Entrepreneurship Is A Mindset: Shopify President Harley Finkelstein On Why Failure Is The Path To Success

Entrepreneurship Is A Mindset: Shopify President Harley Finkelstein On Why Failure Is The Path To Success

Harley Finkelstein is Shopify’s President and an entrepreneur who started his first company at 13. This conversation explores the intersection of commerce and personal growth through Harley’s iconoclastic lens. We discuss democratizing entrepreneurship, the role of anxiety as fuel for achievement, and why this might be the most generative moment in history to start a business. Harley challenges my self-perception as an entrepreneur, forcing me to untether from limiting beliefs about what it means to build something meaningful. Sharp, vulnerable, and endlessly optimistic—this exchange offers a fresh take on modern entrepreneurship. Enjoy! Show notes + MORE Watch on YouTube Newsletter Sign-Up Today’s Sponsors: Roka: Unlock 20% OFF your order with code RICHROLL 👉ROKA.com/RICHROLL Aura Frames: Exclusive $35-off Carver Mat 👉AuraFrames.com Use code RICHROLL at checkout to save! Eight Sleep: Use code RICHROLL to get $350 OFF your Pod 4 Ultra 👉eightsleep.com/richroll AG1: New subscribers a FREE $76 gift: Welcome Kit, a bottle of D3K2 AND 5 free travel packs 👉drinkAG1.com/richroll Airbnb: Your home might be worth more than you think. Find out how much 👉airbnb.com/host This episode is brought to you by Better Help: Listeners get 10% off their first month 👉BetterHelp.com/RICHROLL Check out all of the amazing discounts from our Sponsors 👉 richroll.com/sponsors Find out more about Voicing Change Media at voicingchange.media and follow us @voicingchange

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Dr. Will Bulsiewicz: Heal Your Gut, Reduce Inflammation & Optimize Your Microbiome

Dr. Will Bulsiewicz: Heal Your Gut, Reduce Inflammation & Optimize Your Microbiome

Dr. Will Bulsiewicz is a gastroenterologist, one of the world's foremost authorities on the gut microbiome, and author of “Plant Powered Plus.” This conversation explores the gut-immune connection as...

12 Jan 2h 27min

Mark Manson On Vanity Goals, Self-Sabotage & How To Actually Change Your Life

Mark Manson On Vanity Goals, Self-Sabotage & How To Actually Change Your Life

Mark Manson is the author of The Subtle Art of Not Giving a F*ck and host of the Solved podcast. Back for his third appearance (eps. 476, 882), we skip the backstory and pull questions from a fishbow...

5 Jan 1h 48min

Best of 2025 (Part Two): The Year’s Most Enduring Insights

Best of 2025 (Part Two): The Year’s Most Enduring Insights

The finale is here. Let's close this thing out. Part 2 explores courage, honesty, creativity, relationships, and balance. Bravery. Addiction. Love. Mastery. And why fulfillment doesn't require sacrif...

29 Dec 20251h 51min

Best of 2025 (Part One): Conversations That Shaped Us

Best of 2025 (Part One): Conversations That Shaped Us

Happy holidays from the RRP mothership. Another year in the rearview. Time for what's become one of my favorite traditions, our annual “Best Of.” 12 years running now. This year was packed with an a...

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Kevin Hall, PhD On The Science & Politics of Weight Loss

Kevin Hall, PhD On The Science & Politics of Weight Loss

Kevin Hall, Ph.D., is a physicist-turned-nutrition scientist and author of "Food Intelligence: The Science of How Food Both Nourishes and Harms Us. "This conversation explores why diets fail, the tru...

18 Dec 20251h 58min

Let’s Make The World Wildly Better: Rutger Bregman On Moral Ambition

Let’s Make The World Wildly Better: Rutger Bregman On Moral Ambition

Rutger Bregman is a Dutch historian, bestselling author, and the guy who went viral telling Davos billionaires to pay their taxes. This conversation is a salve for the crisis of meaning percolating t...

15 Dec 20252h

Gregg Renfrew Is Making Counter Moves in Clean Beauty

Gregg Renfrew Is Making Counter Moves in Clean Beauty

Gregg Renfrew is the founder of Beautycounter and now Counter—a pioneer in the clean beauty movement. Five years after our first exchange, Gregg returns with her story about navigating imposed change...

8 Dec 20251h 51min

Rich On Rock Bottom, Resolutions & Reframing Family Dynamics

Rich On Rock Bottom, Resolutions & Reframing Family Dynamics

Roll On returns! Just in time for the holiday gauntlet. Adam Skolnick and I unpack three questions the season demands: how to navigate family gatherings when the same dynamics play out like clockwork...

4 Dec 20251h 25min

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