When Stewart Butterfield was twelve, his parents sent him to the most prestigious private school they could afford. The Butterfields had spent more than a decade rambling around western Canada, including a stint on a hippie commune. The counterculture had lost its charm; remorse was setting in. Maybe their son could make up for lost time by joining the patrician world of St. Michaels University School, on the south tip of Vancouver Island. There would be squash courts, cricket fields, and dormitories carrying august Anglo-Saxon names such as Winslow and Symons. Instead of wearing dirty T-shirts, their son would embrace the preppy dress code and respectful conformity of St. Michaels. At least, that was the hope.
Stewart Butterfield wasn’t about to become anyone’s pawn. He started his rebellion carefully, wearing soft-collared polo shirts to classes and then, when his teachers weren’t looking, slipping into a dark jacket with a mean-looking Iron Maiden logo on the back. Eager to help this newcomer settle in, school administrators invited him to lead the dinner-hour recital of the Lord’s Prayer. Surely the boy would understand the importance of this trusted honor and acquit himself honorably. Instead, Butterfield and an accomplice delivered the entire prayer—“Thy kingdom come,” “our daily bread,” and so on—in squeaky voices that sounded like Donald Duck. Two hundred classmates howled. Teachers seethed. It was Butterfield’s way of telling the world he intended to be a nonstop rule breaker his whole life.
Today Butterfield runs Slack Technologies, a San Francisco software company that private investors have valued at $3.8 billion. It is a tech-industry sensation, attracting more than three million users at organizations such as IBM, Capital One, and the Associated Press. Slack’s workplace-messaging tools are a conjurer’s delight. They combine the addictive pleasure of Facebook with the orderly flow of team e-mails in a way that makes it almost fun to be in contact with colleagues.
As Slack’s founding chief executive, Butterfield owns several hundred million dollars of stock in the company. This giant success is the provocateur’s revenge, the latest twist in a lifetime full of odd events. Butterfield is in his early forties now. He has been zigzagging from project to project for more than twenty years. It’s as if his mission in life is to seize whatever new idea intrigues him, regardless of conventional expectations. When I asked what made Slack so successful, he started talking about eudaemonia, the ancient Greek concept of “happiness that comes from fulfilling your purpose.”
It won’t surprise you to know that Butterfield was a philosophy major in the mid-1990s when he attended Canada’s University of Victoria. The field’s intellectual rigor appealed to him; so, too, did the opportunities to twist ideas in ways only a prankster could appreciate. “It all depended on my state of mind,” Butterfield recalled. “There were times when I felt this could be complete bullshit. At other times, studying philosophy provided the finest opportunities to think. I learned how to write very clearly—and how to follow an argument all the way down.
“Ninety percent of contemporary Anglo-American philosophical writings are really murky,” he added. “It can be a struggle to articulate what it means. And yet, there’s this wonderful, unique feeling of it all becoming clear, at least for a moment. In college, I got a great education in how to think about things. It’s certainly helped me run meetings, and it’s helped in many other ways as well.”
As Butterfield’s example shows, there’s no limit to how far you can rise with a liberal arts degree, as long as you don’t mind considering unconventional paths to the top. That’s how it should be. Your own education doesn’t mirror the orderly norms of business and engineering schools. In college, you hunted for classes that revolved around intriguing questions rather than courses that packed your brain with universally acknowledged facts and formulas. You jumped back and forth in the course catalog instead of taking Marketing 101, 102, and 103. You celebrated originality, clarity, and conviction, even if you weren’t always right.
The world needs your strengths; it just needs them in unexpected places. Let the business and engineering graduates enjoy their moments of triumph at campus job fairs. They have spent four years training for this moment. If a Delaware chemical company needs a fermentation engineer for seventy-five thousand dollars a year, some engineering graduate is the perfect match. That’s not you. You didn’t enroll in college to become the best-trained candidate for a narrowly defined job. Instead, you are hunting for wide-open environments that need your critical-thinking capabilities. The greatest payoff for your college education is likely to be years away, perhaps in your fourth job, perhaps in your seventh. You’re playing a longer game, looking for situations that reward you for being able to say “I’m an explorer,” or “I’m a team builder,” or “I’m someone who can make sense out of situations most people don’t understand.”
