Decoder with Nilay Patel
Square's product chief on the death of the penny and the future of money
08 Dec 2025
Chapter 1: What is the main topic discussed in this episode?
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Chapter 2: What is the background of Square and its evolution?
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It's the only business software you'll ever need. It's an all-in-one, fully integrated platform that makes your work easier. CRM, accounting, inventory, e-commerce and more. And the best part? Odoo replaces multiple expensive platforms for a fraction of the cost. That's why over thousands of businesses have made the switch. So why not you? Try Odoo for free at odoo.com. That's O-D-O-O dot com.
Hello and welcome to Decoder. I'm Neil Apatow, editor-in-chief of The Verge, and Decoder is my show about big ideas and other problems. Today I'm talking with Willem Ave, 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 on the iPhone and let small businesses accept credit cards. Now, of course, Square is much more than a credit card reader, and sadly, the headphone jack is ancient history.
Square itself is part of a new 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, the 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 some reason that no one can quite explain.
And that's where this episode becomes pure decoder bait right from the jump. As you'll hear Willem explain, Block 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.
So I asked Willem about how all of that works, and his answer might surprise you. He says that 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 backend financial automation that companies like Square want to bring to business owners.
So sure, Square might not move as fast as if it was an independent division working autonomously, but Willem says the new structure is already reaping benefits as to how the company develops new products and plans for its next turn, which he refers to as Square 3.0. You'll hear Willem and I dig deep into what it actually means to enable AI for small business owners.
What kinds of questions might a Square user ask a language model about their sales data? And how Square might turn that into actionable input that won't just hallucinate or straight up fail to do what you ask it.
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Chapter 3: How is Square structured under Block's new functional model?
But as you get larger and larger, most of the problems, you know, one or two location seller faces staffing, you know, can I get folks to show up on time? How do I manage my staff schedule so that staff are happy? How can I manage my vendors and all the other costs of goods sold as we know? Costs are going up across almost every dimension in the industry. So the problems keep happening, right?
And I kind of truly believe that you want to democratize technology, right? You want to take technology, and this is really relevant in the AI space. You want to take technology that's usually locked to just the very large corporations, the Wall Streets, et cetera, and bring them down to Main Street, right? And I think if you do that successively...
and make that technology accessible you can actually help society like you can make things better right you can get neighborhoods vibrant again right you can you can help these sellers because you know a lot of these a lot of these small businesses fail unfortunately right and it's because it's hard to run a business and i think if you can apply technology effectively uh you can run a better business um and you can kind of revitalize a lot of the main streets across across the world
That's a big mission. It's interesting, right? That implies that you're going to go from taking payments to helping more efficiently run businesses or helping small business owners more effectively run their businesses. I've heard variations of this pitch from – I wouldn't even call them competitors from other companies that have an entry point into small business.
Intuit was on the show and they're like, we're going to run your whole back office. Squarespace has been on the show. And the slide for Squarespace to go from we set up your website to your website has a booking calendar on it to now we manage your bookings. We should manage your payments. We're going to do all of your invoicing is very easy for them. It was very compelling.
It was like, oh, yeah, I started a website. Now that you're on my front end, you're on my back end too. Get the pitch. And it all starts with we're going to do one thing and we'll expand everything else. Is that how you think of Square and that same ecosystem, that your competitors are other providers who start with one thing and are trying to expand the entire back office?
I would think in broad strokes, yes. I think the unique part about Square is that because we build and design all of our own hardware, kind of from the chip up, that we can provide, I would say, better end-to-end experiences than competitors that may be starting in other areas. And at the end of the day, for the majority of brick-and-mortar businesses, the point of sale is the
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Chapter 4: What role does AI play in Square's product roadmap?
is the artery, so to speak. Like quick serve restaurants, retail restaurants, even a lot of services that need this help make a sale. It's important to think that if you do the core things that a business really needs done super well, then I think it gives you the ability And the believability that you can build additional products.
And then one of the unique things about Square and then Block is that we've also been able to build other business units like Cash App and kind of other complete ecosystems, which is pretty interesting.
