Decoding education

Published on September 21, 2015

In a crappy apartment in east Palo Alto, California, in 2012, Charlie Stigler woke up and started to code. He’d been doing this every day for the past six months—waking up at 11 a.m., writing code and building features all day, getting Chipotle for dinner, working some more, going to sleep, just to wake up and do it all over again.

Just a year before, Stigler’s daily routine had been a lot different. He’d been a first-year and a member of the rowing team at Columbia’s School of Engineering and Applied Science. His days had been filled with practice and classes and dinner at John Jay Dining Hall with his friends. He’d been just a regular 18-year-old, going to college like everyone expected him to.

But that, of course, was before he dropped out.

The myth of the dropout

Stigler is just one prime example of a much larger cultural phenomenon: the dropout entrepreneur. As cofounder of Zaption, an educational technology start-up that raised just over $1.5 million in seed funding, he follows in a tradition that peaks with Bill Gates and Steve Jobs, dropouts near-mythicized by an adoring public. These days, Stigler is hardly an exception. In elementary school classrooms around the country, teachers tell kids that the jobs they’ll have when they grow up don’t even exist yet—and it sure seems like today’s twenty-somethings are the ones coming up with those new ideas.

Why, though, do we see such a deep relationship between dropping out and making it big? First, there’s the question of myth and fact, of whether the people who find success are really all system-bucking rebels. It’s true that plenty of successful entrepreneurs slogged through Core Curriculum classes and doggy-paddled the swim test just like the rest of us. But it’s equally true that some of the smartest, most creative students feel limited by traditional academia—so limited that their only solution is to leave the academic sphere entirely.

Columbia boasts an illustrious dropout history beginning with Alexander Hamilton, who dropped out to join the American Revolutionary War, and continuing through the years to more contemporary figures like Jack Kerouac and Alicia Keys. The well-known names on the list of dropouts belong mostly to writers, actors, and musicians.

Of course, that might soon change: today, the dropout’s biggest goal is to nurture a successful start-up. Many, like Stigler, leave school to pursue some sort of tech start-up. Columbia’s most recent batch of dropouts includes a trio of students—Joey Levy, Joshua Hughes, and Jessica Vandebon—currently on leave from Columbia to develop a fantasy sports site called Draftpot.

The list is so varied that it’s tough to figure out what all these dropouts have in common, if anything. Are they united by risk-taking personalities? Real-world skills? Incredible self-confidence?

Are dropouts fundamentally different from the students sitting in Butler Library—or did they just make different choices?

From Columbia to California

When I talked to Stigler, I was at first surprised by how normal he seemed, for a so-called tech whiz/college dropout/start-up genius. Easy-going and soft-spoken, he joked that he wasn’t too sad about missing out on living in the McBain Hall double from which I was Skyping him.

But Stigler’s low-key exterior belies a history of impressive achievements. During his junior year in high school, Stigler developed an app called SelfControl, which blocks web browsing to increase student productivity. Just a year later, he started working on Zaption, an education start-up that adds slides, discussion, and text to videos to create an interactive learning experience.

So by the time Stigler arrived in Morningside Heights, he was pretty sure that entrepreneurship and software development were meant to be a large part of his life. While Columbia was fun, it was also incredibly unhelpful for his start-up.

Charlie Stigler

He’d expected to have a more flexible schedule now that he was out of high school, but instead he found himself unable to devote enough time to Zaption. He ended up spending all his time in class or at rowing practice—in other words, he had a pretty normal college experience.

But a normal college experience wasn’t quite right for Stigler—although college was fine in and of itself, it was decidedly bad for Zaption.

So instead of putting aside his dream and staying in school like everyone expected him to, Stigler decided to find a way to work on Zaption as zealously as he wanted. In the spring of 2012, he applied for what he very casually calls, “this thing, the Thiel Fellowship.”

Soon enough, he was flying out to San Francisco for a selection weekend. Less than a month later, he was offered the fellowship—funded by entrepreneur and venture capitalist Peter Thiel—which gives winners $100,000 over two years, provided the student drop out of school to pursue their start-up.

“I decided, ‘Well, this makes sense,’ Stigler says. “Then two weeks later, I left school like everyone else and I just didn’t come back.”  

‘We were just kind of winging it’

The Thiel Fellowship is a bit like the Ivy League of the dropout community. With a six percent acceptance rate for its first class, the fellowship doesn’t eschew the competition and selectivity that are hallmarks of today’s universities. But unlike a college acceptance letter, an acceptance into the Thiel Fellowship means $100,000 to pursue a project for two years; mentors who, the fellowship’s website claims, “provide guidance and business connections that can’t be replicated in any classroom;” and the prestige of being part of an institution that has launched over 50 organizations and raised more than $50 million in venture capital. In short, if you’re worried about how dropping out of college is going to look on your résumé, you should try to get your hands on a Thiel Fellowship.

