Probably the most famous childhood story about Richard Branson is the time that his school headmaster predicted he'd either go to jail or become a millionaire.
At age 66, Branson is worth $5 billion. He's been married to the same woman for 28 years, and is the father of two children and grandparent to three more. And, he spends a lot of time reflecting on how his childhood shaped him, and trying to advise parents on how to raise the next generation.
His top advice? Parents should let their kids try things--and fail--over and over and over.
"Too often adults keep kids safe, 'protecting' them from the hurt that's associated with failure. This is a big mistake," he wrote recently. "The more children are told they can't do something, the more they will lose their curiosity and determination. I am grateful to have had encouraging parents, who instead of blockading and trouncing my curiosity, allowed me to figure things out on my own accord."
(Fun fact from that article: Apparently Branson's mother calls him Ricky.)
Recently, Inc.com asked author Simon Sinek for his take on raising kids, and he cited Branson's example for teaching kids be problem-solvers. Sinek said he also advocates for teaching kids independence and resilience; the best teachers I've found on these two points are former Stanford dean of freshmen Julie Lythcott-Haims and former Navy SEAL commander Eric Greitens.
All three are really endorsing that single lesson that Branson keeps referring to, however: raising kids who are brave enough to try new things, and if they fall short, to get back up and try something else.
So, as inspiration, here are some of Branson's most-spectacular and most-publicized failures. Reading this list is good motivation for anyone--parent, child, or entrepreneur--who is afraid of failure.
Student magazine (1968)
"One of my most valuable failures came at an early age, when I failed to convince a major publishing house to buy out Student magazine," Branson recalled. "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. They ran a mile."
Virgin Records (1971)
As Inc.com's Anna Hensel reports, "In 1971, Branson sold discs at Virgin Records that were designated for export--thus avoiding a 33 percent tax. After getting caught, Branson was slapped with a £60,000 fine."
Virgin Cola (1994)
"We hadn't thought things through," Branson wrote. "Declaring a soft drink war on Coke was madness. I consider our cola venture to be one of the biggest mistakes we ever made--but I still wouldn't change a thing."
Virgin Vodka (1994)
This venture "never came close to gaining the same traction" as Virgin Cola, reports The Guardian, and "the entire Virgin Drinks subsidiary has since folded."
Virgin Brides (1996)
This bridal store venture is probably best remembered for the publicity launch, at which Branson showed up wearing a wedding dress. As for why Virgin Brides failed, Branson later quipped, "We soon realized there weren't any."
Virgin Vie (1997)
This was Branson's attempt to create a line of cosmetics.
They didn't call it a social network--but it was one, ahead of its time. It lasted until about the time MySpace became dominant.
Virgin Cars (2000)
"We ... set about revolutionizing the way that cars were being sold. That turned out to be the wrong angle, and Virgin Cars ended up shutting down just five years later," Branson says, adding that in retrospect, "the biggest potential for disruption in the automotive industry had nothing to do with the process of selling cars, but rather with how cars were powered."
Virgin Atlantic "Lie-flat" seats (2003)
"The problem with our proud new 'lie-flat bed' was that while it was flat, it wasn't horizontal. ... [Meanwhile], British Airways had gotten wind of our secret new seat and took their time to develop a truly horizontal lie-flat bed, beating us to the punch," Branson wrote. "That rush to be first cost us a lot. It was an expensive lesson."
Virgin Pulse (2004)
This was a digital music player that never really attracted an audience.
"Some of the best decisions our team at Virgin has made involved exiting markets early, when we could see that our product, service or brand was not making a big enough impression on customers," Branson later wrote.
"One of the most short-lived of all Branson's business gambits, a range of men and women's wear was launched in 1998, targeting high street clothing stores, but wound up within two years," according to The Guardian. "There were hopes for an underwear line after another firm licensed the Virginware brand to produce lingerie, but the firm collapsed in 2005.
Little Red (2013)
This was an attempt to create a domestic airline in the United Kingdom that would compete with British Airways. "The odds were stacked against us and sadly we just couldn't attract enough corporate business on these routes," Branson said as it shut down.
Virgin America (2016)
It's cheeky to call this a failure; the company was acquired for $2.6 billion. However, Branson opposed the merger, and expressed regret that he couldn't stop it.
"I would be lying if I didn't admit sadness that our wonderful airline is merging with another. Because I'm not American, the U.S. Department of Transportation stipulated I take some of my shares in Virgin America as non-voting shares, reducing my influence over any takeover," he wrote at the time. "So there was sadly nothing I could do to stop it."
Branson also tried to take over the British national lottery, but came up short twice.
"Whether it is launching companies ... that fell flat on their face, making the wrong call on investments, or simply forgetting to return a call or send an email," he wrote recently, "I have made hundreds of mistakes. I'm sure I'll make many more this year, and learn valuable lessons from every error. Anybody who tells you they don't make mistakes has just made one."