Shayne Fitz-Coy: The Teaching CEO Redefining Educational Travel
Shayne Fitz-Coy also known as The Teaching CEO, runs a portfolio of companies and guest lectures at Stanford Graduate School of Business and Seoul National University.
But ask him what he really does, and he’ll say: “I run schools disguised as businesses.” Fitz-Coy is a third-generation educator, who serves as CEO of Rustic Pathways - an educational travel company operating in 38 countries and serving 8,000 students annually.
Fitz-Coy’s approach emerged from a lesson at Harvard. Professor Jerry Berlin taught him that “lateness is hostility.” Twenty-four years later, Fitz-Coy still arrives everywhere 10 minutes early, and expects the same from 500+ employees across his portfolio of companies.
But his deepest insight comes from what he calls the “operating in the stretch zone,” a psychological principle drawn from his Harvard psychology background and studies with Tal Ben Shachar. Real growth happens in the productive space between comfort and panic.
Picture a teenager in a Laotian market, trying to order soup while sweating through language barriers, gesturing wildly at a pot of something that might be breakfast or might be fish heads. That moment of productive discomfort is where real transformation begins.
From Student to CEO: A Journey of Intentional Learning
Fitz-Coy’s path reflects his Wooden Shoes philosophy, consistently choosing the harder road with higher long-term payoff.
He chose Harvard over full scholarships to several other schools, taking on $100,000 in debt. The student loan office told him during his sophomore year to take time off school and be admitted to Harvard in two years. He could file as an emancipated individual later, reducing the familial loan calculations. Instead, he worked through school and graduated with crushing loans. During exit loan counseling, the Harvard College Financial Aid Office told him he was graduating second in his Harvard class - in total debt. Fitz-Coy calls it his badge of honor: ‘I chose progress, education, and working through things. That’s me.”
The same pattern repeated with his MBA at Stanford, which he chose over a full ride scholarship to other programs to access the best entrepreneurial ecosystem and network. These were investments in building something.
“I run classrooms that happen to make money,” he explains. This philosophy transforms every business he touches. 90% get implemented because teachers know the best ideas might come from their students.
At Rustic Pathways, he co-founded the Climate Leaders Fellowship with Stanford’s Deliberative Democracy Lab and the Rustic Pathways Foundation, engaging 3,000 students from 17 countries in creating local climate solutions. When one Kenyan student launched a recycling program that now employs 15 people in her village, it proved his point: education at scale means helping a 17-year-old from Ohio discover she can change the world.
A New Model for the Next Generation
Not every lesson lands smoothly. He once promoted managers away from students, thinking it was a reward. Student satisfaction dropped. Now every senior leader comes from and lives in the field. When a student in Seoul got food poisoning at 2 AM, Fitz-Coy was the one cleaning up - kneeling on cold tile, holding back hair matted with sweat, because “Leadership is presence, not distance.”
His commitment shows most clearly in accessibility. Bothered by the fact that many summer programs serve only the privileged, he launched Travel For All, an initiative where private organizations sponsored educational travel experiences for students in need. This summer, he piloted a $745 domestic program this summer, down from $4,800 international trips. As he puts it: “Transformation shouldn’t require a trust fund.”
His insights has been featured in over 35 international media outlets, where he provides expert commentary on youth travel economics and leadership.
As Co-CEO of Sabot Family Companies, Fitz-Coy operates across multiple ventures simultaneously, including portfolio companies like Rustic Pathways (educational travel).
By combining operational leadership with academic rigor and genuine passion for development, Shayne Fitz-Coy isn’t just running an educational travel company. He’s pioneering what happens when you treat every business as a learning plan, every employee as a student, and every challenge as a chance to grow.
