Tyler Oakley applied for a job at Google and got rejected. Now he has a media empire on YouTube

Since 2007, Tyler Oakley has lived a portion of his life on a screen, building a following of over seven million subscribers on YouTube.
During his senior year in college, he applied for a job at Google and got rejected, so he had to get creative. He turned his YouTube vlog into a career.
He's now sharing some of what he learned along the way, mentoring a young woman through the McDonald's "Where You Want to Be" initiative.
Oakley shared some of his career advice with Business Insider.

Sometimes, Tyler Oakley just needs some alone time.

Since 2007, Oakley has lived a portion of his life on a screen — building a following of over seven million subscribers on YouTube. He began vlogging in college at Michigan State University, and that vlog has turned into a media empire.

"At the end of the day, I still very much feel like just a Michigan boy that gets to live this crazy life and dream," he tells Business Insider. Oakley is an author, YouTube and documentary star, podcast host, LGBTQ activist, and a role model for countless people who follow him across social media.

Oakley made his name through his weekly YouTube videos, which feature everything from interviews with former US secretary of state Hillary Clinton, videos answering viewer questions, and a series called "Chosen Family: Stories of Queer Resilience." His most-watched video to-date is "The Photobooth Challenge" featuring Miranda Sings, which has more than 13 million views.

And now Oakley is a mentor to a young McDonald’s employee named Kaila as part of the fast-food giant’s "Where You Want to Be" initiative, which aims to "connect the skills they learn on the job with the education, tuition assistance and career tools available to take the next step in their professional journey."

Through this initiative, some McDonald's employees get to team up with an influencer in the fields of arts and entertainment, technology, entrepreneurship, healthcare, and restaurant and food service. (McDonald's also hopes to use this initiative to highlight new career advice tools on its Archway to Opportunity.)

If you’re a loyal viewer of Oakley’s videos, it’s not surprising that Oakley teamed up with McDonald’s. He got his first job at the fast-food chain, and in 2018 during his "Going Home" series, he worked for a day at his old store — and in a role-reversal, Kaila was in charge of training him.

On this mild January afternoon in Los Angeles, Oakley enters a conference room that has a sterile glow and bright white furniture. A phalanx of people file in, and the interview looks more like board meeting at a millennial-run startup. Oakley, dressed in a gray T-shirt and blue jeans with dark grey rimmed glasses, sits at the head of the table. He has a boyish look, and two tattoos are visible on his right arm (an owl and an acorn).

In person, Oakley isn’t far from his YouTube persona. He’s funny, attentive, and disarmingly nice — complimenting my shirt, and telling me that he feels like we’ve met before, though we haven’t. But he’s also more subdued. He’s spent the day walking Kaila through his work schedule and taping his weekly podcast "Psychobabble" with Korey Kuhl. Completing the synergy, Kaila and Oakley's day was captured in a McDonald's-sponsored video.

And now he has 15 minutes to talk to me. Ready? Go.

In the spirit of Oakley’s new role as a mentor, we decided to ask him for some career advice. Here’s what he had to say:

Oakley says he uses his mornings to focus on the day ahead

He wakes up at 7 a.m. (without an alarm clock), and he hits the gym.

“Every morning when I'm alone waking up in my bed, I'm like, ‘Hey, how do I envision my day?’ ‘What do I have on my schedule?’ and “How do I want it to turn out?’" he said. "Like, that type of mindset is really important."

Teamwork is key to doing 'things bigger and better and more effectively'

As important as alone time is, teamwork makes the dream work.

"When I decided to try and attempt going full-time YouTube, the biggest learning lesson I had was you can do it alone, but you can do it so much bigger if you bring people in who are experts in many different things that maybe you're not an expert in," Oakley explained.

He likens it to his first job at McDonald’s — you need a "team of competent people, who respect the job, and who respect each other” to accomplish a bigger goal.

Taking responsibility goes a long way

Taking initiative is important, whether you're part of a team or directly responsible for your own success, Oakley says.

"I think a skill that goes so underrated is just learning a sense of responsibility," he explains.

In his YouTube career, self-motivation has been a major driving factor.

"It takes somebody who is a self-starter and understands that my successes and my failures are my responsibility," he said. "And so whether I get up in the morning and I decided I'm going to film today or not that's my decision. And to understand the responsibility of 'OK, well if this is going to be my career, I need to rise to that occasion.'"

The importance of authenticity

While being vulnerable on his YouTube channel, or being an unabashed fangirl on Twitter may seem specific to Oakley’s job as a media personality, the basic concept of authenticity can be broadly applied.

"The best I can be as a creator depends on me connecting with people, and if I don't share and be vulnerable in a meaningful way, what can people connect with?" he posited. "If I'm saying the most vague things that can stick against every wall, then what makes the connection deep between me and the consumer of whatever I'm making?"

Being able to learn and pivot from rejection

For Oakley, not getting his dream job doing ad sales at Google forced him to get creative. In his own words, Oakley had "all of his eggs" in the Google basket, and he was "devastated" after getting that rejection, several weeks before Christmas during his senior year in college.

But the crushing moment also "made me open my eyes of what I could possibly do elsewhere," he said.

"I had always thought I was just going to work at a desk, sell ad space on Google, and never in my mind — because I thought for so long that that's what I was going to be — never in my mind did I think, 'oh maybe I could do something in entertainment, or do something in writing or do something like this,'" he said. "If I had gotten that job, I never would have been creative with what I could do."

'My favorite thing that I tap into is alone time'

When asked if there is anything he can’t live without, Oakley says "alone time." And after living so much of your life on the internet, it makes sense that Oakley would need time to recharge.

"I feel like it is so underrated, so underappreciated." Oakley said. "Time with myself, time with my thoughts. Because when you're around somebody, around people all day long — including when you're on your phone, because when you're scrolling you are virtually surrounded."

"To give yourself space from everybody and everything lets you really kind of center and refocus."

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