15 CEOs Who Failed At First

Posted July 28, 2010

The life of a CEO is fraught with peril: Success brings with it the pressure to repeat your performance, while failure brings public scrutiny and stockholder scorn. If you need more evidence that it’s a tough gig, consider the fact that many of the biggest CEOs and other business leaders throughout history have met with major failure on the road to success. Whether you’re a long-time exec or you just started your online degree program in business, let the names on this list serve as an inspirational reminder that obstacles aren’t impossible to pass, just opportunities to grow.

  1. Steve Jobs: It might be hard to remember now, but there was a time when every Apple announcement wasn’t greeted like the second coming, and when Steve Jobs wasn’t worshipped as the leader of the hippest computer company around. Jobs is the CEO and co-founder of Apple Inc., but he wound up on the losing end of an internal power struggle that saw him leave the company in the mid-1980s. He then founded NeXT, a computer company that was eventually bought by Apple, a move that brought Jobs back into the company he’d begun. He was re-installed as CEO of his former home in 1997, and since then has led the company to record heights with a line of iMacs, iPods, and iPhones.
  2. David Neelman: David Neelman founded Jet Blue Airways and served as the company’s CEO, but eventually hit a wall when weather-related flight delays damaged the company’s reputation. He took responsibility for the problems and was asked by the board of directors to resign in 2007. What would’ve been a career-ender for some CEOs was instead an opportunity to move on to something else. In 2009, Neelman launched Azul Linhas Aéreas Brasileiras, a regional airline dedicated to serving Brazil.
  3. Jacques Nasser: Jacques Nasser joined the Ford Motor Company in 1968 as an analyst; in 1999, he became CEO of the company in Michigan. That’s an impressive career, but his time at the top was short-lived. Thanks to economic pressures, Nasser only held the post until 2001, when he was asked to resign. Despite having three decades’ of experience at one company, rising through the ranks to the upper levels, Nasser was shown the door. Yet his failure to hold the reins allowed him to change direction, and he joined One Equity Partners before eventually becoming chair of BHP Billiton, the biggest mining company in the world.
  4. Donald Trump: He’s got terrible hair, a bad reality show, and his hotels have played host to WrestleMania. Yet for all his dubious achievements and pop culture infamy, Donald Trump had his share of setbacks on the road to ridiculous wealth. After a string of real estate successes in the 1980s, a recession and the use of junk bonds brought his business to bankruptcy. It took him years to restructure and reduce his debt to the point where he could return to the top of his game.
  5. David Murdock: Born in 1923, David Murdock was a high-school dropout who got back from World War II without a penny to his name. Homeless and with almost no options, he found a way out when he secured a loan to buy a closing diner that he flipped for a profit. Relocating from Michigan to Arizona and eventually California, he made a name for himself in housing and commercial development before expanding into other business. Now he’s the chairman of Dole. Oh yeah: he’s dyslexic, to boot. What have you done lately?
  6. T. Boone Pickens: An oilman and corporate raider with a controversial habit of trying to take over anything that isn’t tied down, T. Boone Pickens, originally from Oklahoma, is currently the chair of BP Capital Management. (The BP stands for Boone Pickens, though, and isn’t related to British Petroleum.) However, great success tends to bring great failure, and Pickens saw both as he tumbled into debt and saw his gambles on natural gas come up short. However, his business have rebounded in in recent years, and he remains a formidable business presence. Take a look:
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  8. Stephen M. Ross: Stephen Ross is CEO of The Related Companies, L.P., a real estate firm. He also owns 95 percent of the Miami Dolphins as well as 95 percent of their stadium, Sun Life. The real estate game turned on him in the 1990s, sending him to the brink of bankruptcy, but Ross overcame that failure in a big way by developing the Time Warner Center in New York City. Since then, he’s pretty much been on a roll. Forbes pegs his net worth around $2.9 billion. Not bad for a guy who almost lost it all.
