Greatest Transportation Entrepreneurs of All Time

UPDATED: March 29, 2024
PUBLISHED: May 6, 2008

Herb Kelleher b. 1931 What started as a regional carrier serving Dallas, Houston and San Antonio became one of the industry’s pioneering low-cost, no-frills airlines. Founded by Herb Kelleher and partner Rollin King in 1967, Southwest Airlines posted its 35th consecutive year of profitability in 2007. The airline has been known for campy antics—flight attendants singing in-flight travel announcements to the tune of popular songs, pilots telling jokes over the intercom—Kelleher was even known to help load luggage, process tickets or mix drinks onboard. He says happy employees make better employees. “Your people come first, and if you treat them right, they’ll treat the customers right,” Kelleher says.

Quote:”Get to know your people. Everybody, from pilots to flight attendants to baggage handlers to mechanics to janitors. Learn from them.”

William S.Harley 1880-1943 Arthur Davidson 1881-1950 William S. Harley was 21 in 1901 when he drew up plans for an engine to fit onto a bicycle. He and friend Arthur Davidson worked for two years on that 7.07-cubic-inch engine, along with Davidson’s brothers Walter and William, only to find the engine wasn’t powerful to get the bike over the hills in their native Milwaukee. But that didn’t deter them. By 1904, they had a working bike; by 1906, a little factory producing 50 motorcycles. Steady growth and innovation followed—as did competition from companies seeking to emulate Harley-Davidson’s success. Harley earned his mechanical engineering degree, while Davidson honed his sales and marketing skills and started a service school to train certified mechanics. Harley-Davidson went into combat in both world wars and was one of just two motorcycle manufacturers to come out of the Great Depression. It’s the only U.S.-made motorcycle today, with $6.14 billion in sales in 2007. Harley enthusiasts also pay for the brand and the attitude (what other brand would someone tattoo on their body?) licensing of the logo accounts for about 5 percent of net revenue.

Quote: “Life offers few guarantees, but generally the harder and longer you work, the more likely you will succeed.”

Fred W. Smith b. 1944 Before Fred W. Smith purchased a small fleet of planes, the best way to ship your package cross-country was by train or automobile. The Federal Express founder made overnight express delivery possible with his innovative “hub and spoke” package processing system in the early 1970s. The idea, which he wrote about in a paper for an economics class at Yale, was based on a bank-clearinghouse system, with the clearinghouse in the middle of the representative banks. Now FedEx moves approximately 6 million packages worldwide every day, and has expanded into print and copy services with the acquisition of Kinko’s.

Quote: “If your business revolves around one idea, keep that idea foremost. Hammer away at it.”

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