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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Todd Marinovich: The Superstar Quarterback Who Lost Himself In Drugs & Found Himself In Love

Todd Marinovich: The Superstar Quarterback Who Lost Himself In Drugs & Found Himself In Love

Todd Marinovich is a former NFL quarterback, USC Rose Bowl champion, and the subject of the ESPN 30 for 30 documentary "The Marinovich Project." This conversation explores the duality of engineered p...

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The Productivity Myth: Oliver Burkeman On Our Broken Relationship With Time, Embracing Our Limitations & Why More Isn’t Always Better

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Oliver Burkeman is a bestselling author, journalist, and the mind behind “Four Thousand Weeks: Time Management for Mortals” and “Meditations for Mortals.” We explore our broken relationship with time...

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Fasting Compilation: Leading Experts On Water-Only Fasts, Fasting Mimicking Diets & The Optimal Fasting Window For Longevity

Fasting Compilation: Leading Experts On Water-Only Fasts, Fasting Mimicking Diets & The Optimal Fasting Window For Longevity

This Fasting Compilation features Dr. Alan Goldhamer, Dr. Valter Longo, and Dr. Michael Greger to discuss the science of strategic deprivation. We explore why visceral fat behaves like a tumor secret...

20 Nov 20251h 8min

Interview With An Icon: Katie Couric On The State of Media, Institutional Distrust, Cancer Advocacy & What Actually Creates Happiness

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Katie Couric is a journalist and the first woman to solo-anchor a major network evening newscast.  We explore the disintermediation of news media, institutional distrust, and the fragmentation of sha...

17 Nov 20251h 57min

Tig Notaro Is Treading Water

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Tig Notaro is a comedian, actor, screenwriter, producer, and co-host of the podcast Handsome. This conversation explores Tig's legendary 2012 set—delivered days after her cancer diagnosis—and how los...

10 Nov 20252h 41min

Modern Manhood: A Compilation On Redefining Masculinity, True Strength & Igniting Purpose, Community & Vulnerability In Men

Modern Manhood: A Compilation On Redefining Masculinity, True Strength & Igniting Purpose, Community & Vulnerability In Men

This Modern Masculinity Compilation features Scott Galloway (ep. 826), Terry Crews (ep. 676), Jonathan Haidt (ep. 827), Arnold Schwarzenegger (ep. 784), John W. Price (ep. 939), John Pearson (ep. 739)...

6 Nov 20251h 19min

It Begins With You: Jillian Turecki On Why Dating Is Broken, Self-Awareness Is Everything, & What Actually Makes Love Last

It Begins With You: Jillian Turecki On Why Dating Is Broken, Self-Awareness Is Everything, & What Actually Makes Love Last

Jillian Turecki is a relationship expert, New York Times bestselling author of It Begins With You, and host of the podcast Jillian on Love. This conversation explores why intimacy reveals our charact...

3 Nov 20252h 7min

Malala Yousafzai Is Finding Her Way

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Malala Yousafzai is the youngest Nobel Peace Prize laureate, education activist, and survivor of a Taliban assassination attempt at age fifteen. This conversation explores the gulf between icon and i...

27 Okt 20251h 49min

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