Today, I’m talking with Willem Avé, who’s head of product at Square. You know Square — it was started by billionaire Jack Dorsey, of Twitter fame, more than 15 years ago, and it got big on the back of that little magnetic reader that plugged into the headphone jack of the iPhone and let small businesses accept credit cards.
Now, of course, Square is more than a credit card reader, and sadly, the headphone jack is ancient history. Square itself is part of a parent company called Block, which is made up of a really interesting mix of financial services like Cash App, the digital wallet and payment platform, Buy Now Pay Later service Afterpay, and quite a few other subsidiaries. Block also owns a majority stake in the music streaming service Tidal, for reasons that are still a little opaque.
And that’s where this episode becomes pure Decoder bait right from the jump: as you’ll hear Willem explain, Block just restructured the entire company last year into a functional organization, so that it shares resources across all of its units. For Square, that means it’s sharing engineering resources with Tidal, a company that makes an entirely different product serving an entirely different industry.
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So I asked Willem about how all that works, and his answer might surprise you: he says Square, and Block as a whole, are better aligned now that they have a single, shared roadmap — one that, as you might imagine, is pushing very hard into AI and the kinds of back-end, financial automation companies like Square want to bring to business owners.
So sure, Square might not move quite as fast as if it were an independent division working autonomously. But Willem says the new structure is already reaping benefits to how the company develops new products and plans for this next turn, which he refers to as Square 3.0.
You’ll hear Willem and I dig deep here into what it actually means to enable AI for small business owners — what kind of questions might a Square user ask a language model about their sales data, and then how does Square actually turn that into actionable input that won’t hallucinate or just straight up fail to do what you ask.
Willem says the really meaningful shift for this kind of AI is to take the nondeterministic elements of LLMs and agents and link them to deterministic systems. That’s going to be how a company like Square moves beyond the gimmicky, often unreliable era of AI chatbots into meaningful automation for small business owners that helps them be more productive.
It is also a very weird time for money — when you combine what’s happening in decentralized finance and the Trump administration’s interest in crypto with the discontinuation of the US penny and the overall turbulence in the US economy. And Square is pretty deep on all of that, as a company that processes transactions for all kinds of cash businesses every day, while at the same time holding large reserves of Bitcoin and working to enable merchants to actually transact in cryptocurrencies.
It’s been quite a long time since I think anyone, anywhere, has wanted to give up any portion of a Bitcoin to pay for something except well… crime. But you’ll hear Willem make the case that enabling this kind of choice is part of Square’s mission.
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