The most—or least—of one's worries.

EARLIER THIS MONTH, ON A SUNDAY MORNING, the startup world woke up to that rare stripe of news which quietly sends shockwaves reverberating throughout an entire culture of people: Ilya Zhitomirskiy, 22 years old, had passed away. The cause of death "appears to be a suicide," noted a San Francisco police officer who spoke with CNN. A forthcoming coroner’s report will make a final determination. Mr. Zhitomirskiy was one of the four co-founders of Diaspora*, once breathlessly hyped in a May 2010 New York Times article as a “cry to arms” against Facebook, in a story that employed a classic tech narrative: four brilliant young men, on the verge of changing the world, subsisting on ramen and pizza.

Y Combinator’s Hacker News link to the item racked up pages of comments, many devoted to shouting down those who wanted to have a discussion about depression in the technology and startup community, noting it as an inappropriate moment for that topic. One user noted that a breaking news thread announcing Mr. Zhitomirskiy’s death was “a terrible place to have a discussion about ‘the stresses of life … related to tech.’”

Another disagreed: “We don’t talk about suicide in society very well let alone within the startup community. Founders find themselves in extremely stressful situations and living lifestyles that exacerbate the effects of this stress.”

This second comment read in contrast to the first, whose final suggestion on the matter was to “have that discussion inside your head” for the time being, and then go talk about it some other time.

IT'S FRIDAY NIGHT at New York City's startup workspace-cum-mecca General Assembly, and it’s YouAre.TV founder Josh Weinstein’s 25th birthday. A crowded party with a sufficient supply of pizza and beer warms up in the main hall. Mr. Weinstein, however, is found quietly typing at his desk in the South Wing, isolating him from the Startup Weekend New York kickoff raging outside the door.

As we find a place to sit, a few people regard him with quick back-slaps and Happy Birthdays. Another colleague working nearby is surprised to hear of the occasion, quickly offering the same. Along the way, he nods to a nearby colleague, “Chris,” to accompany us as we search out a quiet place to speak; the unannounced third party is joining, Mr. Weinstein explains, because he—another 25 year-old startup founder—has much to say on the topic, the both of them having experienced some stripe of professional failure and the depression that comes with it.

[“Chris” agreed to speak on the condition of anonymity not because he doesn’t want to publicly speak about depression, but because his startup is trying to avoid press in its early stages.]

Mr. Weinstein and Chris sat with Betabeat in a couch-filled cubicle, and immediately begin firing off insight on depression among their contemporaries with the enthusiasm one would expect to be reserved for a particularly fascinating segment of code.

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“I’d be really surprised if you could find a founder who—if you asked them about their emotional state—hasn’t been through depression,” Chris explains. As a computer engineering student working at a startup at a prestigious college, and then as an entrepreneur going it alone after he graduated, he’s experienced in sparring with his own mental health.

“That’s why I asked Chris to come,” Mr. Weinstein explained. “We’ve gone through it at different times. We talked about it; it’s a club. It’s good to have that support network. A lot of people don’t ask for help.”

The World Health Organization cites depression as affecting 121 million people worldwide. The Center for Disease Control estimates one in every ten American adults are suffering from some form of clinical depression. In the 18 to 24-year-old age group, that number goes up to 11.1 percent. To Chris, the startup world is even more susceptible.

“It’s not ‘if,’ it’s ‘when’ it happens,” he sighed. “I’d almost say if they aren’t going through depression, you’re probably not actually pushing hard enough, or taking on enough risk, because that’s just an inherent part of owning something.”

In a phone interview a few days later, angel investor and TechStars managing director David Tisch—who once acted a mentor to Mr. Weinstein—corroborated this theory. “When you as a personality are able to take the risk to start a company, in making that choice, you have to consciously understand that you are rebelling against the easy path,” he explained. “That’s not a foreign concept to the people I work with.”

Mr. Tisch illuminated this with a story he rolls out to young founders on their first day of TechStars that his friend—Thrillist co-founder Ben Lerer—once told in an interview: for the first two years in founding the company, after every important meeting, they’d inevitably take the elevator down to street level, and on the doors closing, jump up and down, laughing hysterically. Or start crying.

“That’s fucking crazy!” Mr. Tisch observed. “In reality, that will screw up anybody. Think about a startup experience like that. Unless you’re emotionally and psychologically tough enough to withstand that roller coaster, you are going to go through [those emotions].”

Jerry Colonna, a venture capitalist turned business and life coach to Silicon Alley royalty, has seen the pressures founders (and particularly young founders) can face. Often. “Every. Single. Day,” Mr. Colonna said in a phone call with Betabeat. “Ten times a day. These pressures are not just unique to this age group, but they are exacerbated in the entrepreneurial community.”

