Juan Trippe was perhaps the first American entrepreneur to think globally. A Yale graduate who worked on Wall Street for a brief period, Trippe in his late twenties became interested in aviation. A quarter century after the Wright brothers' famous flight at Kitty Hawk, Trippe launched the business that eventually became known as Pan American World Airways. From the beginning he conceived of the carrier as an international operation, with service to exotic foreign destinations. Cornelius Vanderbilt Whitney was an early investor and Charles Lindbergh was a technical advisor. Pan Am's first seaplane flight departed Key West for Havana on October 19, 1927.

In the decade that followed, Trippe built the company into a powerhouse. First, he landed federal contracts to deliver airmail, which provided the company with a steady stream of revenue as it built up its passenger business. Meanwhile, he also pursued an aggressive acquisition strategy, buying up a number of small airlines that ran flights between the U.S. and destinations in the Caribbean and Latin America. The company soon expanded to Europe and Asia. Its early aircraft were referred to as "Clippers."

Under Trippe's careful management, Pan Am developed a reputation for safety based on a strict training regimen for both its crewmembers and for its maintenance staff. In 1958, Trippe was the first airline executive to add jet airplanes to his fleet; the switch to larger, more efficient jets allowed Pan Am to reduce prices, making plane travel affordable to a much larger segment of the public. "This is the most important aviation development since Lindbergh's flight," Trippe boasted. "In one fell swoop, we have shrunken the earth."

In an industry not known for excellence in branding, Pan Am also distinguished itself with sophisticated marketing. The company's ads were romantic and graphic; for a time, Norman Rockwell illustrated them. Later, the company's distinctive logo--a blue globe--became a symbol of post-war progress.

Trippe's status as one of America's most admired businessmen was secured in 1963 when construction was completed on the Pan Am Building, a skyscraper located astride Park Avenue in Manhattan, just behind Grand Central Station. Helicopters transported travelers from the building's roof to the major airports in the metropolitan area, while a massive mainframe computer on the building's fourth floor crunched data on Pan Am's passengers, ticket prices, and the weather.

The company reached its peak of financial success in the late 1960s. In 1966, Trippe placed an order with Boeing for the first batch of 747 passenger jets. Two years later, he retired as Pan Am's president. The company he built had become a cultural touchstone. That year, Stanley Kubrick's film 2001: A Space Odyssey featured a Pan Am spaceship, while the airline's Asian fleet ferried soldiers on active duty in Vietnam to Japan or to Hawaii for their R&R leave.

Trippe died in 1981 in his apartment in New York City. A decade later, Pan Am died in bankruptcy. Despite Trippe's many accomplishments, the airline's demise tarnished his entrepreneurial legacy. His story became, for some, a cautionary tale of concentrating power and neglecting succession planning. "Juan Trippe of Pan American was the quintessential example of a charismatic leader," Good to Great author Jim Collins said in a speech at the Inc. 500 conference in Salt Lake City in 1998. "He thought that the ultimate proof of his leadership ability would be for the company to go bankrupt after he died. To that extent, he was an unqualified success."