Of the surfers who chose the alternative content route to a surf career, Pipe master Jamie O’Brien has arguably been the most successful. Photo: Red Bull
In the digital age, no freesurfer has figured out the media landscape quite like Jamie O’Brien. The 42-year-old Pipe master forged a new path of content creation outside of competition, amassing 1.3 million YouTube subscribers — as large as the WSL’s account.
Hacking the social media algorithms led to launching a mini surf empire that has grown into brand partnerships, podcasts, surf schools, soft-tops, and apparel. While O’Brien says some months his YouTube monetization alone can bring in as much as $40,000, he views the platform more as a vehicle to grow his brand, not a primary source of income.
“I always looked at YouTube as, it takes money to make money,” O’Brien said. “Don’t get me wrong, there have been months where we make a lot of money, and months we don’t. It’s expensive. So long story short, I’m not making a ton of money on YouTube, but using it as a platform to leverage my brands.”
A slow month of monetization might only produce $5,000, O’Brien said, not enough to cover the costs of his team. He has two employees on salary, one shooting from the land and another with a drone, and he has to pay for flights and accommodation when they travel.
Over the eight years since he left his Red Bull series to launch his own channel, O’Brien has learned a lot about how YouTube pays its creators. For example, he’s noticed that the CPM (how much an advertiser pays for 1,000 views) varies seasonally, peaking in the summer and again at the end of the year around Christmas and Black Friday. Other tricks, like avoiding swear words and creating longer-form content, can lead to better payouts.
“If every video did 500,000 to a million views, I would tell you straight up, I’m making great money,” O’Brien said. “But sometimes it’s 80,000, 150,000, or 200,000, sometimes you have a horrible month and can’t go over 100,000.”
“There are a lot of moving parts. You can’t control it,” he added. “I learned to understand that you got to ride the wave. When the waves are there, you’re ripping. When the waves are gone, just enjoy it. Keep riding. It’ll come around.”
For O’Brien, the world of content creation is a fluid lifestyle. While he has ideas of places he wants to go, most of the content is adapted on the fly according to swells. And even as a creator with over a million subscribers, it’s hard to guess which content will perform well.
“The algorithm’s a beast, and you’ll never figure it out,” O’Brien said. “It’s all a roller coaster. You never really know what’s going to perform. It’s coming up with a content concept and an idea, trying it, and then if it doesn’t work, don’t do it again.”
O’Brien says he sees his content trending towards a “less is more” principle — putting more production effort into higher-quality videos. However, he notes that he wants to keep it vloggy and relatable.
Few know a Pipeline pit as well as O’Brien. Photo: Red Bull//Ryan Miller
Even though his dad pushed for him to compete and become a world champion, O’Brien said he was always inspired by the approach of Hawaiian surfers like Bruce Irons: filming at the best waves in the world. He credits the values learned from surfing to his success as an entrepreneur.
“I’ve always been driven,” he said. “I’ve been hungry. I’ve worked hard to carve out my place in the industry. I like the grind.”
With an entrepreneurial mindset, O’Brien opened his first surf school at Turtle Bay on Oahu’s North Shore in 2021. Then he opened schools in Waikiki, Maui, and San Diego. In 2024, he added another branch to his empire and launched a podcast in partnership with Mason Ho, whose personality made him the perfect partner.
“You want to see Mason win his heats because you want to hear him in the interviews,” O’Brien said. “When he speaks, he speaks golden. It’s super fun having Mason on board.”
According to O’Brien, the podcast has been particularly successful in retaining audiences. The average view duration is 20 to 25 minutes, compared to the seven-minute duration of a typical 20-minute vlog. He splits the podcast earnings with Ho 50/50, which he calls a “win-win” because he gets to host the content on his YouTube channel.
When O’Brien was starting his channel, he says he encouraged other surfers like John John Florence, Nathan Florence, and Koa Rothman to start building their audiences as well. He joked that he’s done giving step-by-step advice, but for those starting their channels in 2026, the landscape is tricky.
“It’s a hard road to grow a YouTube channel,” he said. “I’m not saying don’t do it. Collectively, there are already so many (channels) out there that it’s hard to engage and entice someone to subscribe to yours.”
And he notes that making a living in the surfing industry, whether producing content or competing, is also getting increasingly harder.
“I think collectively, there’s only a handful, maybe three or five surfers, making over a million dollars a year,” O’Brien said. “Ten years ago was a lot different. There were probably 15 people. It’s getting harder and harder to make good money from pro surfing. I’m just grateful for the time that I’ve been in it, because it ain’t getting any easier, and the talent’s only getting better.”
O’Brien says he’s grateful for the life he’s built through leveraging YouTube. Photo: Red Bull//Jake Marote
He does have one piece of advice that he’s learned doing business: don’t burn bridges in the surf industry.
“The industry is small,” he said. “One guy will work at one brand, then he’ll leave and go work at another brand. Word travels fast and far. So hold yourself accountable.”
While O’Brien says it bugs him if he misses his self-imposed Monday video upload deadline, he doesn’t feel any pressure to perform.
“I look around, and I’m like, ‘This is so sick,’” he concluded. “It’s always been the goal to get some of the best waves in the world. I’ve done that, and we’re continuing to do that. I got a great group of friends to do it with and share the lineup with, and I got a beautiful family. Life’s good.”
