Rob Dyrdek grew up in Ohio (not the typical skateboarding Mecca), and after discovering the skateboard became ingrained in the small but passionate local skate scene. Quickly becoming a pro, he moved to San Diego to engulf himself in the real skateboarding Mecca at the time, San Diego, and received lucrative sponsorships.
Most interesting about Rob’s rise to wealth is that during his early career he would negotiate a small equity stake in his sponsors (similar to Jay Z’s approach when dealing with interested record labels). After this, Rob began to branch out his business enterprise but was unsuccessful in his first few ventures, one of which was a skateboarding retail store (similar to Mark Cuban’s first few ventures failing).
In this video below from Inc., Dyrdek describes his upbringing, and also some of the important lessons he learned while pursuing different business opportunities.
One of the first ventures to really burst Rob’s popularity and exposure was to apply a proven business method to a new demographic. Rob decided to create his own brand of DC shoes within the DC shoe umbrella, similar to how Jordan or Kobe would do this with Adidas or Nike. The Dyrdek brand shoes were a hit.
Rob’s next successful venture was birthed from the fact that he was constantly being harassed by security guards for skating on private property. Thus Rob decided to hire a security guard for himself, now known as Big Black, and create a video to capture all the ridiculousness. Rob then happened to meet MTV producers at a DC sponsored event who fell in love with the video, creating the TV show Rob and Big, and later the TV show Fantasy Factory.
With the television success came many new ventures and expanding current business:
-Black Hotel/Motel snowboarding hotel in Big Bear
-Wild Grinders Skateboarding Toy line
-DC created an entire Dyrdek Collection apparel line