Entrepreneurship & Life w/ Chris “Drama” Pfaff

“What I did know was that was opportunity and it was a greater opportunity than opening a skateboard store”

“I learned so much from shutting up, knowing my role and watching him and the people around me.”

“I realized that I can accomplish things because these people aren’t that different from me.”

“You gotta know what you don’t know.” 

“The way to have a successful business is to have a brand that means something”

“Everyone has those times where they question themselves. It’s not all just rainbows and ponies. Shit happens.”


  • Welcome Drama!: 00:30
  • Background On Drama: 2:00
  • The “Aha” Moment: 7:15
  • Shut Up and Learn: 13:30
  • The Origination of Young & Reckless: 22:00
  • Building Something Sustainable: 27:00
  • Is Entrepreneurship Innate or Trained?: 39:15
  • Favorite and Least Favorite Parts of the Job: 52:15
  • Realizing That People Want To Be Drama: 55:30
  • The Most Trying Moment Of Drama’s Life: 1:00:00
  • Coming Out Of The Shadows: 1:07:40
  • Future Directions and Closing Remark:: 1:015:15


Chris “Drama” Pfaff grew up in a small town in Ohio. He became obsessed with skateboarding around age 10, possibly influenced by his cousin, Rob Dyrdek who he knew of but had never really met at the time. This passion for skateboarding is what drew him to LA, the skateboarding capital. There was no industry for skateboarding where he was from so he had to make the move if he wanted to pursue his passion. Moving to LA is a massive culture shock when you are used to the small town Ohio life. It took a few years for LA to truly feel like home rather than the place he worked.

Drama always had the entrepreneur’s mindset. He used to film little league football games and sell the videos to parents to save money to move to LA. Upon arriving in LA he kept this hustler mentality and he was able to recognize the opportunity when his cousin’s assistant quit. His cousin of course being the famous skateboarder, Rob Dyrdek. He took the opportunity and became Rob’s personal assistant, despite having no clue what the job entailed. It doesn’t matter if you can’t see the full vision or maybe you don’t even think you are worth what you really are. When he made the move, his vision couldn’t see that far ahead. He wanted to open his own skate shop because in his mind, that was the only choice someone like him had.

Even after he had built a clothing empire and began to run a very successful podcast, he still wakes up every day feeling like he hasn’t accomplished anything. He is always searching for that next thing and then once he has that next thing he is chasing something else. Though he has achieved a lot, he feels that if he doesn’t continue accomplishing things then he will wind up working as a barista at Starbucks. Because he has this mindset he was able to recognize the opportunity of being Rob Dyrdek’s personal assistant even though he knew that being an assistant was very low level. He would do Rob’s laundry, polish his floors, drive him to business meetings etc. As he was doing all this he never stopped watching and trying to learn from the experience. They started filming the pilot for Rob & Big and Drama started to come into his own as he appeared on the show. He also began making beats that he would beg producers to put on Rob & Big. The shitty beats that would play during transitions on Rob & Big were Drama’s. Then once Big Black was no longer with Rob, Drama realized that he was now the number 2 guy and he could use this move himself out of TV and really build something that he wanted.

Drama was able to learn so much about how to operate from shutting up, knowing his role and observing the people around him. He was smart enough to realize that he didn’t know everything and had a lot to learn. Not only that, but he recognized that he could learn a lot from the people around him. He also observed a lot of his friends fail and be forced to move back home in their mid 30s. Drama was able to take his observations and use this to help him springboard his own career. He did the research where his idea would fit and just did it.

There is nothing in the world that you can simply read about or look at on your phone, then do it and be any good at it. You need real world observation and experience. The caveat is that you will never get the necessary experience if you don’t learn to shut up and observe people around you. Drama was about 22 years old and partnered up with people who had been in the clothing game for 10+ years. He shut up about everything he didn’t know and learned how to make clothing, learned what margins were, how to run a business etc. He knew how to promote something but had no idea how to run a business so he learned from the people he was around.

When Drama was starting the Young & Reckless Brand he recognized that it had to be bigger than him. The company couldn’t live and die based on his face and him promoting it. After seeing mistakes made by Big Black and tying his clothing line too closely to Rob & Big and other brands tying themselves too closely to Rob, that resulted in the companies struggling when Rob no longer wore their apparel. People often launch a brand that is in their shadow and this is a huge mistake.

