Westfall is chief executive officer of the Natural Selection Tour, which sponsors snowboard competitions

Carter Westfall ’96 and his son, Shepard, after his February 2022 Natural Selection live broadcast event at Jackson Hole Mountain Resort.
Photo: Keegan Rice

Earning a Princeton degree in English and selection as an all-Ivy League football player weren’t enough to allay the career fears of Carter Westfall ’96.

“I was filled with a lot of insecurities about where all of this was leading. At Princeton, you’re surrounded by such accomplished people that you can’t help but judge yourself with your peers,” he says. “I had to remind myself that it was most important that I stuck to my instincts and just tried to listen to myself, versus try to judge myself against others. But it was very difficult.”

Westfall was an offensive lineman and a first-team all-Ivy selection in 1995, when the Tigers won the league championship. “We had a lot of talent on our team, but by far the biggest strength was the brotherhood we had,” Westfall says, noting that connections with Princeton alumni have been key in gaining career opportunities.

Early in his career, the New Jersey native thought it would be fun to work in finance in New York City, so he used some Princeton football connections to become a Wall Street bond trader. He spent nearly three years there before he returned to the gridiron. He was hired as an assistant football coach first at Davidson College and then Rutgers University. Westfall followed former Princeton assistant football coach Joe Susan to those schools but decided the work was too demanding. “I just simply didn’t have the willingness to make the sacrifices to be a college football coach. It’s just a very grueling business,” he says.

From there he moved to executive sports positions beginning in 2005, which eventually led him to the West Coast. Westfall was a vice president of the Pac-12 Conference, promoting the conference’s athletics internationally; he helped lead business development for the Sacramento Kings of the National Basketball Association and for the NBA itself; he traveled extensively, including to China, England, Italy, and Russia, while working in marketing in connection with the Olympic Games.

Now living in Jackson, Wyoming, Westfall is chief executive officer of the Natural Selection Tour, which sponsors snowboard competitions. A snow skier turned snowboarder, Westfall saw it as a ground-up opportunity to “build the Disney of the outdoor world.” The tour’s event sites include the Swiss Alps; Crested Butte, Colorado; British Columbia, Canada; and Valdez, Alaska. Revenue for 2023 is estimated at $3.75 million, but the 4-year-old startup is not yet a break-even business.

Westfall says that despite his accomplishments, he fought doubts about his career progress. He says he always chose jobs that aligned with his interests and never let income dictate those decisions. Taking chances on trying different experiences has been important — “I’ve always been driven by a bit of a fear of regret” — as has trusting his instincts.

Lesson learned: “You’ve got to know yourself and you have to make decisions that are true to yourself,” he says. “Princeton can afford you to write your own story if you’ve got the patience and the perseverance. And, not everyone can do this, but if you can not let maximizing your income dictate things,” satisfaction will follow, he says.