Categories
Micropayments

The Wrong Who

I was in the room for most of the early micropayments conversations. The working-level conversations, where people were genuinely convinced they had finally solved the problem. The demos were always compelling. The unit economics made sense on a whiteboard. And then they died.

They died so many times, and in so many similar ways, that the failure started to feel like a law of nature.

Clay Shirky wrote the autopsy that most people remember: micropayments fail because every transaction requires a decision, and decisions have a cognitive cost that swamps any payment below some psychological threshold. A dollar feels like real money. A dime feels like a question you have to answer. A fraction of a cent feels like being nickeled-and-dimed at sub-human speeds. The advertising model won because it asked users to consent once, peripherally, and then never bother them again.

So I noticed something when I read the transcript of Cloudflare CEO Matthew Princeโ€™s earnings call remarks this afternoon.

Heโ€™s predicting that the internetโ€™s business model โ€” advertising and subscriptions, the twin structures that have governed everything since the late nineties โ€” is about to change. He thinks some part of what replaces it will be micropayments for agentic traffic. Fractions of pennies. Fractions of fractions. At volumes that dwarf anything existing financial infrastructure can handle.

My first instinct was the old skepticism. Weโ€™ve been here before.

But I kept reading, and I think something is actually different this time. And the difference is the one thing all the earlier schemes never had.

The payer isnโ€™t human.

This sounds obvious once you say it, but it collapses most of the objections that killed every prior attempt. Cognitive load isnโ€™t a factor when thereโ€™s no cognition happening. Decision fatigue doesnโ€™t apply to a process with no feelings about fatigue. The agent making the request doesnโ€™t hesitate at a fraction of a penny, doesnโ€™t resent the transaction, doesnโ€™t abandon the session because itโ€™s annoyed at being charged.

All the early micropayments architectures were built on an implicit assumption: that humans could be trained to behave like rational microeconomic actors at browsing speed. They canโ€™t. Nobody does. But agents are rational microeconomic actors by design. Thatโ€™s not a metaphor โ€” itโ€™s literally what they are.

The schemes we watched fail in the early 2000s werenโ€™t wrong about the destination. They were wrong about the who. The internet of human readers and human attention was never a natural fit for per-transaction pricing. The internet of autonomous agents โ€” making API calls, scraping data, assembling answers from dozens of sources in a single second โ€” is a different thing entirely. And itโ€™s arriving faster than most people realize.

Prince mentioned that Cloudflare thinks non-human traffic will surpass human traffic somewhere around 2027. That number stopped me. We are, apparently, closer to a majority-machine internet than to the one we think weโ€™re living in.

The hard part isnโ€™t the concept anymore. Itโ€™s the infrastructure. Prince was candid about this: the transaction volumes the industry gets excited about โ€” a million per second โ€” arenโ€™t remotely sufficient for whatโ€™s actually coming. Cloudflare needs something an order of magnitude larger, and theyโ€™re looking for partners because nothing that fits the spec exists yet.

This is where it gets interesting for those of us who watched the earlier rounds. The original micropayments failures were partly psychological, but they were also partly infrastructural โ€” the payment rails of the early internet werenโ€™t built for high-frequency small transactions either. Whatโ€™s different now is that the need is undeniable and imminent in a way it never quite was before. The traffic is real. The scale is measurable. The pressure to figure this out is coming from something other than optimism.

I donโ€™t know what the solution looks like. Probably not one thing. Prince doesnโ€™t know either โ€” he said as much. Crypto infrastructure is an obvious candidate for parts of it, though cryptoโ€™s history of promising to solve problems and then creating different ones deserves some respect. Whatever emerges will probably be unrecognizable from here.

What I keep coming back to is the simpler observation. We were right that micropayments were the future. We just imagined the wrong future, populated by the wrong kind of payer.

The agents were always going to solve this. We just had to wait for the them to arrive.

Categories
AI Business Work

The Tipping Point Was Last November

Matthew Prince, Cloudflareโ€™s CEO, said something on todayโ€™s earnings call that I keep turning over. He didnโ€™t bury it or soften it. He named a date.

