Financial independence does not make you a braver founder. It quietly kills the hunger that drove you. What actually wins is resources and experience, and they just happen to show up at the same time, so people credit the FI for what the resources did.
AI looks like the great equalizer. The rookies got better, the gap closed, the floor came up. I think that read is exactly backwards, and it falls apart the moment you stop staring at one slice of the picture and look at the whole curve.
WordPress won the small-business web by being the least worst option. With Middleman and Claude, that excuse is gone. A retiree with no technical background just shipped a better site in a weekend.
Your CTO isn't fleecing you on purpose. They're a nerd with toys, a CEO who can't push back, and an AWS bill that's eating the runway. Here's the pattern, the boring fix, and a red-flag checklist.