How Gregg Brockway Thrives As An Athlete Turned Entrepreneur

With a personal and professional life that often feels like a whirlwind, two things help me keep balance. The first is I love having a supportive spouse and three engaging kids. I take every chance to touch base with them, and I find that completely refreshing. More recently, Recently, I have started to practice mindfulness meditation with the help of an app. I find that even 10 minutes a day on a regular basis tremendously helpful in managing life’s stress and anxiety.

As a part of our series about how successful “athlete turned entrepreneurs” thrive both professionally and personally, I had the distinct pleasure of interviewing Gregg Brockway. Gregg grew up with ski racing in his blood — his mother was a member of the 1960 Olympic ski team and his father continued into his 80s to ski race occasionally. Gregg skied competitively throughout his youth and after winning the US Junior National Championships and being the top finisher at the Junior World Championships in 1984, Gregg spent three years competing internationally as a member of the U.S. Ski Team. After failing to realize his Olympic dream and qualify for the 1988 Games in Calgary, he returned to Dartmouth College full-time where he went on to be a two-time All American before he graduated. Today, he is the Co-Founder & CEO of Chairish and enjoys standing on the sidelines watching his three young children continue the family athletic tradition on the ski hill and playing fields in California.

Thank you so much for doing this with us! It is a great honor. Our readers would love to learn more about your personal background. Can you tell us the story of how you grew up?

I grew up in a loving family that enjoyed playing games of all types, sports, cards and board games. Skiing was the one game I took seriously, but I was encouraged to do my best no matter what activity I was involved in. The “be your best self” mindset is something I’ve tried to continue to practice throughout life as it can lead to good places in many areas.

What or who inspired you to pursue your career as a high level professional athlete?

Skiing was an integral part of my childhood thanks to a family who loved the sport and the close friends I made doing it. By the time I decided my goal was to compete with the best, I was fortunate to enjoy the support of a community of people to pursue the dream. In high school, I had the support of my teachers who helped accommodate the travel required to compete at the highest possible levels. I found great mentors in several coaches, as well as family friends who provided wonderful encouragement along the way. It really does take a village!

Can you share the funniest or most interesting mistake that occurred to you in the course of your sports career? What lesson or take away did you learn from that?

I experienced volumes of mistakes and failures over my athletic career, a big takeaway lesson. Skiing is an individual sport with often more than 100 competitors and only one winner, so “failure” was an integral part of the experience. Learning to manage this productively and coming to appreciate that failure is part of growing is something I have tried to keep in mind when dealing with inevitable setbacks that happen in all parts of my life.

Did you ever get a serious sports injury? Do you feel comfortable sharing that story? What was the lesson or take away that you took out of that incident?

My only serious sporting injury happened long after I stopped competing. What sadly seems to happen with age is that the mind remembers performing at a higher level than the body can support, and it sometimes leads to unfortunate injuries. During my rehab I ran into many former athletes with similar observations. My takeaway is that getting old stinks. Today, I appreciate what I was once able to do, and I’m much more comfortable and realistic with enjoying where I’m at today.

As someone with a background in ‘wellness’ I’m interested in stories about interesting wellness experiences. Do you have a story about the weirdest or most humorous wellness experience, treatment, practice, or practitioner that you’ve ever partaken in? If you do, we’d love to hear it.

Well, I grew up in a California family that embraced alternative medicine of all sorts, including herbal therapies, acupuncture, early electrical current therapy and more. My sister is a formally trained medical doctor, so I’m now more traditional in my care and generally turn to licensed medical professionals when needed. Medical science isn’t perfect, but I trust it will generally steer me in the right direction.

OK, thank you for all of that. Let’s now shift to the core focus of our interview. Can you tell us the story of your transition from a professional athlete to a successful business person?

While the athletic skills developed by top athletes are seldom directly relevant to a career in business, I believe the mindset almost always is. The transition isn’t guaranteed and seldom easy (at least mine wasn’t), but having tried to do hard things before helped prepare me to power through difficulties as they inevitably arose. My early jobs ranged widely from pizza delivery to government and banking internships, but in each new situation I tried to work hard and be a quick learner, which I’ve found has proved helpful throughout my career.

What are some of the most interesting or exciting new projects you are working on now?

I’m fortunate to have had an opportunity to work in several interesting fields including finance, technology, travel and now home products and art. I’ve also been able to live in many spots in across the US and abroad including Asia. I’m so lucky to have travelled around the world to meet wonderful people in new places. Today, I feel like I’m able to apply these diverse experiences to my new project Chairish, a marketplace for home furnishings, decor and art and I love the feeling of bringing it all together.

Do you think your experience as a professional athlete gave you skills that make you a better entrepreneur? Can you give a story or example about that?

