12 Historic Failures by Successful Billionaires

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Steve Jobs and Bill Gates
Photo credit: Joi Ito/wikipedia.org

Thomas Edison once said, "I have not failed. I've just found 10,000 ways that won't work." From show business and athletics to tech and the corporate world, the giants of every industry all seem to have one thing in common: They went for something big, failed, and kept trying. Some of the richest and most successful people on Earth built their fortunes on the ash heap of massive, historic failures.
Amazon Fire Phone
Photo credit: Romazur/wikipedia.org

The success of Amazon and founder Jeff Bezos can be traced largely to the philosophy of embracing risk and welcoming failure. And, oh, what a failure the Amazon Fire Phone turned out to be. The foray into mobile phones was such a flop that Bezos at one point lowered the sticker price to 99 cents. It didn't help.
Bill Gates
Photo credit: United States Department of Health and Human Services/wikipedia.org

Sometimes the biggest failure is not what you do wrong, but what you don't do at all. In the early 1990s, Microsoft was the undisputed king of tech and in no hurry to change. Gates failed to recognize the importance of the emerging internet, underestimated the threat and opportunity of the new technology, and Microsoft stumbled hard into the new millennium.
Apple III
Photo credit: Bilby/wikipedia.org

From the personal computer to the smartphone, the late Steve Jobs revolutionized modern society over and over again. Along the way, however, he racked up an impressive list of failures. Jobs proved how ahead of his time he was in 1993 by launching the Macintosh TV, which flopped. The same year, Apple suffered another humiliation with the Newton, which promised to revolutionize handheld devices but was rejected by the masses. Before that was the failure of the expensive Lisa, the first mouse-driven PC, which sold only 100,000 units. All that came after the demise of the Apple III, which overheated and destroyed disks, demanding a recall.
Donald Trump
Photo credit: Gage Skidmore/wikipedia.org

Donald Trump is a billionaire several times over and the master of a global empire — not to mention being president of the United States. But he's also a huge failure. It's estimated that as many as two-thirds of his projects failed or had major problems. For every huge success such as "The Apprentice," there was a string of bombs such as Trump University, Trump Vodka, or the "Trump Tycoon" app.
SpaceX rocket
Photo credit: SpaceX/wikipedia.org

Like Jeff Bezos, Elon Musk has wrestled success out of a bruising string of failures that date back to 1995, when he couldn't even land a job at Netscape. Among his most explosive flops are a literal series of explosions: His SpaceX, one of the most ambitious private ventures in history began in 2006 with its first rocket launch ending in one. The next year, launch attempt No. 2 resulted in explosion No. 2. A rocket failed in 2013 and in 2015. His fourth rocket exploded at launch, as did experimental drone ships. Another rocket exploded in 2016, this time carrying a $300 million satellite.
Warren Buffett
Photo credit: USA International Trade Administration/wikipedia.org

Warren Buffett is synonymous with two things: being the most successful investor in history and as ruler of the massive Berkshire Hathaway. His wildly successful company, however, is also his biggest failure. Buffett has estimated he lost $200 billion — with a "b" — trying to make it work as a textile company for two decades. When Buffett was just a shareholder, owners tried to muscle him out, so he did something he cautions investors never to do: invested based on emotion, and bought the company out of spite.
Virgin Cola
Photo credit: Virgin Cola by Ged Carroll (CC BY)

In 1994, a Sherman Tank rolled through the streets of New York City's Times Square. Riding on top was Richard Branson, the eccentric entrepreneur who had already launched bold ventures into airlines, publishing, and music. The tank demolished its target: a makeshift wall of Coke cans. Branson was launching Virgin Cola, which he intended to topple the mighty Coca-Cola empire. But Coke flexed its muscles, leveraged its relationships, and made Branson's soda nearly impossible to find outside Bangladesh.
Larry Page
Photo credit: Stansfield PL/wikipedia.org

In 1997, young Larry Page was just one entrepreneur in a tech gold rush sweeping the world. He tried and failed to sell his online search tool to a company called Excite for $1.6 million, with the company's offer coming in at a paltry $750,000. Page refused and kept plugging away. The search engine went on to become Google, now worth $132 billion and the world's No. 2 most valuable brand, behind only Apple.
Pizza in a cardboard delivery box
Photo credit: FuzzMartin/istockphoto

While still a graduate student at Stanford, Google co-founder Sergey Brin had a visionary idea — not the one that led him to unify the cumulative knowledge of the human race, index it, and make it available to anyone with a computer. This time, Brin was hungry and had the idea of using the new World Wide Web to send pizza orders through fax machines. But even pizza places with fax machines rarely checked them, and fewer regular people had them.
Harry Potter and the Deathly Hallows
Photo credit: J.K. Rowling by Joits (CC BY-NC)

"Harry Potter" queen J.K. Rowling is one of the most acclaimed writers in history, and the first to become a billionaire. Her books spawned one of the world's most successful film franchises and legions of adoring fans. Before the literary big time, however, Rowling was a depressed single mother living on the British equivalent of welfare. She experienced not one failure, but 12 — a dozen publishers turned down "Harry Potter" before it was picked up for print.
Larry Ellison
Photo credit: Oracle Corporate Communications/wikipedia.org

Larry Ellison co-founded Oracle and built it into one of the world's biggest brands. He's also responsible for one of the most ambitious tech flops in history: a small, basic machine called Network Computer, which was meant to crush the domination of the computer industry by his arch-rival Bill Gates' Microsoft. The internet-focused NC was ahead of its time — and a huge flop.
Mark Cuban
Photo credit: Mark Cuban by JD Lasica (CC BY)

Dallas Mavericks owner star Mark Cuban is probably most famous for his role on ABC's "Shark Tank." But success as a show business mentor came on the heels of failure. Cuban's first foray into television was in 2004 with "The Benefactor," which had such poor ratings that it was canceled before the full first season aired. Cuban went on to become the richest shark on the No. 1 Friday night show among 18- to 49-year-olds, though.

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