Mission: Adulthood

How today's 20-somethings are transforming work, love, and life

The Humbling of a Young Entrepreneur

One tech star's experience reveals how Gen. Y is maturing.

The following is an excerpt from Mission: Adulthood: How the 20-Somethings of Today Are Transforming Work, Love, and Life, by author and journalist Hannah Seligson. Mission: Adulthood chronicles the lives of seven individuals who embody Gen Y, sketching a picture of what life is actually like for young adults today. This excerpt is an account of Josh Weinstein, who was 23 at the time of his interviews. Josh is the founder of YouAre.TV, an interactive video site. He’s the archetypal wunderkind—a chess champion and fluent Mandarin speaker with diplomas from Stuyvesant High School and Princeton University. Right out of college, when he was 22, Josh landed money from established investors to fund his first startup. Yet he still lives at home with his mom.

Josh arrived in Palo Alto from New York at the beginning of July 2011. At first, everything was great. The weather was perfect. Josh was living with a good friend from Princeton, he got to play hockey, started to get back in shape, and his third roommate was an amateur chef. Fairly quickly, though, things started, as Josh put it, “to be not so awesome.”

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“As a city kid, I started to feel the isolation of living in Palo Alto and not working in a co-working space,” Josh said. The CTO, whom Josh calls “Ted,” was acting flaky and not working as much as he and Josh had agreed upon, significantly slowing progress on YouAre.TV. Ted kept pushing back his official start date. That was a red flag for Josh. And by continuing to wait for Ted to start, Josh was going against one of his core principles of running a startup: keep up momentum and get the product in front of people as soon as possible. But instead of listening to his instincts, Josh listened to other people. His advisors and investors told him that it was totally normal that “Ted” was delaying his start date and not to worry.

Those few months in California, Josh said, “It felt like the whole world was passing me by.” He fell into a bit of a funk, but tried to stay upbeat and busy by networking with people at Google and Facebook and plugging himself into the Silicon Valley tech scene. The night before Ted was supposed to start, he wrote Josh an email bailing on his commitment. Josh immediately woke up his roommate and told him he was moving back to New York City as soon as possible. This was one of the biggest professional blows of Josh’s life. After Ted reneged on his offer, Josh started breaking the news to all of his investors. He recounted, “Most of them understood, but I know I lost the confidence of some of them.”

Could Josh have checked Ted’s references more carefully? Paid closer attention to the red flags? Not acted so swiftly in moving out to California? Perhaps. In a self-reflective blog post Josh wrote on his Tumblr account about what happened during the summer of 2011, he owned up, in a very public way, to all the mistakes he made. While social media is usually reserved for flagrant self-promotion and as an advertisement for how awesome your life is, Josh used it to tell the world about his flop. Josh didn’t write the blog post to solicit pity or be vengeful or even out “Ted,” whose real name he never revealed, but rather to dissect the lessons he learned in hopes that they might be helpful to other young entrepreneurs. It was Josh’s way of paying it forward. Moreover, writing a blog post was an important catharsis for Josh in coming to terms with what had happened over those few months, not to mention much cheaper than going to see a therapist.

By September 2011, Josh was back in New York City, living with his mom and working at the same desk at his shared office space, trying to make up for lost time. Something, though, had shifted in Josh. He came across as more introspective and communicative. His trademark one-word answers had been replaced by longer and more thoughtful answers to my questions. The experience with “Ted” punctured the bubble in which Josh had been living. Until that happened, Josh had been lucky enough to have sidestepped much of the random cruelty and unreliability of the real world. This wasn’t because Josh was purposefully leading a sheltered life; things had just happened to work out for him. Feeling slightly more fallible after his brush with failure, Josh seemed to have more capacity for empathy, compassion, and introspection. Some might even call that maturity.

To say that Josh became a font of emotion would be an overstatement, but after his experience with “Ted,” he started talking much more freely about the highs and lows of being the young founder of a startup. When I first met Josh in 2010, the topics of failure, the pressures of running a company when you are fresh out of college, and the difficulty of coping and keeping your head above water in such a competitive industry were topics Josh waved off.

If I asked, “Do you ever feel scared and overwhelmed that investors entrusted you with a million dollars?" Josh would dodge the question or give me a monosyllabic answer. So I would never have imagined that Josh would go on the record to talk about his bouts of depression.

Right after Ilya Zhitomirskiy, the 22 year-old founder of Diaspora, a social network that the founders branded as “the anti-Facebook,” committed suicide, Josh spoke extensively to BetaBeat, a section of The New York Observer that covers technology, about the often-felt, but rarely discussed, phenomenon of “startup depression.”

“There’s no way you can talk about it, because you feel like you’re in this alone. You feel socially vulnerable when in reality everyone else is going through the same thing. The pluralistic ignorance is a big problem. You can talk to your friend, and be like, yo, I’m depressed . . . ‘Yeah, I’ve been seeing a psychologist for the last year.’ And you’d be like, really? And they’re like . . . Yeah.’ Nobody talks about it! You can tell people about your problems, and you'll find out that they have similar problems, too. ” In one fell swoop, Josh made his second public service announcement in three months, making a brave admission about his own struggle with depression. Josh opened up a public dialogue and exposed that, even if this group of young entrepreneurs all appeared to be “killing it,” with their big checks from investors and the opportunity to make fast millions, lurking beneath was the dark underbelly that anyone who is young and untested must feel: doubt, fear, anxiety, and uncertainty about living up to all the hype they’ve built.

“It’s important to relay those experiences to other people, so they don’t think ‘I just took hundreds of thousands of dollars of someone else’s money, everyone in the media loves me, and I should be like Mark Zuckerberg. It doesn’t work that way,” Josh told me as we sat in the living room of his mother’s apartment, looking out at panoramic views of the East River. “Everyone has all these expectations of you—that you are talented, smart, whatever, and it seems like you should execute because you have all the resources. It’s a hard realization, but I thought it was important to go on the record and say all of that.”

 

Hannah Seligson is a contributor to The New York Times Sunday Business Section and author of Mission: Adulthood: How the 20-somethings of Today Are Transforming Work, Love and Life.

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