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5 Things I Learned from Jonathan Cheever

Written by:  

Patrick Boyaggi

Patrick Boyaggi

Patrick Boyaggi

CEO an Co-Founder

Patrick is the Co-Founder and CEO of Own Up. He has a wealth of experience and knowledge as a mortgage executive.

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5 Things I Learned from Jonathan Cheever

When we decided to sponsor Jonathan, we were excited to be a supporter of his Olympic journey because of his strong Massachusetts roots and the clear love of his home.

Earlier this month, we had an intense weekend with Jonathan where we spent a lot of hours together. As I got to know Jonathan, it became apparent that whether he’s recognized as an Olympic athlete or a plumber from Saugus, he is a man of strong character and a person with whom Own Up is proud to be associated.

Here are a five of my impressions from our time together:

1. Humility

Despite being a world-class athlete and one of the best snowboarders in the world, Jonathan is incredibly humble. While we were shooting a short film about his neighborhood, we stopped by the Iron Town Diner, a Saugus favorite. Inside, Jonathan was a rock star. People buzzed around him throughout the dining room. Jonathan shook hands with everyone, showing more interest in what they were up to than in telling them about himself.

Jonathan goes into each competition thinking he is the best snowboarder in the world. Yet, when he’s not competing, he is gracious and modest. I imagine it’s difficult for world-class athletes to not think of themselves as the best all the time, which is why so many are perceived as pompous. This is not the case with Jonathan; humility comes naturally to him, which is something I admire.

2. Introspection

Jonathan is always self-reflecting – on his performance on the mountain, on what he has accomplished in his career and life, and on what he can do to positively affect the world. He explained to me that as an athlete in an individual sport, you have to be critical of your performance. However, it’s off the snow where Jonathan feels it’s important for every person to think critically and to examine their own thoughts and feelings.

Jonathan explained how he uses the serene moments of snowboarding and surfing to evaluate life’s biggest decisions. What’s more, it was obvious in our conversations that he uses his words thoughtfully, which I found refreshing in a world dominated by people that speak before they think.

3. Training to Failure

Jonathan and I spent some time talking about his training regimen. While the workouts he described were dizzying, one story stood out: Jonathan recently adopted a new form of strength training that requires him to complete workouts to the point that his body collapses; no single muscle escapes this structured and purposeful torture.

It was this story that made it blatantly obvious that while we ge get to admire Olympic athletes for two weeks during the year, it’s the countless hours of training to failure that get them there. Nothing comes without hard work, especially becoming an Olympic athlete.

4. Balance

Obviously, Jonathan needs balance to be good at snowboarding, but he made it clear to me that he seeks balance in all aspects of his life. While he wants to be the best snowboarder in the world, he’s equally passionate about his marriage, his family, and his life away from the mountain. He described taking time to study subjects like economic policy and told me stories of partying with friends all over the world.

When I asked him how he makes time for all this, Jonathan’s answer was easy and obvious: “Champions party.” I laughed. His response made me realize that life is short and being great at just one thing means little if you can’t take a minute to enjoy the fruits of your victory.

5. Gratitude

Jonathan repeated how lucky he is to travel the world and snowboard despite all the financial hardship it has caused and all the injuries he has suffered. He has a sincere appreciation for what everyone has done for him in his career, from his parents to his coaches, and even his fellow competitors.

I can attest to his gratitude personally. During a 14 hour, jet-lagged video shoot day, he repeatedly thanked every member of our team for our sponsorship, even though he was the one opening his home, family, and life to us.

Moreover, at the event we hosted for our customers and business partners, Jonathan took the time to meet every person, thanking them for attending in a sincere and appreciative manner.

Thank you, Jonathan. You continually affirm our decision to be on Team Cheever.

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