Making 2.5 Billion People Laugh – Advice from a YouTube Comedy Executive

Going viral isn’t all about luck.

In the age of content marketing and social media, every company or startup is trying to wade through the abundance of virtual information to make their messages heard – or even better – viral. Despite the apparent unpredictability in creating a viral message that appeals to the public’s whims, one man has managed to do it several times.

Remember the famous “I Got a Crush…on Obama” video that garnered over 30 million views? Or the “My Box in a Box” video — the viral hit commented on by both Rolling Stone and Cosmopolitan? They were the brainchildren of former advertising executive and YouTube’s current Head of Comedy, Ben Relles, who also created the popular YouTube channel Barely Political (viewed over 2.5 billion times in total) and the Key of Awesome series (viewed nearly 30 million times per month).

Ben has been working at YouTube since 2011, and is currently leading Comedy for YouTube’s Originals Program. His remarkable ability to create viral hit after viral hit earned him a spot on the Wharton School’s 40 under 40 list, and he returned to the University of Pennsylvania earlier this month to share his insight in finding his breakthrough as a creative person in the business world.

1) You will most likely find your big breakthrough by taking risks

As the leader of an international comedy platform, Ben may strike one as uncharacteristically imposing at first – a fact accentuated by his seemingly ever-present frown. When he finally spoke, however, he revealed his approachable and witty self: humorously self-deprecating at times, always astutely observant. Beside his apparent dispositional knack for comedy, Ben’s wild success is also attributable to a lifelong willingness to take risks and embrace the failures that entail.

“Being willing to fail is a big part of being successful,” Ben remarked, “it’s a cliché thing to say, but I think it’s true.”

One of his failures came during his college days. In his freshman year at the University of Wisconsin, Madison, Ben tried joining a startup business on campus selling discount cards, and he quickly lost the entire $1000 he invested. Recovering from what he called a “big total disaster”, he launched a soft pretzels business during his sophomore year selling pretzels before football games. Taking another risk and investing $1000 on a grill and the pretzels, he started sales at six in the morning and ended up making enough during the season to cover his tuition.

Turning his attention away from discount cards and pretzels to comedy, Ben finally found his big breakthrough in 2007. It was in that year that he took his biggest risk so far: creating the comedic music video “I Got a Crush…on Obama” as the debut piece of the now widely popular channel Barely Political. At the time, the immediate benefits of creating a video of the “Obama Girl” seductively professing her love for then senator Barrack Obama were even less apparent than that of selling discount cards or pretzels. However, Ben took a risk, pulled the resources to produce the video, which eventually became an Internet phenomenon that the President himself said showcased the “fertile imagination of the Internet”.

2) The rest of your career depends on how well you can adapt after achieving your big breakthrough

In 2009, however, dwindling political engagement meant the politically based comedy of Ben’s new YouTube channel was losing traction with its audience. Ben came to that realization when he saw a drop from 30 to 40 million views per month right down to five in his videos within a year.

Not one to call it quits in the face of failure, Ben did the same thing he did after his discount cards business dwindled — he took a risk and adapted. Barely Political started branching out to producing music video parodies (here’s one you may recognize) and the channel was formally acquired by YouTube in 2011 after a surge in popularity. Its parody of rapper Ke$ha’s “Tik Tok” became the most-watched Ke$ha parody in the world (130 million views) – and in a world rife with musical parodies, that is quite a feat.

Ever since joining YouTube, Ben is more involved with what he is truly passionate about — developing quality comedy to a large global audience. He has helped YouTube’s top comedic talents reach billions of people around the world on a monthly basis, even coming full circle: going back to politics by advising the White House on its social media strategy and shaking hands with the President himself.

Looking back at his journey so far, Ben offered a piece of insight that is surprisingly realistic, despite his wild entrepreneurial and intrapreneurial achievements:

“If you have an idea you like and can’t get out of your head, my advice is take a leap of faith and go for it. That said if you’re risk-averse there are plenty of fulfilling and important careers you can pursue as well. I’d take any advice from speakers with a grain of salt — their advice is basically what worked for them. Personally, I’ve benefitted from taking risks and investing in the ideas I’m most excited about.”


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Jason Choi

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