Principles

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. ...

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. ...

The Observation My cousin texted me this morning with a line I’ve heard before but landed differently today: “A ship in a harbor is safe, but that’s not what ships are for.” It’s attributed to John A. Shedd, published in 1928. One of those quotes that gets printed on coffee mugs and LinkedIn posts until you stop hearing it. But context matters. He didn’t send it as decoration. He sent it as a nudge. ...

I’ve been writing thought cards for the past year. Short pieces, usually a page or two, where I try to capture a principle at the moment it forms. I started because I wanted to remember what I was learning. I didn’t realize I was building something. Over the last few months, a pattern kept surfacing. Every card I wrote about how principles form, how conviction develops, how people actually grow, connected to the next one. Not because I planned it, but because the same current kept pulling me back. Looking at them now, they trace an arc I didn’t see while I was inside it. ...

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. ...

Grafe Auction runs about 290 auctions a year across 48 states. Each campaign takes 10 to 14 days from start to finish. I’m the partner responsible for marketing, technology, and operations. That pace doesn’t leave much room for a system that’s clever but doesn’t hold up under pressure. It also doesn’t leave room for losing a thought from January that turns out to be the missing piece in February. The personal knowledge management crowd has an orthodoxy right now: tools don’t matter, just write. The AI crowd has its own: throw everything at the model and let it figure it out. Both are half right. Tools alone don’t create insight. Models alone can’t connect what they’ve never been given. ...

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. ...

The Box There are five of us in a rental car heading from the airport to the hotel. A friend is talking about a book. Nikki Erlick’s The Measure. The premise is simple: one morning, everyone on Earth wakes up to find a small wooden box on their doorstep. Inside is a string. The length of the string is the length of your remaining life. The question the novel asks is the obvious one. Do you open it? ...