Jerry Colonna Makes CEOs Cry

It’s two o’clock on a Sunday morning, and I’m standing outside a Lisbon bar with a pack of techies gathered for the annual Founders conference. The air smells like salt and cigarettes. Inside, someone is passing around shots. Two guys are trying to play pool, but the room is too crowded, packed person-to-person with CEOs, investors, and bankers talking shop. Outside, the breeze on my face is a relief. The guy next to me is maybe 37 years old, with a reddish-blond goatee, and he’s telling me about his enterprise software company, FullContact, which, he says, is based in Boulder.

I’m writing about a man from Boulder, so I ask him: “Do you happen to know Jerry Colonna?”

“Jerry?” he responds. “That guy saved my life.”

He tells me his name is Bart Lorang, and when he went to see Colonna four years ago, his company was faltering and his wife was unhappy with him. Colonna coached him for two years. Today, he says, his company is profitable, and his marriage is strong.

Over the last few months, Lorang’s story has begun to sound familiar to me. Among tech’s founders and CEOs, Colonna’s name carries a certain weight. “When I first started speaking to Jerry, I was a new CEO. Occasionally, people would sheepishly say, ‘Do you know Jerry Colonna?’”says Etsy CEO Chad Dickerson. “There was this moment where you admitted to each other that you were working with him. It’s not an official thing, but there is this almost secret society of people who’ve been coached by Jerry.”

Many of the most successful tech founders have relied on coaches. A small handful of them have risen to celebrity status for coaching some of the valley’s more iconic figures. The most famous was former Intuit CEO Bill Campbell, who passed away last year. Campbell worked with Steve Jobs, Larry Page, and Marc Andreessen, among many others. More than one person has compared Colonna to Campbell. “Campbell had a testosterone-infused Silicon Valley kind of model,” says investor Fred Wilson. “Jerry’s model is more Buddhism and less football.”

Colonna has earned his street cred as a tech coach. After working at one of the first companies to sell internet advertisements in the early 1990s, he joined Wilson to form Flatiron Partners, the high-flying New York venture capital firm that had spectacular wins during the early dot-com years — and then a dramatic demise when the market crashed. He has strong operating experience, and can advise on everything from the terms of a round of funding to the right candidate for a chief financial officer position. But that’s not why he’s an effective coach.

In tech circles, where founders are nearly hardwired to describe everything as awesome, promise every business is growing, and work until they drop, Colonna has empowered them to take on — and tend to — their own mental health issues. He does this by talking about himself. In the early aughts, Colonna was consumed by a deep depression that left him suicidal. His years-long healing process seasoned him, transforming him into a Buddhist empath bordering on New Age. “There are a lot of people you can go to who will teach you to be a better manager,” says Soundcloud CEO Alexander Ljung. “Jerry understands the psychology of leadership.”

His techniques for getting the most out of people are increasingly in demand. Colonna has offices in New York and Boulder. Nearly three years ago, he partnered with some likeminded colleagues to start a firm, Reboot, that has grown to include 16 coaches in Boulder, New York, and San Francisco. Through Reboot, he runs regular workshops—which he calls bootcamps—based on his philosophies. And despite the fact that he now charges clients $5,000 a month, does no advertising, and is constantly trying to pare down his personal client list, founders keep calling him. They just keep calling.

Read more at Backchannel.