The New Republic

Four years ago, a cloud computing company called Rackspace was exploding. Hiring at a rate of 100 people per month, it had bought a 1.3 million-square-foot abandoned shopping mall in San Antonio—soon christened “The Castle”—to house them. Director of social media Rob LaGesse was tasked with making it feel like something other than an abandoned shopping mall. 

Typically, LaGesse might buy some innocuous prints from Ikea, or just leave up easel paper from brainstorming sessions (Facebook lets employees draw on the walls). But LaGesse wanted something more personalized, to keep his burgeoning workforce rooted in its mission. So he asked Hugh MacLeod, a cartoonist he’d met at South by Southwest, to come pay a visit. 

“He just got it,” LaGesse says. “Culture is so important to us. We can’t teach people to love customer service." MacLeod went home, and sent back a suite of simple cartoons with epigrams like “if you’re just here for the paycheck, don’t expect to last long” and “engineers are sexy.” 

Now, Rackspace has spent hundreds of thousands of dollars on original MacLeods—six three-by-five-foot canvases hang in the customer briefing center, and smaller ones are scattered throughout the ex-mall—as well as his designs for t-shirts, thank you cards, an e-book about the company’s history, and employee awards. It's gotten to the point where MacLeod is more of a brand consultant on retainer than just a purveyor of inspirational wall hangings. 

“I’m continually engaged with Hugh,” LaGesse says. “It’s not unusual for him to call me at 10:00 on a Thursday night, and him and I talk about ideas.”

That’s what MacLeod is: An idea man, for companies trying to hang on to their start-up roots. And Rackspace is just the beginning. Over the past seven years, his Miami-based company, Gapingvoid, has amassed a Fortune 500–studded client list including Intel, VW, Dell, SAP, Hewlett Packard, and Cisco, which most recently brought him on for a culture change “intervention” around a still-secret new business initiative. Thousands more people have ordered prints from his online store, festooning their offices with his sloganized cartoons; the dozen-person company pulls in $5 million per year in revenue.

MacLeod’s work is supposed to motivate the masses, just like the those cheesy office posters that have spawned countless satires. But unlike the corporate “art” that might serve as a backdrop for a Dilbert strip, his scribbles are raw and rambunctious, as if scrawled on the back of a napkin at the moment of epiphany (not unlike the cliche about how business ideas are born). His work acknowledges the absurdity of workaday life, while also encouraging employees to respond with passion, creativity, and non-conformity. 

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“Quality Value and Service! So exciting!” shrills a pink lady, sarcastically. “We need to talk,” MacLeod’s chickenscratch begins, against a blue miasma. “After that, you need to shut up.” And for the sporting type: “Be the skin. Be the game.” 

“People’s bullshit detectors are turned up high these days. And you need to come off in a way that’s authentic,” says MacLeod. “Everybody is trying to make a company more human.”

But can a cartoonist manufacture humanity? So far, big corporations seem to think so, and right now it’s an open market that Jason Korman, MacLeod’s business partner, hopes to dominate. “We want to own the office art space,” he says.

ONE REASON MacLeod gets along so well with startups is that he views himself as a disruptive force in his own industry: Marketing. The garrulous Scot got his start in the late 1990s as a copy writer at a Madison Avenue ad agency, doodling on the backs of business cards during lonely nights in Midtown bars. MacLeod started a blog to host them in 2001, along with his musings on life and business. That’s how Korman, a New Yorker with a wine concern based in London, discovered him. 

“I saw his style and his voice, and I thought wow, the problem with wine is everybody’s really intrigued by it, but the conversation about wine is about all this crap nobody cares about,” Korman says. Through techniques like explicitly targeting Microsoft employees and putting a cartoon-labeled bottle on every table at the British Comedy Awards, they doubled sales within a year. After that, Korman and MacLeod decided to start taking clients. 

MacLeod’s blog and cartoon-a-day newsletter had already built up a decent audience (it now goes out to 48,000 subscribers). The commissions started rolling in, especially among like-minded internet evangelists like Seth Godin, who’s published a stack of books about marketing on the web. “When I first saw Hugh’s work, it felt like he was trying to do what I was trying to do: To give people a totem that they can use to rally the troops,” Godin says. “This is about the insurgent manager, the insurgent creative department, that is tired of being told what to do.”

But it’s not just the cartoons: MacLeod’s philosophizing had struck a chord with the new internet economy as well. Inspired by the Cluetrain Manifesto, a set of 95 principles on webby enterprise followed cultishly by a cadre of early blog adopters, MacLeod published the Hughtrain Manifesto, followed by “How to Be Creative.” His teachings align with the golden rules of the startup community, like the value of failure and the importance of ignoring the critics, plus boilerplate bromides about hard work and being passionate about your job. 

