He drops into a 15-foot wave — almost three times his height — his bright pink board disappearing in the dark barrel.
The lip of the wave curls around him, so large that it forms a perfect funnel around his silhouette.
Whitewash forms at the base as the waves crash upon each other. And then he shoots out the other end. It’s like the wave spits him out as the pressure of the water and the air in the barrel compress, leaving nowhere to go except out, bringing him with it.
Jamie O’Brien, or more fondly known as JOB, leans back off his pink board into the water as the barrel dies and another scene of him surfing a barrel comes on the screen, which was set up right in the back of the Hotel del Coronado’s Beach Village on Aug. 10 for the premier of his latest film, “Chasing the Dream.”
Who is JOB
O’Brien was a pro surfer who grew up on Oahu’s North Shore, with the Banzai Pipeline — one of the most famous surf breaks in the world — in his backyard. In 2004, he won the Rip Curl Pipeline Masters at 21, becoming one of the youngest surfers to surf one of the most notorious surf contests at the Banzai Pipeline, and he continues to be active in the surfing world and the online world today.

His YouTube channel has over a million followers where his sponsorship with Red Bull is featured in his videos as he surfs while being set on fire and slides down one of the largest storm drains in Oahu.
The film, “Chasing the Dream,” which documents the last two years of surf trips to places around the globe like Japan, Africa and Tahiti, drew about 400 people to the beach outside of the Hotel Del.
But with all the countries he’s traveled to, O’Brien said he finds himself thinking about Southern California – which is why he wanted to start his surf school in Coronado.
The Jamie O’Brien Surf Experience
His surf schools are known as the Jamie O’Brien Surf Experience, and the Coronado school was started in July of 2023. His surf schools offer group and private lessons at their respective locations to anyone who wants to surf.
“It was cool to partner with the Del here with the surf school and, kind of, just show the world that we’re here as well as give back to all the fans,” O’Brien said as he signed posters. This was his first time hosting an event on the island.

Hundreds of fans lined up on the beach, holding surfboards, skateboards and other knick-knacks they wanted the pro-surfer to sign as the sun set behind them.
O’Brien was supposed to sign posters for just an hour before having an open invite paddle out before the debut of his film, but he signed posters for almost three hours, going through around 300 posters.
O’Brien has opened up other surf schools, two in Oahu and a third just this last year through a partnership with the Del.
“Southern California is such a large market for me and my demographic,” O’Brien said, adding that he chose Coronado because of the surf culture in California and the beginner-friendly waves.
And he wasn’t wrong about his demographics as hundreds of surfers and fans gathered for the event.

“Grab your seat and get psyched,” O’Brien said.
His fans yelled and whooped as scenes of him surfing barrels, cutting in and out of waves and spraying powder on his snowboard on the slopes of Japan played to hungry eyes.
The “Chasing the Dream” premier was two years of surfing in a 25 minute adventure film, and not one second was wasted for the Jamie O’Brien Surf Experience.
“It’s a good life,” O’Brien said.
Those interested in taking part in the Jamie O’Brien Surf Experience can head to his website to book classes at https://www.jobsurfexperience.com/san-diego/.

