AI & Tech
The Fastest Way to Win Meta's AI Contest Is Also the Dumbest
If you want to understand why so many companies are spending fortunes on AI and getting nothing back, look no further than Meta's internal leaderboard for token consumption.
Latest
Systems Thinking
Build It, Buy It, or Borrow It
I have a graveyard of SaaS subscriptions I paid for instead of building and custom tools I built instead of buying. After enough mistakes, a pattern emerged in what made some decisions right and others wrong.
Investment
The Test That Separates a Moat From a Tailwind
When I evaluate a business for the family office, I run one test before anything else. If the wind reversed tomorrow, does the company still exist?
Investment
OpenAI's Retail Investor Play Isn't Democratization, It's a Price Floor
When I evaluate pre-IPO retail access from the family office side, I run a simple test. I ask: who benefits more from this transaction, the buyer or the seller? If the company is engineering broad ownership before a public listing, the answer is almost always the seller.
Entrepreneurship
The Owner-Reliance Discount
Every system you build is equity. Every process only you understand is a liability on the balance sheet.
AI & Tech
Slack Just Turned Slackbot Into the Agent You Actually Wanted
Slack announced more than 30 new capabilities for Slackbot today, transforming it from a simple chatbot into a full-spectrum enterprise agent powered by Anthropic's Claude and connected via MCP.
AI & Tech
OpenAI Kills Sora and the Era of AI Companies That Do Everything
OpenAI is shutting down Sora, the AI video platform it launched to enormous fanfare in late 2025. The consumer app, the API, and the website are all going dark. The billion-dollar Disney deal? Dead.
AI & Tech
Anthropic's Biggest Vulnerability Was a Checkbox
The most safety-conscious AI lab on the planet just leaked its most dangerous model through a misconfigured content management system.
AI & Tech
The AI That Tells the Emperor He's Naked
Interloom just raised $16.5M to map how companies actually operate. The product is compelling, but the real opportunity is much bigger than one startup's context graph.
Systems Thinking
Feedback Loops Are Eating Your Margin
Most operators think about margin as an output. Revenue minus cost equals profit. Margin erosion almost never shows up as a single line item you can point to and fix. It shows up as a pattern, a reinforcing cycle where one problem feeds another.
AI & Tech
Anthropic "Accidentally" Released a New Model. Sure They Did.
Anthropic released a new Claude model this week that wasn't supposed to be public. They called it an accident. The model appeared briefly, got pulled, and the story spread everywhere.
AI & Tech
A Federal Judge Just Told the Pentagon Its Anthropic Ban Looks Like Punishment
A federal judge in San Francisco said today what the entire AI industry has been thinking for two weeks. The Pentagon's decision to blacklist Anthropic looks like an attempt to cripple the company.