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

Habits and Hustle

Jen Cohen

Entrepreneurship, Education, Self-improvement, Health & Fitness, Business

4.5 • 818 Ratings

🗓️ 23 January 2026

⏱️ 149 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 Thank you to our sponsors: Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift. Therasage: Head over to therasage.com and use code Be Bold for 15% off Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE40 for up to $300 off and a 3-year warranty on air purifiers. Momentous: Shop this link and use code Jen for 20% off Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order Amp fit is the perfect balance of tech and training, designed for people who do it all and still want to feel strong doing it. Check it out at joinamp.com/jen Find more from Jen: Website: https://jennifercohen.com Instagram: @therealjencohen Books: https://jennifercohen.com/books Speaking: https://jennifercohen.com/speaking-engagement Find more from Rob Dyrdek: Instagram: @robdyrdek Facebook: @robdyrdek Youtube: @robdyrdek

Transcript

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0:00.0	Hi, guys. It's Tony Robbins. You're listening to Habits and Hustle. Crush it. I am so excited to have
0:07.3	my guests here today. We have Rob Deerick. And I mean, I've never been speechless, but this guy
0:15.0	is above and beyond, probably any guest we've ever had on Habits and Hustle.
0:23.9	He is, you may think of him as a skateboarder.
0:30.1	You may know him from ridiculousness or Robin Big or fantasy factory.
0:35.5	But this guy is one of the most clever entrepreneurs, what he's built, what he's done,
0:39.7	how he's automated his life and designed a life that is way beyond anybody's imagination. You can't even imagine. I am so happy to have you here.
0:46.6	Thank you for being here. No, thank you for having me. I don't mean to make you blush. I don't
0:50.6	even know what direction to go with you because when I delve into, when I told
0:54.2	you, when you walked in, when I delved deeper and deeper into who you are and what you've accomplished,
1:00.1	like, forget about the TV and the world records and all of that. It's, this podcast could be
1:08.4	11 hours, honestly. I don't know what direction to go first yeah and i think that
1:12.4	ends up being a lot of the the problem with um sort of my past sort of reason of not doing press
1:19.1	you know for many years like i didn't even as i built the deer deck machine and built sort of this
1:24.8	entirely new vision for myself and sort of life and legacy,
1:28.6	I didn't talk to anybody. And so by the time I began to share it, it was deeply refined,
1:35.2	and I had lived it and accomplished so much inside the way of thinking that now it's the only
1:42.0	thing everybody wants to talk about.
1:50.0	And that's how I control the narrative that has led to sort of me connecting with a lot of different people that think this way, to be able to have this conversation in a more
1:55.2	intelligent, connected way to who you are and what your brand is.
1:58.7	Then just asking me, what'd you do to become a pro skater?
2:02.3	Yeah, I don't know. But like, it's like you've conquered so many different areas, right? So,
	...

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