He told an Ernst & Young magazine, “I was a very callow youth,” according to the New York Times. But he found direction in his life when he left Washington University in St. Louis to fly Grumman F6F Hellcats off the USS Essex and USS Enterprise in the Pacific. He later named his company after the Enterprise.
Returning from the war, Taylor founded a package delivery business before taking a job in 1948 as a salesman and later manager with Lindburg Cadillac owned by Arthur Lindburg.
At age 35 Taylor noticed cars in the St. Louis area that had been leased by a Greyhound bus subsidiary in Chicago, the Washington Post reported. With the agreement of Lindburg, he took a pay cut and invested $25,000 of his own money for a quarter-share of a car leasing business called Executive Leasing headquartered at Lindburg Cadillac, the Post reported. His customers were at first those of Lindburg Cadillac. Renting, something he had to be coaxed into by his customers, came later but an airport presence was not a major portion of the business until Enterprise bought Alamo Car Rental and National Car Rental in 2007. The company had begun locating Enterprise counters at airports in 1995. The diversity today between local use for those waiting for car repairs or taking a trip and airport rentals allows Enterprise to ride out economic depressions when airline travel is reduced.
His philanthropy has been felt mostly in the St. Louis area, and mostly aimed at helping youth. Estimates are that the private company, which does not report revenues, made $19.4 billion in revenue in 2015, with his personal wealth estimated at $5 billion or more, depending on the source. One of the biggest recipients of his philanthropy is the college he happily left, Washington University, which received a $50 million gift.