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Secrets of Success: Chris Pfaff


There are some “rules” of business success most entrepreneurs abide by. But many also have their own “secrets”—things they do or believe that helped them achieve success. In “Secrets of Success,” a weekly interview series here at’s Small Business Forum, I ask some of today’s smartest, most innovative, most successful business owners to share their insights and success secrets with you.

Meet: Chris “Drama” Pfaff, the founder and CEO of Young & Reckless, a fast-growing apparel and accessories brand. The products are infused with a carefree spirit and the company employs a slick-but-authentic video and social-media strategy, and features hand-picked celebrity collaborations across the fields of music, sports, and fashion.

Pfaff first found fame as the amiable co-star of one of the longest-running franchises in MTV history. You could call Rob Dyrdek’s Fantasy Factory (his cousin’s business) Chris Pfaff’s Startup Incubator. It was there, in a modest “office” underneath the stairs, that Young & Reckless—a line of T-shirts, hats, hoodies, and other accessories—was born. But unlike many accidental TV stars today, Drama has managed to straddle the worlds of “reality” and reality—and parlay a conventional media outlet into a dynamic and expansive social platform, which reaches tens of millions and has catapulted Young & Reckless into more than 3,000 stores nationwide.

You can reach Drama on Twitter @dramadrama, on Instagram @drama, on Facebook (Drama) and on Snapchat (dramadrama). What did you want to be when you grew up?

Chris ‘Drama’ Pfaff: Being honest, I wanted to be a professional skateboarder—because I spent every waking moment skateboarding. And I think with the lack of rules or structure or authority, nothing sounded better than just skateboarding and making a living doing it. But after a few injuries, I realized that everything has a negative side—you’re spending all day hurting yourself and beating your body up. That’s when I got introduced to the entrepreneurial route in life. It appealed to me because it shared a lot of the same authority-free qualities as skateboarding. I decided a normal 9-to-5 would be really tough. Why did you start your own business?

Pfaff: I moved to Los Angeles at 18 and, thanks to my cousin, wound up as a co-star on a couple of MTV reality shows [Rob & Big and Rob Dyrdek’s Fantasy Factory]. It didn’t take me long to realize I didn’t want that to be my lifetime career path, but I saw it was a great launching pad for starting a real business. I always had an interest in clothing. But more so, I saw the gap that existed between the “cool” New York and L.A. streetwear brands and the brands that were offered to Middle America and the rest of the country through mainstream mall distribution. I wanted to create a brand that was accessible to everyone, but also something that customers could really feel connected to. I created “Young & Reckless” because it stands for something, it’s relatable, and I believe it’s something that the 16- to 24-year-old generation can identify with forever. Did you experience a pivotal moment on your way to success?

Drama: Every time I see someone like Puff Daddy or Justin Bieber or any of our celebrity friends wearing Y&R, it obviously feels good. But the real feeling of success came fairly early on. When we first launched the brand, sales obviously coincided with our reality show. The breakthrough moment for me was when they detached from each other—when sales actually went up in between seasons—and the brand truly became its own thing, with its own life. What’s the best small business advice you ever gave and/or received?

Pfaff: Educate yourself before you waste your time. In the sense of really having a reason why you’re doing what you’re doing, and understanding that there’s really a gap in the marketplace, and then dedicating your life to it. I think a lot of people dedicate their lives to bad ideas, and suddenly you wake up and you’re heartbroken and tired and go back to a 9-to-5. What’s one “best practice” more entrepreneurs should be embracing?

Pfaff:I would say it’s discipline. Because when you’re an entrepreneur, you make your own schedule and plan your own day and it’s really easy to a) underwork or b) overwork and forget about balance. For me, I’m a heavy note-taker. Everything is written down in physical form—reminders, to-do lists, updates on projects. Sometimes it’s easy for your ambition to get lost in the cloud. Do you have a prediction for small business?

Drama: Even in the tough economy, I believe that there will be more startups and more ideas than ever—because of how easy it is to share and communicate. I think that it’s important that the ideas sort themselves and the good ideas rise to the top, but I also think there’s something extremely motivating and inspiring about anyone having a shot. What’s your favorite book?

Drama: Start with Why by Simon Sinek. I had the instinct when I was 22 years old to start Young & Reckless and give it meaning and make it something that people could really relate to. But that book really clarified how important that was, how glad I am that I did that, and how other great businesses have been built with a strong “why.” Is there a quote you find particularly inspiring?

Drama: Can’t go wrong with Steve Jobs: “Your time is limited, so don’t waste it living someone else’s life.” I think the biggest mistake that a lot of people make is that they spend a lot of time doing what they think they’re supposed to be doing, or what they’re told to do. And I think that true happiness and success comes from living your life your way. That’s what we celebrate as a brand.