My experience as a competitive athlete has been tremendously helpful to my professional career. Perhaps because skiing was such an individual sport, I had an unbalanced view when I started working about the relative importance of individual contribution and a strong team. Interestingly, my first job in investment banking did not help this belief. Success in this field is often attributed to individual contributors. When I dove into my first start-up, I was absolutely certain it would work, because I was certain I would be the smartest, hardest working guy around. Right. It took an embarrassing business failure (and some sound coaching afterwards) to understand that the team is critical to success and that team building is a learnable skill too. I had to “unlearn” this individual mentality, and it may have been the most important contributor to becoming an effective entrepreneur and leader.

Today, the majority of my time is spent hiring, organizing and enabling the broader team’s focus on our top priorities.

Most athletes have not been able to transfer their success from the sports arena to the business arena. But you have. Can you share with our readers three main strategies you have used to help you succeed?

Yes, several things from athletics have helped me thrive as an entrepreneur:

The first lesson I learned was that there is no substitute for hard work. The people who win over time ALWAYS work harder, and they often find ways to work smarter too. A willingness to push yourself just a bit more than your peers helps with training, in competition and in business too.

Second, I find that top athletes and successful entrepreneurs both need a strong dose of irrational optimism. Anyone who looks rationally at the probability of success of becoming either a pro athlete or a successful entrepreneur just wouldn’t do it. You have to believe your crazy dream is possible and also be just narcissistic enough to believe you’re the special one who will make it happen. The related trait that is helpful for entrepreneurs is the knowledge that the game is never over until it’s over and it really is possible to pull out a win from even the darkest situation.

Finally, I believe, as I think most successful athletes understand, that success comes from continuous improvement, not a single lucky stroke of lightning and that failure is part of the process. No matter how good you are, you always believe there is a way to be better. Top athletes like to learn from every performance, both wins and losses. Failure is unavoidable and often provides the best lessons. I’ve always been curious about new things and how to improve and this has helped me immensely in overcoming new challenges.

In my work, I focus on how one can thrive in three areas, body, mind, and heart. I’d like to flesh this out with you. You are a very busy leader with a demanding schedule. Can you share with our readers two self care routines, practices or treatments that you do to help your body to thrive? Kindly share a story or an example for each.

I grew up believing that I felt better and was more productive when I was in good physical shape. While that belief hasn’t always been enough to stay in good shape, I’m happy to see that more research literature is making the connection between physical movement and good mental health. The activities change, but biking, running, the gym or just going for long walk around the block can all seem to have a positive impact for me.

Can you share with us two routines that you use to help your mind thrive? (Kindly share a story or example for each.)

I have always been curious and I found that having a wandering mind that is a good synthesizer in a great way to help overcome obstacles. At work this manifests as trying to dig into a wide range of topics that may or may not be directly related to my job or the problem at hand. This can happen both through conversations and reading. I’ve loved reading since I was a kid and in the old days of slow chair lifts, I got a lot of ribbing for breaking out a paperback on a long chair ride up the hill.

Finally, can you share with us two routines that use to help your heart, your emotional or spiritual life to thrive? (Kindly share a story or example for each.)

With a personal and professional life that often feels like a whirlwind, two things help me keep balance. The first is I love having a supportive spouse and three engaging kids. I take every chance to touch base with them, and I find that completely refreshing. More recently, Recently, I have started to practice mindfulness meditation with the help of an app. I find that even 10 minutes a day on a regular basis tremendously helpful in managing life’s stress and anxiety.

You’re a high achieving business leader, and you also have family and loved ones that may require a different side of you at home. How do you leave the executive at the door, and be the most loving family member at home?

Well, I have to say this can sometimes feel like a “needs improvement” area. It’s really important, but now that I work with my wife, it is even harder to leave business at the door. I love that we have found each other to be so complementary in a work setting, but I also recognize that for the sake of the sanity of the kids and each other, we need to make time for many other things.

You are a person of enormous influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

A few years ago I supported the founder of a movement to improve the effectiveness of federal and state government through a plan to break the growing political gridlock hampering it. The organization started as The Centrist Project and lives on today as Unite America, but sadly partisanship, polarization and dysfunction seem only to be getting worse. I sure would like to go back to the days we thought our leaders were working together to try to get us all to a better place.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

I love quotes from the experiences of others. One of my favorites is:

“You can never cross the ocean until you have the courage to lose sight of the shore.” — Christopher Columbus

While I don’t remember seeing it when I was competing, it captures how I felt every time I pushed out of a downhill gate on race day and applies to business too. It takes some courage to leave the comfort of seeing the shore to do entrepreneurial things. In my early 20’s, I left the comfort of good job at a successful firm to do a startup and have found that to be the right move several times since. Even though it has not always led to success, it’s been a rewarding journey. This quote also reminds me that there is seldom a perfect time to leave the sight of shore, so it is better to have the courage to get started now.

What are the best ways our readers can follow you on social media?

Well, I’ve been taking a social media vacation for the last several months, but my Twitter handle is @gbrockway. Also, you can follow our team’s progress on Instagram at @chairishco.

Thank you for these fantastic insights. We wish you only continued success in your great work!