Jamie O’Brien Is Better than Everyone at YouTube

It’s not that the rules don’t apply to North Shore native Jamie O’Brien. They do—or attempt to, at least. But the lifelong nonconformist hardly notices as he gives the middle finger to convention and torches his own path. In the face of the WSL’s rigid guardrails and brands looking for someone to “market,” Jamie’s rogue tendencies and unpredictability proved to be too overwhelming for their taste. (Literally burning the ASP’s rule book certainly didn’t thaw any cold hearts.) 

In terms of “industry success,” Jamie never really “made it.” He was a liability that refused to play the game, and endemic brands and surf media largely ignored him. In the meantime, the freesurfing Kahuku kid kept living life the only way he knew how: finding his place within the Red Bull Media House ecosystem, and as a wildcard in whatever competition was happening in his backyard. Jamie O’Brien was living a good life, but it was about to get great.

Why? Well, in a word: YouTube.

The soft board-charging, rivermouth-riding, mischief-causing haole boy whose penchant for pranks is outperformed only by his jaw-dropping (sometimes pants-dropping) Pipe-riding talent, has catapulted himself into algorithmic-driven success beyond what any surf media, brand or organization could hope for.  

“When I got into the YouTube space, I looked at who are the heavy hitters in the industry?” Jamie said. “The WSL pumped out more content than anyone, with more than 10,000 videos — which is crazy great.” 

The World Surf League has been building its YouTube channel for more than a decade and has a whopping 674k subscribers. For reference, Billabong has 93k subscribers. John Florence has 119k. Stab has 134k (subscribe to Stab!).

Jamie only started his channel in 2018, hurling himself onto the front lines of the growing platform with a simple formula — ride waves, pull pranks, and keep pushing until you reach digital domination. It’s worked. He now has above 690k subscribers — even more than the WSL.

“The [surf industry] brands and companies don’t realize how big YouTube is, and the power of the platform,” Jamie said. “ I almost feel like they’re in denial. At the end of the day, it’s the most engaging platform on the planet.”

Engagement — views, likes, comments, shares — yields profit and O’Brien, though goofy manchild at first glance, has a Wolf of Wall Street understanding of how it all works (and how to exploit it). Advertisers on YouTube throw money to guys like JOB on a clicks-per-view or cost-per-clicks basis. The more people you can hook and the longer you can keep them watching, the more commas your next payout will have. 

And while it’s true that YouTube success alone isn’t always a big pay day — one study shows that a YouTuber with 1.4m monthly views might only make $17k a year from the platform — and that sponsored posts are where the money’s at (the same study shows a channel with 100k subscribers can make $12.5k per sponsored post), Jamie’s chosen to do his own thing. Surprise, surprise.

His vlog has an ongoing undercurrent promoting his brand, StayPsyched, allowing him to funnel his audience to his merchandise to further monetize their loyalty. He ships out 500-1,000 boardies, hats, tees, and other ​StayPsyched​ gear monthly.

How’s he doing all this by himself? He’s not. 

“We just got a small group of friends that we surf with on the North Shore. To be honest, we do have a big production as far as the vlogging world goes. I think most people think that vloggers use just one filmer and they do all the editing as well,” he says, referring to other vloggers in the surf world like Koa Rothman with 116K This Is Livin’ subscribers, Zeke Lau’s 8k subscribers with Unleashed (launched in August 2020) and Eli Olson’s 16K subscribers. 

“We have three different filmers and two of the filmers edit as well [​Jackson Lebsack and Justin Graham]​,” he says. “It’s kind of a big team. When you crunch all the numbers together, we’re putting out a lot, but at the same time, it takes money to make money and you gotta put it out there.”

Jamie’s presence on YouTube has elevated his fame as well. The charismatic 38-year-old sees his media success play out daily in real life; returning shakas to fans as young as three and chatting with every Uncle who wants to talk shop on the beach.

“The coolest thing,” he says, “is when you meet these people; they walk up to you and they’re like, ​What’s up Jamie? I feel like I know you, but I don’t. You know, we watch every video. I hope we’re not being weird​. I’m like, ​Nah, it’s all good! I know what I signed up for.”

O’Brien has figured out the value of engagement virtually and IRL.

“I don’t care if you’re up 5 million followers or you bought 2 million of ’em,” he says. “Your engagement sucks.”

It’s those clicks and that interaction that are measurable. Viewers spent 362,374,968 minutes on Jamie’s channel in 2020 alone. But his empire was built on what brands and the WSL will never have — humanity. Jamie’s convinced he’s been successful because he’s relatable—just a dude who likes to catch a few waves and drink a couple beers. After 12 years of contest surfing burnout in the early aughts, Jamie identifies with the divide between The Industry and everyone else. His determination for connection to his viewers is not only financially lucrative, but is a wealth of good feels for the kid from Kahuku who never fully fit in.

“Why do the big corporate companies pay you?” he asks. “It’s because you sell product. How are you ever to gauge who you are if you gave yourself to a big company? I don’t know. It’s weird. It’s like, there’s this big company and you can’t even engage yourself.”

JOB continues to push boundaries and push out content, building up his brand and band of followers, completely on his own terms. As Stab founder Sam McIntosh told the New York Times of surfing’s transition to New Media, “There’s more losers than winners due to the shift, but the people who have done it well carved their own path. [Jamie] wouldn’t have a career if he were waiting for Taylor Steele, Surfer magazine, or us to anoint him.” 

With a crew of friends, filmers, editors and admin helping him put out two videos a week and ship as much StayPsyched merch as needed, Jaime’s got life pretty well figured out.

“You wake up in the morning and you’ve got a friend group that is down to do whatever you want to get involved in,” he says. “Whether it’s getting one of your filmers the barrel of his life or going big-wave rafting. It’s pretty real, you know? It’s not like we’re like making this stuff up.”