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

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