This Man Makes Founders Cry

Jerry Colonna helps CEOs make money by making peace with their demons.

Reboot CEO Jerry Colonna at his Boulder, Colorado office. Reboot is a coaching company for entrepreneurs and leaders of companies.

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.

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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 holds a meeting with Reboot CPO Dan Putt in the Boulder, Colorado office.

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.

Colonna in his Boulder, Colorado office.

I visit Colonna’s Boulder office the day after his 53rd birthday. He tells me he’s feeling low. His mother died recently. It’s December, and the holidays can be hard. Colonna is a fit guy with white hair cropped close to his head. On his left pec, just visible beneath his shirt, is a tattoo of a spider, its body as large as my fist. This, he tells me, is his spirit animal. (The internet tells me that it represents feminine energy and creativity.)

Colonna’s walls are lined with tokens from his travels. There’s a photo of him with friends from Tibet; he took some of the money he made through an early investment in Twitter, which he sold pre-IPO to the Russian investor Yuri Milner, and opened a school there. There’s also a black, rectangular meditation cushion placed before a copper smiling Buddha.

The Reboot offices are in the front right quadrant of a former elementary school, a brick-and-stone Hogwarts of a building that was originally constructed in the late 1800s for the children of the Gold Rush. Today, there’s a coworking space on the top floor and an eating club in the basement. Halfway through our talk, we pop down to pile plates with the kind of food that people serve in Boulder: kale; bean salads; baba ghanoush.

Colonna’s approach to coaching centers on “radical self inquiry.” He believes people can become stronger leaders when they fully understand themselves. We all have things we don’t want to talk about. Usually, our avoidance is so strong that we don’t even know consciously what they are. Those are the things Colonna wants to discuss with us. One former colleague and then client, WME Ventures managing partner Beth Ferreira, sums it up this way: “He asks you the questions that you repress.”

When Colonna listens to your answer, he draws in his lower lip underneath the top in a frown of concentration as he fixes his eyes on you, unwavering but generous. Next thing you know, you are telling him you wanted to be a writer because you were taught the importance of bearing witness as a child when you didn’t feel heard by your parents. And more likely than not, you’re crying. Hypothetically, of course.

Among Colonna’s clients are Gimlet Media cofounders Alex Blumberg and Matt Lieber. Gimlet hosts Startup, a podcast Blumberg produces about building a startup. It’s the reality radio show version of Gimlet Media’s life, which is how any listener knows that last summer Blumberg was feeling a lot of pressure. He hired Reboot to conduct a 360-degree review. The results highlighted a tension he faced: He wanted to take an active hand in creating episodes (and the company was launching six new series), but he needed to spend more time planning for the company’s future. To do that, he felt he had to manage his time in a more disciplined fashion, and this made him feel he’d need to become someone he was not.

In an October episode, he broadcast his coaching session with Colonna. Blumberg tells Colonna he’s feeling afraid. Colonna asks Blumberg about his father, and specifically, about whether his father was free. “He was, very free, in certain ways in that he never took on all the responsibilities of adulthood,” Blumberg says, emitting an uncomfortable squawk of a laugh. They speak about the conflict between his parents which, Blumberg says, never got voiced. There was a tension that existed between his father, who wanted to have fun, and his mother, who wanted him to take on responsibility; Blumberg realizes through the conversation that he has internalized the conflict and is re-enacting it in his present life.

“What are you doing right now? You are looking at yourself. And it’s painful and it’s hard,” Colonna tells Blumberg. He tells him there’s a point in time when you grow past your parents.

Blumberg’s voice cracks. “My dad is over-the-moon proud of me,” he says. “And he always has been.” He notes that he and his dad share similarities, but they are not the same person. He is crying.

Colonna then quotes Jung. “Until we make the unconscious conscious, we will be dictated by it and call it fate.”

Colonna outside his Boulder office.

Colonna has been severely depressed twice in his life. The first was when he was 18. As a freshman at Queens College, he found himself squarely facing down a suicide attempt. He was hospitalized for three months, and with the help of a therapist and friends, he put himself together again. “My mother suffered from schizoaffective disorder, which is a form of bipolar but manifests in schizophrenia, and my father was alcoholic. And so, struggles like these run deep within my family,” he says.

He pulled himself together and worked his way through school, winning a scholarship to pay the $750 tuition each semester. While still in school, he began interning on the copy desk at InformationWeek. Five years after that first internship, he was named editor of the magazine, and then​ later became the director of interactive media for the company that ran it, then called CMP Publications.

In 1996, Colonna joined with Fred Wilson to start Flatiron Partners, which quickly became one of the most notable early stage venture funds of its time and put New York’s tech scene on the map. “He was the person that entrepreneurs always connected to,” says Wilson. “They loved Jerry. Bring Jerry in a meeting and they’d fall in love with us and always wanted to get us to invest in their company.”

