Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee! E245

ℹ️ EPISODE INFO

Released

May 8, 2023

Duration

1h 50m

Channel

The Diary of a CEO

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

In this new episode Steven sits down with the Canadian entrepreneur and president of Shopify Harley Finkelstein. Topics: 0:00 Intro 02:05 Who are you & what mission are you on? 04:03 Why don’t people do the work they want to do? 07:41 What role does passion play in entrepreneurship? 14:21 How to have a good relationship with failure 25:00 The one thing that will make you a great entrepreneur 40:13 The start of Shopify 41:52 Should people be worrying about competing businesses? 50:50 The importance of resilience 54:13 Creating the perfect company culture 01:00:31 How to find the perfect mentor 01:05:51 What companies would you invest in today? 01:11:51 What are you good at? 01:17:40 What’s been your hardest time at Shopify? 01:28:27 Remote working 01:36:10 Something you’ve never said before 01:40:52 The last guest’s question Follow: Instagram: https://bit.ly/3M49FnB Twitter: https://bit.ly/3M3BLPF Join this channel to get access to perks: https://bit.ly/3Dpmgx5 Follow: Instagram: http://bit.ly/3nIkGAZ Twitter: http://bit.ly/3ztHuHm Linkedin: http://bit.ly/3ZFGUku Telegram: http://bit.ly/3nJYxST Follow: Instagram: http://bit.ly/3nIkGAZ Twitter: http://bit.ly/3ztHuHm Linkedin: https://bit.ly/41Fl95Q Telegram: http://bit.ly/3nJYxST Sponsors: Whoop: http://bit.ly/3MbapaY Bluejeans: https://g2ul0.app.link/NCgpGjVNKsb Huel: https://g2ul0.app.link/G4RjcdKNKsb

🎤 SPEAKERS

• Harley Finkelstein

  guest

• Steven Bartlett

  host

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Diary of a CEO, featuring Harley Finkelstein and Steven Bartlett, Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee! E245 explores shopify President Explains Cheap Path To Millionaire-Making Entrepreneurship Shopify president Harley Finkelstein shares how his early family crisis and survival-driven hustles evolved into a lifelong mission to make entrepreneurship accessible to anyone. He argues that the perceived barriers—capital, knowledge, and risk—have collapsed, making the cost of failure “as close to zero” as it’s ever been. Throughout the conversation he breaks down practical mindsets and frameworks for starting, skill‑stacking, handling failure, and building antifragile companies and careers. He also opens up about ego, loneliness, therapy, fatherhood insecurity, and how sharpening a single ‘spiky’ strength transformed his role and happiness at Shopify.

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