Richard Branson, one of the wealthiest people in the world, is worth an estimated $4.9 billion. The serial entrepreneur has built eight billion-dollar companies and continues to innovate wherever he can.
But Branson wasn't always a financial success. During his early years leading Virgin Records, he nearly let the company fall into bankruptcy a number of times, and that's a mistake he regrets, he tells Reuters.
"I can remember a number of occasions earlier in the history of Virgin when the bank manager came to see me on the Friday and told us he was going to close Virgin down on Monday morning," Branson says. But the experience did teach him to get creative with the business: "We would spend the whole weekend scrambling around to avoid going bankrupt and somehow would always find a way to keep going."
After opening the first Virgin Records store in 1971 and the accompanying recording studio in 1972, Branson built the business from the ground up. He signed major acts including the Sex Pistols and, later, the Rolling Stones.
Still, despite how much he loved Virgin Records, Branson wasn't able to keep the label going. As time went on, other ventures competed for his attention. When his airline Virgin Atlantic was taking off, for example, it faced fierce competition from rival British Airways.
Dealing with the back-and-forth demanded the majority of Branson's time and focus and he ultimately decided that the best way to keep everything afloat was to sell the record company.
Although the deal allowed Branson to keep Virgin Atlantic going — and earned him $1 billion in the process — he calls selling Virgin Records to EMI "one of the most painful things I have ever had to do." Still, it paved the way for him to move on to other projects and expand Virgin into the conglomerate it is today.
Whether it is launching companies like Virgin Brides and Virgin Cola that fell flat on their face, making the wrong call on investments, or simply forgetting to return a call or send an email, I have made hundreds of mistakes.Richard Branson
Branson isn't the only mogul who has struggled to turn a profit on a passion project. After her hugely successful TV show "The Oprah Winfrey Show" ended, Oprah Winfrey decided to try her hand at running a television network. She lost an estimated $330 million on the project, and the stress of running a failing network took a serious toll on her mental health.
"Had I known that it was this difficult, I might have done something else," she told CBS in 2012.
However, as with Branson, Winfrey's perseverance paid off in the end. Her network, OWN, eventually carved out its own niche in the television world and pivoted from "what once seemed like a celebrity folly into a major player in the prestige TV landscape," according to Vanity Fair.
For Branson, mistakes are another part of the process. And he's made many of them: "Whether it is launching companies like Virgin Brides and Virgin Cola that fell flat on their face, making the wrong call on investments, or simply forgetting to return a call or send an email, I have made hundreds of mistakes," he writes in a post on his blog.
Still, Branson has always tried to turn his missteps into learning experiences. He remembers the demise of his first company, a publication called Student Magazine he started at age 16. He wanted to sell the magazine to a major publishing house but, "while they wanted to focus on distribution methods and details, I began explaining my vision for a whole host of new Student enterprises, from magazines to travel companies to banks," Branson says.
The publishing house turned him down, and "thankfully, that failure gave me the opportunity to set about doing everything I could to build the businesses I believed in," Branson writes. "Fast-forward half a century and Virgin spans even more sectors than I dreamed of as a teenager."
Like this story? Subscribe to CNBC Make It on YouTube!
Don't miss: Suze Orman: The No. 1 sign you can't actually afford to buy a home
