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.”
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