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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Episoder(1004)

Episode 1,000: Rich & Julie Piatt Celebrate By Going Back To Where It All Began

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This is the 1,000th episode of the podcast. Insane. To mark it, Julie and I take it back to the start. We recap the origin story of this show. A creative experiment, born in a yurt on a Kauai mango f...

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Thrilling Tales Of Modern Men: Danny McBride On Ego, Grievance & The Stories Men Tell Themselves

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Danny McBride is the writer, actor, and producer behind “Eastbound & Down,” “Vice Principals,” and “The Righteous Gemstones.” For 30 years, he's satirized the aggrieved modern male, the guy who grew ...

6 Jul 1h 10min

Play Is The Miracle Drug: Dr. Kelly Starrett On Movement, Recovery, & The Wellness Trap

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Dr. Kelly Starrett is a physical therapist, New York Times bestselling author, and co-founder of The Ready State. This conversation explores human performance and a wellness culture that's become a k...

2 Jul 1h 6min

What Happened To The Vegan Movement? Rich & Simon Hill On The Rise & Fall Of Plant-Based Eating

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By 2020, veganism wasn't a fringe choice. It was mainstream. A few years later, the momentum faded. So what happened? I sit down with nutrition scientist Simon Hill for an honest autopsy – the overhy...

29 Jun 1h 16min

Radiohead’s Ed O’Brien on Depression, Trauma & Finding Light Again

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Ed O'Brien is a member of Radiohead and the artist behind his new solo album "Blue Morpho." This conversation explores the intersection of creativity and mental health, and the ways transformation so...

22 Jun 1h 16min

Fulfillment Maxxing: Why Offline Is The New Online & How to Feel Alive Again

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I think a lot of us are quietly struggling with some version of self-obsession right now. So today I want to talk about a different way to think about all of it: fulfillment maxxing. I get into the ...

18 Jun 44min

Rachel Entrekin Runs On Joy: How She Won The Cocodona 250 Outright By Letting Go Of The Outcome

Rachel Entrekin Runs On Joy: How She Won The Cocodona 250 Outright By Letting Go Of The Outcome

Rachel Entrekin is a professional ultra runner and three-time Cocodona 250 champion who just won the race outright. This conversation explores the mindset behind that feat. We discuss her shift from ...

15 Jun 1h 9min

Touch Grass: Andrew Yang Returns To Talk Phone Addiction, AI's Cognitive Toll, & The Fight For Your Attention

Touch Grass: Andrew Yang Returns To Talk Phone Addiction, AI's Cognitive Toll, & The Fight For Your Attention

Andrew Yang is an entrepreneur, former presidential candidate, and founder of Noble Mobile. This is a conversation about our phones, and what they're doing to us. We get into the machinery engineere...

8 Jun 56min

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