How One Woman Excelled in Athletics, Journalism, Venture Capital—and Aviation

At first, the career path of Joby Aviation executive Bonny Simi may be hard to wrap your head around.

Despite a world with glass ceilings and unconscious biases that often force women to prove themselves again and again, Simi came from humble beginnings to succeed across four different industries: athletics, TV journalism, venture capital, and aviation.

Any one of these career paths alone would be challenging, but Simi mastered all four and raised a family—during an era when opportunities for women were more limited than they are today.

And she’s not done yet.

As part of FLYING’s series celebrating Women’s History Month, Simi shared details surrounding her fascinating path to aviation and how she’s trying to make career opportunities for pilots more accessible to everyone, including women.

Women currently make up only about 5 percent of airline pilots in the U.S. Simi came up during an era when the numbers were even lower: only about 1 or 2 percent. But by keeping her head down and working hard, her passion and fascination for flying drove her forward, leaving her with a resume that reads like a larger-than-life character in a Hollywood movie.

Simi developed her taste for flying as a student pilot in college. Her first takeoffs and landings changed her. “I just felt such a feeling of accomplishment and such a feeling of empowerment,” she recalls. Those initial experiences set her on a path toward earning her private and commercial pilot certificates, as well as her CFI certification.

Later, after becoming a top reporter at a major market TV station, Simi realized her career was off course. In her heart, she knew she belonged on a flight deck. So, she started building hours and eventually flew for an airline.

Not impressed yet?

Through the years Simi also competed as an Olympic athlete and ABC-TV commentator. She was a member of the U.S. luge team in the 1984, 1988, and 1992 Olympics. When Simi learned that women weren’t allowed to participate in Olympic bobsledding, she was astounded. “I just thought it was wrong,” she says. Years later, she actively campaigned to change the rules, helping to open the door to women bobsledders while earning a spot as an alternate on the 2002 Olympic team.

So, how does a career as unique and varied as this get started?

For Simi, it began as a little girl hanging out at Cable Airport (KCCB) in Upland, California, where her mother, who was a teacher, would take Simi and her two siblings to watch GA airplanes takeoff and land.

“I grew up in a family with a single mother and three kids, and later she became disabled so that really made our upbringing challenging,” Simi says. With no money for babysitting, Simi’s mother brought them to a little restaurant at the airport so she could grade papers while the kids watched the aircraft.

“It’s amazing what exposing children to something at a very early age will do,” Simi says. “Usually, you’re exposed to whatever your parents do for a living. But I was exposed because of where my mom brought me.”

Her childhood fascination with airplanes followed her through high school, where a teacher told her class, “You have to have a dream, for a dream to come true.” She assigned Simi and her class an essay about what they wanted to accomplish in life. Simi wrote she wanted to be a GA pilot “because that’s what I saw. I wanted to go to the Olympics because that year happened to be an Olympic year. I wanted to work for ABC-TV because that was the network covering the Olympics. I wanted to go to a good college, and I wanted to build a log cabin.”

She was just 14 years old.

As unrealistic as that list seemed at the time, years later, Simi realized she had actually checked off all of those boxes, except the log cabin. Simi says she is leaving that for a retirement project. 

Simi’s unique set of accomplishments speaks volumes about the value of encouragement and support from mentors.

In the 1980s, Stanford philanthropist and GA pilot Peter Bing spent a lot of time backing Stanford University women’s sports. Simi—who had won a field hockey scholarship to Stanford—met Bing and his wife when they would attend games and cheer on the team.

“His passion in life was aviation and he said if he could have started his life over again, he would have been an airline pilot.” Simi remembers. Taking her up in his Cessna 414, Bing “helped open the door,” she says. At first, flying “just seemed overwhelming and it was so complex. I thought, my goodness, I’ll never learn to fly. It’s just too complex for me.”

Bing told her: “Just go take three lessons.”

Those first lessons in a Cessna 152 “seemed terrifying to me initially,” Simi remembers. “But by the third lesson, I was taking off and landing with a big smile on my face.”

Every time she would return from a lesson, and she didn’t understand something, Bing would take the time to help. “He’d pull out the E6-B and explain it to me. He made it so approachable. To me, in a way, he was kind of like an instructor.”

Bing enjoyed sharing his knowledge about aviation, partially because no one in his family was interested in becoming a pilot, Simi recalls. “I think good instructors and good mentors get as much out of the relationship as the student does.”

“Whether you’re a flight instructor or you’re a captain at an airline—because technically you’re instructing your first officers all the time—it’s mentoring,” Simi says. “I’ve always tried to give back.”

Student pilots looking for mentorships need to be serious about it, Simi says. Put yourself in a position to be mentored. Start by spending time at a nearby airport. Before asking someone to mentor you, invite them for a cup of coffee and start building a professional relationship. Consider joining an aviation organization. “For younger student pilots, [between ages 8 to 17, the EAA’s] Young Eagles program is a great way to find a mentor,” Simi says. Follow your mentor’s advice, she says, otherwise, you’re just wasting time.

As a young pilot, Simi was able to scrape together enough money to earn her private pilot certificate and her instrument rating. But she had no idea how she would find the funds to finish her commercial and CFI training.

Then, her flight school offered her a rare opportunity.

“They really wanted a female instructor,” she recalls. “So they loaned me the money to finish my commercial and CFI, and said, ‘Just pay us back over the next 10 years and you just flight instruct with us as long as you can.’” As Simi is quick to say, this life-changing event was just one of many because “a lot of people really inspired me and encouraged me. They saw the passion that I had.”

