How a Skateboarder-Turned-Serial Entrepreneur Masters Life and Work

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Bailey Maybray
Bailey Maybray



At age 16, Rob Dyrdek moved from a small town in Ohio to pursue his professional skateboarding career on the sunny streets of Southern California. He got paid $1k every month to live his dream before most people graduated high school, let alone college.

Rob Dyrdek standing in front of a graphic featuring productivity tools.

A year later in 1994, he founded skateboarding company Alien Workshop, marking the start of his entrepreneurial journey. Now, nearly three decades later, Dyrdek finances startups through venture studio Dyrdek Machine, while still creating his own companies.

Through his studio, Dyrdek advises businesses in a wide range of industries — including plant-based products, CBD tea, comfortable footwear, and more. His firm has made exits on five brands, with a total value of over $450m.

Below, the serial entrepreneur shared with Trends on how he masters his life, inside and outside the workplace. To get the full guide, subscribe to Trends to access his interview, or watch it on the My First Million podcast.

Lifelong Learning

Dyrdek makes learning a core part of his life. As an entrepreneur, he learned as much as he could about marketing, finances, and operations. As your company grows, he suggests gaining mastery in areas you want to hire.  

Think about it this way: When you interview a marketer, what happens if you know nothing about marketing? This could lead you to hire charismatic but ineffective professionals.

If you recognize a gap in your learning, seek out knowledge from online courses, academic institutions, and even colleagues. The people around you might have a wealth of knowledge you can tap into.

Mental Health

In The Hustle’s survey of more than 300 entrepreneurs, 63% reported experiencing burnout. Dyrdek emphasizes the importance of recognizing burnout — this past year, he found himself exhausting too much energy on two companies he started, so he shut them down.

Entrepreneurs often don’t realize they’re overwhelmed until it’s too late. By managing — and mastering — time, you can prevent burnout from ever happening.

As a preventive measure, Dyrdek builds in time for leisure and adventuring, even when his schedule is filled with tasks and projects. For example, you can box out 30 minutes to go on a walk to break up a slew of meetings.


For entrepreneurs, investing in secure assets helps alleviate the risk inherent to running a business. Once your venture starts making profit, Dyrdek recommends setting aside money for an investment portfolio.

For Dyrdek, he prefers safe, secure assets in a real estate portfolio — including multifamily units, RV parks, and storage — as his safety net.


Dyrdek Machine used to fund tons of startups — before Dyrdek upped his kill rate on ideas to 99%. He recommends investors focus on high-performing opportunities instead of casting a wide net.

Similarly, Dyrdek identifies aspects of work he dislikes and tries to mitigate them. For example, if you find yourself dreading speaking engagements, consider hiring a public relations person to do it for you. Or assess your business’s priorities and determine if public presentations make a difference.

“You either learn them better to where they give you energy, gamify them, or hire somebody else to do it. Or don’t do it at all,” says Dyrek.


Dyrdek has a formula for dealing with personal and professional relationships — cut off anyone who zaps energy. In his words, “reduce, reframe your relationship.”

If a colleague in your organization rubs you the wrong way, make a game plan on addressing your feelings with them. Set up time to chat and see if you can come to an agreement. And, as Dyrdek recommends, alter your relationship with them if needed.

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