If you like such destinations but could use extra help in getting there, spend time with the closing chapters of this book. Chapter 12, “Telling Your Story,” peels away the hidden agendas of common interviewing questions. It shows you how to convey your liberal arts strengths in ways employers will appreciate. Much of your college experience should align with the working world’s requirements. Bosses and recruiting managers simply need to hear your achievements expressed in the language of commerce rather than that of the campus. Whether you’re writing a résumé or preparing for an interview, the techniques explained in that section can help you make a winning impression.
Chapter 13, “Getting Paid Properly,” covers the best ways of improving your earnings power, either with or without an additional round of formal education. Your first-year income after graduation needn’t constrain your pay for years to come. Better days lie ahead, and a seven-step system can help you exploit these opportunities. Over time, it’s often possible to overtake college counterparts who opted for vocationally oriented degrees. They snagged the bigger starting salaries; you won unique expertise that creates infinite possibilities for success.
Need proof? Consider this three-part look at lifetime-earnings trends for college graduates across ten common majors. The liberal arts team is represented by English, history, philosophy, psychology, and political science majors. Your vocationally minded counterparts are represented by peers who chose to major in accounting, civil engineering, computer science, nursing, or business management.
There’s no denying that liberal arts graduates start slowly.
TYPICAL STARTING EARNINGS | |
Annual Earnings, 0–5 Years’ Experience (per PayScale) | |
Computer science | $63,500 |
Nursing | $57,500 |
Civil engineering | $57,200 |
Accounting | $48,300 |
Business management | $45,800 |
Philosophy | $44,700 |
Political science | $44,300 |
History | $42,200 |
English | $40,400 |
Psychology | $38,300 |
Let careers play out for a decade or two, and life gets better. If you hold a humanities or social science degree, by your thirties or early forties, you may achieve complete parity with business and nursing majors. (Catching the engineers, alas, is less likely.)
Most common majors, on average, end up earning somewhere between $60,000 and $80,000 a year.
TYPICAL MIDCAREER EARNINGS | |
Annual Earnings, 10–20 Years’ Experience (per PayScale) | |
Computer science | $111,000 |
Civil engineering | $96,300 |
Philosophy | $84,100 |
Political science and government | $79,900 |
Accounting | $77,200 |
Nursing | $74,100 |
History | $72,600 |
Business management | $72,300 |
English language and literature | $68,200 |
Psychology | $62,100 |
It’s important to remember that annual income is hardly a complete measure of success in life. That’s true regardless of whether people opt for the liberal arts or the vocational track in college. Over time, other questions often loom larger. Are you looking for ways to maximize your social impact rather than your cash income? Are you keeping your work hours manageable enough to have time for life outside the office? Are you doing right by your friends and family? Such factors make it hard to say that a small percentage difference in pay says something meaningful about how successful or unsuccessful a particular education-and-career path might be.
Still, there’s nothing wrong with wanting to rise to the top of a field or earn the outsize income that comes with making an outsize contribution in some form. Within the context of this chapter, it’s worth looking at the data in a different way, to see what we can learn about the highest flight paths available with each major. The place to turn: the Brookings Institution’s Hamilton Project, which analyzes U.S. Census Bureau data that lets us track lifetime earnings by college majors. Zoom in on those findings, and it’s possible to see how much the highest tenth of achievers, major by major, end up earning before their careers are over.
Now you can see the liberal arts in full ascent. Disciplines such as philosophy and political science turn out to be springboards for high achievers—who end up overtaking their counterparts in vocational fields such as computer science. Not every political science major will earn more than $4.8 million in his or her lifetime. But many mayors, senators, and governors do. As for history majors, the high achievers who end up running foundations, hosting television shows, or writing bestselling books reach the same economic stratosphere. Prosperity arrives in a big way for philosophy majors, too, as shown by the success of Stewart Butterfield and some of Wall Street’s most accomplished investors.
HIGH ACHIEVERS’ LIFETIME EARNINGS | |
Top Tenth by Major (Hamilton Project) | |
Political science and government | $4,810,000 |
History | $3,750,000 |
Accounting | $3,650,000 |
Philosophy | $3,460,000 |
Business management | $3,070,000 |
Civil engineering | $3,360,000 |
Computer science | $3,200,000 |
English | $2,810,000 |
Psychology | $2,640,000 |
Nursing | $2,160,000 |
The rest of this chapter will look at three proven paths by which liberal arts majors end up ruling the world (either literally or metaphorically). The first involves bountiful opportunities in the public sector and at nonprofit organizations. Government by its very nature puts the full suite of critical-thinking skills to the test. To be an effective leader, you constantly need to manage the intersection of competing forces and competing objectives.
