It takes us about 90 days to bring a new hire up to speed. Illness or injury can take someone off the schedule much faster than that. A resignation may give us two weeks. I was talking about hiring recently and found myself questioning when we start. We wait for a position to open, then look for someone to fill it. By the time they arrive, we need them to do work they haven’t learned yet. ...
The Observation David Senra asked Brad Jacobs how he differentiates A, B, and C players. Jacobs runs a mental exercise: picture the person in your office saying they’re done. Not a counteroffer conversation. Already moved. Orderly transition only because they respect you. Then feel the reaction. He walks the scale C to B to A. Restated in rank order: C (Jacobs): You shouldn’t smile. Nobody likes firing people. You postponed it. Now you don’t have to pay severance. Problem solved. Replace them. Get the courage to take them off the team right away next time. ...
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. ...
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 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 ...
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. ...