Auctions

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. ...

Five Guys fills your fry cup, drops it in the bag, then scoops another ladle on top. The generosity is staged so you witness it. Jerry Murrell didn’t give customers more fries. He gave them the same fries in a way that felt like more. The question a friend posed: is there an auction industry version of this? Can a business with two customer types (sellers who want maximum return, buyers who want fair access) create a single “fries” moment that lands for both? ...