longer wears his top hat, but he’s still doing the same thing he’s been doing his whole life: finding rich, powerful men and selling them on his notions. His latest now is a partnership with one of the world’s wealthiest men, Jeff Bezos, to spend tens of millions of dollars building “a 10,000-year clock” into a mountain owned by the Amazon founder. Nice work if you can get it.

At one point in time, it was possible to see Brand as the goofy grandfather of a gentler, more thoughtful capitalism headquartered in the San Francisco Bay Area: decentralized but still ambitious; environmentally conscious and techno-optimist; philosophical and even spiritual rather than materialistic and stultified. If Brand had died before the 2008 crash, before Edward Snowden and Uber and Facebook as a tool of genocide and Jeffrey Epstein and coal-fired Bitcoin-mining plants, he might have secured an uncomplicated legacy. Now we all know better, and Brand’s biographer can’t get around that.

At the age of 83, Brand has survived long enough to see himself as the protagonist in a real book, a significant accomplishment for a man of meager talents and what appears to be an exceptionally bad personality. Brand is lucky the book isn’t a better one, for the sympathetic Markoff—a member of the same milieu as his subject, a fellow client of John Brockman who undertook the project at the suggestion of a former Brand deputy, Kevin Kelly—strains to depict him in a favorable light, at significant cost to the work’s quality. The reader is left with a picture that’s suspiciously overexposed, a portrait that illuminates flaws in the attempt to cover them up. Sometimes that’s the most flattering thing anyone can do.