The second big area of opportunity is the money trade, particularly specialties such as venture capital, hedge funds, and private equity. Choose one of these investment-centered domains, and you won’t have twenty thousand people working for you. Instead, you will control vast sums from a small, elegant office with a few dozen staffers taking care of the details. Perhaps you will walk the same path as some of America’s top venture capitalists, such as the ones who bankrolled Twitter, Uber, and LinkedIn. Alternatively, you could be part of the cluster of humanities majors whose stock-picking genius has made them unimaginably rich.
Finally, entrepreneurship is a natural home for restless minds shaped by a liberal arts education. Businesses such as Chipotle and Pinterest were started by political science majors. A background in humanities inspired the founding executives of Whole Foods Market and Salesforce. Spend four years studying the liberal arts, and you work up an appetite for tackling new areas and coming up with unexpected solutions. There’s an old saying you hear from entrepreneurs: “I had to start my own company, because I couldn’t work for anyone else.” That’s still true for free spirits like Stewart Butterfield, and the closing pages of this chapter will explore his journey in more detail.
I’ve found only one area of high-profile leadership where the liberal arts are underrepresented: the chief executive’s chair at big corporations. Let’s take a moment to see the mournful reasons why this is so before turning to cheerier alternatives.
Big Companies, Narrow Path
In 2002, Teachers Insurance picked a Yale philosophy major, Herb Allison, to be its next chief executive. Over the next few years, Allison became an oft-cited example of the ways that even the most “impractical” liberal arts degrees could lead to the top job at a giant corporation. (Teachers Insurance manages more than $400 billion in retirement assets, chiefly on behalf of university professors.) Allison was a man of wide-ranging interests with a career to match. He had spent four years in the U.S. Navy, serving briefly in Vietnam. He had worked in Tehran in the 1970s for Merrill Lynch, when U.S.-Iran relations were smoother than they are today. When Allison fell in love with an Iranian woman and wanted to marry her, her father refused to consent unless Allison started learning Farsi. Delighted by the challenge, Allison built up a thousand-word vocabulary in two weeks, thanks to diligent practice with flashcards.
When Allison retired in 2008, Teachers Insurance did not hunt for someone with an equally eclectic background to replace him. Instead, the New York institution chose Roger Ferguson, a Harvard economics graduate with a nonstop record of business-centered achievement. Ferguson had earned a PhD in economics and a law degree from Harvard. He spent the 1980s working as a corporate lawyer and a McKinsey consultant. After that, a stint as a Federal Reserve Board governor and a leadership post at Swiss Re, a major insurer. Ferguson was a trailblazer in his own right as a pioneering black executive who had scrubbed bathrooms in college to help pay Harvard tuition. When TIAA picked Ferguson, however, his personal journey wasn’t highlighted. Instead, TIAA’s board of directors deemed Ferguson the “ideal choice” because of his background in strategic management, financial services, and economic policy.
It’s sad but true: Large companies have dialed back their willingness to put liberal arts graduates in the chief executive’s seat. Corporate boards may be more cautious after the financial and economic spasms of 2000 to 2002 and 2007 to 2009. There’s less of an appetite for entrusting the CEO’s job to someone with an exciting, eclectic background that could lead to a lot of fresh approaches. Managerial time horizons have shrunk too. At many large, publicly traded companies, success (or survival) is all about handling the pressures imposed by quarterly earnings targets. As a result, there’s more of a desire to play it safe and guard against the unexpected.
The most reliable route to the top of a big company now involves an engineering degree—and “joining a fraternity while you’re at it,” declares Christian Stadler, a management professor at England’s Warwick Business School. He is an expert in CEO succession and the author of Enduring Success: What We Can Learn from the History of Outstanding Corporations. As Stadler sees it, the skew toward engineering-minded CEOs is likely to intensify as multinationals become more open to candidates who came of age in non-U.S. settings such as China, India, and Brazil. In those countries, ambitious students gravitate almost exclusively to engineering programs.
It’s not that big companies don’t appreciate the ingenuity, open-mindedness, sound judgment, and communications strengths of liberal arts graduates. The problem is that as organizations get more complex, there’s a tendency to keep the most creative minds one or two levels below the CEO’s job. Corporate boards prefer to play it safe with the top job, picking candidates who steadily climbed the company ladder via traditional roles. Three-quarters of all Fortune 100 CEOs come from operations; 32 percent have at least some experience in finance. With those priorities, it’s no wonder that engineering and business majors fare best in the race to the top.
