How an old-school skateboarder helps others think more creatively.

With a rebel yell!

Three days later, as we sipped green tea on the balcony of the Redondo Beach home he shares with his girlfriend, Mullen expanded on his distaste for how avarice has altered skating. “Don't frickin' skate in front of the camera, don't practice in front of the camera, don't friggin' publish it on YouTube every time you get a new trick—it's not about that,” he said as he gazed at the setting sun through wraparound shades. “If you do it for the sake of loving it, and you don't care whether you're seen or not, or paid or not, all that stuff will come. But enjoy the process! If you start doing things for the sake of selling up front, for rewards, then it's going to catch up to you. The other guys not chasing money are going to outdo you in the end, because real innovation and grit come from loving the process.”

Those sage words could easily apply to the tech industry too. Just as skaters of Mullen's generation feel nostalgic for the sport's pre-X Games era, when it was a refuge for misfits and outcasts, there are those in Silicon Valley who fear that their culture has strayed too far from its countercultural roots. “There's still at the core of the tech industry this image of transgressive rebels setting their own ethical standards,” says J. B. Shank, a University of Minnesota professor who studies the history of Silicon Valley. “But that's not really the way that world works anymore.” A place where revolutionary companies were started in suburban garages has now been overrun with business majors whose chief aspiration is fabulous wealth. And with them have come the symbols of excess that everyone loves to hate: the fleets of Google buses, the arrogant Uber executives, the entitled Dropbox dudes kicking children off a soccer field.

Concerned that the industry has ossified into something monstrous in the course of its boom, many within tech now have a yen for reminders of its more freewheeling past. “Tech has become so homogeneous, and the culture around it has become pretty stagnant,” says Holly, Mullen's primary mentor. “Media and products and brands are so easy to create that there's brand overload and media overload. So what people are craving is authenticity.” And that is a commodity that Mullen can provide like few others, for no one will ever question the significance of his contributions to a sport so steeped in cool. His true value to the tech world, then, may not be as a fount of novel ideas, of which there is already a glut in this era of social-media punditry. Instead, what he provides is much rarer and more precious: a way for Silicon Valley to validate its heroic narrative about itself. Like the lone entrepreneurial geniuses who loom large in tech lore, Mullen is an eccentric visionary who came west to seek his fortune and in doing so transformed an entire culture. Never mind that he did so as a skater rather than as a developer of software or gadgets; by claiming him as one of its own, the tech industry can bask in the sense that it still exudes an atmosphere of daring and constructive mischief. After all, if the most creative skateboarder who ever lived sees fit to spend time at your conferences and applaud your innovative spirit, then perhaps you aren't doomed to become everything you once reviled.

Silicon Valley's affection for Mullen may signal that the industry is genuinely intent on getting back in touch with its rebellious soul. Or it could just be an empty exercise in self-congratulation. A story that Mullen tells about a lavish tech party provides a tidy parable about the latter possibility. The bash took place in a newly minted zillionaire's San Francisco loft, in which the man had built a skate ramp—a testament to his outsider cred. Yet Mullen was puzzled to see that the loft's owner had placed his expensive wine collection right next to the ramp, where, despite some flimsy shielding, its bottles could easily be destroyed by an errant board. Maybe he was too rich to care. Or, more likely, he only built the ramp for show.