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Whether you’re playing professional sports or leading a company, many of the challenges you experience are in your head. Success requires a high level of mental toughness to think critically and creatively and overcome challenges in your way. For a recent Oh Ship! Show guest, that mental toughness comes from a focus on physical fitness — and vice versa. 

Subscribe and listen to the Oh Ship! Show, then check out these soundbites from my recent conversation with Robin Thurston on the benefits of fitness for leadership.

Meet Robin Thurston, CEO of Outside

Robin is the founder and CEO of Outside — a portfolio of active lifestyle brands Whether you’re passionate about running, biking, climbing, hiking, skiing, fishing, yoga, or any other outdoor activity, Outside likely has you covered. Previously, Robin served as the Helix, a personal genomics company. He was also the Chief Digital Officer of Under Armour, a role he attained after selling the Map My Fitness app. Through each of his roles, Robin has continued to share a deep personal passion for sports at a professional level.

Freddie: How does spending time outdoors and training for professional sports prepare you to be a better entrepreneur?

Robin grew up in Colorado and was constantly surrounded by outdoor activities. He feels fortunate enough to have grown up in a world where he got to spend time outside. But aside from having nature built into his blood, Robin believes that being in situations where he learned to lose has helped him to grow as a professional.

“Whether you’re running a professional marathon or playing any type of team sport, you lose a lot. You’re in the game all the time, but the reality is that you lose 99% of the time. I’ve honed my ability to learn and adapt through this type of failure. I don’t think there are many avenues that allow people to learn through failures like sports and the outdoors. Every loss makes you pause and think about how you can go after a win.”

Robin likens his time on a Swiss cycling team to his “college.” “I was in Europe for four years. When a colleague during my investment days would complain about a hard day, I’d think to myself, ‘This seems a lot easier than racing.’ Truly the biggest lessons in life have come from losing over and over.”

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Freddie: Going from the finance world to entrepreneurship in the fitness and outdoor space is a big leap — what led to your “Aha!” moment?

Having worked in mutual funds at Reuters and later serving as an investment director for Wellington Management, developing the Map My Fitness app doesn’t seem like a logical next step. But that was the reality for Robin, who realized that life is too short not to do what you love. 

“A good friend of mine passed away on a rafting trip. He and I had spoken often about the businesses we might try together. But when he died, it gave me the confidence I needed to go try something different. 

One night I was sitting in Andermatt in the Swiss Alps. A friend spoke up and said it would be cool to come back to these roads without being here. And that was immediately an Aha! moment. Back then, we didn’t have a way to share a route I created with someone. I knew a little about Google Maps at the time. And then, I met my co-founder, Kevin Callahan, who is now the VP of Product at Outside. He was the runner, and I was the cyclist, and it just evolved. There was a lot of serendipity in it even before mobile, which we got very lucky with and had two of the first 100 iPhone apps. We had a million users on the web before the first iPhone even launched. It was the right product at the right time.”

Freddie: What was your inflection point where you knew that life was changing in a major way?

When you’re building a business and watching it grow, eventually, something clicks, and you know you’re set for success. But Robin always took his success one step — and one download — at a time.

“Building a business is just a lot of little steps. Sometimes you have small wins. Sometimes you have big wins, like how we got featured many times by Apple. But when the App Store launched in June 2008, it was like crickets. We had a few users downloading the app here and there. By Christmas, the markets were melting down. Lehman Brothers had gone under. But we were hopeful because AT&T had an exclusive contract with the iPhone and was doing a huge Christmas ad campaign, and Map My Run was featured across advertisements. I was thinking, This is going to be huge, but even in 2009 and 2010, we struggled to raise venture capital. VCs didn’t see its potential. But we sold it to Under Armour in 2013, and it’s been such a game-changing app for fitness and outdoors enthusiasts.”

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Freddie: Entrepreneurship is very much like an endurance sport — how do you reach your desired intensity level?

As with any sport, the more effort you put into it, the more you see returns on that effort. But just like a stock chart, progress isn’t always up and to the right. Even Map My Ride was a decade-long endeavor. The same holds true in business.

“You wake up and incrementally put in effort every day. Just like in training, sometimes you have to rest. Sometimes you work longer hours. You need to be able to see the bigger, longer-term picture, but you also have to put in effort every single day. Some days that’s harder to do than others. Some days you get caught up in the minutiae. Some days you take steps back. But you have to keep putting one front in front of the other, get people aligned, and push on.”

Subscribe to the Oh Ship! Show to hear the full conversation with Robin Thurston.

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