Of course, not every dropout worries about such details. Take School of General Studies senior Ilya Vakhutinsky, for example, who dropped out of Rutgers University in 2010 entirely fundless to work on a health care start-up with a friend.

“I left in the end of the fall semester and the accelerator didn’t start until summer, so from January to June there was a good quarter of the year where we were just kind of winging it,” he admits.

Waiting until a grant came his way didn’t seem important—every day spent in school was a day he could be spending working on his project. Vakhutinsky was convinced that dropping out was the right thing to do, no matter the risk.

“Risk wasn’t necessarily on my mind,” he says. “I always said I’m gonna go for it now, I can always go back, [dropping out is] not gonna throw my life off course.”

But in keeping with the all-roads-lead-to-San-Francisco dropout tradition, after spending a summer at an accelerator in Boston, Vakhutinsky won the Thiel Fellowship and went off to San Francisco to pursue his own project: a start-up that helps connect home caregivers to elderly people.

An intentional education

Stigler and Vakhutinsky both seemed to have put a lot more thought into education—its value, its methods, its role in their lives—than I have. Even though the vast majority of the people I interact with on a daily basis either have a college degree or are pursuing one, I realized I had never really had a thoughtful conversation about pedagogy until I spoke to Stigler and Vakhutinsky.

Though they certainly think about education differently—Stigler hasn’t gone back to school since dropping out, while Vakhutinsky is currently a student in General Studies—both have thought long and hard about what higher education is supposed to do and why the traditional university system didn’t work for them.

“In general it’s really bad that there’s such a default [to go to college],” Stigler argues. Most people don’t spend a lot of time thinking about it.”

Rather than really choosing to go to college, Stigler says, most people simply allow a wave of tradition and expectation to carry them there. If there’s nothing standing in the way of your education— money, say, or grades—you’ve probably opted into college without really considering it.

Stigler thinks that’s a problem.

Vakhutinsky, like Stigler, found school a trial rather than an opportunity. Even from a young age, he was far more focused on entrepreneurship than on school.

“When I was at school I was very slowly kind of escaping. I would spend weekends at a hackathon and less and less time focused on schoolwork,” Vakhutinsky says. “It became too much of a burden to go through with it so I decided to just leave.”

His bet paid off. Just a few years later, he’s working at Quartet, a company that helps healthcare providers and primary care physicians care collaboratively for patients. All his life, Vakhutinsky has been interested in health care. To see his entrepreneurial skills put toward changing people’s daily lives and to sense that he has a hand in keeping his customers healthy, he says, is incredibly satisfying. But more importantly, he never found this sense of tangible impact at school.

Vakhutinsky differentiates between college as a choice and as an unexamined next step. Before dropping out, he says, “I was so focused on going to college for the career-oriented version of it. I was taking x, y, z classes so I could get a job.”

And because Vakhutinsky proved that he could create his own ideal job simply by dropping out of school and working with skills he already possessed, he was sure that the purpose of a college education had to be more than just career preparation.

He’s back in school now—but with a completely different mindset. First, he chooses his classes based on what seems interesting rather than purely useful. This semester, he’s taking a class on public health. It relates somewhat to his work, sure—but it’s important that he chose the class because he really wanted to take it, he says.

Learning for the sake of learning, in Vakhutinsky’s mind, is what college should be.

The temporary CEO

Stigler and Vakhutinsky both exemplify one specific type of dropout: the type who feels pushed out of school, who feels like academia is decidedly wrong for them. There’s another kind of dropout, though: the kind who likes school just fine, who would’ve stayed had an irresistible idea not pulled them out into the real world.

Hughes, Vandebon, and Levy, a former sales analyst at Spectator, are some current examples of this second type. The trio is on leave from Columbia to work on a fantasy sports website called Draftpot, which just raised $2.2 million in funding.

When I talked to Levy, he bristled at the word “dropout.” He made very clear that he and his co-founders are simply on a leave of absence.

“I fully intend—as long as Columbia will allow me to—to go back,” Levy says. “It’s very important to me, and to my family, and I genuinely want to complete the education, because I really enjoyed my time at Columbia and I think it’s a great school and I want to come back.”

Instead of feeling that college quashed his ideas, he simply stumbled into an idea with too much potential to ignore. After hearing his uncle complain that he didn’t understand how to use a fantasy sports website, Levy thought he could do it better and the idea for Draftpot was born.

