Decision-Making

The Observation We require identity verification on the website: a picture of your ID and a selfie. A few customers a week call and say, there’s no way I’m giving you my ID. Almost always, the reason is identity theft. So I ask them, what do you think they do with that stolen identity? They target businesses that aren’t doing identity checks like we do. To that, they almost always go, “Oh, I’ve never thought about that side of it.” Almost selfishly, if you ask me. They’ve only ever pictured themselves as the victim, never the business that gets stuck with the bill. ...

When we ran simulcast auctions, with people bidding in the room and online, I heard the same suspicion time and again. The people in the room thought the internet had an advantage, and the people online thought the floor did. I think putting those two methods of bidding into the same auction can create distrust. Each group competes against people whose way of participating differs from its own. That gives bidders another reason to question whether everyone has the same opportunity to compete. ...

The Observation Mel brought Chinese for lunch on August 19. I went to break the fortune cookie and it was kind of soggy. Bit into it anyway, then read the slip: “Let go of the past and embrace July’s opportunities.” The first card I wrote treated that as a miss. July was later until it wasn’t. The cookie certified the window closing. That was the joke I thought I had. ...

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. ...

The Observation Touch it once. When something lands, finish it or triage it on the first touch. Do not pick it up, set it down half-handled, and pay the full re-entry cost later. Touching without deciding is how piles become careers. I learned that young. At sixteen, through business class and Business Professionals of America, I interviewed for an On the Job Training slot and got hired as a teller at Norwest Bank, the company that became Wells Fargo. Stillwater in May 1993. Through March 1998 I moved from that floor to the Norwest Center downtown Minneapolis (now Wells Fargo Center), then across the street to IDS as lead teller, then to sales and service supervisor with a second drive-up branch on Portland Avenue while they found a new supervisor. Somewhere in that stretch, leadership training put the line in my mouth: touch it once. ...

The Observation I was listening to Lex Fridman with Julia Shaw on the bystander effect, and the piece that stuck was simple: if you’re not first on the scene, you look at the other faces to figure out what this is. Calm faces mean “not an emergency.” Your calm becomes data for the next person who walks up. Lex’s point was that most people think they’d resist evil, or step up on a street when something bad is happening. Most people don’t. You have to simulate the hard act of resisting, or of intervening, because in the moment it’s not easy. ...

Today I rebuilt the routing rules for my AI agents: which model handles mechanical work, which handles hard reasoning, which validates the output before I see it. The setup looked rigorous. Every substantial piece of work got checked by a validator agent running at high effort on my most capable model. The critique that stopped me: the validator was the same model as the thing it was checking. Same model, same characteristic errors. When the producer and the checker share a mind, the check confirms the work is consistent with itself. It can’t see the errors that mind is inclined to make, because it’s inclined to make them too. ...

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. ...

Most leaders don’t actually leave doctrine behind. They leave the way people remember them leading. Mission statements claim transparent, equitable, research-led, open. The qualities show up in the language. They rarely show up in the practice. The honest version of the legacy claim is smaller and harder. It’s not “I built a great system.” It’s “I knew the way my own thinking gets stuck, and I built a tool that breaks me out of it.” ...

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. ...