For a long time, the executive-search firm Spencer Stuart analyzed the educational backgrounds of every CEO working at one of the five hundred leading U.S. companies. In 1999, about 15 percent of these bosses had liberal arts backgrounds. In 2008, the liberal arts presence had dropped to 6 percent. By contrast, engineering majors in 2008 held 22 percent, while the next three most common majors, economics (16 percent), finance (13 percent), and accounting (9 percent), together accounted for more than a third of the sample. It would be nice if Spencer Stuart had even fresher data, but the firm halted such studies after 2008. Clients weren’t interested in the results anymore. Pedigree had become a settled issue.
Ask corporate boards how they pick CEOs, and the answers are likely to focus on pedigree-neutral factors such as leadership skills, strategic clarity, and a proven record of success in recent jobs. Directors rarely acknowledge a deep, explicit interest in candidates’ long-ago academic choices. Even so, today’s most-favored career trajectories at the twenty largest U.S. companies keep adhering to the same patterns. At eight companies, including ExxonMobil, Microsoft, Procter & Gamble, and Verizon, an engineering degree is the path to the top. At another eight, including Walmart, Coca-Cola, AT&T, and Oracle, the CEO holds a business or economics degree. Only one full-strength representative of the liberal arts appears in this top-twenty list: history major Brian Moynihan, who runs Bank of America. (The CEO of JPMorgan Chase, Jamie Dimon, holds a dual degree in economics and psychology.) Even the ultimate renegade company, Apple, is playing it safe now. With the death of founding CEO Steve Jobs in 2011, the company no longer is run by a Reed College dropout extolling the importance of liberal arts thinking in high-tech settings. The big boss at Apple now is Tim Cook, an Auburn-trained industrial engineer.
Such trends can feed on themselves for a long time. Current and past CEOs tend to be directors of one another’s companies. While corporate boards are responding to pressure to increase gender and racial diversity, they aren’t facing major calls to bring in directors with nontraditional educational backgrounds. As a result, boards full of business and engineering majors are likely to keep picking CEOs with business and engineering backgrounds. Without the right connections, liberal arts graduates find it harder to break into the club.
At some point, all this might change. In the meantime, if you want to soar with a liberal arts degree, plenty of other pathways await.
What the Social Sector Admires
Justin Davis graduated from the University of Maine in 2014 with a degree in political science. Alix Rudzinski majored in the same field, graduating from Assumption College in 2015. Both work full-time in Washington, DC, now, and there’s nothing glamorous about their duties as staff assistants. They answer phones, they do a little document research, and sometimes they make coffee for their bosses. Their annual salaries: less than twenty-nine thousand dollars.
Don’t feel sorry for them.
In politics, traditional career escalators operate as efficiently as ever. Entry-level jobs may be low paid and include a lot of menial work, but the opportunities for advancement are bountiful. The average congressional staff assistant stays in the job for just 1.9 years. Look alert, make friends, and become known as a doer. It won’t take long for better jobs to emerge.
The path upward is especially obvious for strivers like Davis and Rudzinski because their boss, Maine senator Susan Collins, got started in Washington as a congressional staff assistant herself. She had just graduated from St. Lawrence University in 1975 with a degree in government. Maine’s junior senator at the time, William Cohen, needed extra help in his office. She took the job, low pay and all. She put up with a group house and a spending budget so tiny that she couldn’t afford more than sandwiches for dinner. That penury didn’t last long. By 1981 she was a staff director for a powerful subcommittee and eventually a candidate for statewide office herself.
What worked well in the 1980s works even better today. Your liberal arts education provides you with excellent instincts for the give-and-take of modern-day politics. You can make sense of voting blocs; you can understand angry constituents’ real issues beneath the furious insults that are hurled your way. You know how to persuade people and perhaps even inspire them too. In Collins’s own words, a liberal arts education “enables you to cite both Plato and Spider-Man in the same speech.”
