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Inside Tyler Oakley’s Unlikely Rise to Fame and Fortune

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When Tyler Oakley was invited to meet with Larry King, he couldn’t quite believe his luck.

“Just being in the waiting room and seeing all the pictures on the wall — there was the Dali Lama and Oprah!” says the bespectacled online star, 28, who had dinner with the legendary radio host in March. “This is a man who has interviewed presidents and icons. The fact that he had an interest in talking to me was just so surreal.”

There have a been a lot of surreal moments for Oakley, who still seems in awe that his YouTube channel has 7.9 million subscribers — and that he’s made even more millions (as in dollars) by just being himself.

Ramona Rosales

“I feel like every month there’s a moment where I’m just, like, ‘Wow. This is happening?!'” says Oakley, who was featured on Forbes‘ 2017 30 Under 30 list in January and reportedly raked in $6 million during a 12-month period ending last June.

“5 years ago — even a year ago — I could never have imagined any of this,” says the online personality, who also competed with his best friend Korey Kuhl on The Amazing Race in early 2016 and recently saw their podcast, Psychobabble, transform into a show that’s broadcast on Fullscreen. “But I’m open to it all — and whatever it could turn into.”

  • To see Oakely in the pages of PEOPLE, pick up the latest issue of the magazine — on newsstands now

Born in Jackson, Michigan, Oakley is the third- youngest of “a bunch of steps and halfs” — 12 brothers and sisters in all.

“Me and all my siblings would put on plays for our parents,” says Oakley, whose mother and father split when he was an infant. “I was always a ham and I loved attention.”

At 14, he came out as gay.

“I felt like it was going to be the end of the world,” says Oakley, who has raised over $1 million for The Trevor Project to combat LGBTQ youth suicides. “But I was really fortunate. My family and friends were really receptive.”

Keeping in touch with those good friends is what led Oakley to YouTube.

“We’d all gone to different colleges and it was a way for me to let them know what was going on in my life — just making videos about my dorm or Welcome Week or people on my floor,” says Oakley, who studied communications at Michigan State University.

Oakley and his mother
Courtesy Tyler Oakley

He knew his vlogs were being viewed by more than just his friends, but it wasn’t until a few years into his YouTube journey that he truly comprehended the size of his growing fan base.

While at an MSU football game, “I looked around the sold-out stadium and said, ‘I could fill this with the people who watch my stuff.’ That was insane,” he says. “It had grown into something so much bigger than I expected.”

Oakley had dreams of working at Google’s Ann Arbor campus after college, but when that opportunity fell through he decided to move to San Francisco.

“I applied to ever single job on Craigslist and I got an internship, which turned into a full-time job doing social media for a website,” says Oakley.

But he soon realized doing social media for a company was not as fulfilling as doing it for himself.

“I could go into my bedroom, turn on my camera and do it my own way,” he says. “I was doing my 9-to-5 job, but for myself. And in 2012, I decided I hated my job enough that I wanted to try YouTube full-time.”

RELATED VIDEO: See How These Amazing Fans Wished Tyler Oakley a Happy Birthday!

 

Oakley’s sphere of influence has now grown way beyond YouTube — he’s written a bestselling memoir, Binge, has his own glasses line with Warby Parker and hosts a talk show on Ellen DeGeneres’ digital platform Ellentube — but the social media star admits evolving his brand hasn’t been easy.

“People are used to seeing a 3-minute, edited, fun version of me. It’s a ‘social’ job but I usually create in solitude. To go out on a stage or do a meet-and-greet is a whole different thing,” says Oakley, who embarked on a world tour in 2014.

Now living in Los Angeles, the media mogul says he makes sure to put down the phone and turn off the camera a little more than he used to.

“I’ve decided I need to step away every so often and that’s okay,” he says.

But that doesn’t mean he’s planning on letting any new opportunities pass him by.

“I want everything,” Oakley says with his signature guffaw. “Because, I feel like, why not?”