In this tightly knit community, he continued, the factors unique to young entrepreneurship can add up. “When you layer status against the pressure cooker of, say, Broadway between 23rd Street and the Village, that whole corridor”—where General Assembly is, of course, located—”what you end up with is a sort of high school [scenario]. Who are the cool kids? Who aren’t the cool kids? Whose popularity is rising, sinking? You get this incredible pressure on people.”

Mr. Colonna illustrated a scenario that isn’t all too uncommon these days, specific players aside: “Imagine that you’ve just raised a million and a half dollars from Fred Wilson. Exactly. Scared shitless. Oh, and by the way, you’re worried that everybody’s going to find out that you have no fucking clue what you’re going to do.”

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Cody Brown, the 23-year-old co-founder of NYU Local and the recently-launched Scroll, corroborated this point by phone from his apartment in Bushwick. “The fact of the matter is: there are a lot of people in their early 20s being handed thousands of dollars, multimillion dollar checks, and having this self-imposed pressure,” which is in addition to the pressure of trying be a normal, young, 20-something. Like, for example, “trying to find a girlfriend,” he laughed.

He went on to point out a distinct irony for those like him in this specific moment in technology startups: “It’s funny how many help enhance that feeling of stress. Like, foursquare! Oh, god. I really don’t need to know every party that I haven’t been invited to, routinely and beautifully laid out on my phone!”

Even the most cursory of looks reveals young startup founders living lives that are potential incubators for depression. If that’s the case, we offered, then why have many of the people we’ve spoken with felt that the past week is the first time a discussion concerning tech startups and mental health has happened at a significant volume? After all, these are the same scientifically and socially progressive creative types brought together by the mandate to bring the world new and improved ways to hack everything from their workweek to their own bodies, let alone socialize.

Back at General Assembly, Chris sighed: “In the startup community, there’s a real stigma to depression. Every time someone comes around and asks ‘Hey, how’s it going?’ you’re always like”—and here, he vamped a disposition familiar to anyone who has ever had a discussion with a startup founder—”‘Best day ever, man! Killing it! We’re crushing it!’ You have to do that, because your job as founder is, to some extent, to create the Steve-Jobs-Reality-Distortion-Field.”

As conversations about mental health and depression in startups stay at hushed tones, the idea that anybody else is going through a common experience is a difficult prospect to embrace. “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,” Mr. Weinstein kicked his feet up on one end of the couch, in what one could have easily been mistaken for a therapy session, continuing, “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, and they’re like,” and with this, he smiles: “‘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!”

Mr. Brown echoed this sentiment: “Founders don’t want to discuss this,” he explained. “They want to have the public appearance of always being in control, and always being on top of their game.”

A 24-year-old female startup founder was at first reluctant to speak at all, noting over an email that it “makes me nervous as a young company to admit ever wavering.” She finished: “I feel like you might run into other entrepreneurs who might decline [speaking out] for fear it’ll make their investors look twice at them.” We did. She eventually relented, explaining her own experience with the problem over an instant message:

“Sometimes you get run down and depressed because your product is fucking awesome, your team is great, and you can’t stop yourself from working ’round the clock on it because you love it. But, your body rebels against that. Makes you tired unexpectedly, makes small problems inflate. And then you freak out, thinking that one off day is going to set into motion many, many more. So,” she finished. “You keep it inside.”

But, we asked her, wouldn’t it befit all parties involved to make this an open dialogue? Founders could get the help they need and investors could be satisfied with knowing the full condition of their investment. The idea was roundly rejected, one Gchat ping at a time:

“No
I don’t even think it would help
I think I’d get replaced”

IN A SITUATION so obviously built for so many involved to experience some form of depression or anxiety, be it mild or severe, one could reasonably assume the venture capitalists handing over money to these bright young things would have trained themselves to see it coming in their founders, and actively intervene. Some, Mr. Tisch argued, do: “The best investors out there get to know the entrepreneurs to the point where they’re there as a friend. It’s a very honest relationship that gets built. The best VCs pay attention to these things,” but, he qualified, “like in every industry, not everyone’s the best.”

“I don’t think [these issues] are getting brushed under the rug, but,” he concluded, “It’s probably something we can all do better in exposing.”

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Of course, the first and most rudimentary answers to these problems are as obvious as they are readily available:

“Stay focused on that self that exists outside of work,” Mr. Colonna explained. “Make sure you are dissipating the anxiety through physical exercise, eating right, all the things our mothers taught us.”

Mr. Tisch’s advice was more philosophical: “Understand where you are in the process. Consciously understand that you are rebelling against the easy path,” he suggested.

Chris noted: “Be comfortable having others know about it.” He nodded at Mr. Weinstein: “You have to identify people you can talk with about it.”

