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The evolution of YouTube musician Chester See

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It’s been a year since my first interview with Chester See, and while many things have stayed the same—the minimal decorations in his pool house-turned-home, his warm hospitality, the white baby grand piano in the corner, the whiskey drinks—there is a certain enthusiasm about See as he prepares to capitalize on all the great things this year has to offer. 

His motto: Be surrounded by good people, keep writing songs, and enjoy the fame he’s gained from seven years on YouTube.

“I’ve always wanted to be an entertainer," See excitedly exclaims. "I just now embrace the fact that I am an entertainer and I get to do it the way that I want to. I love the way I do it. I love it.”

See’s legacy on YouTube has been built upon a genuine personality that fans can't help but fall in love with and years of trying the unexpected. His channel, which boasts more than 1.4 million subscribers, is a mix of stripped-down pop covers, viral original songs, comedy videos, and vlogs documenting See’s everyday life.

But like most Internet personalities, it was never in See’s plans to become a YouTube star. Upon graduating from UCLA in 2005, See began hosting the short “Disney 365” while simultaneously songwriting with popular artists signed with Warner/Chappell. It was through this partnership that See met YouTube musician David Choi, who convinced See to start putting his work on the platform.

“That was the start of YouTube. David help my laptop and recorded in iMovie HD and held it to the best of his abilities trying to keep it steady,” recounts See. “It wasn’t until 2010 I started thinking, 'This is actually something more than just a place to have music heard. You can start creating a brand.'”

From there, See began making a name for himself as a songwriter, musician, actor, producer, and activist campaigning for traditional media’s respect for the digital platform. But looking back, See admits that he was originally inspired to pursue a career in Hollywood for incredibly superficial reasons.

“I think I was the same age from 20 to 28 mentally. By that I mean I was naive to what was going on in the industry and had my eye set on becoming a musician and actor, [but] I was doing it for the wrong reasons,” states See, throwing his hands into the air with a laugh. “It took me a while to look back and see in hindsight I wanted those things for the wrong reasons. I wanted to be a musician or actor because I felt it came with a certain unwarranted respect, and it was the greatest thing ever when I realized that’s not why I do what I do.”

Through his many years on YouTube, See has always worked to push the boundaries of how an audience interacts with content. In 2013, See produced and starred in “Side Effects,” a 40-minute feature film released specifically on YouTube. And while critics scoffed that the film would never hold the attention of millennials, the project racked up 2 million views in the first week alone. Earlier this year, See also acted alongside YouTube’s golden trio—Hannah Hart, Grace Helbig, and Mamrie Hart—in the highly anticipated feature film Camp Takota.

“I’ve had so much excitement with what’s happening with the space that I’ve almost become anti-TV, anti-film, to the degree [that] whenever I’m on a panel, I’m always arguing with anyone who is taking the other side," See says. “I go into meetings and there is a lack of respect for what is happening online, and it’s absolutely ridiculous. When you step back and you look at it completely rationally, the work that someone does on YouTube compared to the work that someone does on TV, I think the person who has found success on YouTube, nine times out of 10, probably works harder because they’re not just creating content, but they’re having to play so many roles.”

While See has already achieved a level of success felt by few creators, he readily admits he doesn’t care if he becomes a fat, old songwriter. In fact, he sees everything from this point on as just icing on the cake, including his debut album set to be released this year.

“I feel so happy and content with what I’ve already done that now, it’s become some much more fun and less about needing to reach whatever stupid, fake, successful level I thought I needed to reach. Now, I’m in this really amazing situation where I feel like I can create things and people are listening. I only want to put out content that I wanted to make from here on out,” smiles See.

For creators looking to branch into the YouTube scene, See has one piece of advice: consistency.

“Nobody's changing the amount of time they spend watching YouTube. That’s a fixed number; that’s a fixed amount of time,” advises See. “What does change is the content within their fixed time. So if my fixed time is, I spend an hour watching YouTube every day, if I stumble across something I want to watch, I’m going to unfortunately bump something out, and being that consistent and retaining that attention is key right now in the game of YouTube.”

As for his new year’s resolutions, See is keeping his promise, employing friends such as Grace Helbig, Andy Lange, Josh Golden, and Andrew Garcia to help him fill his channel with great music and vlog collaborations.

“Because none of this shit matters. None of that shit matters at all. All that matters is if you’re smiling and you’re happy,” See insists. “Figure out what makes you happy; pursue that. Everything else is bullshit.”

Photo via Chester See/YouTube