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What Richard Branson Learned From His 7 Biggest Failures The mark of a true entrepreneur is the ability to adapt to changing circumstances.

By Alp Mimaroglu

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Billionaire Richard Branson owns so many businesses he's said that he has a hard time keeping track of them all. Worth more than $5 billion, he's been knighted by the British government for his services to entrepreneurship and has a well-earned reputation for success.

But Branson's career has had its share of wrong turns and miscalculations. Here are a few examples of failures in his career and the lessons we can learn from them.

Related: Billionaire Richard Branson Credits To-Do Lists as a Key to His Success

1. When his first company didn't make money.

Branson dropped out of school in 1967, at the age of 16, to start his first business: Student magazine. He wanted Student to become the voice of his generation, and the magazine earned some big name interviews -- but not a lot of money. Cash flow soon became a problem for the would-be publisher.

If he had stuck to his original plan, Branson might have gone under. Instead, he decided to be flexible and pivoted into what would end up being a much more successful territory -- music. He launched a mail-order discount record business, and what began as a way to pay for the magazine grew into a billion-dollar recording empire called Virgin Records.

2. When Virgin Atlantic Airlines almost crashed before it started.

Branson launched Virgin Atlantic Airlines in 1984 to give passengers a better flying experience. He saw a big opportunity but had little experience, and his new venture almost failed before it got off the ground.

During the initial test flight of Virgin's only plane, a rented Boeing 747, a flock of birds flew into an engine, causing extensive damage. The airline couldn't get certified to start carrying passengers without a working plane, and it couldn't get money for repairs without being certified.

Instead of panicking or giving up, Branson stayed optimistic. Working fast, he restructured his companies and pulled money from other ventures to get repairs done quickly. His airline got the certification it needed, and Virgin's inaugural flight from Gatwick to Newark was a success.

3. When his soda company fizzled.

Virgin moved into new territory again in 1994 with the launch of Virgin Cola, a soda designed to compete with Coke and Pepsi. Early taste tests were promising, and early on, Branson had high hopes. "Coke is the best known brand in the world, and if we could topple Coke, we thought it would be a lot of fun," he once said.

Before long though, it became clear that Virgin Cola wasn't selling. It was too similar to other sodas to build its own identity. The company folded after a few years, teaching Branson an important lesson in the process -- if you're not unique, you won't get noticed.

4. When his trip around the world almost killed him.

Branson's personal ambitions are just as big as his professional ones. He's attempted several adventurous world records and was the first person to pilot a hot air balloon across the Atlantic.

But his trip around the world wasn't as successful. After accidentally losing most of their fuel, Branson and his co-pilot found themselves above the Pacific Ocean facing gale force winds. With no hope of rescue if they ditched, they calculated the likelihood of their survival at only 5 percent. Branson has said they were faced with two choices, either lay down and accept their fate or stay up for three days straight trying to reach North America.

They managed to make it to safety, and Branson's experience taught him the value of resilience. "Never give up," he said in an interview. "Even if it sounds slightly corny. Fight, fight, fight to survive."

Related: 11 Powerful Quotes to Make You More Successful From Billionaire Entrepreneur Richard Branson

5. When Virgin Cars missed the mark.

The Virgin Group has found plenty of success in planes and trains, but automobiles were a different story. In 2000, Branson decided to launch Virgin Cars, an online business that aimed to change the way cars were sold. While the company started out strong, it soon lost steam and shut down within a few years.

Branson blamed a failure to focus on the right form of disruption. In hindsight, he decided that what needed to change about the auto industry wasn't how cars were sold, but how they are powered. He's since invested heavily in creating more sustainable environmental fuels.

He's also applied a new rule across all his businesses. "There can be no profit without a well-defined purpose."

6. When shoppers didn't say yes to his dresses.

Branson has made several forays into the fashion world without success. He's had a clothing company, a cosmetic brand and even an underwear label that was meant to compete with Victoria's Secret.

Perhaps the most surprising of the Virgin fashion ventures was Virgin Brides, a wedding dress and bridal boutique that opened in 1996. Branson shaved his beard and donned one the brand's wedding dresses for the launch event, but his short-lived modeling career failed to drive sales.

Branson's multiple attempts to make Virgin fashionable reflect his willingness to fail. While he doesn't easily give up on projects, he's also unfazed when things don't work out as planned. He starts over with a new approach.

7. When Virgin Digital didn't get downloads.

Virgin Digital opened its doors online in 2005. A music download site in the style of iTunes, Branson's music platform boasted a massive library of songs. It also featured a digital music subscription service that foreshadowed later platforms like Spotify.

Unfortunately, what Virgin Digital didn't have was the iPod. The service fought a losing battle against Apple and pirated music sites for two years before shutting down for good in 2007. The loss was a reminder for Branson that it's always better to forge your own trail than it is to follow in other companies footsteps.

Related: Why 'Fail Fast, Fail Often' Is All Hype

Everyone fails. The people who fail most succeed.

Any one of Branson's failures could have derailed his entire career if he'd allowed it to, but the mark of a true entrepreneur is the ability to adapt to changing circumstances. A true adventurer in both business and life, Branson will continue pushing his limits -- and we can all stand to learn a bit from his bravado.

What is holding us back from achieving our dreams? Perhaps not as much as we think.

Alp Mimaroglu

Demand Generation and Marketing Technology Expert

Alp Mimaroglu is a digital marketing team leader who specializes in creating highly effective marketing engines for companies that range from startups to Fortune 500 companies.

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