Soon, his new venture loomed larger than school—he couldn’t focus on his classes because he was putting so much time into Draftpot. But instead of talking about wanting to leave school, Levy says he felt compelled to take time off—as though he would be acting irresponsibly by staying.

“It’s less about me being disillusioned with my experience at Columbia and more about me being all in with Draftpot,” Levy says. “It’s a tremendous opportunity from a business standpoint, having the opportunity to operate a site that could be an industry leader.”

Levy seems to have felt a sense of responsibility to leave school—for the good of his business.

“I would never go to school while working at Draftpot because that’s not fair to the people invested in Draftpot or to anyone involved in Draftpot—people are investing time and money,” he says.

Should I stay or should I go?

Clearly, then, not all college students feel that they’re on a thoughtless treadmill to fluorescent-lit cubicles and midlife crises. Connor Abbott, a sophomore in SEAS, like Levy, loves studying at Columbia. Abbott is a gifted programmer who spent the past two summers working at Intel.

The idea of dropping out has certainly crossed his mind. In fact, one of his professors once asked him why he didn’t leave school and get a job.

I was like, ‘Um, there are reasons I’m still in college!’” he says.

Abbott has never wanted to drop out, despite the fact that he possesses skills that could make him very successful even without a college degree. But to him, college is more than a step toward future success.

Once you drop out, “You can’t learn just random things anymore. You can’t learn whatever you want to learn,” Abbott says. “You’re sort of forced into this one little domain and if you’re not learning from that then you’re wasting your time.”

Connor Abbott

His time in school is an entirely unique learning experience that he can’t get anywhere else, even if he’s writing brilliant code and making great money.

Of course, it helps that Abbot’s bosses at Intel—who recruited him after he posted an open-source code he had written to a mailing list frequented by Intel staffers—want him to graduate. He hasn’t had to make the choice between going to school and working there.

“For larger corporations there’s more of an incentive to have people with degrees working,” he says. “They were like, ‘You should graduate so as soon as possible we can come get you to Portland.’”

But Abbott’s very real skill set gives him a unique perspective on his education. Rather than learning in a vacuum, he says, he spends his time in class making connections between the problems he solves for homework and those he solves at Intel.

“I feel like I learn best when I have a goal to do something and then, oh, by the way, here’s this thing you have to learn in order to achieve that goal,” Abbott says. “I later look back and think it’s so easy, and everyone else finds it difficult because I’ve just practiced it so much and I’ve practiced it in pursuit of a goal.”

His practical knowledge of what he’s studying not only makes the concepts easier to grasp but also reveals the importance of seemingly thankless tasks. In his programming classes, some people get frustrated at having to show the changes they make as they edit their code. But Abbott, having worked side by side with other software engineers for years now, understands the importance of explaining your process to other people. To him, these rules feel necessary—and sensible.

In many ways, Abbott has stumbled into the perfect balance between work and education. He hasn’t been forced to put aside his projects to focus on school or to drop out of school to pursue his work. He wants to go into a field full of established companies rather than start his own business from scratch. His education and his future vocation work in tandem rather than in opposition.

And this is in large part because Abbott has never considered a start-up. He has the tech skills that entrepreneurs today want and need, but he feels no need to create his own company.

So staying in school makes sense if you’ve got tech skills but no entrepreneurial yearning. But what if you’ve got the spirit of an entrepreneur and you still love college? Can you do both?

The road more traveled by

A host of people and organizations at Columbia have devoted themselves to making sure entrepreneurship and college aren’t mutually exclusive. Columbia Entrepreneurship and student group Columbia Organization of Rising Entrepreneurs are two prominent players in the attempt to nurture start-ups at Columbia.

Columbia Entrepreneurship is an organization run by the University that facilitates entrepreneurship by making connections between schools, students, and alumni. The organization also aims to change the way entrepreneurship is taught at Columbia. I talked to Chris McGarry, the director for entrepreneurship in the University Office of Alumni and Development, and when I mentioned that dropping out of school seems to have worked for many a young entrepreneur, he was quick to correct me.

Steve Jobs, Bill Gates, they dropped out of school. Peter Thiel says he’ll give you $100,000 if you drop out,” McGarry says. “That’s the mythology around the start-up community. But those are the outliers.”

“What’s driving innovation in this country is people who are much less glamorous and much more stable and much more practical than Steve Jobs or Mark Zuckerberg,” McGarry says.

And he’s right; we hear a lot more about the dropout stories—kids who made it big, quick, after taking a huge risk—because they’re compelling and fun and out of the ordinary. The dropouts live the new American dream because they make something out of nothing. The stories of people who went to school and did just what everyone expected and worked their way slowly to success just isn’t uncommon or incredible enough to be interesting.