Mr. Weinstein agreed that so much of dealing with the emotional rigors of startup life was simply a matter of battling the character traits that helped those like him get there in the first place.

“Depression is so common, especially with people who are Type A,” Mr. Weinstein shook his head. “When you’re wired to execute and accomplish, it’s a challenge that you need to overcome. If you don’t recognize it yourself, or talk to people about it, it’s not going to be fun.”

Earlier that evening, when we first found out it was Mr. Weinstein’s 25th birthday, we couldn’t help but ask him:

It’s Friday night. It’s your birthday. You really going to stay here coding all night, or are you doing anything for it?

“Yeah,” he smirked, “we’ll be fratting our brains out at happy hour.”

As it turns out, Josh spent the rest of the night working.

fkamer@observer.com | @weareyourfek

Photo by Jackie Snow

Betabeat has written before about Jerry Colonna, also known as the Yoda of Silicon Alley, who is a business and life coach for a lot of big name start-up and tech CEOs. Mr Colonna is travelling out to Berlin soon to teach one his famous Disappearing Into the Fire sessions, and gave an interview to Tech Berlin over Skype.

He explains that he became a coach after Flatiron Partners folded and he worked a brief, unhappy stint with JP Morgan. "What I wanted to do was to really help other people who are in the exact same place I was in. Kind of the existential question, how do I make sense of this life I have created, especially as it relates to work and the definition of myself."

Business is booming now, says Colonna. As a journalist, investor and now coach, he says his interest has always been in two things. "To have the right brain speak to the left brain and vice versa, kind of being an interlocutor between two separate world. The other thing is the conversation, a really significant dialog, between two people."

It was this attitude that meant, when a CEO was having a problem he couldn't discuss with the rest of the board, Mr. Colonna was the one who was singled out as a confidant. As he says in the video, Fred Wilson is still a big supporter and recommends that many of the CEOs from Union Square Ventures portfolio companies seek out Jerry's advice. Flatiron Partners may be a thing of the past, but the partnership between these two men continues to bear fruit for entrepreneurs.

SKYPE A FOUNDER #6: Jerry Colonna, Professional Coach from TechBerlin on Vimeo.

Jackie Snow for The New York Observer

On a spring morning back in 2008, Lockhart Steele, the precocious prepster who helped Gawker Media turn a snarky take on current events into an online juggernaut, sat down for breakfast at Pastis. He was meeting with Joanne Wilson, one of the investors in his new company, Curbed Media, which focused on residential real estate.

"She's telling me about how everything is going so well," said Mr. Steel. "And I'm thinking, uh oh, the other shoe is about to drop."

Ms. Wilson, wife of local venture capitalist Fred Wilson, had made her first angel investment in Curbed, and as the pair sipped coffee, she pushed Mr. Steele to consider the challenges the future might hold. His miniature empire was expanding quickly but still not profitable, and the tremors that would crumple the financial markets were already reverberating through real estate. “She asked me if I was familiar with Jerry Colonna and would I consider going to see him,” Mr. Steele recalled.

Mr. Steele was aware of Mr. Colonna, a former venture capitalist who had recently embarked on a new career as a business and life coach, serving entrepreneurs and CEOs, but the Curbed founder took a dim view of self-help. “In my head I’m thinking, no fucking way,” he remembered. "I’m an upright New Englander, just naturally averse to any kind of New Age crap.”

At Ms. Wilson’s insistence, Mr. Steele agreed to give it a shot. Entering Mr. Colonna’s office in the Flatiron District, Mr. Steele couldn’t decide what bothered him more—the Buddhist altar or the Yankees memorabilia (he was a Red Sox fan, after all). “Jerry started out asking me how I was feeling, how things were with my body,” he recalled. “And I’m thinking, It’s 11 a.m. on a Wednesday, I should be at work … ”

- -

“I see myself as sort of an emotional consigliere,” Mr. Colonna told Betabeat recently, sitting in his office on Broadway. “I like to have the deep conversations with people that really dig into their problems.” He was dressed a bit like Steve Jobs: blue jeans, white Nikes, a blue turtleneck and wire-frame glasses. He spoke with a soothing, monklike calm—a style that has proved surprisingly popular among high-strung local techies.

Mr. Colonna’s touchy-feely ethos makes him something of an outlier in the city’s competitive, high-stress tech scene. Under the “recommended reading” section of his website, Mr. Colonna touts such titles as Start Where You Are: A Guide to Compassionate Living and When Things Fall Apart: Heart Advice for Uncertain Times. A post about a recent trip to Tibet includes a lyric from the Tracy Chapman song, “Changes”: If you knew that you would die today / Saw the face of God and love / Would you change? / Would you change?

