The skateboarder and businessman Paul Rodriguez sat on a restaurant patio not far from the Santa Monica Pier when a movie crew member tapped his shoulder.
"Hey, guys," the man said. "They just put 500 bucks on Buchmann to ollie the stairs!"
A small crowd had gathered nearby to see if he could launch both himself and his board into the air, but the trick was to do it while falling downward. At the top of a concrete staircase, cinematographer James Buchmann, from the skate movie they were shooting, "We Are Blood," was building up his courage.
Rodriguez's eyebrows shot up.
"Oh no," Rodriguez said, grinning. "That's dangerous."
After an aborted first attempt, Buchmann was stalling. He paced out a few more steps from the edge. Rodriguez, watching, said, "Man, I'm scared."
Buchmann pushed off hard and made a heroic attempt through the air. For a moment, it seemed he might make it. The crowd broke out in cheers.
Then it fell silent.
Buchmann didn't quite make it.
"Ouch," Rodriguez said.
This is pretty much how Rodriguez has been spending his time recently. It's decidedly atypical for someone who started his own company and is worth millions in sponsorships.
For Rodriguez, it is part of a journey to answer one of skateboarding's lingering questions. When must a skater stop skating?
That question helps explain why he's here in Los Angeles, filming this movie, skating in the Dew Tour that arrives downtown Friday, and generally goofing around with dudes like Buchmann (who soon limped away without major injury).
Rodriguez, 30, is both the most famous active skateboarder in the world … and a bit on the old side. He has been skating professionally since he was 14, has filmed skate videos around the world and has won years' worth of competitive skating medals.
Ty Evans, Rodriguez's director in "We Are Blood," said Rodriguez is "one of the very first people that have crossed that bridge between core and non-core skateboarding and brought skateboarding to the masses."
As filming was wrapping up, Rodriguez began musing on stagnation. One morning, he said, he woke up and wondered: What's next?
"You reach a point where, like, what's motivating me?" Rodriguez said.
In the past, many skaters with his resume have scaled back in favor of more entrepreneurial ventures. Rodriguez has the cachet to do the same: Last year, Sports Illustrated called him the "Michael Jordan of Skateboarding."
It is an unusual career arc. Jordan, after all, didn't retire early to start running his shoe brand.
"As skateboarding developed, all these guys build a name for themselves and then they can move on and start their own businesses," explained Chris Colbourn, a 24-year-old skateboarder who costarred in "We Are Blood" and will also compete in the Dew Tour.
Rodriguez did start his own company, Primitive, and has expressed a desire to build an empire.
Despite the anxiety over stagnation, Rodriguez decided he wasn't ready to give up skating.
"I'd feel lost," Rodriguez said.
This presented a problem. He still loved the sport, but he had grown bored with the routine of movie-competition-movie-competition.
And so began Rodriguez's contemplative period. How would he maintain his drive?
The first traces of an answer came from sushi.
Specifically, it was a documentary that followed a master Japanese sushi chef, "this dude" in his 80s who was completely dedicated to his craft, Rodriguez said. His standards were painstakingly high. The best fishmongers held out their best fish for him. He thought of little else.
"He literally goes to sleep and dreams about it and he'll wake up with a new sushi roll in mind or a new dish that he'll want to work on," Rodriguez said.
When he was younger, Rodriguez would lie awake thinking of his next trick, playing it in his mind until it felt right. He decided to chase that again.
Rodriguez still has shoes to sell and skateboards to hawk. But his career path has tilted to what drew him to the sport initially, when he'd skate a place so often he'd know the feel of its pavement and the tilt of its rails.
"We Are Blood," which was to premiere Thursday at the Ace Hotel, felt right to him because it was a big-scale movie with a small crew. They traveled across the world, and filmed on top of skyscrapers, but he had enough time to hang and watch as a crew member ollied over his first water bottle.
"He was looking for something else in this film," Colbourn said.
Rodriguez said he found it.
Rodriguez still averages at least three hours of skating daily, but he knows his career will end eventually. He hopes that will be far in the future.
While filming the movie, he was more preoccupied with the next day's schedule. He obsessed over every detail, as he once had.
"It's torture, man," he said on one of the film's final days. "It's torture. Like I won't fall asleep because I'm thinking, thinking, thinking, dreaming, dreaming, dreaming, envisioning a trick, envisioning a trick. And I can't wait until tomorrow, because I want to try this trick."
He smiled, and added, "And I won't go to sleep all night."