15 Historic Failures by Successful Billionaires

Steve Jobs and Gates at D: All Things Digital in 2007

Steve Jobs and Gates at D: All Things Digital in 2007 by Joi Ito (CC BY)

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Elon Musk
Elon Musk by Heisenberg Media (CC BY)

The Small Idea

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 have one thing in common: They went for something big, failed, and kept trying. As Twitter's board members consider Elon Musk's surprising $43 billion offer to purchase the company and turn it into a free-speech zone, remember this: Some of the richest and most successful people on Earth built their fortunes on the ash heap of massive failures. 

Related: 12 Tech Flops of the 1970s and '80s That Were Ahead of Their Time

Elon Musk
Wikimedia Commons

Elon Musk: Rocket Man, Oh Man

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. Amazingly, SpaceX has turned things around — even launching two NASA astronauts into space to help them reach the International Space Station. Now Musk is back in the news for making a non-solicited offer to buy Twitter, where he recently became the biggest shareholder, and it remains to be seen whether that will blow up on him, too. "I invested in Twitter as I believe in its potential to be the platform for free speech around the globe, and I believe free speech is a societal imperative for a functioning democracy," he said in his letter to the company. "Since making my investment I now realize the company will neither thrive nor serve this societal imperative in its current form."

Related: Surprising Things Tesla Makes That Aren't Electric Cars

Jeff Bezos
Steve Jurvetson

Jeff Bezos: Amazon's Physical Bookstores Fold

The success of Amazon and founder Jeff Bezos partially stems from a willingness to embrace risk and welcome failure. But even though Amazon was able to drive bookstores like Borders out of business, it hasn't been able to take over — at least in the physical space. Amazon has announced it will close all 68 of its brick-and-mortar bookstores, pop-ups, and "4-star" shops carrying highly rated toys and home goods in the United States and United Kingdom. Not that Amazon is giving up on physical locations entirely — there are still plans to open a fashion store in greater Los Angeles, and an effort to expand Amazon Go convenience stores into the suburbs.

The store closings aren't Amazon's first flop, either. For instance, the Amazon Fire Phone was such a failure that Bezos at one point lowered the sticker price to 99 cents. It didn't help.

Related: 30 Things You Should Never Buy on Amazon

Mark Zuckerberg

Mark Zuckerberg: Wirehog and Whistleblowers

Most people know Mark Zuckerberg for his success with Facebook, but they may not remember his interest in the peer-to-peer file-sharing service Wirehog in 2004. The service let Facebook users swap documents, files, and music, resulting in a flurry of lawsuits and the plug being pulled on Wirehog in 2006. Of course, Zuckerberg has managed to thrive since then — until now, at least. Meta, the company formerly known as Facebook, recently had its worst day ever on the stock market, losing a staggering $240 billion in market value. With that loss, Zuckerberg's personal wealth dropped by $31 billion. All this also comes on the heels of a whistleblower's damaging reports in late 2021 that cast doubt on Facebook's efforts to stem the rising tide of misinformation on its platforms. 

Related: 33 Companies That Changed American Culture for Better or Worse

Bill Gates Missing the Internet
Wikimedia Commons

Bill Gates: Missing the Internet

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. Bill Gates failed to recognize the importance of the emerging internet, underestimated the threat and opportunity of the technology, and Microsoft stumbled hard into the millennium. But don't feel too badly for Microsoft — the company hit a market cap of more than $2 trillion in late June as Gates was spending billions developing vaccines for the coronavirus.

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Steve Jobs
Steve Jobs by Bilby (CC BY)

Steve Jobs: A Big List of Failures

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. But if you have an old Lisa computer? It could be worth over $50,000.

Donald Trump
Donald Trump by Gage Skidmore (CC BY-SA)

Donald Trump: Too Many Failures to List

Donald Trump claims to be a billionaire several times over and the master of a global empire — not to mention that he was 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. The release of his tax returns by the New York Times suggested other problems, too.

Warren Buffett
Warren Buffett by USA International Trade Administration (CC BY)

Warren Buffett: Buying Berkshire Hathaway

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
Virgin Cola by Ged Carroll (CC BY)

Richard Branson: Virgin Cola Tanks

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. Branson's failures don't end there — in 2020 his attempt to launch his first rocket for Virgin Orbit also failed, though he quickly put more rockets into production.

Larry Page
Larry Page by Stansfield PL (CC BY-SA)

Larry Page: Failure to Sell

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 valued at $1.8 trillion in August and the world's No. 2 most valuable brand, behind only Apple.

Sergey Brin

Sergey Brin: The Pizza Fax That Wasn’t

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.

J.K. Rowling
J.K. Rowling by Joits (CC BY-NC)

J.K. Rowling: 13th Time’s the Charm

"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 (though some recent controversies have tarnished Rowling's reputation among readers). 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
Larry Ellison by Oracle Corporate Communications (CC BY)

Larry Ellison: No to the Network Computer

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
Mark Cuban by JD Lasica (CC BY)

Mark Cuban: Small Screen, Big Failure

Dallas Mavericks owner star Mark Cuban is probably most famous for his role on ABC's "Shark Tank." But success as a 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 enduringly popular broadcast show, though.

Related: 13 Small Business Tips to Borrow From "Shark Tank"

Sheldon and Miriam Adelson, at the Woodrow Wilson Awards
Sheldon and Miriam Adelson, at the Woodrow Wilson Awards by Union20 (CC BY-SA)

Sheldon Adelson: Lost His Fortune ... Twice

Sheldon Adelson got an early start by selling newspapers at age 12 and, after a stint in the U.S. Army, becoming a mortgage broker and investment adviser. He did pretty well — and was worth $5 million by the age of 38. But he blew it all not once but twice thanks to a dip in the stock market and a failed attempt at condo conversions in Boston. Fortunately, he always loved computers, and when he created the Computer Dealers Expo in 1979 he finally landed a big-money idea. COMDEX became one of the largest computer trade shows in the world. Later, got into the casino business. Adelson died in January owning more than half of the Las Vegas Sands gambling empire, valued at $14 billion, and worth $30 billion.

Michael Bloomberg 2013

Michael Bloomberg: Got Fired

A failed run for president of the United States (remember?) wasn't Michael Bloomberg's first flop. He was canned from the investment bank Salomon Brothers in 1981 and says he funded his own company because no one was offering him a job. Salomon Brothers probably regretted its decision, since Bloomberg LP now rakes in more than $10 billion annually. Bloomberg was also the mayor of New York City from 2003 to 2012.