That sentiment stands in sharp contrast to the city’s predominant start-up culture, which romanticizes sleepless work weeks, solitary struggle and scrappy resolve in the face of failure.“You’ve either started a company or you haven’t,” Chris Dixon, founder of local start-up Hunch and a well respected angel investor, wrote on his blog recently, in what might stand as a stirring manifesto of the Founderist ethos. “‘Started’ doesn’t mean joining as an early employee, or investing or advising or helping out. It means starting with no money, no help, no one who believes in you … and building an organization from a borrowed cubicle with credit card debt and nowhere to sleep except the office...It means lying awake at night worrying about running out of cash and having a constant knot in your stomach during the day fearing you’ll disappoint the few people who believed in you and validate your smug doubters.”

Founders, in this construction, are digital-age martyrs, Red Bull-chugging dreamers who sacrifice personal friendships and physical well-being so that bold new ideas can make their way into the world.

During the first dot-com boom, Mr. Colonna was a founder himself. His venture capital firm, Flatiron Partners, which he stared with Fred Wilson, was the first in town to specifically fund early-stage internet companies, including Geocities, which sold to Yahoo for $3.7 billion in 1999 at the height of the Web 1.0 bubble.

Despite racking up some very impressive returns, however, the fund was dissolved following the crash of 2001, as the tech industry violently imploded. Some of Flatiron’s most high-profile portfolio companies—Kozmo, Urban Box Office, Scout ElectroMedia—were among the biggest casualties.

Mr. Colonna went to work at JP Morgan Partners, one of Flatiron’s principle backers, but he felt lost there. “I became depressed, suicidally so, thinking about where my life would go,” he said.

In under a year, he’d decided to resign, telling colleagues he was going to work on a novel about a man having an existential crisis.

On Mr. Colonna’s personal blog, the now-shuttered Madeleines, readers could follow his spiritual evolution in real-time as he discovered Buddhism and then sought certification as a business coach through the Open Center. There’s a touch of Jack Handy to some of his language, as Mr. Colonna grapples with the process of his reinvention. After leaving JP Morgan Partners, he wrote of telling some new acquaintances about how he used to be a venture capitalist. “But I really wanted to say, ‘I’m still important. I’m still smart.’”

There are now more than 50 clients on Mr. Colonna’s roster, and many more on the waiting list. They come for his unique mix of tactical acumen and emotional insight. He offers sessions in person at his Broadway office, as well as via phone and video chat with clients as far away as China. Fees are on a sliding scale.

Sitting on Mr. Colonna’s office couch during that first session back in 2008, Mr. Steele deflected the coach’s questions with a practiced vagueness honed at countless New York cocktail parties. “Jerry looked at me and said, ‘No, what’s really on your mind?’”

The truth? Mr. Steele had been stewing over his next round of fund-raising. He wanted to return to his original investors, whom he liked and trusted, but knew they wouldn’t want the valuation to rise if they backed him again. His employees, meanwhile, would be unhappy if the new round of funds didn’t raise the valuation of the company, and with it their stock options. The fretful disclosure poured out of him.

“Jerry didn’t even blink,” he recalled. “‘Oh,’ he said, ‘that’s called the inside round problem.’ He spent the next half an hour dissecting it, and when I left that day, I felt like someone had lifted a hundred pounds from my shoulders.”

“When I first started, it was like a secret club,” Mr. Steele said. “Now it feels kind of like half the downtown tech scene has been to see Jerry.”

“Jerry is like Barbara Walters,” Joanne Wilson noted. “Get him one-on-one with anyone and he can make them cry.”

As Betabeat got up to leave our interview with Mr. Colonna, we received a free sample of his services. He pointed at the large duffel bag we had brought along to the interview. “Travelling?” he asked.

It was actually a gym bag, we explained. Betabeat had taken up Brazilian Jiu-Jitsu.

“You see, I love that!” Mr. Colonna exclaimed, sitting forward. “It’s so vital to have a passion outside of your work. You’ve just launched a new site, that’s like a start-up. When you create a new business, there is a narcissistic impulse to connect your self-worth to your company.”

The Observer took a seat on the couch again, next to a stuffed Yoda doll Mr. Colonna had received as a gift from a client. Our mood, we told him, was squarely pegged to the performance of The Observer’s newly launched tech site, Betabeat.

“How has your stomach been feeling?” Mr. Colonna wanted to know.

In fact, for the past few days, our stomach had not been good, we admitted, dumbstruck. Not good at all.

“It’s not X-ray vision, I’ve seen this a thousand times,” Mr. Colonna declared. “Oops, we’re having a session now.” He laughed.

“Look I’m not trying to tell anyone what to do,” he said. “You could be an investment banker or you could be Mother Teresa, but if you let work take over your life, you’ll be miserable. To be an entrepreneur takes a single-minded focus, but to do that without an awareness of its cost is a tragedy.”