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6 Famous Entrepreneurs Tell Us Their Biggest Failures And How They Overcame Them

These incredible stories prove the golden rule: It’s not how many times you fall—it’s how many times you get back up.

1. Hugh Hefner (founder, Playboy Enterprises)

“When I founded Playboy, I couldn’t find a single investor. I was told over and over that nobody would pay to see one naked woman a month when they could mail out a nickel for a pair of X-ray specs and ogle all the ladies they liked. But I didn’t blink. I hired a PI and had him track down and smother the magician who gave X-ray specs their mystical properties, and then—bam! Playboy subscriptions skyrocketed.”

2. James Dyson (founder, Dyson Ltd)

“We spent millions on a vacuum that was designed to turn on whenever the user shouted the phrase ‘It’s time to clean up the big mess I’ve made.’ It was a total flop. The voice-recognition technology was still years away from being fully functional, and people said they felt insane shouting this phrase at an unresponsive vacuum. Luckily, I invented the bagless vacuum cleaner a few years later, and people were so excited that they forgot Dyson was the company that made them shout at vacuums.”

3. Larry Page (co-founder, Google Inc.)

“The first search engine I ever built was a plywood jukebox-type machine called The Whizzler that spit out results on ping-pong balls. It worked terribly and ruined me financially. But it laid the groundwork for the search engine that would become Google.”

4. Pierre Omidyar (founder, eBay)

“I once had a hockey stick autographed by Bobby Orr that a kid in my class stole from me, so I created the online marketplace eBay to tempt him to put it up for auction. He never has, but I’ve made a lot of money, which is its own kind of reward.”

5. Mark Zuckerberg (founder, Facebook)

“I should have never created those goddamn twins. Those boat-rowing monstrosities from hell. I was young and proud, thought I might play God. I tried to breed two male boat enthusiasts who look exactly the same. But I overestimated my abilities and ended up creating a mad two-headed paddling antichrist for the new millennium. It is the great failure of my life. The whole world suffers for it. I’m so sorry.”

6. Richard Branson (founder, Virgin Group Ltd)

“I died in 2006. I am not at liberty to divulge how I overcame that.”


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