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The Apprentices: Learn-By-Doing Entrepreneurship at Enstitute

Meghan Casserly, Forbes

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.”

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