UPDATED: February 20, 2015, at 1:42 a.m.

John Capodilupo, a former member of Harvard’s class of 2014, works just a few minutes away from Fenway Park. His office, located in Boston’s Landmark Center, spans two floors. It’s right under the basketball court, Capodilupo notes as we climb up a narrow stairwell with exposed brick walls.

The space has all of the typical features of tech-industry decor—hand-written equations scrawled on glass walls, bright Post-it notes covering whiteboards, flat white desks strewn with Mac computers. Employees sit (or bounce) on exercise balls and occasionally get up to fetch a Luna Bar from a snack-laden table in the center of the room.

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Capodilupo comes from a family of academics; he matriculated expecting to pursue a Ph.D in computer science. That all changed, however, during Capodilupo’s sophomore year, when friends connected him with Will Ahmed ’12, a former captain of the men’s varsity squash team who wanted to create a wearable exercise monitor—a Fitbit-like device for serious athletes. The idea became a prototype, the prototype became the company Whoop, and Capodilupo became a Harvard drop-out.

Of course, Capodilupo, now 23 years old, may return for his junior year of College whenever he wishes, thanks to the Faculty of Arts and Sciences’ generous leave of absence policy. The chief technology officer, who still wears a Harvard rugby shirt with his jeans and thick-rimmed glasses, looks more like a grad student than a truant.

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“I talked to the resident dean of Quincy House, and the way she put it was, Harvard’s always going to be here,” Capodilupo remembers. “It was kind of a no-brainer to try this out.” Capodilupo’s parents took some further persuading, but friends and faculty agreed with Chapman. After all, many of his friends had applied for the Thiel Fellowship, a prestigious program that offers entrepreneurial students $100,000 to drop out of school for two years.

Mark Zuckerberg, Bill Gates, Matt Damon—Harvard has had its fair share of famous drop-outs. Popular culture depicts these figures as the ultimate rebels, the entrepreneurial renegades with the brains to get into Harvard and the balls to leave it. Now, though, with supportive faculty, programs like the Thiel Fellowship, and an accommodating return policy, students considering dropping out have few reasons not to do so. While entrepreneurial and artistic opportunities are often time-sensitive, Harvard, these students believe, can wait.

Harvard Innovation Lab mentors, as well as professors who teach classes about innovation and entrepreneurship, seek to enable students to pursue these opportunities on campus. Still, given the difficulty of fully utilizing Harvard’s resources while maintaining a full course-load, many students find that at a certain point, it becomes easier to leave. When students reach that point, they discover that many of the same mentors and faculty they’ve already been working with are eager to help them move beyond Harvard’s gates.

LATE NIGHTS

If Whoop’s space looks like a cross between the Google headquarters and a fitness center lounge, then the Her Campus office in Boston is a girl-world mecca. I meet with Annie Wang, formerly a member of Harvard’s class of 2011, in the magazine’s “living room,” a small area with red walls and a white corner couch. Wang sits under three framed drawings: a pair of red lips, a bottle of Chanel No. 5, and a nail-polish set. Most office accessories are a particular shade of pink—“our pink,” Wang explains.
The magazine, an online platform for college women, now numbers 20 staff members and about 5,000 contributors worldwide. It merits its own shade.

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But the company traces its beginnings to a less glamorous setting—Quincy dining hall—where Wang and her co-founders, Stephanie K. Lewis ’10 and Windsor H. Western ’10, first began working on their proposal. After winning Harvard’s i3 Innovation Challenge, which offers a variety of awards for promising entrepreneurial proposals, the team moved to a space that Harvard Student Agencies offered to the contest’s winners. The three founders worked there for another year before Lewis and Western graduated and Wang took time off to work at the company full-time. During that year, the magazine garnered national attention and the founders were featured in Inc.com’s “30 Under 30.”

“I felt that this opportunity was once in a lifetime,” Wang says. She wears a faux-fur vest and her long black hair in a high ponytail. “It was a speeding train and I needed to get on board.”
Beyond material success, though, Wang explains that had she not left school, she would have lost the chance to follow her passion. “People feel like they need to go on the path set by others…that’s such a denial,” she says.

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The level of that passion—as measured in late-night hours and skipped lectures—often provides a litmus test for students wondering when it’s time to drop out. Erik C. Schluntz ’15-’16 and Merrill H. Lutsky ’15 decided to pursue funding from Y Combinator, a seed accelerator that provides $120,000 to fund startups, when their consumer technology start-up Posmetrics took off during their sophomore year.

