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Today I’m talking to Harley Finkelstein, president of Shopify. Shopify is one of those companies that makes the modern internet go — it makes software that allows businesses of all sizes to set up online stores, and from there it can handle everything from shipping orders to financing loans for expansion. The company went public in 2015, and as online commerce has exploded during the pandemic, it’s been on a tear ever since — it just posted $988 million in revenue in the first quarter of 2021, a 110 percent increase from last year.

But while things are going extremely well right now, I was very curious to talk to Finkelstein about how he sees competition from the tech giants — a lot of online shopping starts with targeted ads on Facebook, which is building out its own shopping platforms. Facebook and Apple are fighting over how those ads are tracked and served overall. Apple is, as of this week, also in the middle of a nasty trial with Epic Games about the cut it takes on digital purchases in iOS apps. And of course, there’s Amazon, which dominates online retail.

Finkelstein says that Shopify provides tools for businesses to compete with all of these giants, and that Shopify itself can sometimes act like a giant because it has so many customers to represent. The phrase he used was “being the empire vs. Arming the rebels,” which, yeah, that’s pretty good. Except for the part where the empire routinely strikes back. Still, Finkelstein is a true believer in entrepreneurs, and that really came through in this conversation.

One thing to pay attention to: every time I talk to an executive from a platform company, we wind up talking about moderation issues, and Shopify did ban Donald Trump’s store after the January 6th Capitol riots. But Shopify doesn’t really fit into the same category of laws as Twitter or Facebook or other social media platforms — so it has a different set of moderation challenges, and it’s worth thinking about whether the enterprise software that powers online stores should have to meet the same moderation standards as TikTok or YouTube. It’s complicated, and Finkelstein and I wrestled with it a little.

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