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 [Read more...]