Auctions

The observation On July 1, Cloudflare shipped something called the Monetization Gateway. Any site behind their network, which is roughly a fifth of the web, can now charge for anything it serves: pages, datasets, APIs, tools. The mechanics run on HTTP 402, a status code that has sat in the spec unused since the 90s, literally reserved as “Payment Required” for a future that never showed up. An agent requests a resource, gets a 402 with a price, pays in stablecoins, and the content comes back. Sub-second, wallet to wallet, no account signup, no API key. It’s built for machine buyers, and Cloudflare says the quiet part out loud: AI crawlers request content a hundred to tens of thousands of times for every human visitor, and you can’t sell a subscription to a crawler. ...

On June 3, 2026, Matthew Prince, the CEO of Cloudflare, posted a number from his own network’s live data. For the first time in the history of the internet, more than half of all web traffic was not human. Bots, crawlers, and AI agents made up about 57 percent of the requests. People made up the rest. Prince said he’d figured the crossover would come at the end of 2027. Agentic traffic got there a year and a half early. ...

A seller calls a few days after the auction closes. The line of equipment they bought new in 2021 came back at 40 cents on the dollar, and they’re sore. They paid top money for it. They expected more than this. So you do the thing the business trained you to do. You send the marketing report. Look at the reach. Look at the registered bidders, the ad spend, the page views, the email opens. We ran the play. We found the market. ...

Two observations stacked on the same Friday morning. The first one I’ve lived. Marketing agencies typically charge a percentage of marketing spend as their fee. The agency makes more money when the client spends more money. The incentive is to grow the budget, not the results. I’ve been quietly dismantling that arrangement in our vendor stack for the last couple of years. The second one I heard this morning. Pavel Durov on the Lex Fridman Podcast (#482, Sept. 30, 2025), making the point that drug companies aren’t actually incentivized to find the root-cause cure. They’re incentivized for you to keep taking the drug. Recurring revenue. Maintenance, not resolution. ...

Definition The agentic shift is not an upgrade to existing infrastructure. It replaces the assumptions that infrastructure was built on. “Each level isn’t defined by what the AI starts doing. It’s defined by what the human stops doing.” – Five Levels of Agentic Commerce “The cost of modern convenience is an involuntary autobiography that someone else owns.” – Digital Exhaust “The agentic web is the marketplace trap with different actors.” – Two Trust Systems ...

I told someone last week that his business couldn’t survive him. He’d called to pick my brain. Decades in the auction industry, multiple divisions, good revenue. But every decision in the company routed through him. Sales, operations, finance, client relationships. He’d spent his career being the best person on the microphone, and the rest of the business just happened around that skill. There were no documented processes. No decision-making frameworks anyone else could follow. If his potential successor took over tomorrow, they’d fail. Not because they’re incapable, but because the architecture underneath was never built for anyone else to run. ...

I was listening to Acquired’s Google episode this morning, the Alphabet deep dive, and one detail stuck with me. Google launched Google Video before YouTube even existed. Google had the engineering talent, the infrastructure, the money. YouTube had nothing except a webcam, a website, and almost zero friction. YouTube won because anyone could upload a video in minutes. Google Video required you to fill out forms, wait for approval, deal with format restrictions. Same basic product, totally different levels of friction. The low-friction version attracted the creators, and the creators attracted the audience, and the audience attracted more creators. Users did the scaling. Google just had to buy it afterward. ...

Two weeks apart, two completely different conversations, the same sentence came out of my mouth. On February 24, I told a bidder verification startup to make their pricing model “super simple, my mom can read it.” They’d built a tiered structure with base fees, per-bidder charges, monthly active user fees, revalidation windows, and a bidder-pay option. Smart people solving a real problem. But the pricing had become a mirror of their engineering, not what they were actually selling. I pushed them to kill the MAU charge entirely because customers would think they were being double-charged. Simplify to two price points: one flat fee for new bidders, a lower one for returning. They agreed. ...

Stripe’s 2025 annual letter lays out five levels of agentic commerce, and what makes the framework stick is that each level isn’t defined by what the AI starts doing. It’s defined by what the human stops doing. Level 1: Eliminating web forms. You still research and decide. The agent just handles the typing, the checkout fields, the payment details. It’s a clerk, not a buyer. Level 2: Descriptive search. You stop searching for specific products and start describing situations. “I need back-to-school supplies for a third grader in Chicago, nothing too itchy or tight, he likes KPop and tennis.” The system reasons across weather, materials, sizes, taste, reviews, and delivery timelines. ...

Last August, I had a conversation with a colleague that stuck with me. We were talking about whether auctions actually find true market value. My argument was simple: how can it be true market value when maybe 5-10% of potential buyers ever see our marketing? We’re calling it market value based on whoever happened to show up. I wrote about it at the time. My answer was to build communities, find your own lake, pursue smarter marketing instead of more marketing. I believed it. I still do. But six months later, I think I was thinking too small. ...