Chris “Drama” Pfaff (@dramadrama) is a former reality TV personality, host of the Short Story Long Podcast, and founder of streetwear clothing line Young and Reckless.

What We Discuss with Chris Pfaff:

  • Why Chris decided to take his skateboard from suburban Akron — where escaped cows made the evening news — to Los Angeles, where high-speed car chases barely raise eyebrows.
  • What it’s taken so far for Chris to make it in today’s cutthroat fashion business climate — especially when he has to work twice as hard to overcome what others expect from his “dumb” reality TV persona.
  • How to stay tenacious — like someone raised in the Midwest — when you fail over and over again.
  • Why sometimes running a business — even something as fun and exciting as a top-level streetwear brand — can be more of a curse than a blessing.
  • How Chris feels about regretting something he has done versus regretting something he hasn’t done.
  • And much more…

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Jordan first met Chris “Drama” Pfaff in their building’s elevator when they were neighbors in Hollywood. Back then, he was the butt of every joke on reality TV show Rob & Big, and had dreams of starting a clothing brand (like everyone else their age in Hollywood).

What follows is a very frank discussion of what it takes to make it in today’s business climate, how to stay tenacious when you fail over and over again, and why sometimes running a business — even something as fun and exciting as a top-level streetwear brand — can be more of a curse than a blessing. Listen, learn, and enjoy!

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More About This Show

So many startup businesses — especially ones that center around fashion — don’t last beyond the attention span and pocket capital of their founders. But Chris “Drama” Pfaff — former star of reality shows Rob & Big and Rob Dyrdek’s Fantasy Factory, host of the Short Story Long Podcast, and creator of streetwear clothing line Young and Reckless — isn’t an ordinary founder. And contrary to whatever impression you may have of his role on reality television, he’s no dummy.

“In the beginning, I tried everything I possibly could to not be that,” says Chris. “The main thing was this: when I launched the brand, it was ‘Drama the dummy from reality TV’ mixed with ‘This guy from reality TV is starting a merch line’ mixed with the fact that the show, for good and bad, was so massive that it was so connected to me and merch no matter what I did. So the main thing that I did was found really good business partners. I didn’t go try to print shirts myself and sell them. I went and found guys who had had a clothing line for 10 years before me. They made full collections of clothing and that kind of gave me a head start in actually producing and making a real clothing line.

“The second thing was I did as much marketing as I possibly could outside of myself. I tried to shy away from [going on] Facebook saying, ‘Go buy my shirt! Go buy my shirt!’ We did a really big project with Meek Mill early on and we had every single actor and influencer and everyone coming by the office and taking pictures in the shirts because I knew I had to do twice the amount as everyone else so that you would see it as ‘The New Clothing Line’ — not ‘Drama’s Little Project.'”

Perhaps some of Chris’ tenacity comes from his upbringing. Like Jordan, Chris grew up in the Midwest — suburban Akron, to be exact — where he passed the time skateboarding in a town where an escaped cow was the featured story on the evening news. Chris had ambitions to skate as a career, but he knew he’d have to endure the culture shock of moving to a town where things moved at a faster pace: Los Angeles.

“L.A. is the world capital of skateboarding,” says Chris. “It’s where all the brands are. It’s where all the famous skate spots are. It’s where all the pros live. I was just obsessed with skateboarding, so the next logical move was to move to L.A. So I think from age 14, I just knew: ‘The moment I graduate high school, I’m going to L.A.’ I knew around 16 I wasn’t good enough to be a pro skateboarder — even though that was my dream — so I was like, ‘Whatever. I’ll work at a skate shop. I’ll film skaters. I’ll do something,’ but I was just so obsessed with skateboarding; I just followed that.”

Listen to this episode in its entirety to learn more about what led Chris from dreams of connecting with the skateboarding world to landing a gig as a reality television star, how this path has been a boon and a hindrance to Chris’ current entrepreneurial ambitions, why Chris feels it’s better to regret something he has done than regret something he hasn’t done, how it feels to see other celebrities wearing his clothes rather than having to play the role of celebrity himself, and much more.


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