Tobi Lutke and the inevitability of Shopify

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I think I’m in the clear for a little bit on the mega-conference front, with both CES and NRF’s Big Show now behind us.

Of course, many titans of business and society are spending this week at the World Economic Forum in Davos. I hope to join them there with The Aisle in the future.

For now, I tuned in on Tuesday to watch Amazon CEO Andy Jassy’s interview with The Information founder and editor-in-chief Jessica Lessin because, of course, agentic commerce was bound to come up. Spoiler: it did.

Jassy made the case that while horizontal, or generalized, AI assistants or agents (like those from ChatGPT or Perplexity) do an OK job matching Amazon’s breadth of selection in e-commerce, they lack Amazon’s advantages in personalization based on purchase history, express shipping speeds, and customer service.

“Those things you don't get in agents typically,” Jassy said, while talking up Amazon’s own shopping assistant Rufus.

But he did reiterate that he expects Amazon will eventually partner with other third-party AI assistants or agents when the shopping experience on them improves. To me, that still sounds like a backup plan. But if one of those deals does happen, I’d expect the terms would have to be quite favorable to the e-commerce giant with a market cap approaching $2.5 trillion.

It’s a fascinating dynamic for anyone building or investing in this space, and one I’ll be tracking closely. Have any insight into Amazon’s discussions with AI app companies like OpenAI, Google, or Perplexity? I’d welcome a conversation. You can reply here, or message me confidentially on Signal. I take source trust and discretion seriously.

Now on to the good stuff…

In 2018, during an onstage interview with Shopify CEO Tobi Lütke at a Code Commerce event I hosted, I asked whether Shopify might one day make sense as part of a larger tech company.

"The power of Shopify is its independence," he told me then.

The company's mission, as he saw it, was to help make life better and easier for e-commerce entrepreneurs and merchants wherever they wanted to sell: social platforms, marketplaces, or on their own websites. And to do so effectively, Shopify needed to resist pledging allegiance to any single distribution channel, or “quasi-monopoly,” as Lütke said.

Nearly eight years later, e-commerce is on the cusp of perhaps the greatest transformation since its inception and, in a recent discussion, it became clear that Lütke’s vision is still very much intact. Only Shopify’s leverage has changed.