Strategy

The Best Way to Create Luck


Rob Dyrdek went from a high school dropout to become a world-renowned skateboarder, media mogul and founder of a new sports league. His success, a story of taking opportunities and leveraging small successes into larger ones, has lessons to teach anyone looking to build a career.

Rob took his credential as an early professional skateboarder, expressed a message that resonated with a small tribe, said yes to going deeper into media, and eventually served that expanded tribe with a legitimate platform.

Leverage from Strength

Rob’s first leap emerged from a frustration. He was a professional skateboarder, but those early years weren’t especially lucrative. Worse still, practicing his craft required trespassing and having altercations with security and police. Frustrated by their continuous interference, he made a mockumentary style video in which he hired a security guard to guard against security. It was intended as a one-off and to make a point, but in today’s terms it went viral. As he said in last night’s “Real Sports with Bryant Gumbel” that was the start of his side-gig became his main gig.

The video’s success caught MTV’s attention. He was signed to create a reality TV show (an early Jack Ass model) in which he and his side-kick security guard put themselves in ridiculous and entertaining situations. The pretext expressed a fundamental skateboarding ethos and he gradually became the media representation for a community. The success of his voice then grew that community. With each new venture, he found a way to blend boyish hilarity with increasingly serious entrepreneurship.

That first MTV show eventually expanded to four. He adapted to changing media preferences (shifting from creating his own videos to featuring and sharing crowd-sourced videos) and even targeting a younger audience with a cartoon series about skateboarding friends.

He used each success to create a safe foundation for more experimentation which drove his next investment of time and energy.

Most recently Rob launched a new sports league (Street League) to finally give skateboarders a platform for professionalization (and earning potential) beyond the periodic X-games. He devised a clever points scheme and course layout that heightened the stakes for each skater’s performance–each run had the anticipation of a Hail-Mary or walk-off homer. The league now enjoys sellout crowds across the country and has likely enhanced the career legitimacy of skating for kids (and their parents) across the world.

Place Bets and Say Yes

What I liked so much about Rob’s story was that he experimented freely and took advantage of opportunities whenever they came. As we grow our careers, we all should be experimenting with what we love, trying new ways of expanding those skills, and investing in what gets traction.

Rob took his credential as an early professional skateboarder, expressed a message that resonated with a small tribe, said yes to going deeper into media, and eventually served that expanded tribe with a legitimate platform.

The Main Lesson: Continually experiment with what you’re good at, find ways of sharing it, and say yes to small opportunities to grow it. Don’t wait for the big opportunity, create it instead.