It’s 6.45 am, 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 four 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 hopes to 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, PR and recruiting companies. Ittycheria focuses on housekeeping, 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 programme 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 Street, 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, capitalisation 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 co-founder 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 percent 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”.