Growing up, I fell in love with the idea of being an entrepreneur. While it’s probably in my DNA, I did not fall in love with the idea until I read Bo Peabody’s Lucky or Smart, which started with, “I based Tripod in Williamstown…not because it made much business sense, but because I really like to ski.” These were my people! At 7, I told my parents, “I want to go to a college with its own ski resort.” There were two, and, luckily, I went one of them.
While I like to tout predicting my destiny for going to college, the rest of my career has been anything but linear or destined. First, I made money in my career trading equities from a small portfolio that I started in college than actually working in a job. Then, it took a while for me to take the plunge into startups. I started my career as a Technology Strategy Consultant: I stayed in this job a while because I loved becoming an expert in writing business cases for large transformations in IT organizations.
When I did take the plunge in working in startups, I realized that there was a lot that I took for granted in large enterprises: culture, process, etc. Not that these things were directly beneficial to me, but rather, they insulated me from extraneous details, which allowed me to become an expert and do a job well. So in this journey, I have had to grow up a lot personally and learn to deal with a lot more adversity than before.
There are so many lessons to learn in startups. However, I think the biggest one is to take control of your own success. What defines people’s own success is personal to them. For me, it’s first and foremost about providing an opportunity for people to live a great life, have great families, and be great. Growing up in a family of healthcare providers, great simply means, “a person who you can trust with your life.”
For me, this started young. I have several life-threatening food allergies. At a young age, I started injecting myself with an EpiPen when I had a reaction: I have used my EpiPen over 35 times. Then, in high school, I started to push my limits in mountaineering. “There are only three sports: bullfighting, motor racing, and mountaineering; all the rest are merely games,” by Ernest Hemmingway became my mantra. I stayed close with the friends who would climb fourteeners with me because we were well aware that our decisions could be our last. Finally, after retiring as a competitive mogul skier, I ventured into the backcountry. Here it’s necessary to find partners because, if you are buried in an avalanche, your only chance of survival, is your friends digging you out in 15 minutes.
There is a virtuous cycle to this. If you rely on your friends saving your life, you need to advocate that they can also live a great life. A great life where they have the character and ability to trust with your life. Character comes from experience in adventure and empathy. Ability comes from all the financial means that make life possible.