Life Lessons From A Flight Attendant Turned Silicon Valley CEO

life lessons from a flight attendant turned silicon valley ceo
life lessons from a flight attendant turned silicon valley ceo 1

“We always hear about the men who built companies in Silicon Valley, but what about the women?” asks Maryles Casto. In 1974, this pioneering entrepreneur from the Philippines turned a $1,500 startup into the go-to travel agency for the titans of Silicon Valley. Her new book, A Hole in the Clouds: From Flight Attendant to Silicon Valley CEO (Silicon Valley Press), tells the behind-the-scenes story of what it took to build her company, Casto Travel, and what it took to stay on top.

“I wrote this book to tell my story—the story of an immigrant, the story of a woman without a college degree who built a company that at its height made $200 million a year in revenue. We helped the tech industry grow and it helped us grow, too,” says Casto. “I want people to know what Silicon Valley was like as it was taking off.”

Casto originally came to the U.S. as a Filipino immigrant with no college degree and tapped into her skills as a former Philippine Airlines flight attendant to create Casto Travel, which became the largest privately owned travel management agency on the West Coast. In 2019, she sold most of the company, retaining Casto Travel Philippines. She is now the founder and chairwoman of MVC Solutions, a travel industry services firm with dual headquarters in Silicon Valley and Manila.

In the book, Casto reveals what it was like to interact with famous tech leaders like Apple’s Steve Jobs, Intel’s Andy Grove and Oracle’s Larry Ellison. She also shares the career highs and lows she had as the founder of a company—from the struggles to growing too rapidly to facing near-bankruptcy during economic downturns. “I didn’t let obstacles stand in my way,” she says. “I moved the obstacles.”

Here, we got the scoop from Casto on what it took to create her company, her tips for career success, her advice on travel and her favorite vacation destinations.

My Inspiration: “My love for flying started as a young girl, growing up in a remote section of the Philippines on a family farm. As it was sizable, my father would travel from one part of the island to another in his small plane and would have me join him—we chased clouds and did acrobatic maneuvers. My assignment was to look for the hole in the clouds so we could climb higher to a smoother altitude. I was hooked. The transition to travel as a flight attendant was a natural one. The opportunity to be a stewardess, as we were called back then, combined my love of travel and caring for others.”

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A Father’s Influence: “Much is talked about the mother-daughter relationship but not much about the influence of fathers on their daughters. I was fortunate to have one who encouraged me. He considered my questions relevant, he allayed my fears and hesitations and as busy as he was, he always had time for me. As noted in my book, in my younger days I wanted to be a hairdresser and he willingly allowed me to practice my skills on his hair. We need more fathers today to be aware of the influence they have on their daughters and encourage them to play a big supportive role in their lives. Girls are just as much a part of our future as boys are.”

Starting My Company: “I had a travel background as a flight attendant and flight manager. I enjoyed taking care of people and being proactive and service oriented. I could no longer fly because I was married—in those days, once you were married you were out. I flopped in being a salesperson, going door-to-door for Avon. I flopped at Macy’s, wrapping gifts. When it was suggested I join a travel agency, I thought, ‘Well, that I can do.’ And later, when I created my own, I never expected it to take off the way it did.”

What I Learned From the Tech Leaders: “So many people presume that to succeed here, one needs to be like Steve Jobs and Larry Ellison. They act aggressive; they are callous, brash and opinionated. They did not succeed because of their personalities—they succeeded in spite of them. Both were geniuses in their own way but they were difficult people. I learned one thing: not to be like them. I gave myself permission to be me and not try to copy anyone. My goal was always to engage with people in a way that I thought was both genuine and respectful. It worked for me and I hope I became a better leader for it.”

Advice for Women Who Want to Get Ahead: “Listen to your heart as much as you listen to your head. There is a place for compassion in business. There is a need for leaders who genuinely care. The days of the alpha male are no more. It is time for women to create their own path—and we can do it so much better.”

Why Being Quiet is a Powerful Tool in Business: “Business is often a series of negotiations. The goal is always an agreement that meets the interests of both sides of the table. The only way to learn about the people, clients and employees you interact with is to genuinely listen to them.”

