Scaling

In August 2025 I wrote a thought card about structured data. The argument was simple. Treat your data as a long-lived asset that should be findable by any system, and you build infrastructure that compounds. The card said nothing about agents. I had no idea WebMCP was coming. Six months later, Google announced WebMCP and the agentic web, the standard protocol for AI agents to act on structured web data. A protocol I’d never heard of, designed for a use case I hadn’t predicted. And the platform I’d been building already fit it. Not because I saw the future. Because the principle didn’t depend on seeing the future. ...

I was working through the details of bringing a small team in-house. Purchase price, salaries, org chart, who reports to whom. Normal acquisition stuff. And I caught myself thinking about it like a hiring decision. How many people, at what cost, doing what work. But we weren’t hiring. We were acquiring. The distinction matters, and I think it matters more in the auction industry than most people realize. When you hire someone, you’re renting their skills for as long as they stay. The moment they leave, whatever wasn’t documented or embedded in a system walks out with them. That’s not cynical, it’s structural. I wrote about this a few weeks ago in a different context: the relationships someone builds on your platform become yours, but the person is always rented. Everyone is. ...

Definition I’ve been circling this idea for six weeks, and it keeps showing up in different shapes. 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 ...

Dave Plummer is a retired Microsoft engineer. He created Windows Task Manager, ported Space Cadet Pinball to Windows, built the ZIP folder support, and wrote the Windows activation system for XP. He’s been coding since the TRS-80 days. Dropped out of high school. Worked at 7-Eleven. Went back to school, cold-emailed his way into Microsoft from Saskatchewan, and stayed for years building tools that billions of people still use daily. He now runs a YouTube channel called Dave’s Garage. Lex Fridman had him on episode #479, and four things from their conversation stuck with me. ...

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. ...

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. ...

The Synthesis Niche saturation isn’t the opposite of coalition. It’s the prerequisite. Daniel Ek’s principle is right: saturate your niche before you expand. But the card was incomplete. It assumed the niche is a standalone unit. It’s not. Niches that share a method, a market structure, or an identity sit on top of shared infrastructure, like lakes fed by the same aquifer. Auto auctions, livestock auctions, industrial equipment, personal property. Different surfaces, same water underneath. ...

The Observation I didn’t build structured data systems because I predicted WebMCP or the agentic web. I built them because “touch it once, make it findable by any system” is just good practice. “Computers do the mundane, humans critically think” is just a sound division of labor. These are principles, not predictions. But those principles, arrived at independently, produced exactly the infrastructure the agentic web needs. A straight line runs from a thought card I wrote in August 2025 to a platform that’s accidentally ready for a protocol Google announced six months later. ...

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. ...

Building better markets instead of chasing perfect prices Let’s talk about something every auctioneer thinks about: Are we actually finding true market value? I had an interesting conversation recently with a colleague about whether auctions reveal what something’s really worth. Sure, they can. But here’s what bothers me. We’re calling it “true market value” when maybe 5–10% of potential buyers ever see our marketing. How’s that the true value? This isn’t just theory. It creates real problems. ...