Then, it all blew up. In the spring of 2000, the dot-com bubble burst. Over the next two years, the NASDAQ would lose 78 percent of its value. “In the midst of all of that, I’m staring down the gun barrel of turning 40,” Colonna remembers.

Here, Colonna pulls a signature Colonna. He recites poetry, quoting from memory a stanza by Donald Justice: Men at forty/learn to close softly/the doors to rooms they will not be/coming back to. His eyes return and he says, “The age from 35 to 45, it’s a fucking rocking period.”

Colonna felt awful. He weighed 250 pounds, 75 more than he does now. He wasn’t sleeping. Flatiron Partners had stopped investing in new businesses. Earlier, he had led a $30 million round of funding at The Industry Standard, where he was on the board. By August, it was facing bankruptcy. Colonna had just begun a week-long rafting trip in the Grand Canyon when The Industry Standard announced it would shut down. “I came out of the Grand Canyon trying to figure out what to do with my life,” he remembers. Colonna returned to New York, and signed on to work full-time for J.P. Morgan Partners, the private equity arm of the bank. That was on September 10, 2001.

On the morning of September 11, Colonna flew to Washington, D.C. He was in a meeting with several senators and tech executives, sitting next to Tom Daschle, then the Senate Majority Leader, when the Secret Service rushed in to say the US was under attack. “There we are in a hotel across the street from the capital,” Colonna recalls. “That day was fucking surreal.” He and two New Englanders arranged for a car to drive them home; I-95 was closed, so they traced backroads west through Pennsylvania into New York. Thirteen hours later, Colonna finally hugged his kids on Long Island.

For a while, Colonna avoided his mess of feelings by making himself very busy. He helped start the Financial Recovery Fund, an $11 million fund that made grants to small businesses hurt by the attacks through something called the Partnership for the City of New York. He also stepped in as co-executive director for New York’s failed 2012 Olympic bid.

But he was anxious and unhappy. The more anxious and unhappy he became, the more activity he took on. The busier he was, the more impressed the people around him became. “Jerry’s great!” they thought. But Colonna was not great! He was not! Inside, he was spiraling downward into a vast blackness from which he didn’t know how to extricate himself.

One February day, he left an Olympic bid meeting. The committee had free office space in downtown Manhattan because no one wanted to be there. The offices were on Liberty Street, just a block from the remains of the World Trade Center. All around him, he could smell the charred odor of burnt steel. The metal-on-metal clash of the cranes came from every direction. It was 20 degrees outside. He stood there on Broadway, just up the street from St. Paul’s Chapel. “Something was wrong,” he remembers. He began to cry, and his body spasmed into a panic attack. He felt like he couldn’t breathe. He pulled his phone from his back pocket and called his therapist. She told him to get in a cab and come immediately to her Long Island office.

“I said to her, ‘Put me in a hospital, because I’m done,’” Colonna remembers. “And she said, ‘You’re rich, what do you want to go to a hospital for? The food sucks. Go to Canyon Ranch.’” So he packed a pile of books (When Things Fall Apart and Let Your Life Speak), and headed out on a two-week trip to Arizona.

Things didn’t get easier right away for Colonna, but they did eventually get easier. After a year at J.P. Morgan, he set out to “live life without a business card” for awhile. He taught leadership, though his students tended to call it “Jerry’s Money and the Meaning of Life Class.” He sat on boards — 21 of them. He spent a lot of time researching a novel he never wrote about a man in the middle of a midlife crisis. For four years, he went on medication to help treat his depression. He traveled to Greenland and skied across the top of parts of the polar ice cap. He started attending frequent yoga and meditation retreats.

Colonna meditates at his Boulder, Colorado home.

Colonna calls this period of his life his “hermitage.” He met with people only occasionally. In 2006, a lawyer in his late 20s — a friend-of-a-friend — stopped by for a coffee. The guy wanted to get into startups. It was obvious to Colonna that this guy hated being a lawyer. So Colonna asked why he made the decision to go into law in the first place: “He started to cry,” recalls Colonna. “And he started to tell me about his father and pleasing his father and how miserable he was,” In the process of talking through the lawyer’s next career move, something clicked: Colonna realized that he should go into coaching.

He trained. He got a catalogue from the Open Center in New York and signed up for a coach training program. But soon, even before he’d completed any formal credentialing, Colonna had taken on clients a couple days a week. “I remember one woman with whom I was meeting on a fairly regular basis, just to help her. One time we were sitting in the conference room and I sort of mapped out her life on a dry erase board,” says Colonna. “She called me up and she said, ‘You know that thing you did last week? Can I pay you to do that once a week?”

Chad Dickerson started working with Colonna within a couple months of becoming the CEO of Etsy in 2011. He had already been at the company for nearly three years as chief technology officer, but in some ways he was an unusual pick for the top job. Dickerson was a thoughtful and introverted engineer—a respected Yahoo veteran with a strong tech background. He had never helmed a company, let alone a high-profile, six-year-old startup with several hundred employees in need of a growth jumpstart strong enough to propel it toward an initial public offering.