“The summer between freshman and sophomore year, I was waking up thinking about the company, going home thinking about the company, and going to sleep thinking about the company,” Schluntz says. Now, having sold Posmetrics to a software company, the pair is back at school; Lutsky will even use advanced standing to graduate with his class.

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Conversely, investors often interpret students’ willingness to drop out as an indication of their passion (and their confidence in their companies’ financial prospects).

“Investors say, we want founders, not students,” Lutsky says. “If it’s an idea I want to put a million bucks into, I want the person on the other end to truly believe that it’s a billion dollar company.” Lutsky added that while some accelerators like Rough Draft and Dorm Room Fund target current students, these companies typically invest smaller amounts.

THE LIFESTYLE

Rory O’Reilly, formerly class of 2016, and Kieran O’Reilly, formerly class of 2017, wear nearly identical glasses. They’re Skyping in from Berkeley, Calif., though they still have “kind of a house” in San Francisco; Paul A. Bottino, a Harvard School of Engineering and Applied Sciences lecturer who teaches Engineering Sciences 95r: “Startup R&D,” helped set them up there. That was back when they were working on Glyphic, a GIF-messaging app. Once the two moved to the West Coast, they realized that the market for such apps had already been saturated.

Now, the two have a new project, GIFYouTube, a site for users to upload videos and convert them into GIFs. They’re joined over Skype by Patrick H. Pan, a 16-year-old freshman and former member of the class of 2018. Right now, Pan, an inactive Crimson arts editor, sits cross-legged on his dorm room bunk bed, but he’s scheduled to fly out early the next morning to meet Kieran and Rory on the West Coast. A fourth student, Aaron Neuman, formerly a member of the class of 2017, also previously worked with the team.

“I just felt like it was my child,” Kieran says. “I couldn’t abandon it. I wanted to see it grow. I actually have nightmares that the website will break.”

Before settling first in San Francisco and then Berkeley, the team set up temporary work stations in hotel lobbies. Now that they’re pulling 17-hour days, they often have to remind each other to leave the house.

“Yesterday I went to a friend’s party, and I asked Kieran to come, and he was like, ‘Nope, I have to keep coding,’” Rory says.

But that’s standard in the tech industry, and start-up teams operating under deadlines must operate on even tighter schedules. A Thiel Fellowship only funds two years, and the Y Combinator sponsors teams for three-month periods, culminating in product presentations on “Demo Days.”

“The YC mantra was...write code and talk to customers,” says Lutsky, who would start making sales calls at 9 a.m. on the East Coast and finish at 5 p.m. on the West Coast for a total of 11 straight hours of sales work every day.

Eventually, Schluntz says, “they added exercise.”

Even during down time, many start-up entrepreneurs find themselves still focused on work. In fact, it’s hard to get away from it on the West Coast. “We live in this pretty large house in San Francisco with eight other people, and between all of us there are four companies,” explains Colton T. Gyulay, a former member of the class of 2015 who left Harvard to develop a mobile game app with Connor N. Zwick, of the same class. “So we always talk and bounce ideas off each other.”

One of the aforementioned roommates walks across the screen as we talk via Skype; he’s a drop-out, too—they all are. Though Zwick originally left school on a Thiel Fellowship whose two years have passed, he says that it seems unlikely he’ll return to school in the near future.

It’s the 17-hour days and households of dropouts that lure many tech-minded students out of school. This path appeals to many not because it seems exotic, but because it seems typical.

“When we tell people [that we dropped out], they’re like, oh, of course, Harvard-drop-out-start-up,” Kieran says. “Since I got [into Harvard] I told my parents I would drop out.”

That doesn’t mean all students interested in technology or computer science choose that path. According to Bottino, of the 232 students who have enrolled in his start-up class, only five have left school. Harvard College has a 97 percent graduation rate; of those students, 86.2 percent graduate within four years.

Michael P. Burke, the Faculty of Arts and Science Registrar, says that about 200 students take a leave of absence for a variety of reasons every year, and roughly an equal number return. He does not collect data on the lengths of individual students’ leaves of absence, but estimates that most return after a year.

“We make every possible condition [enabling graduation] available to them,” Burke says. But when a student comes to a thoughtful decision to take time off, it’s “not at all” a problem. The leave of absence policy does require that students returning after a leave of five years or longer petition the Administrative Board, and leaving in the middle of a term may interfere with financial aid.

Still, most house and resident deans respond encouragingly to students considering taking time off.

“Harvard can wait,” says Luke A. Leafgreen, Mather House dean. Leafgreen estimates that roughly 10 percent of his students take time off for a variety of reasons.

