The Man Warren Buffett Called the Greatest Businessman He Ever Knew The Enterprise Rent A Car Saga

In the central Pacific during the final 18 months of the Second World War, a Navy fighter pilot from St. Louis was flying F6F Hellcat aircraft off the deck of a Yorktown-class aircraft carrier called the USS Enterprise. His name was Jack C. Taylor, and he flew combat missions in the squadron rotation that carried American naval aviation to the doorstep of the Japanese home islands by the summer of 1945. When the war ended, Jack Taylor came home with a Navy Air Medal and no clear sense of what a Midwestern aviator without a college degree was supposed to do for a living. He took a job selling Cadillacs at a St. Louis dealership, and spent the next 11 years on the showroom floor. In 1957, with seven cars in the basement of the dealership and a 25 percent stake personally guaranteed by his employer, he founded a small leasing operation called Executive Leasing. Twelve years later, in 1969, he renamed the company after the aircraft carrier he had flown off in the Pacific. In this in-depth episode of Old Money Luxury, we trace how a Navy carrier pilot turned Cadillac salesman became the founder of the most valuable family-held rental fleet in the world — a global operation of more than 2 million vehicles across more than 10,000 locations, still 100 percent privately held under Taylor family ownership almost 70 years after seven cars were parked in a St. Louis dealership basement. ------------------- Gain FREE access to secret full-length documentaries on wealthy families "too scandalous for YouTube" by joining our newsletter: https://www.substack.com/@oldmoneyluxury ------------------- We open on Enterprise Holdings today — the parent company behind Enterprise Rent-A-Car, National Car Rental, and Alamo, with over $35 billion in annual revenue, more than 90,000 employees, more than 10,000 offices worldwide, and the largest fleet of rental vehicles ever assembled under a single private owner. We trace the family's ancestral origins in the American Midwest — the Taylor line, the St. Louis mercantile world, and the aviator's childhood that pushed Jack Taylor toward the deck of a Yorktown-class carrier the year he turned 22. We follow Jack C. Taylor through his early life — Washington University in St. Louis, the wartime enlistment in Naval Aviation, the Hellcat squadron in the Pacific, the Navy Air Medal, and the 1945 return to a country that no longer required combat pilots. We watch him arrive on the showroom floor at Arthur Lindburg's Cadillac dealership on Natural Bridge Road — 11 years selling cars, the customers who kept asking about longer-term leasing, and the 1957 conversation that produced Executive Leasing with seven cars in the basement and a 25 percent stake personally underwritten by his employer. We reconstruct the pivot from leasing to daily rental in 1962 — the insurance-replacement niche that no national competitor had bothered to occupy, the neighborhood office footprint away from airports, the free customer pickup, and the operating model that Hertz and Avis would spend the next 30 years trying to catch up to. We trace the 1969 rebrand to Enterprise Rent-A-Car after the aircraft carrier that had carried Jack Taylor across the Pacific, and the deliberate refusal to compete on airport counters — the geography, the customer, and the pricing that let Enterprise grow underneath the industry's radar for nearly two decades. We follow the second generation into the executive suite — Andy Taylor's rise from local branch manager to chief executive in 1991, the succession Jack engineered with the patience of a man who intended his company to outlast him, and the family-first management philosophy Warren Buffett publicly identified as the model for the ideal American family business. We trace the peak-power years — the acquisitions of National Car Rental and Alamo in 2007, the consolidation into Enterprise Holdings, the industry-leading market share, and the private-ownership structure that let the family invest through recessions the public competitors could not survive. We watch the third generation take control — Chrissy Taylor's rise to chief executive of Enterprise Holdings in 2020, the granddaughter of the Cadillac salesman now running the largest privately held rental fleet in the world, and the ownership structure Jack Taylor engineered to keep his descendants in the building. And we close on the founder's death in July 2016 at the age of 94 — the seven cars in the basement in 1957, the 2 million vehicles on the road at the end, the personal exemplar Warren Buffett kept returning to whenever he was asked what an American family business could look like when the family actually refused to sell, and the single decision — never go public — that made every other decision possible.