Not exactly revolutionary stuff, but MacLeod says it with enough regularity to convince entrepreneurs he’s on their side. 

“There’s definitely a kinship in what he's interested in outside of work,” says Stuart Johnson, who’s hung dozens of MacLeods on the walls of his 40-person law firm in Michigan. “If I thought all he was doing was trying to come up with an idea for something he could sell, that would take away from what I get out of it.”

Now, MacLeod’s doodles have practically become dogma: He’s the official cartoonist for Babson College, the top entrepreneurship grad school in the country. President Len Schlesinger stumbled upon a particularly resonant Gapingvoid cartoon while browsing the internet—“Don’t try to be the best when you can be the only,” a paraphrase of Jerry Garcia—and used it for his first State of the College address. Then he started buying prints for the library, which is now nicknamed the Hughseum.” Last year’s strategy presentation consisted entirely of cartoons. 

“We had hard copies available for people, and the hard copies just flew out,” Schlesinger says. “It was such a powerful way of being able to talk about what we do.”

CAN CUTE DRAWINGS actually change a workplace environment? Gapingvoid argues yes, and often points to the Blue Monster as an example. 

The Blue Monster was a crudely drawn head with pointy horns, gimlet eyes, and a gaping mouth full of sharp teeth that MacLeod created for some friends at Microsoft, accompanied by the phrase, “Change the world or go home.” The goal: Counteract the prevailing attitude that Microsoft, the Evil Empire, had stopped innovating and was only trying to squeeze out competition. A manager in the company’s UK office adopted the Blue Monster, putting it on his business cards and e-mail signature, endorsing a Blue Monster Reserve run of white wine, hoping the ethos would spread virally and buck up a discouraged workforce. It helped, a little; one guy even got a Blue Monster tattoo. 

But then it faded away (the tattooed guy got laid off). And though MacLeod says more Microsoft commissions followed, Gapingvoid never got paid for the Blue Monster beyond a few limited-edition prints; it was more a demonstration project for the power of what MacLeod calls a “social object,” which stimulates feelings, conversations, and action. His corporate campaigns, instituted by management in order to inspire the rank and file, are much more banal—like Intel’s processor “as an expression of human potential,” a poster for Cisco covered with light slogans, and smiling blue monsters proclaiming the coolness of nerds for Hewlett Packard’s cybersecurity division (“Just because we’re paid-to-be-paranoid security gurus doesn’t mean we don’t leave our caves once a year”). 

In large part, corporate commissions are less threatening because Gapingvoid tries to reflect the company’s values back at them, not provide a tool for disruption. "If you can really take people’s true beliefs and sentiments and aspirations, and give them ways to communicate that, it’s really powerful,” Korman says. “I think that’s why the whole office art thing works, is because the voice isn’t shallow platitudes.”

In fact, you can find plenty of shallow platitudes in the Gapingvoid online store: “A story without love is not worth telling.” “Inspire → Be inspired.” “Learn. Love. Live. Legacy.” Which may speak to the fact that there is still an appetite for cheesy truisms. Hallmark still makes a bundle off of them, after all.

MacLeod talks a lot about the importance of working for some purpose other than a paycheck. “If it was just the money, everyone would join the mafia and be done with it,” he says. But he doesn’t appear terribly excited by the airy inspirational stuff himself. MacLeod’s page of favorites from his own ouvre is much more dark—about relationships, poverty, New York. The insights are sharper, but not much use for galvanizing a staff of hundreds or thousands. Johnson, the Michigan lawyer, also says he puts more upbeat Gapingvoid cartoons in the common areas, keeping the more cynical ones for his own office. “We need to know at least once before we die that our life isn’t shit,” for example, is not something he’d use to get people jazzed about coming to work in the morning.  

MacLeod’s work is undeniably an improvement over the office schlock of yore. At its best, it’s more honest, and more cognizant of the entrepreneurial psyche, while still retaining some idealism. But it’s hard to imagine a truly dynamic company like Google bringing in Gapingvoid—their famously positive office culture arises organically, from employees who have ample freedom to create (the free food doesn’t hurt, either). In a way, inspirational office art is doomed from the outset: A poster put up to motivate others inevitably admits that something fundamental is already missing. Passion, for workers laboring in the bowels of the typical American megacorporation, might be too much to ask.

All images courtesy of Gapingvoid.

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