โ€œInternally, the tipping point was last November.โ€

Thatโ€™s a specific thing to say. Not โ€œweโ€™ve been on a journeyโ€ or โ€œAI has been transforming our industry.โ€ A month. A moment. The thing changed, and he knows when.

What changed, by his account, is that Cloudflareโ€™s teams began seeing productivity gains so dramatic they were hard to describe โ€” people who were two times more productive, ten times, in some cases a hundred times. โ€œIt was like going from a manual to an electric screwdriver.โ€ Usage of AI tools internally is up more than 600% in just the last three months. Every line of production code is now reviewed by an autonomous AI agent.

And then he said goodbye to 1,100 people โ€” about 20% of the company.


Today wasnโ€™t just Cloudflare. Earnings season has become something like a drumbeat. Meta is cutting 8,000 employees this month. Amazon cut 16,000 in Q1. Oracle eliminated roughly 30,000 to fund AI infrastructure. Block cut almost half its workforce. PayPal is reportedly planning to cut 20% of its staff over the next few years. Coinbase cut 14%. Snap cut 16%. As of this week, more than 92,000 tech workers have been laid off in 2026 alone.

The scale is striking. But what strikes me more is the framing โ€” the specific language being used to describe whatโ€™s happening. These arenโ€™t being announced as cost-cutting moves or post-pandemic corrections, the way they might have been in 2022. Theyโ€™re being announced as architectural decisions. Structural adaptations. Evolution.

Prince was careful to be explicit: โ€œThis isnโ€™t a cost-cutting exercise or an assessment of individualsโ€™ performance. Itโ€™s about defining how a world-class, high-growth company operates and creates value in the agentic AI era.โ€ Thatโ€™s not empty corporate language, or at least not only empty corporate language. The distinction heโ€™s drawing โ€” between trimming fat and reimagining how a company is built โ€” maps to something real about what AI agents can now actually do.

Thereโ€™s a legitimate version of this argument and a convenient one, and theyโ€™re being delivered in the same sentence by the same people, which makes them hard to separate. Some analysts suspect companies are using AI as cover for cuts they wanted to make for other reasons โ€” rightsizing from pandemic-era overhiring, funding massive infrastructure buildouts, chasing margin. Oxford Economics flagged this: maybe some firms are โ€œdressing up layoffs as a good news story.โ€ The cynicism is warranted.

But then thereโ€™s the Cloudflare number: 600% increase in AI usage in three months. Thatโ€™s not a narrative. Thatโ€™s a measurement.


Whatโ€™s different about this moment โ€” what makes Princeโ€™s โ€œtipping pointโ€ language feel accurate rather than convenient โ€” is that the people making these decisions are themselves users of the tools. Theyโ€™ve seen the productivity numbers internally before anyone else has. Theyโ€™re not theorizing about what AI might do to their workforce; theyโ€™re describing what it already did.

Thatโ€™s the thing that changed. For years, AIโ€™s labor impact was a future tense conversation. Economists studied it, think pieces warned about it, conferences debated the timeline. Then, somewhere around last November apparently, a cohort of technology companies crossed from hypothetical to empirical. The future tense became past.

Whether you read that as tragedy, as transformation, or as both depends on where youโ€™re standing. 1,100 people at Cloudflare today are standing somewhere very specific. Prince acknowledged this with what felt like genuine difficulty: โ€œA number of friends will no longer be colleagues.โ€ Whether that difficulty changes anything material for the people leaving is a fair question.

But the acceleration itself โ€” the thing he named โ€” is real. The tipping point was last November. And if it was last November for Cloudflare, it was some nearby month for Amazon, for Meta, for Block, for all of them. Whatever these companies learned that changed everything, they all seem to have learned it around the same time.

Thatโ€™s what I find myself sitting with today: not just the scale of the disruption, but the synchrony of it. The realization arrived, and then the decisions followed. Quietly at first, then all at once.