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. ...
A seller calls a few days after the auction closes. The line of equipment they bought new in 2021 came back at 40 cents on the dollar, and they’re sore. They paid top money for it. They expected more than this. So you do the thing the business trained you to do. You send the marketing report. Look at the reach. Look at the registered bidders, the ad spend, the page views, the email opens. We ran the play. We found the market. ...
If you choose convenience, you decline. That’s a human law. In business, commentary is the ultimate convenience. It is easy to write a forecast, spin a narrative, or make a decision because “it makes sense at the time.” But commentary naturally drifts and flatters us, and human memory decays too quickly to defend the truth. A typo can sit wrong by $1.2M for eleven months because nobody was forced to check the record. ...
I’ve been wrestling with how easily we slide into convenience. When AI makes writing effortless, our natural gravity is to accept the first thing the machine spits out. This default drift is a human law of decline. If you choose convenience, you’ll gain weight, you’ll stop reading, your brain will go soft. You’ll decline. The only way to survive this is active resistance. For myself, I’ve built custom agentic tools to force Socratic friction into my writing. But as a leader, the question is broader. I can’t build custom vaults and code-level friction for everyone in the company. Most people just want the frictionless path to get the task off their plate. ...
When AI commoditizes text generation, the natural gravity of human behavior is “normal drift,” gravitating toward low defaults and “easy peasy chat” while expecting a “silver magic bullet.” To survive this without losing my own original thinking, I’ve realized I cannot rely on self-discipline or raw willpower alone. I need a triple-layered cognitive defense system: The Tactical Defense (The Code Layer): Encoding Socratic pushback, friction, and accountability directly into the custom agentic skills I build. I don’t just open a ChatGPT tab; I build systems designed to actively resist my own laziness. The Contextual Defense (The Data Layer): Operating under the law of reciprocity. Deep sparring requires deep context. If I don’t build a dense, custom vault of actual thinking, the system has no leverage to push back, and the dialogue collapses back to generic out-of-the-box templates. The Meta-Cognitive Defense (The Mindset Layer): Active self-awareness of my own blindness and non-original thinking. Recognizing that I am naturally prone to low-effort defaults, and deliberately hunting for those defaults inside my daily work. Without these layers, I am just defaulting to convenience and calling it innovation. ...
Two observations stacked on the same Friday morning. The first one I’ve lived. Marketing agencies typically charge a percentage of marketing spend as their fee. The agency makes more money when the client spends more money. The incentive is to grow the budget, not the results. I’ve been quietly dismantling that arrangement in our vendor stack for the last couple of years. The second one I heard this morning. Pavel Durov on the Lex Fridman Podcast (#482, Sept. 30, 2025), making the point that drug companies aren’t actually incentivized to find the root-cause cure. They’re incentivized for you to keep taking the drug. Recurring revenue. Maintenance, not resolution. ...
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 just don’t understand how people are asking for a 1% life without understanding it takes 1% sacrifice effort. You have to be a 1-percenter if you want a 1% outcome…” Gary Vaynerchuk, The GaryVee Audio Experience, “Starting a Business, Building Brand and Overcoming Doubt,” September 25, 2025 Heard this Vee bit yesterday and the word “sacrifice” kept rattling. Sacrifice is the word doing the work in the quote. A 1% life takes hours, but the hours are downstream of what you’re willing to do without. What you don’t get to have, who you don’t get to be, what you don’t get to chase. That’s the dimension the hustle genre keeps missing. 1-percenter mode has two faces: the things you add (hustle, grind, output) and the things you subtract (sacrifice). The genre talks endlessly about the first. Vee names the second. My read is sacrifice is the word that completes the picture, the thing left behind, not just the thing being added. ...
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. ...