Chapter 1.  
BusinessOutside

“Thousands of tired, nerve-shaken, over-civilized people are beginning to find out that going to the mountains is going home; that wildness is a necessity.”

—John Muir

Fifty-five people showed up at 5:00 a.m. on a Wednesday morning to hike the Boulder Skyline Traverse. I couldn’t believe it. This twenty-mile hike, with 6,000 feet of elevation gain, isn’t for beginners. The group had started modestly enough, with a few friends who were going to hike every major peak in the mountain range in Boulder, Colorado. Within three weeks, it had evolved into a curated group of entrepreneurs and business owners who all had one thing in common: a growth mindset.

I shouldn’t have been surprised; this was one of the reasons my family and I had moved to Boulder in the first place: the opportunity to surround ourselves with people who prioritized getting outside. And when I formed this group, I had set the intention that it be a place for deep connection. Still, seeing my dreams come to fruition felt unreal. Here I was, doing what I had set out to do—to create a whole new life.

Three years before, in 2014, I found myself at a crossroads. After I left SoloHealth, a technology company I had founded seven years earlier, I took time off to travel with my family and discover my identity without the CEO title. I reconnected with friends and family I hadn’t seen in years, and engaged in meaningful discussions. My wife, Aly, and I spent countless hours reflecting on what was most important to us. It didn’t take long for us to acknowledge that our lives had become too routine. We needed to shake things up.

I thought back to the several cross-country moves in my life—one from Illinois to California when I was eight years old and a second from California to Florida when I was fourteen. After college I moved from Florida, to Texas, to Michigan, with Kellogg’s, then to Atlanta where I worked with the eye care division of Novartis. With each move, there were dramatic environmental and cultural changes that shaped who I became. I learned the value of getting out of my comfort zone at an early age, which expanded my capacity to be adaptable in all areas.

As these thoughts ran through my mind, I reached out to friends who I knew could add perspective to our situation. Jim Sharpe, fellow member of Young Presidents’ Organization (YPO) and respected business school professor, told me about the “zip code strategy”: pick where you want to live first, and then figure it out from there. I had never heard of this concept, but it made sense to me. Why not live in a place that reflects your ideal lifestyle?

Soon enough, Aly and I were Googling all the best places to do the things most important to us:

• Best places to raise a family
• Best cities to walk
• Healthiest cities
• Best cities for entrepreneurs
• Best places for outdoor adventure

It turned out that Boulder, Colorado, was at the top of nearly every list. So off we went to see why people seemed to love th