Decoder with Nilay Patel (The Verge)

Episode: Square's product chief on the death of the penny and the future of money

Guest: Willem Ave, Global Head of Product, Square
Date: December 8, 2025

Overview

This episode explores the evolution of Square (now part of Block), its ambitious roadmap to enable AI-driven financial tools for small businesses, and the practical and philosophical implications of changes in money—from the death of the US penny to the future of crypto. Host Nilay Patel and Willem Ave dive deep into how Square structures itself in a rapidly changing landscape, the tension and promise of AI automation, and why Square keeps investing in both tangible hardware and the digital future.

Key Discussion Points & Insights

1. What Square Is (and Isn’t) Anymore

• From Card Reader to Commerce Platform
  • Square began as a simple way for small merchants (e.g., coffee shops, farmers’ markets) to accept credit cards via a mobile device and a headphone jack attachment.
    • “A lot of people have seen us in coffee shops or farmers markets...We serve sellers that are very small all the way up through Chase Stadium and everything in between.” (06:52, Willem)
  • The company now offers an integrated commerce platform serving a wide variety of businesses, from small sellers to stadiums.
  • Square’s initial unique selling proposition—plug-and-play hardware—has evolved to tap-to-pay and full hardware/software integration.
    • "That is the selling point for a lot of small merchants. It's just that easy and it's the hardware they already have." (09:50, Nilay)

2. Open Ecosystems and Apple’s Role

• Square supports both open connectivity and platform-specific integrations like Lightning and USB-C.
  • Transitioned from headphone jack readers to Bluetooth and now “tap to pay.”
• While there has been industry controversy over Apple’s NFC restrictions, Ave downplayed any issues:
  • “Apple’s a fantastic partner of ours as we continue to innovate.” (10:35, Willem)

3. The Journey from Payments to Platform

• Square aims to “democratize technology”—moving up the value chain from merely accepting payments to providing full business solutions (inventory, staffing, analytics):
  • “One thing we say at Square is like, you know, a seller should never outgrow Square...That means we need to meet them where they are.” (11:45, Willem)
• The strategy: Expand offerings so businesses can run entirely on Square if they choose.
  • “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.” (15:23, Willem)
• Differentiator: End-to-end control of both hardware and software yields better, more reliable customer experiences.
  • “We can provide, I would say, better end-to-end experiences than competitors…If the point of sale goes down, that's the end of that.” (16:16, Willem)

4. Competitors and Industry Position

• Square sees itself as uniquely positioned because it serves many verticals (food and bev, retail, services).
  • “When you think about our competitive set…a lot of the needs across these industries rhyme. Right. And I think that's where you can leverage platform in our ecosystem.” (16:25, Willem)

5. Transparency and Roadmap: The Power of Public Commitment

• Square publicly shares its product roadmap—tiny and large features alike—to drive accountability and openness.
  • “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.” (21:36, Willem)
• Real-world example: Building combo meal support for restaurants isn't just a technical tweak—it's about reflecting real business needs.
  • “The software has to work for how you want to run your business…It's important to be able to help sellers model their business the right way.” (21:54, Willem)

6. How Square Makes Decisions: Design, Customer Focus, and Alignment

• Square emphasizes a design-led organization, aiming to learn from both top-down vision and bottom-up creativity.
  • “The art...is one of the reasons why Square and Block as a company is a very design led organization...time and time again I'm always surprised and delighted by the creativity that comes out of basically a design team…crafting these experiences.” (24:51, Willem)
• Different customer types need different kinds of flexibility: an open platform for large, complex needs; easy “one-stop” for small sellers.
• Prioritization flows from customer needs, top-down company strategy, and an open but focused process (“pit stops” and “unblock meetings”):
  • “You want to make sure teams…have rituals that they can get decisions made quickly...We aim to have decisions made within 48 hours or less.” (44:37, Willem)
  • “Your gut is the best-trained ML model on the planet. It's just the synthesization of all the things that you've seen over your entire career, day to day, in and out.” (44:37, Willem)

7. Block’s Reorganization: Functional Structure and Strategy

• Jack Dorsey (CEO) recently reorganized Block into a functional rather than divisional structure to boost alignment and cross-pollination.
  • “We created a single set of priorities. So a single shared roadmap. If you have a single shared roadmap with clear DRIs…makes a lot of these decisions a lot clearer.” (35:11, Willem)
• Engineering, product, design, and teams now serve the whole company ecosystem (Square, Cash App, Afterpay, Tidal, etc.), rather than separate business-unit silos.
• Benefits: Tighter alignment, fewer conflicting priorities, clearer accountability.