What’s more, you enjoy every college student’s familiarity with blogs, podcasts, Tweet storms, social-media campaigns, sentiment analyzers, and all the other tools of modern digital communications. For older bosses, it’s all a mystery. As a result, when openings for press secretaries and directors of communications arise, it’s often a staffer in her or his twenties who is seen as the ideal pick. In the days of black-and-white films, political press secretaries were grizzled old newspaper reporters. Now, the press secretary is more likely to be a newcomer such as Christopher Knight, a 2013 political science major from Stonehill College who deals with the media for Senator Collins.
No one knows what specific achievements in coming decades could propel someone to the highest levels of government. Public tastes keep changing. In different eras, people have prized everything from military service to union activism. That fluidity plays to your liberal arts strengths. Historical records show that during every period from the 1960s onward, a substantial number of U.S. senators and representatives with college educations earned liberal arts degrees. This ability to improvise never goes out of style; it helps you stay in command amid ever-changing norms.
In philanthropy, too, a liberal arts degree turns out to be the best credential for making it to the top. People with humanities or social science degrees run eight of the twelve largest foundations, including the Ford Foundation (government and communications); the Getty Trust and the MacArthur Foundation (history); the Hewlett Foundation and the Lilly Endowment (religious studies); and the Moore Foundation and the Mellon Foundation (psychology).
These leaders are the sorts of explorers that we’ve met in earlier chapters; they take a semester off from college, switch majors, work in warehouses after graduation for a stretch to get their priorities sorted out, teach in universities… and then let their own curiosity guide them through a lot of different jobs. In fact, I’ve just given you the condensed bio of James Cuno, the Willamette history major who now serves as the J. Paul Getty Trust’s chief executive. As Cuno observes, there is no proven master plan for getting to be a foundation head. If anything, boards are looking for people who have lived on both sides of the income divide. It’s crucial to understand the world from different perspectives, to know what it’s like to be poor as well as prosperous.
Conquering the Stock Market
Liberal arts degrees on Wall Street? You won’t find such credentials everywhere; much of the financial sector is staffed by people who loved money as little children and went on to earn a bachelor’s degree in economics or finance so they could chase riches as briskly as possible. All the same, there’s an island of diversity when it comes to people who excel as professional investors. A surprisingly large number of these money managers hold humanities degrees, most commonly in philosophy.
Consider George Soros, who studied philosophy at the London School of Economics before building an investment fortune that Forbes magazine estimates at $24.9 billion. In books such as The Alchemy of Finance, Soros argues that his entire life has been an exploration of the interplay between thinking and reality, with successful trading strategies emerging as a happy by-product. His favorite zone of exploration: the ways crowd mentalities can take hold and briefly distort reality before eventually disintegrating. By exploiting this dynamic, which he calls “the principle of reflexivity,” he has made billions trading oil stocks, betting against the British pound, and so on. Investment successes made him famous, but in Soros’s words, “the abstract came first.”
The two biggest mutual-fund companies in the United States, Vanguard and Fidelity, are both run by people with strong liberal arts backgrounds. Vanguard CEO Bill McNabb was a government major at Dartmouth, and Fidelity CEO Abigail Johnson studied art history at Hobart and William Smith. Both of them earned MBAs a few years after graduating from college; they can hold their own just fine in meetings focused on the usual business metrics. Still, both acknowledge in media interviews that their companies’ biggest opportunities call for a curious, open-minded perspective that isn’t bounded by what’s on today’s spreadsheet. “Don’t assume that the answers are out there in the form of somebody else already doing something,” Johnson told Forbes.com in 2013. “Sometimes they are. But you have to think beyond that. The right answer for you and your organization might not be something that’s been done before.”
Large-scale investing is where the cerebral types hang out. Professional investors read incessantly. They join organizations such as the Council on Foreign Relations, partly because they want geopolitical insights that could help them make money and partly for the impractical reason that it’s interesting to ponder China’s future. A disproportionate number end up as college trustees, allowing them to reconnect with academia. (Being willing to advise a school’s endowment managers helps too.) Even the hunt for bargain stocks is conducted in quasi-academic fashion, in conferences packed with leading New York money managers who deliver heavily footnoted lectures to one another.
One of America’s most combative (and successful) investors is Carl Icahn, a bearded, voluble man famous for buying stakes in underperforming companies and then pressing for strategic shake-ups. Executives resist, he hectors them, and before long, they usually capitulate. While working as a Wall Street Journal reporter in the early 1990s, I talked with Icahn half a dozen times in the midst of these controversies. Each time, I was struck by his eagerness to analyze both sides’ positions. Our phone calls wouldn’t end until he had explained why he was right, why management disagreed, what the other side was missing, and why he expected his views to prevail. He managed to be both strident and professorial.