After college, while moving up the ladder as a TV reporter, Simi also worked as a CFI and started doing some charter flying. “I just had this insatiable desire to keep learning different planes.”

In the early 1990s, another life-changing event occurred while Simi was at the top of her game, reporting at San Francisco’s KGO-TV. When forced to make a choice between her reporting duties and teaching student pilots—she had an epiphany: “It was at that moment I said: I need to be a pilot—not a TV reporter. I had already built up my flight time and I started applying to airlines.”

At United Airlines (NASDAQ: UAL), Simi “happened to get in at the right time in the early ’90s when airlines were hiring large numbers of civilian pilots,” she recalls. Prior to then, the airlines hired mostly military pilots. She started as a flight engineer on a Boeing 727-200 and eventually moved up to first officer. That led to FO slots on the Boeing 777 and then a promotion to 727 captain. After moving to the 737-300 and 13 years at the airline, Simi decided she wanted to do more. But she still wanted to fly.

“I did what people think is crazy: I gave up my seniority number at United.” She left the airline to start as a junior FO at a new startup airline called JetBlue (NASDAQ: JBLU), where she could continue flying while exploring other operational roles. Next, Simi helped launch a venture capital firm for JetBlue in Silicon Valley—all the while continuing to fly as a JetBlue pilot.

It was at JetBlue Technology Ventures where Simi heard about something new. The aviation industry was buzzing about the development of new electric vertical takeoff and landing (eVTOL) aircraft. JetBlue—as well as Uber—had invested in a Silicon Valley eVTOL startup called Joby Aviation (NYSE: JOBY). Soon, Simi was all in. She signed on as head of air operations and people.

“I think electric propulsion will fundamentally change aviation,” Simi says, “just like jet propulsion did in the ’50s and ’60s.”

Simi acknowledges that much has improved for women in aviation recently, but when she was starting out in the airline industry there were even fewer female pilots than now.

“When you’re young and aspiring to do something, you like to see others like you. You say, ‘Well, if they can do it, I can do it.’” But when Simi was a rookie, being a female airline pilot “was very much an anomaly,” she recalls. “At times it was hard. You always felt you had to prove yourself more than someone else—and I always just put my head down and proved myself. Then, everything was fine. But every new trip—prove myself.”

Although she says airline pilot opportunities have improved somewhat for women in the decades since Simi joined the workforce, what hasn’t improved, in her view, is financial accessibility. In the 1980s, it was difficult to find the money to build enough hours to become an airline pilot—although the requirement was 250 hours—much less than today’s threshold of 1,500 hours.

For many pilots with limited funds who are trying to build hours, the only option is to take out loans and go into debt. “But at least back then you could see there was a way to get paid after that,” she says. “Now it’s far less accessible. And that’s a problem.” Joby aims to solve this challenge by establishing a direct pathway for students to become eVTOL pilots.

Joby Aviation expects that—in 2024—its eVTOL air taxis will be flying passengers on short hops over traffic congested cities. Because they’re powered by lithium-ion batteries, these single-pilot, four-passenger aircraft will emit zero carbon operating emissions—thereby helping the environment.

Joby has been flying full-sized prototypes of the six-motor, tilt-rotor aircraft since 2017, completing more than 1,000 test flights.

“The aircraft is just incredibly simple to fly,” says Simi, who has racked up some time on the aircraft’s flight simulator. “The transition from forward flight to hover…it’s very easy. It transitions itself. You just command a lower speed, and the transition happens automatically. But it still feels weird to do that, initially, if you’re a fixed-wing pilot.”’

Once commercial operations get started, Joby’s airline pilots will have the opportunity to enjoy a more balanced lifestyle, compared to traditional airlines, Simi says. For example, there will be no all-nighters, because Joby plans to operate air taxis that fly short, local routes. Four-day pilot layovers will disappear, Simi says, making family life easier. 

With the help of her husband, Simi points out that she “raised a family as a female airline pilot. That’s hard—really hard. With this, now you’re home every night.”

To compensate for industry growth and generational retirements, Boeing (NYSE: BA) projects 612,000 new civilian pilots will be needed globally over the next 20 years. To satisfy that demand, the company says the industry must work together to build a “diverse talent pipeline through more educational outreach and recruitment.”

Joby plans to build a flight school to create a pipeline for its eVTOL pilots—shepherding them from students to being fully prepared to fly a new kind of aircraft at a new kind of airline.

When Simi began dreaming of becoming a professional pilot, “you had to be part of an insider’s club to figure out how to make a path.” This new model, she says, “makes a very clear path. A very defined path, in a very rigorous way,” in the form of a Part 141 pilot school program.

The school also eventually plans to be an academic institution, she says, offering an associate degree in aviation. “If you think about the access to underserved communities when you’re an academic institution, that allows you to have scholarships and grants—that gets back to my background,” Simi says. “I wouldn’t be in this career if I didn’t have access to scholarships and grants.”

Her advice for women interested in learning to fly: “Just start. Stop thinking, ‘I ought to, or ‘I should’ or ‘I wish.’ Just do it.”

Helping to create a normal path to aviation careers for women and people in underserved communities has become one of Simi’s top life goals.

In addition to opening up new career options for an entire generation of pilots, it would bring her life full circle—back to that young girl, hanging out with her mother at the local airport, who would eventually realize the dream of learning how to fly.