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“Take the competition seriously, but not yourself.” For Sir Richard Branson that’s not just a passing quote -- it’s a motto he lives by.

Branson is no stranger to hard work. He founded Virgin Records in 1973, which sold for $1 billion, he owns Virgin Money, Virgin Airlines, Virgin Galactic, is and numerous other Virgin business ventures.

But despite being one of Forbes’ “ World Billionaires,” taking himself too seriously never seems to be a problem. Branson captured national headlines this year by posting a goofy photo on Twitter with a sleeping employee, and he even brought attention to National Oceans Day by wearing a mermaid tail.

Related: 8 Times Billionaires Got Wacky on Twitter

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He holds the title for the first crossing of the Pacific in a hot-air balloon, he bungee jumped out of a building in Las Vegas and has a flying submarine (which yes, he has used).

Branson turns 66 today. To celebrate, we have curated 8 times the silly billionaire made us smile.

1. When he was interviewed by Entrepreneur.com’s Kim Shandrow
Branson’s a busy man, that no secret, but he made sure Entrepreneur.com’s Kim Shandrow got all of her interview questions in, plus a few extra, when she interviewed him in Los Angeles for the Virgin Atlantic’s “Business is Adventure” event.

When his PR team asked Shandrow to finish the interview, the billionaire cut them off and made sure she had time to get all that she needed.

He then shared some of his most classic advice for starting a business, “Screw it, just do it.”

2. When he writes his own Tweets
Branson is one of the most active billionaires on Twitter often linking out to his blog. Many busy CEO’s have their team for that, but the billionaire says he writes every word.

“My first rule of social media is to make sure everything I post is absolutely authentic,” Branson said in a blog on LinkedIn. “If it wasn’t really me writing on LinkedIn or posting my virgin.com blogs, people would spot it a mile off.”

In fact, there’s a lot to smile about when the billionaire takes to Twitter, it makes us smile. He once dressed in a mermaid outfit, blue scales and all, for World Ocean Day.

3. When he crashed a hot air balloon into the Atlantic ocean

Branson is not only an incredibly successful businessman, but he also loves adventure. In July of 1987, Branson, then 36-years-old, and a co-balloonist attempted to be the first to cross the Atlantic in a hot-air balloon.

“The next thing, we found ourselves being hurtled through the water at something like 100 miles per hour with water coming in the capsule,” Branson told the New York Times. “We climbed out on the roof, and the capsule started rising.”

4. When he lost a bet, and paid up
Branson lost a bet to Tony Fernandes, AirAsia Group CEO, after his Formula one racing team finished after Fernandes’. The bet? The loser dresses up as a female flight attendant for the other’s airline.

Branson didn’t back down from the bet and wore bright red lipstick, fake eyelashes and he even shaved his legs (but not his mustache).

5. When he wrote this adorable letter to a 12-year-old
When 12-year-old Olivia Hill reached out to Branson to be the topic of her business studies project, she probably didn’t expect to hear back.

Sure enough, Branson made time to respond to the young girl. He even adds to the end, “Have you thought about your own first business idea yet? When you do, be sure to let me know.” Adorable.

You can read the full letter here.

6. When he announced a full year of maternity and paternity leave for his employees
Not only does Branson offer his employees unlimited vacation days, but June of last year he offered Virgin Management employees in London and Geneva an entire year off for maternity or paternity leave. If the employees were working there for four years or longer they receive all of their salary for the 52 weeks.

He posted in a blog, “If you take care of your employees, they will take care of your business.”

7. When he bungee jumped off a casino in Vegas
He probably doesn’t remember this 2007 bungee jumping adventure too fondly, as he crashed into the side of the building a little harder than expected (and ripped his pants), but the video certainly made us laugh.

He jumped off of the Palms Hotel Casino in Las Vegas, a 407-foot-tall building to celebrate his first Virgin America flight.