Long before those exchanges, Icahn was a Princeton philosophy major, writing his senior thesis on “The Empiricist Criterion of Meaning.” I tracked down a copy of the eighty-page tract, and it reveals early signs of his famously argumentative style. How do we know sugar dissolves in water? college student Icahn asks. We run an experiment. How do we know a typewriter won’t dissolve in water? We infer it, based on our existing knowledge of water and metals. Experiments, inferences… he dances back and forth between the two, developing his theories. Only at the end does Icahn betray his reasons for pursuing philosophical questions so keenly. Experts haven’t fully defined meaning, the college senior contends, but they are drawing close. It’s as if we live in a city that “suddenly finds itself in possession of a great homogenous mixture of gold and sand. If the gold could be separated from the sand, it would prove a great deal more valuable.”
Ever since, philosopher Icahn has been pushing away the sand so he can amass a seventeen-billion-dollar fortune with what remains.
On the West Coast, humanities majors opt for a different type of investing: bankrolling start-ups via venture capital. Each year, Forbes magazine highlights the top one hundred venture capitalists in its Midas List, and a surprising share of them have nontechnical, nonbusiness backgrounds. Among them is Matt Cohler, a Yale music major. Another is Peter Fenton, a 1994 Stanford graduate with a bachelor’s degree in philosophy. Both work at Benchmark Capital, a firm renowned for being an early investor in eBay, Instagram, Snapchat, and Twitter. Ask each about his investment approach, and the answers pay homage to the central concepts of critical thinking. They’re comfortable working through a lot of ambiguity. They look for executives with a strong desire to learn and an ability to attract outstanding people.
Enter venture capital with a liberal arts background, Fenton points out, and you “ask questions that are by nature expansive.” Often that means stretching beyond product and engineering technicalities, he says, in favor of seeking essential insights about people and businesses most likely to rise to greatness.
LinkedIn’s best-known founder, Reid Hoffman, now doubles as a venture capitalist with Greylock Partners. He earned his Stanford degree in symbolic systems, an interdisciplinary blend of psychology, linguistics, and philosophy with computer science and statistics. Being schooled in so many disciplines at once has proven hugely helpful, Hoffman says. Instead of focusing on companies that solve narrow problems, Hoffman concentrates on something much more ambitious: “improving human ecosystems through tech finance and entrepreneurship.”
Press ahead in any liberal arts discipline, and at some point you will encounter giant ideas in conflict. Those Hegelian tensions make investing both exasperating and intoxicating to liberal arts majors, contends Dan O’Keefe, a Northwestern philosophy graduate who now runs mutual funds for Artisan Partners in Milwaukee. To be a great investor, O’Keefe explains, “you need two almost-incompatible traits—or at least ones that create extreme tension. You need extreme conviction you can step into the market, regardless of what everyone else thinks, and develop unique ideas that will make money. But you also need an incredible amount of humility. You must be open to new information, even if it could be overtaking all your earlier work.”
Building Greatness from Scratch
We’ve all heard this refrain: Engineers and computer science majors know how to start companies. Some are so brilliant they can drop out of college and create companies like Facebook, Spotify, or Microsoft that are worth billions. Business majors know how to launch start-ups too. They use their college years to get highly focused training in identifying markets, creating business plans, wooing customers, and achieving profitability. But liberal arts majors? What can they possibly know about starting companies that endure?
They don’t get mad; they get even. Liberal arts graduates shred their own stereotype every day. For full-fledged proof, just take a look at Inc. magazine’s annual ranking of the five thousand fastest-growing start-ups in the United States. You’ll see what people with degrees in psychology, philosophy, and studio art are capable of creating. You’ll encounter thriving start-ups in fields ranging from business services to talent agencies, organic juices, and party planning. And in nearly a third of the most successful start-ups, you will find liberal arts graduates are part of the founding team.
People with liberal arts backgrounds have a knack for “starting a business which is driven by ideas and doesn’t require lots of capital,” says Robert Sprung, a seasoned venture capitalist. A perfect example involves Globalization Partners, which is one of Inc. magazine’s ten fastest-growing companies. It provides tools and contacts to help thousands of U.S. companies expand into countries ranging from Peru to Singapore. Its founder, Nicole Sahin, originally planned to become an anthropologist after studying humanities at Maryville College in St. Louis. After extended fieldwork in Colombia’s highlands, however, “I realized I didn’t want to keep visiting one village for the rest of my life,” Sahin told me.
