Contrarian takes on AI, markets, and technology from Stephen Messer — the arguments nobody else is making yet.
Opinion
The oldest rule in venture was bet on the jockey, not the horse. Something changed. The biggest funds, now $235B in combined AUM, have quietly become investment trusts, paying up for access to founders who already made it, running the exact playbook J.P. Morgan ran on the railroads in 1901
Opinion
Wall Street calls it a bubble because the money moves in a circle: Nvidia into OpenAI, OpenAI into Oracle, Oracle into Nvidia. This is the third time a tech industry has run this experiment. AOL was the first. WeWork was the second. Here is what's actually different this time.
Opinion
Two mega-trends land the same year. One ends privacy for anyone in public life. The other makes wiretapping impossible forever. Both reshape society more than the AI everyone still writes about — and neither has entered the conversation yet.
Opinion
Two respected CEOs spent July 2026 running the same play: build a wall around your data. Both are selling the wall. But only 10% of what makes you competitive lives inside it. The other 90% is externality — visible only at network scale, invisible from behind their walls.
Opinion
Every personal social network evolved. Every messaging app evolved. Only professional networking is still a résumé site with feeds glued on top. That ends now, and it changes how anyone with a network gets to use it.
Opinion
Every AI debate is stuck at the model layer — bubble or not, whose benchmark wins this month. All interesting. None of it decides who owns AI. The real fight is one layer up: whoever owns the orchestration layer gets the next twenty years.
Opinion
The debate over the AI data center buildout has been about whether OpenAI, Anthropic, and Oracle can generate enough revenue to justify what they are building. That is the wrong question. The right one is what a stockpile of general-purpose GPUs is worth if one island stops shipping chips.
Opinion
Spire Global started with a question most people in the satellite industry considered absurd. What if a satellite could be the size of a wine box, cost $200,000, and do more than the ones that cost a billion dollars? Here is what happened next.
Opinion
Most companies apply AI to what they already do. The ones who win ask whether what they're doing should exist at all. The sales forecast is the perfect place to start.
Opinion
Part 1 made the case for urgency. Part 2 covered the people problem. This part is operational. Not philosophy. What the companies pulling away are actually doing, and how to start.
Opinion
Part 1 made the case for urgency. This part is about who you put in charge of it, and why most companies get that decision backwards.
Opinion
There is a sentence moving through boardrooms right now that sounds like wisdom and functions like a trap. "We are taking a responsible approach to AI." It gets nodded through. And it is the most expensive position a company can take right now.