Save Time for Yourself: “I never started Casto Travel because I just wanted a job. (Of course if you read my book, I desperately needed one.) I did it because I love travel and I believe in the value of extraordinary service. At all times, I wanted each of our clients to have the perfect experience in all their travels. No client was alike and each one needed personal attention. But to serve my clients best, I also needed to take care of myself. I knew when I was off, when I was not in top form. I needed to invest in myself just as I would in other parts of my company, as well as for my family.”

Challenge Equals Opportunity: “The one constant in the travel industry is change and challenge. From the rise of the online booking engines to the 9/11 attacks to multiple recessions, we had to face our own fair share of downturns. What I learned from the downturns is the need to always focus on the core business and the core values of the company. A strong downturn completely forced business leaders to communicate clearly with their team members and clients alike about company values and priorities. As a result of the [current] pandemic, many companies are struggling to return to their prior glory. Many will fail. I believe this is because they did not invest enough in the culture of their companies, in providing value to their employees or personally engaging with their clients. You must be visible at all times but more so during a crisis. I have seen too many people hiding during the pandemic and their companies are hurting because  of it.”

My Current Company: “MVC Solutions is the parent company for all of my interests. The principal asset it holds is ownership of Casto Travel Philippines. As shared in my story, I acquired a firm in the Philippines in anticipation of significant changes within the industry around pricing and distribution of airline tickets. This firm allowed me to do trials with a number of concepts to support that business model. To support Casto, I built a series of call centers designed to support my agency. While the change I anticipated didn’t develop, I soon started fielding calls from many of my competitors seeking to contract with us to provide support for their business services. Since then, Casto Travel Philippines has provided all manner of business process services—largely to the travel industry. We provide everything from after-hours services to accounting, IT, training and more. One of our clients describes our service as ‘his secret force multiplier’ that enables him to grow faster than his competitors.”

Travel Strategies and Advice:

• Security lines are going to get worse, not better. Be sure to enroll, at minimum, in TSA PreCheck. It gets you access to expedited screening in the U.S. Even better, enroll in Global Entry, which is a huge time-saver for international flights. 

• Always book morning flights. Flight delays are extraordinary these days. As planes often fly to three, four, five or more cities in a day, one challenge early in the day will cascade throughout. 

• Get the vaccine. It’s effectively a requirement for travel. Also, travel with a COVID-19 test kit,  especially for international travel. 

• If you want to improve your chance of an upgrade, get status with an airline or hotel. The better the status, the significantly higher your likelihood of an upgrade.

 • Link your mileage accounts. Most airlines will have reciprocal programs with a number of hotels. You link them together to get more miles. Same goes with your favorite shared car service and credit card. 

• Both the Centers for Disease Control and Prevention and the U.S. Department of State issue frequent updates to their travel advisories for international destinations. These updates are a wealth of information about what to be aware of and what to be wary of. These are in almost all circumstances only advisories. You create your own adventures. 

Favorite Places to Decompress:

Rancho La Puerta – México: “I can say I grew up at the ranch. I’ve been going there for about 30 years and it’s my home away from home. They are family and you know them as one. I like the longevity of their staff, their knowledge of their guests’ wants and needs, and their motto, ‘Siempre Mejor’—always better.”

• Alphaland Balesin Island Club, Inc.Philippines: “This is a private island. The all-inclusive club contains different nation-themed resorts within the island. You can stay in Bali for lodging, have breakfast in the Philippines, lunch in France and have dinner in Italy. Only locals on the island serve the guests. Good hiking, sailing, and fencing lessons.”

• Wakaya Club & Spa – Fiji: “This resort’s founder was David Gilmour, who discovered Fiji Water during one of his island explorations. When I visited, the resort was all-inclusive and Gilmour provided the villagers who lived there jobs, a school, and a church. It was just an amazing resort where no one knew the word ‘no,’ only ‘yes’ to any request.”

Where I Want to Go Next: “My goal moving forward is to start discovering America again, now that travel restrictions are lifted. I’d like to fly over the Grand Canyon in a small plane to view its majestic canyons, go river rafting on the Russian River and helicopter skiing in Nevada and visit the Mauna Loa Observatory on the Big Island of Hawaii to see the stars in a new way.” 

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