Rob Dyrdek mastered entrepreneurship—in business, and in life.

Flight Templates are templated flights, or sets of questions, written by some of the world’s preeminent business leaders. With Flight Templates, Balloon users get unparalleled access to seasoned perspectives and proven business strategies across all areas of business, including leadership, product, marketing & sales, innovation, employee experience, culture, and more. This feature is part of a series on The Insight that profiles Balloon’s Flight Template authors.



“Skateboarding stacks.”

That’s how Rob Dyrdek—the former pro skateboarder who rose to pop culture fame as the host of the MTV series Rob & Big, Rob Dyrdek’s Fantasy Factory, and Ridiculousness—described how a few foundational moves turn into more complex tricks, which can turn into spectacular combos, which can turn into mastery.

Now, at the helm of his venture creation studio, Dyrdek Machine, Dyrdek translates this philosophy into operational systems that allow him to consistently achieve lofty goals for himself, his brand, and the companies which he co-founds.

“You have to clearly define what you want, then create the pathway to get there by breaking it down into as small of steps as possible,” Dyrdek said. “It’s about simplifying and trusting that there are a million ways to achieve the vision. You should always be rethinking, creating, and exploring new paths to achieve your goals. Then, success is inevitable.”

Dyrdek explained that while there will always be infinite paths to achieve any goal, the attitude you have while you tread the path you choose is ultimately what determines whether or not you’ll succeed. Looking back, the 46-year-old recognizes that his deep-seated sense of hope and self-belief played a pivotal role in going from a 16-year-old high school dropout to the leader of a multi-million dollar brand.

At Dyrdek Machine, he looks for this resolute sense of purpose in the founders he builds ventures alongside. Dyrdek takes a notably hands-on approach with his partners, who he calls “Do-Or-Diers.”

“To be a Do-Or-Dier, you have to have incredible patience. You have to have a deep sense of who you are and what you’re setting out to achieve, even if you’re not able to articulate it in a way that other people will understand,” Dyrdek said. “It’s what I seek the most in the people I do business with. They have to have that deep, unwavering belief, because that’s what it takes to truly find success.”

Since launching in 2016, Dyrdek Machine has created 15 brands, five of which have exited with a combined $450 million value. The brands span industries and have created products from apparel to alcohol to VR tech to the world’s first professional skateboarding league, and their success is nearly inevitable. Dyrdek and his team of “Machinists” guide each company through the Machine Method, a highly systematic, five-phase process that refines a big idea into a profitable business.

“So often in this day and age, entrepreneurs are idea-driven, as opposed to operations-driven. I think that’s one of the biggest things that’s overlooked in this space, and it’s one of the big reasons so many businesses fail,” Dyrdek said. “So many people have an idea that they think can be a successful business, and they wrap some sort of service or need or disruption around that idea without clearly understanding how to evolve that into an operationalized business that makes money. It’s a huge gap.”

But Dyrdek wants to demystify the process of bridging the gap. Using the Machine Method philosophy, Dyrdek has written a five-part flight template series, “The Machine Method for Manufacturing Amazing Companies,” so even teams outside of the Dyrdek Machine umbrella can benefit from the principles that helped Dyrdek himself evolve from an athlete to a celebrity to a businessman to the master of his own destiny.

  • Growth Visioning Exercise
  • Balance Data with Intuition
  • Milestone Planning
  • Position for Growth Opportunities
  • Perfect Your Brand’s Scaling Story

The series underscores efficiency, actionability, and productivity, but Dyrdek emphasizes that creativity and passion will always be at the heart of great companies. To him, true entrepreneurship—which he thinks of as the ultimate theme of his life, even before he was creating businesses—is ultimately about loving the journey, rather than dreaming about the destination.

After all, he didn’t first pick up a skateboard because he wanted to go pro. 

He picked up a skateboard because he loved to ride.

Check out Rob Dyrdek's Flight Template Series

Entrepreneur, venture capitalist, TV personality