8. Jack Dorsey’s Leadership and Vision

• Jack is seen as a stabilizing, visionary force—“lives in the future”—and is currently pushing hardest on automation and AI.
  • "Jack is an incredible visionary leader. I sometimes joke...he, like, lives in the future. This has a great intuitive sense about what's important for customers and where markets and things are going." (48:20, Willem)
  • “There hasn't been a technology in, let's say, past 20 years that improves by an order of magnitude every 12 months [like AI].” (50:32, Willem)

9. AI: Hype, Promise, and the Determinism Dilemma

• Square sees the next big shift as bringing AI and automation to small businesses—helping with everything from proactive insights to internal automation for support/sales/risk/compliance.
• The “interface” is changing; AI makes querying and action natural-language-driven, asynchronous, and potentially “agentic” (autonomous).
  • “For the first time, these kind of agentic systems give sellers a natural language way to answer questions about their business, like kind of letting their curiosity run free.” (57:02, Willem)
• Importance of combining non-deterministic AI (large language models) with deterministic traditional systems for reliable outcomes.
  • “These large language models are becoming more like the CPU...You need to give the CPU different things...data, sandboxes...the realization is: humans using computers are also not deterministic.” (64:58, Willem)
• Future UI might be largely generated by AI, allowing user-customized workflows rather than developer-specified forms.
  • "For the first time ever, the interface is generated by the customer or the user." (67:17, Willem)

10. The Death of the Penny: Operational Impact

• The penny is being discontinued in the US; Square already had similar features for Canada/Australia and is ready for the transition.
  • “We’ve had to build the features and capabilities to let sellers do roundups and all that other stuff. So we're excited to just enable that for US Sellers now.” (78:07, Willem)
• Operational impact: minimal; rounding up will not significantly change transaction patterns.
  • “I believe that elimination of the penny and kind of rounding up a little bit isn't going to like meaningfully change the behaviors we see just in the industry. Time will only tell though.” (78:49, Willem)
• Trivia: Square moves more than 16.7 million pennies between merchants and customers per week—a number the company had to double-check after the show.

11. Crypto and the Future of Money

• Square (Block) believes in giving sellers and customers maximum choice, including accepting bitcoin and fiat.
  • “Our goal is to make bitcoin everyday money. It doesn't mean you have to hold bitcoin. You can choose to hold fiat if you'd like to.” (73:49, Willem)
• Offers conversion tools so sellers can settle in fiat even if payment is in bitcoin. Most payment volume is still fiat-based.
• The company invests heavily in the Bitcoin Lightning network for instant transactions.
  • "Lightning is fast enough. And this is where block has made, I would say, monumental investments in the lightning network. We're one of the largest lightning nodes.” (73:55, Willem)
• However, philosophical and practical barriers remain: for many, the incentive is to “hold” bitcoin, not spend it.
  • “I'm just going to say I've been asking for years, why would anyone spend a bitcoin? And no one has ever given me a reason.” (77:39, Nilay)

Notable Quotes & Memorable Moments

On AI and Automation:

• "There hasn't been a technology in, let's say, past 20 years that improves by an order of magnitude every 12 months. There just really hasn't in a long period of time." (50:32, Willem Ave)
• “These large language models are becoming more like the CPU of a lot of these different products we're building.” (64:58, Willem Ave)

On Company Culture and Decision Making

• “Your gut is the best-trained ML model on the planet.” (44:37, Willem Ave)
• “Alignment is super, super important in a large organization. If you create different, effectively different mini startups...you're usually going fast in like different directions." (36:35, Willem Ave)

On the Death of the Penny:

• “We've had to build the features and capabilities to let sellers do roundups...We're excited to just enable that for US Sellers now.” (78:07, Willem Ave)

On Crypto Philosophy:

• "Our goal is to make bitcoin everyday money. It doesn't mean you have to hold bitcoin. You can choose to hold fiat if you'd like to. And again, giving sellers that choice, I believe is super important." (73:49, Willem Ave)
• "I'm just going to say I've been asking for years, why would anyone spend a bitcoin? And no one has ever given me a reason." (77:39, Nilay Patel)

Timestamps of Key Segments

• 01:59 — Episode introduction: Key Square/Block context and AI ambitions
• 06:05 — Willem Ave joins, Square’s evolution and expansion
• 08:29 — Square vs. Apple and the changing “open-ness” of payment platforms
• 11:45 — From payment acceptance to full business management
• 16:16 — On competition and the differentiator of Square's hardware/software integration
• 21:36 — Roadmap transparency and accountability
• 33:37 — How the Block reorganization to a functional structure works
• 44:37 — Decision making frameworks and the importance of alignment
• 48:20 — Jack Dorsey’s leadership, priorities, and impact
• 55:37 — Deep dive: What AI can tangibly do for small business
• 63:06 — “Deterministic” vs “non-deterministic” compute in future Square AI products
• 73:49 — The real status and vision for bitcoin/Lightning in Square
• 78:07 — Killing the penny: Preparing for and surviving the transition

Takeaways

• Square is no longer just a payments provider; it’s a platform aiming to cover every business need, buttressed by deep, hardware-driven integration and a future-facing, AI-empowered vision.
• The move to a functional organizational structure at Block was designed to align priorities across all brands for greater velocity and cross-pollination.
• AI is viewed not just as a trend, but as a core technological shift that will reshape business interfaces, automation, and the very architecture of financial tools for small business.
• Crypto remains experimental for most merchants, but Square/Block is betting on giving users maximum freedom of choice—and on the infrastructure (like Lightning) to someday make bitcoin “everyday money.”
• Death of the penny? For Square, it’s just another software update, but a symbol of how money and payments never stand still.

“If you don't show people what they can do, they won't even try. And then what scrambles that with AI is you can ask it to do anything and it will just confidently say it's happening, whether or not it actually is happening, happening.”
— Nilay Patel, 69:00