When Andy Taylor, Executive Chairman at Enterprise Holdings, was a young boy, his father Jack Taylor took him along to work on Saturdays at Executive Leasing, the business he owned within a St. Louis car dealership. Spending time at the dealership with his father, Andy observed early and often the spirit of fun and entrepreneurship that drove Jack and characterized the business he built.

In the candid stories that Andy generously shared during the two days he hosted Tugboat Institute @Enterprise at his headquarters last week, the Evergreen leader noted that among other essential learnings he benefitted from as he grew up in the family business, a key encouragement of his father was: “Every day is going to be fun.” Listening to Andy, it was clear that having fun has been an essential part of his and his team’s journey scaling Enterprise from $78M to a now $24B global business.

During his fireside chat with Tugboat Institute founder and CEO Dave Whorton, Andy graciously provided an in-depth look at the history of the company and of his tenure, from his days as a 16-year-old washing cars and riding along on repossession missions with his father, to his appointment as president in 1980 and his current role as Executive Chairman. He shared how his dad’s founding philosophy of “take care of your customers and employees, and the bottom line will follow” continues to be the guiding philosophy of Enterprise Holdings.

In addition to his own experiences, Andy introduced Tugboat Institute members to key Enterprise leadership team members, who presented on their unmatched talent acquisition and management training programs, the evolution of their management system and incentive practices over time, the revitalization of the company’s original fleet management business, the creation and scaling of their commercial trucking division, the evolution of their global expansion approach to match global customer needs, and their approach to addressing disruption in the transportation space today.

Throughout the sessions, the strategic role of the Taylor family in the formation, growth, and success of the company—and their unwavering commitment to the business—was a consistent theme. In the final session of the event, Tugboat members heard from Andy’s daughter and Jack’s granddaughter, Chrissy Taylor, Chief Operating Officer of Enterprise Holdings, and Andy’s niece, Carolyn Kindle Betz, Executive Director of the Enterprise Rent-a-Car Foundation. As third-generation stewards of the company, the women’s deep commitment to Enterprise, the company’s employees, and the wider community of St. Louis was an inspiring example of the impact of abiding Evergreen principles in business and life. And, they have adopted the family philosophy of working hard and having fun.

The new and old deep connections between our members, built upon their alignment around Evergreen principles, were on display during our evening events, where we introduced our community to two St. Louis landmarks. On Wednesday evening, we learned about the Donald Danforth Plant Science Center’s remarkable research in solving the world’s food challenges (while tasting Clase Azul tequila), and on Thursday night we had the pleasure of touring the recently completed Gateway Arch Museum, dining in the modern facility, and taking in the stunning views of the surrounding area from the top of the iconic Gateway Arch.

On Friday morning, about 40 of our members opted to continue their learning journey by participating in the Olin Family Business Symposium at Washington University in St. Louis. Hosted by Olin School of Business Adjunct Lecturer and Tugboat friend Spencer Burke, Principal of the St. Louis Trust company, this event offered a keynote presentation by Dave Whorton and three panels consisting of local Evergreen business leaders and Tugboat members from the area and beyond. Dave and the panelists discussed the competitive advantage of Evergreen ownership and the importance of Evergreen values to business, families, and local communities.

Across the educational sessions, evening events, and more informal moments, our days in St. Louis were characterized by the inspiration, warm connections, and shared learning that defines Tugboat Institute. We are grateful to the Taylor family and Enterprise Holdings for a once-in-a-lifetime experience together.

Diana Price is the content manager at Tugboat Institute.