The $5 Millionaire: Shopify’s President on Building Wealth & Purpose

In this The Diary of a CEO episode, Harley Finkelstein, Shopify’s President—an absolute force in the world of e-commerce—reveals his take on becoming a millionaire. And not in the way you’d think. It’s mind-boggling, really: he suggests that the cost to get started is no more than a Starbucks coffee. Yep, just a few bucks, and you’re on your way to a life you never even dared to dream about. But hold on—there's a lot more to it than just spending pocket change.

Finkelstein dives into Shopify's core mission, this almost radical belief that anyone, absolutely anyone, can become an entrepreneur if given the right tools. He talks about resilience and mindset—not just those corporate buzzwords, but real stuff like facing fears, picking yourself up, and learning to take hits that keep coming (you know, like in those Rocky movies). And it’s not all rainbows and quick wins; he admits entrepreneurship can sometimes feel like a lonely, endless journey. But, as he describes it, there’s also magic in the madness.

And here’s something I hadn’t really considered before—Finkelstein talks about “skill stacking,” combining talents and skills, even those you think have nothing to do with business, like some crazy fusion dish. Mentorship, he says, is invaluable; he actually lights up when discussing his own mentors and how they shaped his life and career, like guiding stars he still follows.

Plus, he gets real on passion. I mean, we hear it all the time—“follow your passion,” right? But he pushes it a step further, asking, “Is your work connected to who you are, or is it just a paycheck?” And when he said that, I felt it. It's like he was daring us to actually feel our work, to know deep down that we’re creating something that might just change lives.

You can catch the full episode on YouTube here – trust me, you’ll want to watch this one. Get inspired, maybe even a little fired up—and who knows, it might just be the nudge you need to jump-start something amazing.