What’s the first job that taught you real responsibility?
While working for Nike Golf, I had the rare privilege of having a one-on-one lunch with our legendary founder Phil Knight. It wasn’t planned. We were just at the same place at the same time for lunch, both having sandwiches.
I asked if I could ask him a question, he said yes, and we just started talking. I asked
him about what had driven his success. He told me, “You’ll never have all the knowledge you want. So, at some point, you need to trust your gut and pull the trigger or you’ll miss the opportunity.” It was simple yet incredibly wise advice.
A few months later, we signed a young kid named Tiger Woods and my marketing education took off as I began working with him. Phil and I would be in a lot of events and meetings after that. But at the time of the one-on-one, it was pretty rare for a kid like me in his 20s to sit down with the CEO. It stuck with me.
What’s a decision that changed the direction of your career?
My wife and I both received job offers on the same weekend in 2003—mine was in Colorado, where we were living, and hers was in Hawai‘i with The MacNaughton Group. We flipped a coin, she won, and we moved to Maui two weeks later. I left the global sports marketing world and eventually started over in tourism.
I didn’t know anyone when I arrived and was turned down for plenty of jobs. Everyone told me, “Sorry, you don’t have any experience.” It was humbling. I had to listen more, drop the swagger I needed for Nike, but focus on what my work there was all about: connections.
I learned quickly that on Maui your reputation is everything, much more than the company you work for. The shift taught me a lot about respect and developing relationships. It ended up opening doors I never expected. And I’m still on
Maui and still happily married.
What’s a daily habit you can’t live without?
Meditation and daily gratitude are habits I really rely on. We all have frustrating days, so taking a moment to breathe, reset, and let go of some of the bad stuff helps me keep perspective and get ready for what’s next. I meditate at night to clear my head and actually turn off my brain before bed.
Then in the morning, I start fresh and ask, “Okay, what can I do today?” Meditating has made me more empathetic and a better listener. I also like showing gratitude every day—thanking the team for their hard work, especially those working out in the fields in every kind of weather. When it comes from a real place, gratitude is always a good thing.
What’s one thing you’ve learned about failure?
We all fail. The real question is: How do you respond? I adopt an athlete’s mindset of getting back up and trying again. It goes back to my high school and college days as a competitive ski racer. There was a final race where the winner would earn a spot at state championships. It came down to me and one other skier. We ended up right next to each other at the finish line. Then the officials told us the timing gates had failed, so they’d relied on hand-held stopwatches to time the race. The stopwatches placed me second.
I congratulated the winner, but I knew I hadn’t failed—it was a failure of the moment, something out of my control. The failure of a situation. I just cleared my mind and moved on to my next race. I’ve carried this into my work: Do a quick post-mortem, learn, adjust, admit when you’ve miscalculated, and avoid the blame game because it’s what erodes work culture.
What’s one leadership quality you admire in others?
I really admire strong time management. We all have 24 hours in a day. Leaders have to make decisions while still creating mental space to think clearly and plan for the future—not simply react all day.
There’s so much compression of time now so safeguarding your schedule is critical. If as a leader you’re constantly in a decision-making hamster wheel, you lose the ability to think one, two or even five years down the road. I’m really impressed by leaders who handle huge demands on their time yet still avoid burnout and show up as good spouses, parents, or caregivers.
I’m also impressed when a leader can lead their company, do community service, take care of family needs, and still take care of their own mental and physical health. That balance isn’t easy so I really try to manage my time carefully and watch for signs of burnout.
