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Rob Dyrdek merged his skateboarding league and production company with Nitro Circus, sold the combined entity for $300 million, then bet $10 million that he could negotiate a TV deal worth an extra $100-150 million in profit.

Rob Dyrdek merged his skateboarding league and production company with Nitro Circus, sold the combined entity for $300 million, then bet $10 million that he could negotiate a TV deal worth an extra $100-150 million in profit.
What's been the biggest bet? Where, where have you plowed in something like $10 million into? My professional skateboarding league, my production company merged with Nitro Circus and created Thrill One Media. We sold Thrill One Media for $300 million, and then the group that bought Thrill One, I invested $10 million with them because I knew I was going to negotiate for a bigger television deal and hopefully make another $100 to $150 off of it a couple years down the It was the most I made and the most I invested in one