It took Sahin more than a decade to settle on her business ambitions, with many detours along the way. (She set up a school in Cambodia at one point; she spent enough time in the Philippines to gain local-language competency, and so on.) When she finally did form her own company, in 2014, her haphazard ramblings had graced her with an invaluable network of contacts around the world. Spin the globe, pick a country at random, and Sahin knew someone who could act as a sales agent there. Differences in local business customs didn’t faze her; in fact, she relished the chance to build cultural bridges. “It’s like applied anthropology, every day,” she told me.
“Liberal arts graduates know how to sell their products,” said Patrick Chung, a Silicon Valley venture capitalist. “They’re good at helping customers think about the world differently.” A case in point: Paint Nite, which organizes painting parties in bars and restaurants that are suitable for everything from corporate off-sites to bachelorette parties. In Inc.’s 2016 rankings, it’s the second-fastest-growing company in the United States, far ahead of half a dozen other companies trying similar ideas. What’s Paint Nite’s edge? Everyone else focuses on signing franchise deals with bars willing to pay top dollar. Paint Nite instead builds a network of likable artists/hosts who stage events wherever they want. Credit Paint Nite co-founder Sean McGrail (a psychology major at George Washington) with winning instincts about his customers’ desires.
Two more traits belong in the liberal arts arsenal, even if they aren’t talked about as much as others. One is the temerity to imagine yourself succeeding on a giant scale—ruling the world, if you will. Let the business and engineering grads stress about increasing operating margins by two percentage points. They belong at big companies, grinding ahead on a predictable path. The secret dialogue inside your head is much bolder, reflecting the big ideas and open horizons of your college days. If you’re John Mackey, the University of Texas philosophy student who founded Whole Foods Market in 1978, you become obsessed with something called conscious capitalism, in which businesses serve all major stakeholders—including customers, employees, communities, and the environment—instead of fixating solely on what’s best for shareholders. You imagine yourself adding a fourth great virtue to Plato’s triad. Skeptics’ doubts hardly matter. You have been chasing giant ideas since your student days, and there’s no reason to stop. Why should you? In Mackey’s case, you end up running the world’s premier organic grocer, with more than fourteen billion dollars a year in sales.
Rounding out the list of liberal arts virtues for entrepreneurs: an endless desire to get better. Entrenched businesses are notorious for reaching a certain level of performance and then deciding such a showing is both satisfactory and sufficient. (You can see the results in everything from toothpaste to airlines. Past a certain point, it’s just more of the same.) By contrast, the best start-up founders never settle. They see themselves as constant learners, forever dissatisfied with the current version of their offerings, always eager to keep improving. Humility and ambition fuse together in a way that invites comparison to the heady spirit of discovery on a college campus. “We’re always experimenting with features,” says Ben Silbermann, the political science major who started Pinterest in 2009. His company’s themed photo pages now attract more than 110 million monthly users, yet to Silbermann, “this is still an early product.”
To see how all four of these traits interact, let’s take a closer look at Stewart Butterfield’s career. For the past two decades, his fascination with philosophy has inspired him to create elaborate online worlds. He and a few friends spent years developing these “infinite games,” convinced they were tapping into something profound about the ways societies build culture. Butterfield’s projects seldom caught on with the public, but each failure contained the first stirrings of a future success.
The sheer intricacy of these projects repeatedly forced Butterfield and his developers to develop game-playing shortcuts—which found new life as wildly popular business tools. Everything happened by accident. In 2004, Butterfield woke up from a fevered dream, convinced a digital-imaging tool inside GameNeverEnding could become a business in its own right. He had stumbled onto the basis for creating Flickr, a wildly popular photo-sharing service that Butterfield later sold to Yahoo for twenty-five million dollars. Luck struck a second time, in 2013, when an internal chat tool that engineers used to share ideas while working on Butterfield’s Glitch game became the basis of his biggest business success: Slack.
Between those two triumphs, Butterfield discovered he simply could not work for a big company. He spent three years inside Yahoo trying to shepherd Flickr’s continued growth for his new corporate masters. It didn’t work. There were too many rules, too many meetings, and too many business targets tied to short-term performance. There wasn’t any room to make Flickr into the best possible service it could be, especially if it would take a year or two for the benefits to show up in any financial metrics. In 2008, he decided to quit. On his way out, he wrote an allegorical e-mail that never said a bad word about Yahoo but presented a wry, surreal glimpse of his frustrations, couched in the metaphor of how a simple tinsmith would feel in such a situation.
