You can be on Entrepreneur’s cover!

8 Times Billionaires Got Wacky on Twitter They may be highly respected professionals, but here they let their fun sides shine.

By Grace Reader

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

Walter McBride | Getty Images
Oprah Winfrey

An employee of Richard Branson is now Twitter famous, but maybe not for the reason he had hoped. Branson posted a tweet with an employee who was sleeping on a coach in the Virgin Australia office reading, "checked in on @VirginAustralia staff & caught this guy sleeping. I gave him a wake up call!"

For Branson, posting goofy photos is not out of the ordinary, but for other billionaires, posting a funny tweet can be quite the rarity. Here are eight times billionaires took over Twitter by being whacky:

1. Richard Branson

Richard Branson posted a tweet with a sleeping employee that went viral, but quickly assured the Twitter community that the man was simply getting some much needed rest while on standby.

Shortly after Branson had captured the media's attention, he took it a step further. On World Oceans Day Branson dressed up like a mermaid, with a shiny tail and everything.

2. Warren Buffett

Warren Buffett is one of those billionaires who doesn't generally use social media, but he did generate some attention when he tweeted a photo of himself dressed up like Walter White's alter ego Heisenberg from Breaking Bad. The photo has been retweeted 5,396 times so far. Buffett only has eight tweets, the first being, "Warren is in the house."

3. Oprah Winfrey

Oprah Winfrey tweeted out a video about how much she loved bread. Yes, bread. Oh and she made $12 million from the tweet. Oh, to be Oprah.

4. John Henry

John Henry, owner of the Boston Red Sox, tweeted out a photo of a Boston cop celebrating a David Ortiz home run. The photo of the police officer, a massive Red Sox fan, went viral and the owner soon tweeted out a photoshopped version.

5. Bill Gates

Bill Gates is usually very stoic in his tweets, but he brought attention to a serious issue in a goofy way when he tweeted about poop. Despite the silly connotation, the tweet was meant to bring attention to the fact that 1.5 million children die each year due to severe diarrhea.

6. Bob Parsons

GoDaddy owner Bob Parsons must not be an ophidiophobe because he used a snake as a golf club. He only got 10 retweets and 25 likes for this tweet, but it sure got his wife's attention. Below the tweet, Renee Parsons commented, "HONEY!!"

7. Mark Cuban

Mark Cuban is always a little bit of a goof when it comes to Twitter. Just look at this tweet that he sent out using a urinal while holding the NBA Championship Trophy. Mavericks fans thought the picture was so funny that the team starting selling socks with that very image on them.

8. T. Boone Pickens

T. Boone Pickens got some attention for taking on rapper Drake in a tweet. Drake handled the episode well though, tweeting to his followers "@boonepickens just stunted on me heavy." To make it even juicier? Pickens biography is titled The First Billion is the Hardest.

Grace Reader


Grace Reader is a former editorial intern at and a current freelance contributor. She is a third year journalism and media communication major at Colorado State University. Grace is the PR and marketing manager at Colorado State University's Off-Campus Life, and a sports anchor at CTV Channel 11. 

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business News

James Clear Explains Why the 'Two Minute Rule' Is the Key to Long-Term Habit Building

The hardest step is usually the first one, he says. So make it short.

Business Solutions

Set Your Team up for Success and Let Them Browse the Internet Faster

With ad blocking, Control D is $35 through April 21.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Side Hustle

This Dad Started a Side Hustle to Save for His Daughter's College Fund — Then It Earned $1 Million and Caught Apple's Attention

In 2015, Greg Kerr, now owner of Alchemy Merch, was working as musician when he noticed a lucrative opportunity.

Business Solutions

Grab Microsoft Project Professional 2021 for $20 During This Flash Sale

This small investment is well worth the time it will save your team in organizing and monitoring project work.

Business News

Microsoft's New AI Can Make Photographs Sing and Talk — and It Already Has the Mona Lisa Lip-Syncing

The VASA-1 AI model was not trained on the Mona Lisa but could animate it anyway.