Do you think of like Toast as your competitor? Like Toast makes hardware. It's in point of sale in restaurants. Is that the big competitor? Is it other hardware companies? How does that work for you?
You know, while I think about competitors, I don't obsess over competitors. I think it's better to obsess over customers. But one of the unique things about Square is that we can serve effectively almost any type of seller. Retail, food and bev, health and beauty, services, etc. And the reason why that's...
I think really interesting is that when you think about our competitive set, yes, like, you know, for Food & Bev at the large end of the market and quick serve and full serve restaurants, it's Toast, it's Q, it's a couple other folks. In retail, it's like Lightspeed and Shopify. Health and Beauty, there's a bunch of scheduling products out there.
Services, you know, mainly Intuit, QuickBooks, Service Titan, et cetera. And then I just kind of come back to what a lot of these sellers need is like they need a rock solid platform and software to help them run their business. And as you kind of build some of these capabilities, a lot of the needs across these industries rhyme, right?
And I think that's where you can leverage platform in our ecosystem, especially on help me understand how my business is running, help me grow my business, help me manage my staff. There's a lot of very core similar needs so that we can then build capabilities that we can apply across industries.
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Chapter 5: How does Square plan to leverage AI for small business owners?
I'm fascinated by the fact that you said you think the hardware is a big differentiation, right? You design it from the chips up. That's a big investment. The cliche is hardware is hard. That has to run all the time. If the point of sale goes down, that's the end of that, right? Your sellers are probably moving on.
How do you think about managing the hardware roadmap next to the software roadmap next to, hey, maybe the future of all these capabilities are on an AI roadmap somewhere else?
We have an incredible hardware team. Thomas Templeton leads our hardware team, and it's, I think, one of the best in the industry. So we partner very closely on making sure that we can form fit seller need, right? Like the form factors that they need to run their business with then the software workflows that work best. And it's a partnership.
And the faster that we can iterate and deliver both software and hardware experiences together, I think the better off all the sellers will be.
I'll make the comparison to Apple or even to Google, right? Like every year Apple shows off iOS and then a few months later they show off the phone and it sort of embodies whatever new features of iOS happen. Google does the same with Android and the Pixel.
Are you on that kind of roadmap where you're like, I've got a bunch of software ideas and the next version of the point of sale terminal will really bring them to life or are they separate in your mind?
A lot of the reasons why different hardware companies have different strategies is largely how much the underlying hardware exposes APIs and enables the software behaviors. I think ultimately for Square, we can decouple those to a larger degree where we don't need kind of monolithic kind of hardware software release cycles where we can be more nimble on the software side.
And then, yes, there's like step function improvements and things that get unlocked from a hardware capability side. But it's not as monolithic as some of the other kind of hardware companies out there.
What I'm really pushing on is the idea that it's the hardware that is the big differentiator here. What's the evidence for that? Is it the customer saying, boy, we love these square terminals? Is it just that it's easier and more convenient? Is it that they're more reliable? What are the factors that make it the big differentiator?
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Chapter 6: What is the significance of the US discontinuing the penny?
We want our seller's brand to stand front and center. There's a lot of design decisions that we've made to make sure that that stays true for a seller.
Do you ever do the Steve Jobs things where you pick up the pictures of like the Blackberry and the Palm Trio and you're like, this is why they suck and this is why ours is better?
No, I haven't. I think it'd be funny to do, but no, we haven't.
That's like a big vision, right? We're going to enable sellers of all kinds at every scale. We're going to have hardware that's better, that is a better literal customer experience. And then I was looking at your public roadmap, and it is extraordinarily tactical in places. One of the items is there's going to be support for combo meals at quick service restaurants.
Where do you think that balance is, that Square has to do the work to support combo meals, not the restaurant has to decide it wants combo meals and it can make Square do that?
The genesis for the public roadmap, and it's pretty unique for larger businesses in the space, is that We wanted to build out in the open, and we wanted to drive accountability for what we say we're going to do, we're going to go do, and we're going to do it with speed, velocity, and quality. As far as the granularity and the details of what we show in the roadmap, it's really a judgment call.
