It’s the curse of the YouTube personality. Amass over 20 million fans across various platforms, have an audience with Barack Obama, and appear on the cover of a major magazine and still leave most of the country hearing your name and wondering, “Who?”But with YouTube supernova Tyler Oakley leading the way—his luminescent shock of white-gold hair and megawatt Cheshire Cat grin surely the guiding lights—#TeamInternet, as he affectionately calls his peers and their loyal fans, is steadily marching towards legitimacy.The 26-year-old openly gay Michigan native posted his first video on YouTube eight years ago, an awkwardly shot greeting card meant for just his close friends that accidentally amassed around 100 views. Now, he may be the first person to have screamed, “Yaaas queen!” at Michelle Obama while interviewing her with blue hair.“When I started doing it in 2007, nobody had a million views,” he tells The Daily Beast, rambunctious after a flight back home from Australia, where he concluded the international leg of his Slumber Party tour, on which he meets fans and chats with them while everyone wears pajamas. “The most subscribed person I remember when I first started might have had 40,000 subscribers or something. Now you can really be in charge of your own trajectory.”For Oakley, that means an unexpected career as the gay BFF of millions of hashtag-wielding Internet fiends, the majority of whom might be found beaming with their glistening orthodontics at the two “vlogs”—video blogs—Oakley posts each week. It’s a following that’s led to Oakley being named one of TIME’s Most Influential People on the Internet and described by OUT magazine as the leader of “The Cult of Oversharing.”With his name garnering a bit of media omnipresence and Oakley himself appearing on traditional TV outlets and even as a guest on Ellen—Oakley refers to DeGeneres as “my queen and also my doppelganger and we are twinsies for life”—it’s hard to shake a feeling that #TeamInternet is on the cusp of a mainstream crossover.Certainly an indication of this is this year's Streamy Awards, which recognizes excellences in online video and is in its fifth year. This year’s lineup is the best example yet of the marriage between this community of online stars and old-school Hollywood entities, with names like James Franco, Weird Al Yankovic, and James Van Der Beek joining Oakley and his Internet famous brethren as nominees.For the first time, the awards will be broadcast on actual television, with its telecast airing Thursday night on VH1, a curious case of online awards airing on actual TV. Oakley, who won Entertainer of the Year at last year’s ceremony, will co-host the proceedings with fellow YouTube-to-mainstream crossover success Grace Helbig.And the timing of the awards is certainly noteworthy, too, taking place just days before the 2015 Emmy Awards, which honors more traditional television entertainers. Are we on the verge of an old vs. new turf war? “I think that it’s been pretty evident for a while now how traditional [media] has wanted to go a little digital and digital has wanted to go a little bit traditional,” Oakley says about the awards shows’ timing. “I think we’re all meeting in the middle. The lines are getting blurred, and the fact that the Streamys are on TV this year shows how much that audience is there.” As a pure numbers game, it should make total sense that the Streamys are getting a telecast as legitimate as the Emmy Awards. Oakley alone has over 7.5 million subscribers to his YouTube channel, which is multiple times the average viewership for most of the shows that are nominated for Emmys. Mad Men averaged just 2 million viewers in its last season, for example.In an entertainment industry fraught over the splintering of viewers and declining ratings, #TeamInternet has an astronomical reach.But numbers don’t always add up to credibility. (Donald Trump is leading the GOP polls, after all.) Despite his millions of followers, sphere of influence, and validation in various business pursuits—Oakley has a book, Binge, set to be released next month and turned his predilection for Taco Bell into a legit business relationship—there are still hurdles to jump before he’s taken seriously, at least in some circles.Perhaps a modicum of skepticism from “traditionals,” as Oakley refers to those who are dubious of the influence of digital media stars, is justifiable when one considers how hard it is to really describe what exactly he and hordes of YouTube personalities like him do for a living.He’s a self-described “professional fangirl,” with many of his vlogs dedicated to quick-witted and ebullient gushing over his favorite celebrities, chiefly Darren Criss and One Direction. You know when your mom says things like, “Why would I join Twitter? I don’t need people to know what I ate for dinner.” Oakley’s YouTube channel is, in some respects, just like that.He’s mastered the art of the confessional, and figured out the power of authenticity and dialogue. Oakley’s videos alternate between breathless recaps of his week and Q&As with his followers about everything from whether he will see a movie coming out the next weekend to what age he was when he lost his virginity—he was 18 and it was on St. Patrick’s Day.Basically, it’s just giddy talking, but with a candor, accessibility, and sunniness that vacillates wildly between silly and serious with nimble ease. It’s a quality that online communities clearly crave from role models and weren’t getting from the PR-controlled TV and movie stars who stand on glamorous pedestals. It may be all the more powerful coming from Oakley, a