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After $192M IPO, GrubHub’s Mike Evans Embarks on New Venture: Biking Across America

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“I’m quitting my job and riding my bike from Virginia to California!”

And so goes the first line in a blog post written earlier this month by GrubHub cofounder Mike Evans. After working on GrubHub these last twelve years, and successfully raising a much higher than anticipated initial public offering of $192 million, Evans has decided to take some time away from the business world and has embarked on a bike tour though the American landscape.

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Evans’s proposed bike route. (via Mike Evans)

Back in March, when the company filed for its IPO, Evans jointly announced his plans to leave GrubHub and seek out new challenges for himself and in the Chicago startup community. At the time, no one had any ideas as to what was up his sleeves – I mean, what new ideas can one expect from someone whose last venture led to a nearly $200 million IPO? Indeed, even for Evans, the idea for this trip hadn’t yet fully materialized; he was playing around with ideas for a cycle tour or a backpacking trip, but it wasn’t all there, yet. One thing, though, was sure: that he needed to take a break. As he told me:

“At the time, I knew that I wanted an intentional period set aside for transition instead of jumping straight into my next project. I didn’t know what shape that would take.”

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Evans started his trip at Jamestown, VA. (via Mike Evans)

On his bike tour, Evans plans to go from Virginia and eventually make his way to California. Prior to the first day of his trip, he made his way from Chicago to Virginia Beach, launching the tour from nearby Jamestown, VA. According to the route map he posted on his blog, Evans plans to pass through ten states total, including Illinois, Colorado, Montana, and Idaho. In a blog entry posted yesterday, Evans documents his experiences in Auburn, Kentucky (day 16 of his trip).

As to his reasoning for going on this transAmerica tour, Evans wrote:

“First, I hope to spend a lot of time in reflection, contemplation, and prayer about the direction of the next stage of my life.

Second, I hope to grow in compassion and contentment. I was once described as a ‘happy go lucky’ person, but I’ve lost that over the last twelve years at a very stressful job.

Third, I hope to experience the trip for whatever it presents and not load it down with a lot of expectations. That said, I do have two important expectations. I expect the country to [be] beautiful. I expect to meet people that represent kindness, hospitality, and joy as opposed to what our TVs tell us the world is like.”

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Throughout his trip, Evans will be documenting everything from sights he sees to people he meets. This is a train spotted on Day 16 of his trip, in Auburn, KY. (via Mike Evans)

While startup founders fervently pursue their ideas on a daily basis, there comes a point when even they can burn out from the stresses of startup life. Evans himself was certainly not immune to the immense workload and pressures, especially when you consider how large GrubHub has grown since it was first founded by him and Matt Maloney.

“Founders live and breathe their idea and execution of that idea 24/7,” said Evans. “Over an extended time, some kind of equilibrium can be created, but ultimately stress, responsibility, and authority change a person: sometimes for the better, and sometimes for the worse.”

For founders who fear going through this similar experience of self-changes, Evans offered some advice: “Personally, two good control mechanisms for this change have been self-awareness and a willingness to adapt.”

Throughout his trip, Evans will continue to post updates on his blog. While still in its early phases, he shared some insight on his experience thus far:

“Facing each day free of expectation maximizes how much I enjoy it.  If I’m not looking for a particular set of things to happen, I can much more readily enjoy whatever happens to come my way.  I’m finding that each day, each town, and each personal interaction surprises me, so coming to it openly allows me to learn and enjoy those things more.

Focusing on the amount of miles left to pedal for the day ruins the experience.  Focusing on enjoying the current mile as each mile comes my way is the only way to really enjoy them.

Fresh food and good beer are very hard to find in most of America unless you’re willing to drive long distances.  I’m going to start a garden and do more home-brewing when I get back.”

Keep up with Mike Evans as he bikes westward from Virginia to California.

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About the Author

Ronald Barba is an associate writer and reporter for Tech Cocktail. Formerly a DC native, he's now based in New York City. He reports on the Mid-Atlantic and Northeast, looking at startup communities like Boston, Chicago, D.C., and NYC. He's especially interested in venture capital, M&As, and tech/business trends. Aside from startups, Ronald is interested in philosophy, cognitive science, politics, social justice, pop culture, and all things geek. He reads Murakami and Barthes, and alternates binge watch sessions of 'Doctor Who' and 'The Mindy Project'. Got something to say? Then email me (ronald@tech.co). Follow me on Twitter: @RonaldPBarba. Subscribe to me on Facebook. Find me on Google.

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