It’s 6:45 a.m., and Ben Darr is coming back from the
gym to a hideous smell from the refrigerator. A roommate shuffling past the
kitchen shrugs. Another confirms the bad news: Last night, in a cleaning
frenzy, someone moved the fridge and forgot to plug it back in. Darr just
shakes his head and unloads the dishwasher.
That’s life at Enstitute, where 11 wannabe
entrepreneurs, aged 18 to 25, are packed in a Lower Manhattan loft. Shopping,
cooking, eating and cleaning together, they share one remote control and many
secrets in three bedrooms at night. Come daylight, they’re off to work. Just
under half the “kids” have already founded a company; only three have graduated
from college. Maybe they’ll come out of this experiment knowing if they have
the right stuff.
No one knows if you can really teach entrepreneurship.
InSITE offers a one-semester mentorship in finance and tech to business and law
students. Billionaire Peter Thiel pays kids $100,000 to drop out of college and
pursue a startup idea. Enstitute’s edge: learning by doing for two years with a
key founder—a model it will expand to three new cities next year.
Shaila Ittycheria, 31, and Kane Sarhan, 26, created
Enstitute last year as a nonprofit, draining their savings and raising $300,000
from Boston Celtics co-owner Jim Pallotta and the deLaski Family Foundation,
which backs social entrepreneurs. Sarhan handles fundraising, p.r. and
recruiting companies. Ittycheria focuses on everything internal, taking care of
the kids and overseeing the mentors, who include the likes of Fabian
Pfortmüller of Holstee (a lifestyle brand) and Hilary Mason of Bitly (which
shortens URLs for social). The mentor-entrepreneurs pay the apprentices $200 a
week.
To get the matchups right, Enstitute spends months
vetting apprentice candidates through video and in-person interviews, essays
and self-assessment, then reaches out to startups that will offer real work—not
to an “intern,” says Ittycheria, but to a “wingman.” Apprentices meet
one-on-one with Ittycheria at least once a week. The review can be devastating.
“Sometimes you think you’re doing great,” says one fellow, cringing. “Shaila’s
always going to be the one to tell you when you’re wrong about that.”
How well is the program working, less than halfway
through the first year? To find out I spent a couple of long workdays with
Samman Chaudhary, 24, who is paired with entrepreneur, incubator and venture
capitalist Mark Peter Davis, 34, and with Ben Darr, 20, who is attached to
Thrillist Media Group’s Ben Lerer, 31.
It’s their first day in a rented work space on West
24th St., and the heat isn’t working. Chaudhary and Davis, who have worked
together for five months, huddle at a single desk in a stark white office.
“Pull up your PDP,” Davis says, referring to the personal development plan of
skills to master. Last week, term sheets. This week, capitalization tables.
It’s Fundraising 101.
“When you take an investment you issue new shares, and
that increases the denominator,” Davis explains as Chaudhary builds a document and
starts mocking up a series of investments. “I started as a VC, and someone said
we needed a cap table, and I was like, ‘Whaaaat?’ I flailed for weeks before
figuring it out,” he says. “Samman’s going to get it in two hours.”
Chaudhary was doing postgraduate work at Sheridan
College in Toronto when she read about Enstitute while scrolling her Twitter
feed during a dental checkup. She was a straight-A student but unsatisfied.
Enstitute offered practical skills—and a pass to Manhattan. Davis’ habitat is New
York’s Flatiron District, where he’s a partner in early-stage fund High Peaks
Venture Partners and cofounder and board member of four companies via his
incubator Interplay.
Two weeks into her apprenticeship Chaudhary says she
felt she was doing great—showing up on time, completing every task with a
smile. “I would have given myself a B+,” she says. Her mentor thought
otherwise, telling Shaila at their first check-in that Samman was failing. “It
was the wake-up call I needed, and it really changed the way Mark and I
operate,” Chaudhary says. “I became 1,000% more proactive, and we now have a
rule of the most brutal honesty.”
Chaudhary says she’s no longer sure whether she wants
to found her own company—or continue her education. While she loves New York’s
startup culture, she’s also interested in emerging markets. “If I have a
brilliant idea and follow it, great,” she says. “If I move to China and keep
learning, even better.”
Ben Darr, on the other hand, is hell-bent on becoming
an entrepreneur. “After these two years I’ll be ready to start my own company,”
he says. Can he survive the apprenticeship? He spent a restless two years of
college at three very different schools. Working for someone else, he says, “is
like staying at a friend’s house: It’s fun, you do cool stuff, but it’s still
awkward every time you take something from the fridge.”
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