“As you know, tin is in my blood,” Butterfield’s memo began.
For generations my family has worked with this most useful of metals. When I joined Yahoo back in ’21, it was a sheet-tin concern of great momentum, growth, and innovation. I knew it was the place for me.… Since the late 80s, as the general manufacturing, oil exploration and refining, logistics and hotel and casino divisions rose to prominence, I have felt somewhat sidelined. By the time of the Internet revolution and our expansion into Web Sites, I have been cast adrift. I tried to roll with the times, but nary a sheet of tin has rolled off our own production lines in over 30 years.… Please accept my resignation.… I will be spending more time with my family, tending to my small but growing alpaca herd and, of course, getting back to working with tin, my first love.
Butterfield’s e-mail delighted Silicon Valley. The silliness about tin and alpacas was a handy façade; the rogue philosopher was quietly getting ready to build another business—his way. This time, the big breakthrough happened inside a Butterfield-created game company called Glitch. The game itself never thrived, but everyone working on the project loved a slick online-messaging tool. Use it, and a tiny online window alerts you to just the right amount of detail about what your colleagues are doing. No torrents of spam messages, no risk of being isolated or out of the loop. Suddenly something as basic as rounding up half a dozen people for the three o’clock meeting didn’t need to be such a chore. Glitch was destined to perish, but the messaging tool—named Slack in 2013—was a keeper.
Part of Slack’s edge came from a sassy automated buddy providing usage hints and guidance as needed. Its name: Slackbot. Its mission: to make even the briefest interaction with Slack seem fun and efficient. Early on, anyone who typed in Hey, Slackbot, could get replies ranging from Hello to ’Ssup and Hay is for horses. Get snarled in Slack’s system and you would be told: We’ve seen this clear up with a restart of Slack, a solution we suggest to you now only with great regret and self-loathing.
Within twenty-four hours of a private rollout in August 2013, Slack had eight thousand users. By mid-2016, that number had grown to three million. The snarky middle-schooler who refused to say the Lord’s Prayer properly (and then became the rebellious corporate executive who pretended to be a tinsmith) had turned into a very successful CEO. Now Butterfield prospered by knowing when to be silly in a world that took itself too seriously. Maybe he hadn’t needed to evolve at all. Perhaps success just meant finding the right setting for a personality that never changed.
When the jokes subside, Butterfield’s ambitions emerge. In fact, he possesses all the temerity you’d expect from a liberal arts major building his own company. In a 2014 interview with Toronto’s Globe and Mail newspaper, Butterfield declared his goal was to establish Slack as dominant in communication as Microsoft Windows was in software. Never mind the giant size disparity between the two companies; he dreamed of being a unified hub for everyone.
Is he there yet? Not at all. When I met with him in 2015, he talked about the importance of craftsmanship and about how much Slack’s success depends on getting a never-ending list of tiny details right. In a mordant moment of self-reflection, Butterfield told another journalist: “I feel that what we have right now is just a giant piece of shit. It’s just terrible, and we should be humiliated that we offer this to the public.”
Ask Butterfield about Slack’s users, and a more compassionate side emerges. Their problems are his problems, and he’s committed to being as sympathetic and helpful as possible. Tech companies have been thrashing around for more than a decade trying to get smart about knowledge-sharing within organizations. It’s a murky, messy area, because it’s far more than a software challenge. It’s also a test of human dynamics, Butterfield explains, particularly “the ability to interpret people who aren’t necessarily great at articulating what they want.” The more Slack can decode hazily expressed preferences, he knows, the more valuable its software becomes.
In 2008, Butterfield returned to his alma mater, the University of Victoria, to give a talk as a distinguished alumnus. He was jokey at the outset, promising to explain “how to make a fortune in applied philosophy.” Quite quickly, though, he turned serious.
“Entrepreneurism is a good avenue for exercising the kinds of things you learn with a humanities degree,” Butterfield declared. “If you have a good background in what it is to be human, an understanding of life, culture and society, it gives you a good perspective on starting a business, instead of an education purely in business. You can always pick up how to read a balance sheet and how to figure out profit and loss. It’s harder to pick up the other stuff on the fly.”