ORLANDO, Fla. — For the past 10 years, Ricky Dillon, 27, has documented every major moment of his life on YouTube.
He started posting videos when he was a junior in high school — funny music parodies at first, then more personal stuff. The concept of a YouTube star was still in its infancy; his peers who knew about his channel bullied him.
“Back then you made videos for no one,” Mr. Dillon said. “People didn’t get it.”
By the end of 2010, he had amassed 50,000 followers; in 2012, the count was up to about 200,000. That year, he and six of his internet friends started Our Second Life (O2L), a collaborative YouTube channel. They had watched each other’s videos from afar — Minnesota, Texas, California, Alabama — and thought that together they could build a much bigger following.
The boys moved into a sprawling home in Los Angeles in 2013, paving the way for collab houses like the Team 10 house, 1600 Vine and Hype House, and embarked on a 19-city tour across America the following year. Thousands of fans came out to meet them. The group won a Teen Choice Award. Their subscriber count spiked to 2.5 million.
It all seems a bit quaint compared with how quickly young creators are able to become famous and financially independent in 2020.
“It’s a night-and-day difference between then and now,” Mr. Dillon said. “It’s become a cool thing.”
He was speaking in Orlando, Fla. He had traveled there from Los Angeles for Playlist Live, an online-video convention now in its 10th year. When Mr. Dillon first began attending Playlist, YouTubers and their fans were still an emerging community. There wasn’t a lot of money in it.
After O2L disbanded in December 2014, Mr. Dillon reinvented himself. He released 20 original songs, a music video with Snoop Dogg, a memoir and a card game called Ricky Dillon’s Twisted Truth or Dare. He also kept posting videos to his personal channel, taking part in viral challenges and recounting hilarious stories from his daily life.
More recent times have been tough, he sad, noting that 2018 and 2019 “were dark years for me.” Mr. Dillon had financed his music videos himself and spent carelessly, eventually landing in financial trouble.
“I hired a team to pay my taxes in 2015, and I was under the impression they were being paid,” he said. “I don’t know what happened, but three years rolled by and I hadn’t paid. All of the sudden I had to pay all these taxes off.”
He was also coming to terms with his identity. Growing up, he didn’t believe he was allowed to be gay. “So many times I didn’t want to make videos because I was in a dark place,” he said.
Just days before arriving at Playlist, Mr. Dillon came out to his fans in an emotional video. Brandy Smith, 18, said she was inspired by his authenticity on social media. “His confidence made me think how much confidence I could have,” she said.
At the convention, Mr. Dillon assumed the role of sage elder. According to the event’s organizers, 70 percent of the creators in attendance were first-timers, many of them newly TikTok famous. For Mr. Dillon, Playlist was one in a long line of public appearances.
“A couple years ago I started to feel like, am I going to get too old for this?” he said. “But people like Shane Dawson are paving the way for older people.” Mr. Dawson, 31, has been a mainstay on YouTube since 2008 and is one of the most prolific YouTubers working today.
Aside from a stint in retail — he was a sales associate at PacSun in high school — Mr. Dillon has never had a traditional job. However, maintaining momentum in the online video world can be cutthroat. Some influencers start fights or engage in cruel pranks for views. Mr. Dillon has steered clear of controversy and become somewhat thrifty.
In addition to running his YouTube channel, Mr. Dillon has recently taken on a part-time job editing videos for the 20-year-old Dolan Twins, which helps him pay the bills.
“When you stare at your own face for eight hours, it’s hard,” he said. “When I edit for them, it’s fresh material. It’s not myself. It’s a new way to be creative.” He lives on a quiet street with a roommate, his dog and a pet pig. Between shooting and editing, he works out and binge-watches TV.
Mr. Dillon said he’s finally feeling positive about the future for the first time in a while. The money from editing has freed him up, so he doesn’t have to upload or post when he doesn’t feel like it. He wants to release new music. He’s been experimenting with TikTok.
But he no longer feels the need to keep up with the latest thing. Throughout the conference, while most of the attendees were glued to their screens, he posted only one photograph to Instagram. In it, he is surrounded by flowers with a slight smile on his face.
“I used to feel really pressured to post the whole weekend,” Mr. Dillon said. “Now I just enjoy the ride.”