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It takes a lot to keep out of the water. But last March, the pro surfer and his crew were getting skunked by some of the worst surf conditions seen on the Oregon Coast—50-mph winds, lashing hail, and line after line of pounding 15-foot waves. The boys gamely tried to paddle out, but even O’Brien, a Pipeline Masters champion, couldn’t make it past the break for the first time in a surfing career that started at age three. “I almost made it, but at the moment I asked myself if it was even a good idea, I didn’t make it out,” says O’Brien.

From the shelter of his RV on shore, he turned to social media in search of an alternative. To his 684,000 Instagram followers he posted: “We really want to try to surf a river wave! Would be stoked if you guys could recommend anywhere we can hit up!” On the advice of one of O’Brien’s local fans, they pulled up to a wave on the Clackamas River, in the Cascade Mountains southeast of Portland, for O’Brien’s first go at surfing a mountain river.

Although he was a regular on the pro tour by age 18, O’Brien’s considerable fame stems more from the web TV show he created five years ago with Red Bull, called . The 10-minute episodes follow Jamie and his crew, including his best friend Sean “Poopies” McInerny, around the world as they search for epic waves. Some of the series highlights include waterskiing massive waves on Oahu’s North Shore, tandem rafting those same waves, and surfing the fearsome Teahupo’o wave in Tahiti while lit on fire. This trip brought them to Oregon for an RV-powered multi-sport adventure: from surfing along the coast to snowboarding on Mount Hood with all their gear in tow. And in the best JOB style, they weren’t going to let the weather get the best of them.

At the Clackamas, the foursome took turns ripping it up on their new friend’s specialty river surfboard, which is a little wider and fatter than an ocean board. “The forest and clear water were really cool,” says O’Brien.  “I was also really impressed by how powerful the river is—it was a little overwhelming.” They each tried to catch the wave in a “sumo tube,” an inflatable orange cone you climb inside and “wear” like a suit (and is usually towed behind a power boat). Then they pulled out one of their favorite toys, the Supsquatch, an enormous 16-foot inflatable stand-up paddleboard that they’ve been using to surf iconic breaks the world over. “Neither worked very well,” says O’Brien, “but we had a blast.”

The upside of the storm that thwarted O’Brien’s coastal surf was that it hammered 11,250-foot Mount Hood with fresh powder. An incredible 74 inches fell in 72 hours—more than an inch and hour for three days. The Who is JOB crew drove northward toward Mount Hood Meadows to join the resort’s famous RV encampment, where a dozen RVs filled with diehard skiers congregate during every storm. But it was snowing too hard for the boys to make it. In the stormy darkness, they pulled over just downhill of the resort in the town of Government Camp and then fired up steaks in the RV to fuel up. In the morning, the crew feasted on the epic powder until they had had their fill.

“One of the best days I’ve had,” says O’Brien. “They sandbagged me with a 20-foot drop they said was just five, and I ate it, but no problem—it was all powder.”

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