From the start, Dickerson found Colonna’s coaching invaluable. “On the outside, some of the way Jerry talks can look touchy-feely, but he’s also been an investor and an executive before,” says Dickerson. “You could have a very good conversation with him about the puts and takes of round valuation and who to take money from, and who not to take money from.”

Dickerson needed to hire a chief financial officer, a general counsel, and someone to run human resources, among many others, as soon as he possibly could. He met regularly with Colonna as he filled these positions. Nearly six years later, Etsy has gone public and grown into a thousand-person company. Colonna continues to coach Dickerson, as well as several other senior Etsy executives. Around Etsy, Dickerson calls him the fifth Beatle, saying, “He’s been able to help me cut through some of the dynamics that I might not see because I’m in it and all the executives are in it, too.”

In the process, Dickerson has grown into a confident and effective CEO. He credits Colonna for helping him master the communication skills and resilience necessary to do it. “There are tons of ups and downs to running a company,” says Dickerson, ticking off a list: The stock soars; you land a big hire; the stock tanks; your best engineer quits. “Learning how to understand yourself and manage your emotional state during all of that turmoil, it sounds touchy-feely but it’s actually a great source of strength,” he says. “You can act forcefully and with clarity.”

Two years ago, Colonna moved to Boulder full time. His good friend Brad Feld lived there and encouraged him to come. Colonna was on the board of Naropa University, a Buddhist-inspired liberal arts college in Boulder. And as a deep introvert often pulled to be in the company of people, he craved a bit of distance; he wanted to live somewhere where he could be alone a lot and spend time in nature.

In mid 2014, he teamed up with some likeminded thinkers to start Reboot. It has grown to include 16 coaches spread between offices in New York, Boulder, and San Francisco. Each has her own approach to the craft. Colonna and one of his cofounders, Khalid Halim, provide a light form of supervision, and make themselves available to talk through things that come up. Once a quarter, the group joins a coaching call. The company also takes on performance reviews, and provides peer groups and organizational leadership development. More recently, Reboot has gained a reputation for its four-day workshops called Bootcamps.

Reboot has held these gatherings for VCs, CEOs, and founder pairs. Later this year, the company will hold its first women-only bootcamp. Often held in Colorado, the retreats cost between eight to ten thousand dollars, and include roughly 15–24 people. The application process is lengthy, and includes references. Its stated goal is straightforward: “Uncover your authentic leadership style and become the best board member/investor/supporter you can be.”

But attendees come for something more. They’re often tired, burned out, frustrated with cofounders or board members, and they’ve forgotten why they wanted to work on startups in the first place. It’s a feeling Colonna knows well, and one that often goes unremarked upon in the valley. The startup grind has a way of wearing you down. They come to recharge. After a recent VC bootcamp, seed stage investor Jacob Chapman blogged about how powerful the experience was, writing: “The Reboot team possesses an otherworldly talent for coaxing authenticity and truth out of people. They can even coax truths out of people who, like myself, have been lying to themselves for years.”

Jerry Colonna outside his Boulder, Colorado office.

The bootcamps serve a second purpose. At this point, there’s not enough Jerry to go around. Colonna isn’t really interested in becoming a coach to celebrity CEOs. He doesn’t want to raise his rates to the point where only large company CEOs can afford him, and he is always trying to shrink his client list. But even though there are other Reboot coaches, “if you want Jerry,” says Wilson, “you kind of have to have Jerry.”

Colonna gets to New York for about a week a month, where he works out of a tenth-floor office on 21st and Broadway. When I stopped by to see him there at the beginning of January, he was wearing jeans, a navy sweater, and a string of prayer beads around his wrist. Everything about his presence was lighter. With the holidays behind him, he said, he said he was feeling much better, more grounded.

Colonna’s depression still creeps up, but these days he manages it well. It’s work. He needs a lot of time to himself every day. To let off steam, he boxes because, he’s often said, “sometimes you just need to hit something.” And he relies on his Buddhism practice, beginning each day with a 20-minute meditation. He also journals each morning.

Taken together, it has left him resilient. That’s what Colonna aims for in his coaching. Sure, he’d like the entrepreneurs with whom he works to kill it at their jobs. He’d like them to be happier, because who doesn’t want to be happier? But really, he wants everyone to figure out what he has figured out the very hard way: “Life sucks and it’s okay. Life is great, and it’s okay. Life goes up and it’s okay; life goes down and it’s okay,” he says. “If we can instill a sense of resilience in people, we mitigate suffering.”

And, as Bart Lorang would tell you were you to encounter him outside a bar in Lisbon, often our marriages and our businesses fare better as well.

Creative Art Direction: Michelle Le 
Photography by: Matt Nager