But Columbia Entrepreneurship doesn’t aim for flash or glamour. Instead, it attempts to incorporate entrepreneurship into traditional education—to eliminate dropouts rather than encourage them. McGarry believes in the power of a college degree not just to launch a start-up but to mint a lifelong entrepreneur, and that the entrepreneurs who feel that college holds them back just aren’t looking at the big picture.

In fact, Columbia Entrepreneurship uses the University’s resources to support start-ups. They connect aspiring entrepreneurs to alumni in their field, like supplying law school students with the marketing guidance they need to create a legal start-up. They also provide something as simple as a co-working space for entrepreneurs to work in.

McGarry explained to me that an entrepreneur’s path isn’t all that different from anyone else’s. It involves hard work, knowledge, and a whole lot of failure. He argues that, in fact, being part of a university’s community is a massive boon for entrepreneurs—you get incredible academic experiences, relationships with powerful or soon-to-be powerful people, and a community wherein you can test your ideas with relatively little risk.

“We’re investing our resources in the entrepreneur, not necessarily the start-up. The start-up that they’re working on today might fail, but that founder will have learned a lot for the second start-up that she works on,” McGarry says. “And then if that fails it’s important that she understands and documents and internalizes that so the third start-up has a much better chance.”

College isn’t just a unique academic environment—it’s also a very specific kind of incubator, one that isn’t focused solely on start-ups but supports them all the same.

Columbia Entrepreneurship and CORE seem to share a similar goal—they both want to create an environment at Columbia that allows entrepreneurs to pursue their ideas. CORE aims, in the words of its president, Simon Schwartz, to inspire, educate, and launch. It offers programs that give Columbia students the resources to build their start-ups—initiatives like workshops, panels, and networking sessions. One of CORE’s newest projects, for example, is Almaworks, an eight-week intensive accelerator meant to launch student start-ups.

CORE president Simon Schwartz

Throughout my conversation with Schwartz, it became clear that the people running CORE get even more out of it than the participants.

“We run CORE like a start-up. We have our product, which is our programming. We have our market, which is the greater Columbia community,” Schwartz says. “And how do we deliver that product and get the most benefit to the Columbia community?”

CORE aims to create entrepreneurs that can tackle the world’s problems—an especially appropriate project for an organization that is already grappling with an issue that’s confounded many others.

Creating a successful start-up incubator at a university, Schwartz tells me, is a pretty daunting task.

“Nine times out of 10, in the scenarios in which people have tried this, it fails,” he says. “And that’s because you can teach business practices, you can teach how to do interviews, you can teach how to pitch things, you can teach design processes and systems of management but the one thing you can’t teach is … an idea.”

The entrepreneurs with whom CORE works are markedly different from Stigler and Vakhutinsky. Rather than coming into college knowing exactly the project they want to accomplish, the entrepreneurs at CORE just know that they want to run a start-up—even if they don’t know quite what that start-up will be.

And that’s why CORE is so important. Entrepreneurs like Stigler, who know exactly what they want to do and who possess the skills to do it, are rare. But smart people with the drive to solve problems creatively are relatively common at Columbia. CORE helps take these still-malleable entrepreneurs and adds an important practical facet to their Columbia education.

“We provide this dual education,” Schwartz says. There’s this rigorous liberal arts education at Columbia that’ll teach you how to think, and CORE will teach you how to do.”

Throughout the process of writing this article, I didn’t come across a single person who thought they had the secret code to success. No one said that dropping out guaranteed that you’d make it big, but nobody could say that dropping out barred you from success, either.

Instead, the key to making it—and by making it, I mean not just solving a problem or creating a product or making money, but also finding personal fulfillment—seems to hinge on real, careful thought.

That might seem obvious—but then, doesn’t going to college seem obvious for most of us?

Everyone I talked to had reached a point in their life, usually after they’d already gone to college, when they realized that they didn’t have to do what everyone expected them to do. For Stigler and Vakhutinsky, that realization gave them license to drop out. For Abbott and Schwartz, it informed the way in which they interacted with their school.

As entrepreneurship becomes increasingly common, the narrative around dropouts needs to shift from myth to parable. While dropping out doesn’t guarantee success, it does indicate thought and intention around education. Dropouts aren’t just people who have opted out of the educational system; they’re people who have chosen to learn differently.

Stigler recently discussed going back to school with his dad, a professor at the University of California, Los Angeles and co-founder of Zaption.

“My dad was saying, ‘What do you think about college?’ and I was saying, ‘Well, if it’s the best way for me to learn, but I don’t see that right now there’s any way it could be the best way for me to learn,’” Abbot says. “And he said, ‘Yeah, of course not.’”

“Because I’m learning a lot more right now just doing what I’m doing.”


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