Power-Down Boot Camps for Venture Capitalists - OZY | A Modern Media Company

Power-Down Boot Camps for Venture Capitalists

Power-Down Boot Camps for Venture Capitalists

By Zara Stone


Because VCs also need places where they can recharge their batteries.

By Zara Stone

Every year in Boulder, Colorado, Jerry Colonna would host four-day boot camps on radical self-inquiry under his firm, Reboot, designed for target demographics: CEOs and founders. Then he realized there was an underserved community of venture capitalists. “They have a unique expression of power, not a traditional command and control structure,” he says. This can lead to anxiety, depression and self-doubt — which Colonna, a former venture capitalist turned executive coach, alleviates through group discussions, exercise and guided mindfulness. “We’re helping people develop stronger and more resilient leadership,” he says. He wishes something like this had existed in his VC days — “I was fucked up and lost!” he exclaims.

This January, Reboot hosts its third VC boot camp. Such camps are part of a growing number of venture capitalist–targeted getaways, all offering far more than the usual meet ’n’ greet. This partly falls into the bracket of “adult summer camps” — searches are up 43 percent from 2016 on Pinterest travel boards — combined with VCs’ desire for a more elite and introspective experience. There’s Summit, launched in 2008, an invite-only event series — an average day might include making a 3D-printed bird’s nest, learning meditation techniques from an Olympian and listening to Quentin Tarantino. In July 2017, Farm + Land launched, a company creating invite-only urban retreats for “urban creatives, makers and doers” — think tiny-house building, yoga and CEO keynotes. This past fall, the European Venture Retreat launched in Italy, and then there’s Further Future, ostensibly a conference on futurism, but in reality, a three-day party for venture capitalists and their cronies. For VCs who attend, these camps offer a path to recapture — or reinvent — their childhood, engaging in wholesome fun, with an adult bent. 

We’re working harder than ever before, and the only medicine is the outdoors.

Freddie Pikovsky, founder, Farm + Land

“I don’t see what we do as a retreat,” Colonna says. “A retreat feels like rest, whereas a boot camp is leaning in and doing hard work — you see the difference?”

Around 20 to 30 VCs apply for each $10,000 spot Colonna offers — he tries to keep groups to fewer than 20 people. Some participants try to use the retreats for networking, he says, which isn’t what he wants — his goal is willingness to work and authenticity. “What they need is equanimity and resiliency, and the capacity to deal with the fact that sometimes things suck,” he says. “Five years from now, I’d like them to not feel depressed and aggressive, but [to] feel at peace.” One session titled “VCs Behaving Badly” involves venture capitalists owning their past mistakes and working out how to change.


Steve Schlafman, a principal at RRE Ventures, found attending a boot camp invaluable. “The boot camp went deep and had a profound effect on me,” he wrote on his blog. “Throughout the weekend, I was able to recognize that many of the things that I wrestle with as a board member and an investor are quite common.”

The chance to reconnect with nature while reflecting on personal goals is what inspired 33-year-old travel entrepreneur Freddie Pikovsky to found Farm + Land (it’s also the subject of his upcoming book). Farm + Land is a wilderness retreat that’s also a country co-working space with plenty of Wi-Fi and handcrafted tiny houses and cabins. The beta test is in 2018. “We’re working harder than ever before and the only medicine is the outdoors,” Pikovsky says. “It’s the escapism that urban dwellers are needing.” A co-working garden with hammocks is available for those who can’t switch off. “This is a modern, relatable idea of what a retreat should be,” he says, adding he’s looking to curate attendees. VCs are one demographic he’s looking at — “they have a lot to share,” he says. Amenities-wise, luxury — hotel-quality sheets, organic food and artisanal crafts — is a key part of this project.

That’s admirable, but it also leads to a homogeneous group (read: white male) attending and participating at such retreats. Lack of diversity is common in tech, which also means that in these cases, mindfulness becomes the domain of men.

Why there’s such a desire for this type of soul-searching getaway for VCs is hard to quantify, but the current climate of self-awareness plus the revelations of rampant sexual harassment are likely playing a role. Colonna thinks the growth may be related to people feeling more confident in talking about their struggles. “If that’s the case, I’m super fucking happy,” he says. “We’re pointing a way and saying you don’t have to feel like shit every day in your job and your life.”

Personal development rather than profit is becoming a priority for many, and the different offerings emphasize  an opportunity to make real social connections rather than just network. From extravaganzas like Summit to reflective events like Reboot, the VC world is getting more woke. And we’re all better off for it.

Sign up for the weekly newsletter!

Related Stories