“In some cases, they’re so excited about their career and they find they don’t need a degree, and that’s fine, too,” Leafgreen says of students who never return.

“I think that generally when students want to take a leave of absence, it’s a good thing,” says Adams House dean Adam Muri-Rosenthal, adding that he often assuages the concerns of students worried about falling behind.

So for those who have promising opportunities, the choice often seems obvious.

Receiving YC funding, Lutsky says, made the decision a “no brainer.”

“It was like getting into Harvard—you can’t say no to it.”

THE ARTISTS

Like tech-whizzes, talented artists are often presented with time-sensitive opportunities. At 3 p.m. on a Friday afternoon, Kaledora Kiernan-Linn (who goes by Kaledora Fontana), a former member of the class of 2018, has just finished rehearsal. Now, she’s re-lacing her pointe shoes in an empty studio, adjusting her purple leotard and translucent skirt in front of a wall of mirrors.

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It’s a short day for Fontana, whose rehearsals often go from 9:30 a.m. to 6:30 p.m. Someone else needs the studio—a bearded man carries a camera through the room and and two legging-clad dancers stretch just outside the door—so we walk to an independent coffee shop down the street, across from the apartment Fontana shares with a roommate.

Fontana is starving—rehearsal often goes through lunch—so we order some food and coffee and sit down to talk. As hectic as her days might be, Fontana feels relieved that she’s no longer juggling a full course load along with dance. When the Boston Ballet first hired her before her freshman year at Harvard, Fontana asked her director if she could commute from Cambridge. He said yes, but Fontana soon realized that she had taken on too much.

“If I had five minutes during rehearsals, I’d be reading a book,” she says. “That was really fun because I like being really busy, but eventually I got to the point where I thought I was superhuman and could survive on four hours of sleep.”

Though Fontana tried to manage her schedule by finding a fourth class whose lectures she could watch online, midterms and finals brought unavoidable conflicts—she had four exams at the same time as performances. After a weekend of two performances per day, Fontana scheduled three make-up exams back-to-back on a Monday.

“I set up a meeting with my resident dean [Madeline Currie of Oak Yard], and I was like, I can’t do this anymore.”

While Fontana can come back to Harvard anytime, age matters in ballet; this might be her only opportunity to dance. After all, as a graduate of the School of American Ballet, she’s been training for it her full life.

“This was the only time I could do this, so it would be stupid not to,” she says.

Anna B. Lee, a former member of the class of 2017, Skypes in from Germany, where she’s studying with a violin master. Like Fontana, she had first tried to balance a burgeoning career as an artist with the normal demands of school. “I had concerts on the weekends in Europe, so I got an excuse to be absent for three days during orientation week. So already orientation week I wasn’t there,” she remembers.

After missing several German classes (Harvard language classes allow no more than three absences), Lee realized that she could no longer sustain her schedule. She could return to school later, but she needed to study violin now—her teacher was reaching the end of his career. “I can do literature at any age, but in terms of my body, things like learning how to do certain techniques or learning with this particular teacher, there is an expiration date,” she says.

Unlike tech-oriented students, however, artists don't necessarily have a set path to follow after leaving school. For some, it’s just about pursuing an idea when it strikes.

My Ngoc To, formerly a member of the class of 2015 and an inactive Crimson editor, wrote a memoir while taking time off after freshman year for personal reasons. She returned to school in the fall, but then came across another project.

“I was having lunch in the Signet [Society], talking to this nice old dude, and I was saying I love writing and art, and he was like…you should write a children’s book,” she recalls. Now, To is on her second leave of absence, writing and illustrating a children’s book based on Vietnamese fairytales.

Having written both at school—in creative writing classes and as a member of the Harvard Advocate—and outside of school, To believes that the latter better facilitates her creative focus. “At Harvard it’s hard to fully immerse yourself because there are so many distractions,” she says. “[Art] takes diving really deep into whatever you’re creating.”

Students who drop out of Harvard to write set their own schedules and work on their own terms.
“It would be 11 p.m. on a Friday and I’d be turning off the lights in the common room and turning on the lamp in my room,” says Charlie Horan, a former member of the Class of 2018 who’s taking time off to write a novel. Now he writes from 10 p.m. to 2 a.m. without disturbing roommates.

LAUNCH PAD

Harvard might not be able to provide an alternative to the Boston Ballet or full time study with a master violinist, but it has sought to bring the tech industry closer to campus. Based across the river at an edge of the Harvard Business School campus, the Innovation Lab does not look unlike Capodilupo’s office.