My general preference is to show more. and make it kind of more raw and utilitarian rather than maybe more polished. So I think that's why you kind of see everything, tiny little features, but also really big things will show up there.
Specifically for combos and kind of some of the capabilities, it's important for when you run a business, the software has to work for how you want to run your business. And that's how you merchandise your sales, how you present those goods or food or services that you're creating and present them to customers.
So that's why it's important, and sellers tell us this, but it's important to be able to help sellers model their business the right way.
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Chapter 7: How is Square integrating Bitcoin and crypto into its services?
Is that the kind of thing you want to do for people is templatize a restaurant so that they have combo menus? Because the other way of doing it is I run the restaurant. I invent the combo menu and I just put it into the menu with a price and that's fine. And no metaphor required. No further like the combo meal is made up of these three separate items.
I mean, I think what you need for any software, and I generally agree, a lot of software is like forms and lists of things, which is interesting as a reflection. But you need the core foundational primitives and constructs, right?
Like, for example, in the hierarchy that those things, kind of how they're designed and engineered in the backend, are important to get right and are important to be flexible. You can't offer infinite flexibility, right? I think it's important for any software product to provide guardrails to a certain degree and take opinions because...
you know, a lot of, you know, if you don't, it could just end up in like a super complicated kind of cockpit of knobs and levers and kind of forms and buttons that are really hard to use and understand.
Yeah, it's funny. I use the cockpit of knobs and levers all the time. But the thing I was thinking about is, okay, I run my little team. And if this was a submarine, my managing editor needs to sit at a console with a lot of buttons. And how can I put the buttons in front of her so that she can do her job most effectively? She does not like this metaphor, and I don't think it actually works.
And I think I'd be bad at driving a submarine because I don't think that's how a submarine works either. But that's what you're describing, right? It's like how do I put the various tools of the business in front of the person who operates the business?
What's the dynamic between Square saying these are the tools we think you need that will be most effective and the customer saying these are the tools we actually want?
Yeah, that's the art and kind of mainly the art of building great products. It's one of the reasons why Square and Block as a company is a very design-led organization. I think design in its kind of most simplest form is kind of helping understand the core needs and building solutions and designing solutions to help solve those needs.
And I think time and time again, I'm always surprised and delighted by the creativity that comes out of basically a design team and org working closely with engineering to craft these experiences. I think if you have too much of a top-down view of exactly what you want to build, I think that A, limits the creative process.
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Chapter 8: What challenges does Square face with Bitcoin transactions?
I think that's one. I think two, though, it's also really important to make sure that the teams and the squads are stable.
at kind of the kind of ground level that they're building they have autonomy mastery purpose they can go kind of go build the things for customers and you kind of need to synthesize both kind of uh stability at the squad team level with kind of top-down strategic prioritization that's kind of happened and i think that's been the biggest change and benefit from going from a divisional business unit structure to a functional structure
is that alignment is super, super important in a large organization, right? And if you create kind of different, effectively different mini startups or kind of product areas, which happens in a divisional org, then like, yes, you can kind of go fast in each of those directions, but you're usually going fast in like 14 different directions, right?
Versus going fast and making trade-offs and being able to build together and kind of build something really incredible.
I'm just going to push on this a little bit. I think I understand what you're saying, but just assume I'm much dumber than maybe people think I am. DRI is directly responsible individual. You said you had squads. I understand why you would want shared engineering resources for Square and Cash App and maybe even Afterpay, right? These are payment rails.
Why does title need strategy alignment with Square?
So not everything has to harmonize at like exactly the same strategy or exactly the same things that we're working on. It's more that when you functionalize a company, you can also make sure that each discipline is operating kind of at the highest, highest levels, right? So both from a performance perspective, but also an accountability perspective. I think that's one of the key points.
It's not like we're trading off people necessarily between title and Square all the time. It's Title as a team, Square as a team, Cash App as a team, et cetera. And at the margins, we might make prioritization trade-offs. But in the broad strokes, that's, you know, kind of we have our strategies and we go execute on them.
This is the argument that I've heard for functional organizations and companies that have lots of disparate
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