4 steps to living a more adventurous life and becoming a better entrepreneur

These four words can help you become a better entrepreneur

Jon Levy was, by his own admission, a painfully awkward, geeky kid. He was big into science and computers well before it was cool.

"Back then, I would watch 'Star Trek,' play on my computer, kind of be into science. But back in the '90s, there were no dot com billionaires, there were no iPhones, there were no mainstream superhero movies," says Levy. He is now 36, and he wore a not-at-all geeky man bun and black leather bomber jacket when he came to the CNBC offices for an interview.

"So if you were a geek, you were relegated to the fringes of society. Now you can be a geek and be everybody's hero."

Jon Levy as a child on an Israeli military base, visiting his cousin who was a tank commander.
Photo by Benjamin Levy

When he was in 8th grade, the teacher had students pick two names of classmates they would want to sit next two and two they didn't. The teacher would use that information to create a crowdsourced seating chart. Levy came to find out that he was the one student that virtually nobody wanted to sit next to. "I had a choice. I was either going to figure it out, or I was going to being relegated to being a geek in an era when geeks weren't cool," says Levy.

Levy chose to carefully observe human interactions so that he might mimic them. He went on to become a human behavior scientist and a master networker.

Jon Levy in Antarctica, "in a penguin suit hanging with penguins."
Courtesy of Jon Levy

Today, Levy hosts a series of dinner parties called The Influencers that bring together some of the most elite, successful, and creative professionals of the day. He does human behavior research with Moran Cerf, a renowned professor of neuroscience and business who works out of Kellogg, NYU, and MIT.

And next week, Levy's book, The 2 AM Principle: Discover the Science of Adventure, comes out. In it, he breaks down the key ingredients in a good adventure and pairs instruction with stories from his own life.

Levy is proud of his transformation. While he admits he isn't an extreme athlete scaling the walls of live active volcanoes, he lives an adventurous, remarkable life. He has traveled extensively, run with the bulls in Pamplona, battled Kiefer Sutherland in Jenga, and crashed multi-million dollar weddings.

Jon Levy cliff jumping off Santorini Island in Greece.
Courtesy of Jon Levy

"My interest in social interaction was bread from my lack of popularity. Without a doubt. And so now I am a human behavior scientist. Who would have figured. It couldn't be more cliche!" says Levy. "But what I discovered along the way was a commitment to inspire and enable people to live exciting and remarkable lives and so I started looking for patterns in what causes these things."

"If it were truly random, all of us would live similarly exciting lives. And we don't. That means there has to be some sort of method to the madness. There has to be some governing dynamic."

Here are the four main ingredients that go into creating any grand adventure, as Levy sees it. Conveniently enough, the acronym for the recipe is "epic": Establish, Push Boundaries, Increase, Continue.

Our brains are obsessed with novelty.
Jon Levy
human behavior scientist, author


Position yourself intelligently. You won't stumble across adventure sitting in your living room alone. Hang out with inspiring people. "The most important thing, by far, is the team of people you select," says Levy. "The right group of people can make a terrible experience fun and the wrong group of people can make the best experience miserable."

And go to new places. "Your brain actually operates differently in an unfamiliar environment. Our brains are obsessed with novelty," says Levy. "When something novel happens, our brains respond in a positive way because we want to explain and explore it and this feeds the desire to be out there."

Push boundaries

"You have to cross some kind of social, physical or emotional boundary. You have to push your comfort zone. Because an adventure isn't an adventure unless you grow from the experience," says Levy.

Pushing a physical boundary would be like trying a new athletic endeavor, while pushing an emotional boundary might involve acting outgoing if you are an introvert. The point is to step outside of the boundaries that we have either dictated for ourselves or adhered to as a result of a subconscious decision to follow society's suggestions.

The key is to realize that you can push these perceived limits.

At the Sydney zoo in Australia. Jon Levy was in the process of visiting all seven continents in one year.
Courtesy of Jon Levy

"They are not real, it was just made up at some point and we all agreed on it," says Levy. For example, "there is nothing stopping you from walking around barefoot in New York, just society sees it as odd."


Maximize the potential of the environment you choose for your adventure. This step of the process is situation-specific and requires the adventure-seeker to be creative in whatever way context allows.

For example, if you go to a bar with new friends, perhaps there is a game you can play or a question that everybody can pose that will elicit group participation. Or, if you are participating in a physical challenge, there could be a way to create competition.


Start the process over again. Go to a new place with new people, cross a boundary, and maximize the potential experience available in that situation.

And, perhaps more importantly, figure out when to call it quits.

"Most people try to push their experiences long past the point of enjoyment," says Levy. The key to some adventures is knowing when to stop. And that can be a challenge. "I think that's something that entrepreneurs really suck at, frankly, and I am guilty of as well."

The entrepreneurial experience is impossible without a willingness to be uncomfortable and to grow.
Jon Levy
human behavior scientist, author

Levy started a business that aimed to apply online dating principles to make the college admission process more efficient, and the startup wasn't working. He held on for too long, toiling away for two years when he would have been better to pull the plug.

When it is time to curtail an adventure that's either wrapped up or become staid, Levy says to be sure to conclude with a flourish. People remember the beginning and the end much more acutely than they remember the middle slog of any experience, he says.

Why is this beneficial for entrepreneurs?

There is no heroism in making foolhardy business decisions. Nobody wants to lose their own money or the money of their investors. But learning how to live a more adventurous life does have the potential to teach an individual how to be more okay with uncertainty, and that's a threshold that every entrepreneur has to confront sooner or later.

"The fundamental element is that the size of our life, the scope of it, is in direct proportion to how uncomfortable we are willing to be, how much we want to grow," says Levy. "The entrepreneurial experience is impossible without a willingness to be uncomfortable and to grow."

Jon Levy in the emergency room in Pamplona, Spain, after being trampled in the running of the bulls.
Courtesy of Jon Levy

Further, seeking out, creating and living through adventures forces individuals to hone skills that will benefit an entrepreneur. For example, learning how to talk to strangers on a solo-traveling adventure helps entrepreneurs network at business events. Summarizing yourself, explaining who you are and what you do, is a skill you improve with practice.

"I perfected pitching when I was in a foreign cities and I had to quickly explain what I do over and over and over again to each person I was meeting on a bar crawl," says Levy.

There's no direct correlation between reaching a mountain peak and running a fast-growing tech startup, but putting yourself in the mindset for one is going to open your way of thinking for the other.

"In my mind, a wealth of experience and understandings of cultures is one of the greatest gifts and entrepreneur can give themselves," says Levy. "It catalyzes creativity, it gives you a better understanding of how to communicate with people and so exploration has the potential to feed innovation."

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