A Hole In The Clouds: From Flight Attendant to Silicon Valley CEO

by Maryles Casto

A resource for anyone who has ever dreamed of building their own business, from an entrepreneur who started from scratch, aimed high, and reimagined an industry.

A Hole In The Clouds is the true story of how an unemployed flight attendant from the Philippines transformed herself into the CEO of the go-to travel agency for Intel, Apple, Syntex, Kleiner Perkins, and more.

When Maryles Casto left her father's sugar plantation in the Philippines and moved to the United States as a new bride, she brought with her a love for travel and the stellar customer-service experience she'd gained as a flight attendant for Philippine Airlines. She never imagined she'd be building a business from the ground up in an unfamiliar country. But when her husband went back to school, she needed to find a job.

After a disappointing attempt at door-to-door sales, Maryles landed a job at a local travel agency and dedicated herself to learning everything she could. She took her knowledge to her next employer, along with her characteristic determination, energy, focus, and grit. By the time she left to start her own travel agency, Maryles was the only agent Silicon Valley giant Andy Grove trusted to handle his travel plans.

In this book, Maryles shares how she built her business from a $1500 startup to a $200 million company, with the respect of Silicon Valley's pioneers. She talks about the advice she received from Andy Grove, Robert Noyce, and Steve Jobs, and she has the notable distinction of possibly being the only contractor to hang up on Steve Jobs without losing his business. Beyond that, she offers invaluable lessons about how she shaped her business and what it took to thrive in an industry threatened by extinction.

What people say about it

Poignant, touching, and insightful. I enjoyed reading A Hole in the Clouds so much. Maryles is brilliant—a legend, a class act, and an inspiration
to women, mothers, entrepreneurs, and humanity in general.”

—Charlene Leiss, president, Flight Centre Travel Group, The Americas


Maryles Casto’s journey and insights provide a case study in courage, compassion, and  principle-based decision-making. It is a must-read for anyone seeking inspiration and  insights for navigating uncertainty, adversity, and the continuous pursuit of the next horizon.”

—Brad D. Smith, executive chairman, Intuit

About the Author

Maryles Casto

Maryles Casto is a pioneering travel industry executive and entrepreneur with 48 years of experience in founding and leading companies to profitability. A former Philippine Airlines flight attendant, Casto created and helmed Silicon Valley-based Casto Travel, the largest privately owned travel management agency on the West Coast. Throughout its history, Casto Travel was frequently ranked among the Top 100 Fastest Growing Businesses in Silicon Valley and San Francisco, and was also ranked second in revenues in Silicon Valley women-owned businesses by the Silicon Valley Business Journal in 2006. Separately, Casto is the founder and owner of Casto Travel Philippines, Inc., based in Makati, Philippines. Most recently, she founded and is chairwoman and CEO of MVC Solutions. Casto has served on many business, civic and philanthropic boards, and currently lives in Silicon Valley and San Francisco.

Maryles Casto