AI & Tech
Two Roads for AI Regulation and Why Both Are Dead Ends
The AI regulation debate has collapsed into two camps, and I think they're both wrong. The answer might be hiding in the last place I expected.
Systems Thinking
AI & Tech
The SaaSpocalypse Is Real. The Diagnosis Is Wrong.
A trillion dollars in SaaS market cap vanished in a few weeks. Wall Street looked at a few impressive AI demos and concluded that enterprise software is dead. It isn't.
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.
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?
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
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.