Building a brand around yourself is a huge problem in the world of entrepreneurship today. Stardom is not guaranteed to happen at all and it certainly isn’t guaranteed to be sustained. Many people get their ’15 minutes’ but few turn that into a lifetime. When building a brand if it tied to your 15 minutes too much then when that time runs out, the company will fail. On the flip side if you can capitalize on your strengths while building a brand that could sustain without the lead guy. Drama’s biggest fear was the company living and dying with him. He didn’t want to be big with successful merch, he wanted to run a really big brand. These YouTube stars who are selling clothes are fucked he minute they stop putting out funny videos everyday or the minute people no longer find them funny.

Something Drama is working on improving with Young & Reckless is navigating the world of social media influencers. It used to be, the brand would pay a lot of money to someone who is famous and recognizable and that person would wear your brand for the season. Now, there are thousands of people who are “influencers” that kids look to for trends. Its not like someone just looks at what ASAP Rocky is wearing anymore. There could be some 16 year old girl who has a youtube channel that carries far more clout than ASAP Rocky in the world of fashion influence. This brings up the question, do you really want some kid who hasn’t done anything in life aside from grow a following to represent your brand? In Drama’s opinion you need to protect your brand at all cost. Protect everything that gets put onto your site and you put out directly with everything you have. So if at any moment someone hears about the brand and goes to look it up on your site, your culture and feel is rock solid. That said, there is benefit especially in the fashion industry, to have someone with a shit ton of followers wearing your clothes. Where people go wrong is on the extremes. Whether that be selling out and working with anyone and everyone no matter their values or holding on too tightly and not working with anyone who doesn’t meet your qualifications specifically. In either scenario your brand never grows to the point you want it to. The epitome of executing on this strategy is the brand Supreme. People line the streets to buy a $50 T Shirt and now Supreme has received a billion dollar valuation.

There are certain characteristics that are required to succeed as an entrepreneur. Whether these can be learned is a little sketchy. The relentlessness and thick skin are required to succeed in the world of entrepreneurship. That said there are a lot of people that have what it takes, but don’t attempt it because of their environment. So many people could do it if they worked to cultivate these skills a little more. Identifying what these skills are and working on them is the most important thing.

Chris’ advice to young entrepreneurs is to figure out how you can “Starbucks a business.” Meaning, identify something old that people love and figure out how you can make it new again. This is something the biggest companies have done. The people who are able to take something old and boring and make it newer, better and more fun. This is where the big wins are at. Tech is making entrepreneurship the Wild West. Anything can happen and you can disrupt any space with the right idea and execution.

Everyone has things in their jobs that they enjoy doing more than others. For Drama, he really enjoys creating content, putting it out and seeing how it is received. He loves receiving the feedback. He will literally hit refresh over and over to see how people are reacting. His least favorite is operational things of the business. For example, people who are asking for a raise, people who need to be fired or just people who are getting their feelings hurt because of the way someone else in the office is talking to them. The babysitting and navigating politics of coworkers is what he dislikes.

Drama is incredibly grateful for everything in his life. All the work, all the luck, all the love has received, he is incredibly grateful for. There used to be times where he was getting so bogged down in the work that he would become down on himself and his life but he has implemented practices that helped him do a 180. He now starts every morning by writing down a list of what he is grateful for. He realizes that he has an incredible life and says it is ridiculous for him to ever go to bed upset or wake up upset because he has it better than so many other people.

Drama had a light dosage of not feeling good enough for a long time. He had an older brother who was always better than him at given tasks. Then he started to develop this complex that he was always the one who was second tier. Then even when he moved to LA everyone looked at him as Rob’s little cousin. Then people would look at Young & Reckless, recognize that it was doing well but would say ‘yeah but it wouldn’t have happened without Rob.’ These things slowly caused more damage than he thought they did. There was a phase where Young & Reckless was hitting a rough spot, the tv show was over, some negative personal relationships were dragging him down and these all came to a head at once. This lead to a phase where he was just waiting until 9:00 at night so he could chug a bottle of wine, take a Vicodin and pop a Xanax so he could go to sleep at night. Nothing seemed to matter and it all seemed to be for no reason. It was out of this darkness that started his podcast, Short Story Long. He decided that he wasn’t going to be defeated by this darkness and wanted to get his story out of who he really is.

Put an hour or two in your calendar every week and meet up with someone who you think is really cool and just sit and talk with them. There is something about having great conversation that enhances your quality of life. This is one of the reasons Drama started his podcast with all the amazing guests he has. It has been a way for him to have the conversations he enjoys with people he admires and share it with the world. Since the podcast has taken off he has been able to come out of the shadows of Rob. People no longer look at him as Rob’s cousin or a second tier guy. He has become the guy people want to meet.



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