  9. Mark Zuckerberg: When David Fincher makes a movie about your life, you know you’ve made it. Mark Zuckerberg founded Facebook with a few of his classmates at Harvard in 2004, and despite his massive success — in March 2010, his net worth was $4 billion — he’s dealt with failure at every turn. Users have often bristled at perceived abuses of privacy, and Zuckerberg has fought an almost constant battle with the press over the site’s expanding role in online society. Still, there’s no denying his business savvy.
  10. Bruton Smith: Bruton Smith, from North Carolina has had a life-long love of stock car racing, and he built Charlotte Motor Speedway in 1959 for $1.5 million. By 1961, he was bankrupt. Smith lost control of the track and relocated to Illinois, working down his debts. He wouldn’t regain control of the track until the 1970s. However, Smith’s adversity bred success: As founder and CEO of Speedway Motorsports, he owns eight NASCAR tracks. Speedway was also the first motorsports company to be traded at the New York Stock Exchange, going public in 1995.
  11. Richard Branson: Long before he was picking fights with Stephen Colbert, Richard Branson was struggling to make a name for himself. He wasn’t the best student: dyslexia hampered his academic performance and affected his personal relationships, and a few attempts to make money as a teen met with disaster. However, those early failures only strengthened his resolve, and by age 20, he’d started up a mail-order record company that would soon move into physical retail. The name: Virgin Records. Branson’s Virgin brand now encompasses everything from airlines to mobile phones.
  12. Henry J. Heinz: The business giant whose name is now synonymous with ketchup started out by going bankrupt. In 1869, Heinz formed his first company, Heinz Noble & Co., with L.C. Noble. The intent was to market horseradish, capitalizing on Heinz’s love of produce and gardening. Within a year, the company went out of business. Thankfully (especially for those of us who like a good burger), he rebounded soon after and teamed up with his cousins to start F&J Heinz, which would eventually become the H.J. Heinz Company. The rest is tasty, tasty history.
  13. Yasumitsu Shigeta: One of the richest people in the world according to Forbes, Yasumitsu Shigeta earned billions thanks to his mobile phone sales but lost it all when the dot-com bubble burst. He was knocked completely out of the game, and by all accounts, should’ve stayed there. But he rebounded by changing direction, moving from mobile media into businesses like office equipment and medical insurance. By the mid-00s, he was a billionaire CEO once more.
  14. Tim Blixseth: After trying his hand at everything from songwriting to real estate, Tim Blixseth found himself broke and struggling to realize his dreams of financial gain. But instead of chasing the money, Blixseth made it work for him: He turned some of his Montana land into the Yellowstone Club, a private ski and vacation resort that brought him success.
  15. Donald Graham: The Graham family is a media institution: Donald’s mother, Katharine, was the publisher of The Washington Post for more than 20 years, his daughter works at Slate, and his son works for The Onion. Donald joined the Post as a reporter in 1971 and eventually worked his way into the management ranks, becoming publisher in 1976 (succeeding his own mother) and CEO in 1991. However, his time at the post began with a major setback when, in 1994, he lobbied Sen. John Danforth to include a special provision favoring the Washington Post Company’s cell phone holdings in the General Agreement on Tariffs and Trade treaty. This ethical breach cost him credibility and earned scorn from critics, but the paper’s soldiered on and is one of the few media outlets managing to weather the Internet-driven demise of newspapers.
  16. Sam Walton: Sam Walton is known for founding two stores that seem to define modern America: Wal-Mart and Sam’s Club. But before the Wal-Mart stores made him famous, Walton learned some hard lessons as the owner of a Ben Franklin store in Newport, Arkansas, in the 1940s. His low prices and longer hours brought in the money, but as a result, his landlord refused to renew his lease and bought out the store’s inventory. His business career was almost over as soon as it began, thanks to some cutthroat practices. It took a few years for Walton to rebuild his businesses, but with the help of his family, he was able to get Wal-Mart off the ground.

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