Episode 522: The Best of Habits & Hustle: Rob Dyrdek (Serial Entrepreneur and Ridiculousness Creator)

Jan 23, 2026

Rob Dyrdek, a serial entrepreneur and former professional skateboarder, dives deep into designing a life of intent. He explores the pitfalls of losing self-belief after initial success and how to rebuild it through techniques like hypnosis. Rob shares his insights on mastering time as a strategic asset, emphasizing the importance of creating systems for wealth without burnout. He also discusses optimizing health through biomechanics and daily routines, ultimately framing success as a balance between hustle and intentional living.

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INSIGHT

Systematic Venture Creation

The Dyrdek Machine is a venture creation studio that systematically builds businesses from idea to exit.
Rob frames success as art (vision), science (proven principles), and magic (timing/luck).

ANECDOTE

First Cold Call Sparked Belief

At 11 Rob cold-called a skate shop and offered to bring paying skaters to use their ramp to skate for free.
That early acceptance validated his talent and planted a foundation of self-belief that fueled bigger shots.

INSIGHT

Belief Can Collapse With Direction Loss

Losing clarity on direction breeds doubt which erodes long-standing self-belief.
Rob lost his self-belief in his mid-20s as businesses failed and identity fractured beyond skateboarding.

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Relentless drive isn’t the problem for most high performers. The real breakdown happens when self-belief collapses after early success and hustle turns into motion without direction.

This episode is part of The Best of Habits & Hustle, a series where we revisit some of the most impactful conversations we’ve shared. In this one, I’m joined by Rob Dyrdek to challenge the idea that working harder fixes everything and explore why success stalls when it isn’t intentionally designed.

We also talk about rebuilding belief after hitting bottom, mastering time as a strategic advantage, and designing systems that create real wealth without burning your life down.

Rob Dyrdek is a serial entrepreneur, producer, and former professional skateboarder. He is the creator of Ridiculousness and the founder of Dyrdek Machine, a venture studio that has built 18 brands with six exits totaling over $550M. Rob is also the CEO of Existence and the mind behind Time Creationism, a framework focused on engineering time at scale.

What We Discuss:

(00:02) Losing self-belief after early success and why hustle stops working

(11:38) How subconscious belief shapes trajectory more than effort

(13:27) Hitting rock bottom and the decision to reprogram belief

(19:18) Why self-belief isn’t motivation, it’s data and mastery

(46:41) Designing time as a strategic asset instead of reacting to life

(52:03) Why balance must come before scale, not after

(56:47) Building systems that create wealth without burning your life down

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Find more from Jen:

Website: https://jennifercohen.com

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Books: https://jennifercohen.com/books

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Find more from Rob Dyrdek:

Instagram: @robdyrdek

Facebook: @robdyrdek

Youtube: @robdyrdek