The Ramblings
of a Serial
Entrepreneur

Trusting your gut is risky, and over-analyzing isn’t practical. Field notes on what actually works for most decisions.

We can't see the future, but with the right framework we can spot failure before it happens. That turns out to be most of what we need.

My oldest leaves for college this month, and I've already started grieving her departure. It taught me something about the bigger picture of losing someone.

The most dangerous moment is when everyone in the room agrees. A field-notes case for why agreement isn’t evidence - and what to do when you can’t change who’s in the room.

An AI passed its taste for owls to another AI using nothing but a list of random numbers. I think it taught me something about my own kids.

They file thousands of cookie-cutter privacy suits a year and bank on you settling. Here's how I made two disappear - and you can too.

Nobody can define consciousness. Not the philosophers, not the neuroscientists, not the AI researchers. But now it's at the center of AI ethics, regulation, and moral status. That's a problem.

Doomers and optimists both assume superintelligent AI will be relentlessly motivated - but biology and history suggest it will be lazy.

If AI frees humanity from work, most people won’t paint or philosophize. They’ll sit on the couch and scroll until they die. The technology is engineered to make sure of it, and you won’t even notice.