In a lounge area in the center of the room, a couch wraps around a black rug, facing a flat screen TV and Wii controller equipped with Guitar Hero paraphernalia. Most of the white walls feature doodles, written quotes, and tacked photographs. It’s dinner time, but a dozen or so students sit at flat white tables, hovering over laptops and occasionally leaning over each other’s screens.

One wall holds about 10 sheets of paper that read “___ is a ____ looking for a ___ to help with ___,” the spaces filled in with requests for investors, technicians, and team-members. Yin Liang, a student at Harvard Business School and a founder of Potluck Energy, one of the iLab’s Venture Incubation teams, tells me that she’s used the help board several times. “It’s set up so people can support each other,” she explains.

The Venture Incubation Program attempts to mimic that San Francisco atmosphere—eight people and four companies in a room—here on campus. Between 50 and 60 VIP teams each season receive office space, participate in workshops, and collaborate with iLab mentors for 12 weeks.

For some students, though, the iLab cannot provide a permanent alternative to dropping out. Several iLab alumni—Capodilupo, Lutsky, Schluntz, Gyulay, and Zwick, among them—went on to pursue resources outside Harvard. The O’Reilly brothers started an application for the program but never followed through.

Gordon S. Jones, the managing director of the iLab, says he does not see this as a failure on the part of the iLab. Rather, he says he understands that the iLab can serve as a launch pad for students who will ultimately go on to work in the industry full time. “We’ve had students who have left after finding some resources here that gave them the confidence to step out and run with their ideas,” he says.

Jones says he believes that the iLab serves students best by meeting them at their individual stages of development, and then connecting them with the appropriate resources. Jones maintains that the iLab “makes it easier to stay in school.” But for students who ultimately leave, Jones says, “we’re supportive from a distance.”

The iLab offers monetary funding through the President’s Challenge and the Dean’s Challenge; other entrepreneurial students, like Wang, apply for the i3 Innovation Challenge. These competitions are meant to provide students with the resources—monetary and otherwise—to develop companies during the semester. For many students, though, supporting a full-time company while at school proves unsustainable, not because of a lack of resources, but because of an inability to take full advantage of them.

“We’ve had an overabundance of resources thanks to the iLab and the amazing faculty here,” says Reylon A. Yount ’16, whose start-up, a performance interface application called Worldi, won the Dean’s Social Entrepreneurship Challenge in 2013. “We’ve just had so many mentors that we find ourselves still processing advice before we can go ask for more.”

“But there are some fundamental challenges that come along with having a full time academic career and doing this thing that’s supposed to be like 100 hours a week,” he continues.

Yount says that looking back, he wishes that he had known more about the time and effort that would be involved in maintaining a Dean’s Challenge project. “I sort of became aware of the challenging balance after talking to a lot of my own mentors,” he says. “It would be helpful for some of these very idealistic students to know early on that it’s not just a side business. The people from the Dean’s Challenge can be very direct and honest about this.”

According to Jeremy S. Sabath, a former member of the class of 2016 who left Harvard to pursue a job as a user experience strategist for a company called Freshly Tilled Soil, students who attempt to grow companies on the side end up “in no-man’s land.”

“There are people who seem to have more hours in the day,” Sabath says. “But in general it’s a disservice to encourage people to do both [school and a start-up] at once. They’re going to do worse at both.”
Sabath says that while at school, he wished he could take two classes and count residency at the iLab for another two credits. “People have to decide between doing well, pursuing their passion, and sleep,” he says.

For others, like Gyulay, the iLab just cannot compete with the start-up environment in the Bay area. “It’s unparalleled the way it can happen [in San Francisco],” he says.

The iLab might better serve students for whom entrepreneurship has not yet become a fully-fledged passion. Many who work at the iLab have little or no experience in starting a company. “Most people here have not done it before,” Jones says. For them, the iLab allows for experimentation without risk; it also requires less of a time commitment.

Others, like Liang, have already completed their undergraduate degrees and entered the professional world. Liang says that outside of her two HBS courses, she has a large amount of free time to spend at the iLab. “Most of the people I work with [at the iLab] have two to four years [professional] experience and are grad students,” she says.

According to Jones, 30 percent of students who swiped into the iLab this past year attend the Business School, 40 percent attend the College or the Graduate School of Arts and Sciences, and 30 percent attend Harvard’s other schools.

IN-CLASS EXERCISE

It’s 9 a.m. on a Thursday morning, but the students in Fernando M. Reimers’s education and social entrepreneurship course look eager to get to work. Desks face each other at odd angles, and the students form haphazard groups of threes and fours; Reimers has asked them to identify a challenge in contemporary education. The walls of Longfellow Hall are painted bright green.

