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Be Relentless: Rob Dyrdek’s 7 keys to taking risks and winning big

Rob Dyrdek isn’t your average skater. He definitely isn’t your average TV star and he damn sure isn’t you average business mogul.

The journey he’s been on for the past 30 years has been a wild one and it’s far from done. But just studying the moves he’s made so far, the risks he’s taken, and the success he’s had shows one very important thing — it’s all about his mindset that he has to learn more and conquer that’s gotten him this far.

So how did a skater kid from Ohio turn out to be one of the most successful self-made businessmen today? It’s all about taking the biggest risks.

For Dyrdek, it started when he decided to make the leap of faith and dropout of school at the age of 15 to move to Los Angeles and pursue a career as a pro skater. That was just four years after he actually started skating! He knew what he needed to do and would let nothing stop him.

Rob literally sat down with his teachers and school counselors and convinced them that he didn’t need to finish high school, and he did it! It was that fearlessness early on that developed over time and helped him transition into anything he ever did.

By the time he was 16, he was already treating his career like a business — keeping track of all his board sales, solidifying his place in companies like DC Shoes, and planning out his next moves. He once said,

“When I was 16, I told people I had to treat this career like a business.”

From there he continued his relentless pursuit of perfection and when it looked like his skate career was over by 24 when DC told him that they wouldn’t renew his contract, he took that as motivation to become better than he ever was. His skating abilities improved and he made them pay up.

That moment provided the spark he needed to step out of his comfort zone as a skater and start to push the limits to become something truly great. Whether it was opening a new skate shop or trying his hand at a bunch of different business ventures, he made a name for himself that eventually caught the attention of MTV execs.

By 2006, he starred in his first show Rob & Big and his public persona took flight from there. Soon he was able to master the craft of reality TV, which led him to start his own syndicated series for Fantasy Factory and Ridiculousness.

Over the years Rob has invested in a ton of businesses, made some mistakes, and learned some valuable lessons. This also led to him launching his own VC company called the Dyrdek Machine where he invests in insane ideas and likeminded individuals not scared to take risks just like him.

Now, as a married man, a father, and 43-year-old man who’s conquered more than anyone could’ve imagined, many wonder what could be next? The answer is whatever the fuck he wants.