person who is unabashed and unapologetic about his gayness.Sure, it’s nice to have the Tiger Beat poster pulled out of the magazine and plastered onto your wall, but it’s even better when the person on the poster will talk to you—like, directly to you and share, or at least be willing to talk about, all of your concerns.In a video uploaded just last week, Oakley posits, “me being me may have even helped some of you guys be you.” It’s almost insufferably cheesy, were it not completely accurate. (Again, this guy has an international tour to prove this.)It’s an influence he takes seriously, too, having parlayed his YouTube influence into advocacy for the Trevor Project, not just speaking on behalf of the organization, which fights bullying and prevents suicide of LGBTQ teens, but often fundraising for it through his channels. Two years in a row, he raised $500,000 for the organization.“I understand that with the audience comes a sense of responsibility,” he says. “Although I’m there to entertain, I also want to make sure I’m using my opportunity in the best way possible. Because although I don’t have an obligation, necessarily, I feel like it would be a missed opportunity if I didn’t try using it for good.”That’s especially true when it comes to young gay people. He thinks about being from a small town now versus when he was growing up and coming out. There may have been no opportunity to seek guidance from an openly gay person then. “Nowadays if somebody in America is feeling alone and wants to find a coming out story, they just search ‘coming out’ and they’ll find millions of first-person examples of people telling their story,” Oakley’s included.If it sounds a little bit like teenage self-help, it might be just that. The swift rise of Oakley’s YouTube channel—and his fame and sponsorship deals (watch how seamlessly he weaves product integration into his videos)—might be simply because teenagers are rabid for self-help, or at least affirmation or acceptance, and thrilled to have found easy access to it on the smartphones their thumbs never leave.“I think social media has amplified a lot of voices that maybe traditional media hasn’t perfectly portrayed,” he says.Further proof of this community’s influence on the culture at large—not just the thriving online community that turned these personalities into stars—is the conversations the content created by these people are starting.There certainly was evidence of that with the response to Oakley’s “It Gets Better” video, but it’s never been more evident than with the current firestorm surrounding YouTube comedian Nicole Arbour, whose “Dear Fat People” video has been criticized for its aggressive fat shaming.(Sample line: “I don’t feel bad for you because you are taking your body for granted…What are you going to do, fat people? What are you going to do? You going to chase me? I can get away from you by walking at a reasonable pace.”)Arbour has since defended the video, which seems a cardinal sin according to the Bible of positivity and anti-bullying that #TeamInternet seems to worship and live by. Oakley himself had just spoken about his own past eating disorder to Seventeen magazine when Arbour’s video was published.“As somebody who has gone through body image issues and who has been pretty vocal about all that and trying to amplify voices in other communities going through that, it’s disheartening that somebody could make content like that and deny responsibility,” he says.“I feel like everybody, whether you have one follower or a million followers, has an opportunity to either positively or negatively affect people,” he goes on. “I’m the first to appreciate and accept growth, if that were to come from that creator, but from what I’ve seen I haven’t seen anything like that. But it can take time. Not everyone is born with a sociology degree. It’s just disappointing sometimes when people who have a lot of influence are a little bit resistant to growth.”It seems appropriate, particularly with the Streamy Awards—basically the online Oscars—approaching, that Oakley, the event’s co-host is speaking a sort of State of the Union on all issues related to YouTube.The medium is a red-hot conflagration kindled by all the ambitions that seem to drive young people today: confession, community, candor, self-branding, and self-marketing. It’s selfishness and selflessness rubbing together like sticks: I going to make money by just being me; also, I’m going to help people. And if the community is generating heat, Oakley is the star that is most on fire.President Obama seemed to have gotten the smoke signals. He invited Oakley to the White House as part of a group of YouTube influencers he hoped would help his administration get more young Americans signed up for the Affordable Care Act.But more visibility breeds even more criticism, as Oakley has learned throughout his ascent (he says he’s been accused of “acting gay and putting on a lisp” for views), and so his White House visit brought even more scrutiny to the idea that he should be taken seriously.“To me it was like, oh my god, the most powerful person in the world cares about me and my peers and what we do and how we connect with our audiences and is wanting to learn from us? It boggled my mind,” he says. “It was a cool moment, but even then people were like, ‘Why is he wasting his time with YouTube blah blah blah?’ Whatever the success might be, there will always be people that don’t get it.”Thursday night’s Streamy Awards then, in which Oakley is not just hosting, but hoping to repeat his Entertainer of the Year then, is one more crucial step in that direction.