Reimers wears a sweater with a sport coat and tie. He circulates the room, approaching each group for a few minutes, asking students to share their ideas with the class.

He passes the microphone to a girl wearing a blue sweater. She’s concerned that online education is too solitary. Over the course of the GSE-listed course A132, Reimers will work with her—and the course’s other students—to develop entrepreneurial projects that will address these identified challenges. Yount, who took Reimers’s class, developed Worldi after noting how arts education might be improved if students were more aware of contemporary performances.

“You should be able to gain experience that connects you with the world while you’re in college,” Reimers says. The professor of the practice in international education explains that when students have come to him considering dropping out, he’s discouraged them; he believes a student’s desire to leave indicates a failure on the part of the school to engage with her.

“I think when a student drops out it’s because they didn’t make a connection with someone who challenges them,” Reimers says.

That might have been the case for the O’Reilly brothers, who say that their schoolwork did not engage them to the extent that their independent work did. “Our start-up is pretty much our life,” Rory says. “At school our [academic] work isn’t our life, it’s something we do for classes.”

Sabath also noted that he felt disengaged with Harvard due to a lack of “experiential learning.”

But most faculty at SEAS and Harvard’s Computer Science department view the decision to take time off as a personal one. That decision might be motivated by a desire for an experience that Harvard cannot provide, rather than experience that Harvard has failed to provide. James H. Waldo, Harvard’s chief technical officer and a professor of the practice in computer science, works with students to develop independent projects in courses on distributed systems and privacy.

“I’ve surprised some students when they’ve come to me thinking of [withdrawing],” Waldo says. “I think they expect me to say ‘stay in school’ like a parent, but I generally don’t do that. I say, ‘If you think this is really interesting, go do it.’”

Waldo recognizes that working in the industry teaches students skills he could not possibly impart in the classroom. “Craftsmanship is learned by doing the craft, not teaching it,” he says. “I try to teach some of these things in my class, but how do you teach people to maintain a piece of software over several years in one course?”

Waldo, who designed software for Sun Microsystems Laboratories and Hewlett Packard before joining Harvard, argues that industry training is about experiential, not monetary, value. “There are much easier ways to get money if you’re a Harvard student than starting your own company,” he says. “But even students who come back after their company has crashed and burned—they’ve learned a lot.”

Bottino says that students who manage their time wisely can grow a company without dropping out, he would not discourage a student from taking time off if she came to the decision thoughtfully. “Harvard is fantastic in its liberal policy that you can come back at any time,” he says. “If you come to it as a reasonable decision, if you really want to do this, if now’s the time, if it’s just too hot, then yeah, take time off.”

Harry R. Lewis ’68, interim SEAS dean and a former dean of the College, also supports students of his considering leaving school. “There’s no downside risk,” he says. “If they are paying more attention to things other than Harvard at Harvard, go do the other thing for a while. So I don’t mind people leaving—the ones who don’t come back aren’t coming back because they’ve been very successful.”

He notes that popular portrayals of start-up culture often portray drop outs as defying or one-upping their former schools. “One of the things I found slightly curious is people who try to say, ‘Haha, we got you, so-and-so dropped out,’” he says. “People drop out all the time for all kinds of reasons.”

Like Jones, Lewis says he believes that students can manage companies without leaving school; in 2001, he pushed to rescind a rule that prohibited students from starting businesses in their dorm rooms.

FINAL PROJECT

Outside Whoop’s conference room, a glass door—also covered in equations—reveals a room full of coders hunched over their laptops. Upstairs, the hardware room is empty, save for a board labeled with the Whoop logo. They’re not company products, just props from a party the office hosted over the summer.

Capodilupo can’t show off the product he dropped out three years ago to create; he has to keep it under wraps before the spring launch. I can’t help but wonder whether he’s nervous—after so much time dedicated, an education halted. “The start-up world is a roller coaster,” Capodilupo says. “One week you’re on top of the world; the next week an investor pulls out.”

Knowing the unstable nature of the job, did Capodilupo see dropping out as a big risk? Not really. “It was just a total thing to do in the tech world at Harvard,” he says.

On the salted and ice-hardened streets of Boston, Harvard’s campus is just a T-ride away. It’s separated from the city only by a narrow river, only by an iron gate. 

This article has been revised to reflect the following correction:

CORRECTION: February 20, 2015

A previous version of this article incorrectly stated that Aaron Neuman works with the team behind start-up project GIFYouTube. In fact, while he previously worked on the project, he is no longer involved.