Bonny Simi: Navigating from Olympian to Pilot to Venture Capitalist

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Bonny Simi’s dreams led her down an untraditional career path. | iStock/wedninth

Bonny Simi has an eclectic resume. She’s a three-time Olympian and former broadcast journalist with three degrees from Stanford. She later became a commercial airline pilot and executive, and now leads the venture capital arm at JetBlue.

And she roughly mapped out her life at age 14.

Simi recently spoke to Stanford students at the School of Engineering about her life experiences, the guiding principles she picked up along the way, and why it’s so important to make a bucket list.

Dare to Dream Big

Simi was 14 when American adventurer John Goddard spoke at her school about the 127 goals he set for himself as a teenager in 1940. He encouraged the teens in the audience to go home and draw up their own list.

Simi thought about it and wrote down five goals: Go to a good college, go to the Olympics, become a TV commentator, become a pilot, and build a log cabin. These were big goals for Simi, who was raised by a single mother who worked as a schoolteacher and was on public assistance.

“People talk about dreams coming true, but have you ever stopped and thought, What are your dreams?” Simi says. “A lot of people hold themselves back, because, well, ‘I can’t do that. I don’t have enough money.’ Or, ‘I’m afraid to fail.’ I want you to stop for one second and think, if you were 100% guaranteed to succeed, what would you do with your life?”

Develop Transferrable Skills

In high school, Simi was a good writer and a decent athlete, competing in swimming, track and field, and field hockey. Her academics and athletics, coupled with her writing skills, helped Simi craft a college entrance essay that caught the attention of Stanford’s admissions office.

Simi was accepted into Stanford on a field hockey scholarship, ticking off her first goal. As a freshman, she saw an opportunity to tick off her second life goal, by entering a national writing contest to become an Olympic torchbearer at the 1980 Winter Olympics in Lake Placid, New York.

Her essay earned her a ticket to the Olympics, where she sat in the stands as the U.S. men’s hockey team famously defeated the Soviet Union for gold.

Take the Less Obvious Route

Being surrounded by Olympians for a few weeks inspired her to think about returning in four years, this time as a competitor. While the easiest route for Simi might have been to graduate on time and enter the workforce, she instead signed up for a beginner’s luge class to learn a sport that sends racers on thin sleds down a twisting track.

She took a break from school to fly to Germany and train with the German national team, which was ranked best in the world at the time. In those early training sessions, she crashed 52 times in a row.

“I had the confidence, and I wasn’t going to leave,” Simi says. “And because of that confidence, they kept coaching me. By the time I finished, I came back and became the best [luger] in the U.S.”

It took her seven years to graduate from Stanford, with a degree in communication. She ultimately competed in the 1984, 1988, and 1992 Winter Olympics.

Pursue Goals Simultaneously

Simi encouraged students to pursue their goals in parallel, to eliminate some of the risk in the equation. While training for the Olympics, Simi got a job as a TV reporter at the ABC station in San Francisco. The steady paycheck allowed her to train as an Olympian and pursue the fourth goal on her list, learning how to fly.

She signed up for an introductory course at the Palo Alto Airport and fell in love with flying, eventually earning her pilot’s license and becoming a flight instructor.

By 1990 — just 10 years after attending the Olympics as a teenage spectator — Simi found herself at a crossroads: She was working as a TV reporter and teaching flying lessons on the side while preparing for the 1992 Olympics. Rather than stay on that track, she decided to make another big change.

Follow Your Passion

Simi recalls one Saturday when she planned to teach a flying class and her editor in San Francisco asked her to come in on her day off to file a story he needed.

“It was going to be a slow news day,” Simi says. “And I was going to have to cancel all my students. I thought about it. I was going to make $100 teaching that day, or $500 to do the story. And I said no. I realized at that moment that my passion was around aviation, and I firmly believe you need to follow your heart.”

She applied to become a commercial pilot with United Airlines, eventually getting hired in 1990 to fly jets out of San Francisco. For the next 13 years, she flew full time, piloting 727s, 737s, and 777s. By 2003, Simi was a senior pilot at United, flying desirable routes and making a great salary.

Anyone else might have decided to maintain the status quo, flying for another 13 years and preparing for retirement. Simi didn’t. In 2003, she joined a fledgling airline called JetBlue, which had taken its maiden flight just three years before.

Find the Perfect Job For You

Every person has an ideal job, Simi says, where they’re passionate about the work, have the necessary skills for the role, at a company that represents a good culture fit for the person. Simi found that in JetBlue, which had gone public a year and a half before she joined.

Although she initially took a pay cut, the company felt like a better culture fit for her than United, Simi says.

She flew commercial jets for JetBlue, but set a goal to join senior management.

“People who wind up in the senior leadership of an airline tend to either grow up through the industry and don’t have a solid business background, or have a very solid business background but don’t grow up in the industry,” she says, placing herself in the first category.

She took a career break and returned to school, earning a master’s degree in human resources in 2006 from Regis University. Simi joined JetBlue’s senior leadership in 2007 as the director of airport and people planning, and was a Sloan Fellow at Stanford GSB that year.

While working as a JetBlue executive, she earned two additional degrees, both from Stanford: one from the Graduate School of Business and one from the School of Engineering.

Today, she runs JetBlue Technology Ventures, the company’s early-stage investment arm.

Looking ahead, she has just one thing left to achieve from her original list: Build the log cabin she envisioned at 14.

“My husband says, ‘But log cabins aren’t energy efficient.’ I said, ‘Yeah, but it was goal I wrote when I was 14 years old, and I’m going to get the goal.’”