Three teams made reasonable decisions. The product broke. Anthropic's postmortem is honest about the bugs - but silent about the organizational pattern that let all three ship at the same time.

Atlassian replaced its CTO with two 'next generation AI talent'. The point isn't the headcount. It's that the CTO's job has changed and most people haven't noticed.

Uber burned through its annual AI budget in four months. The lesson isn't that AI is expensive - it's that ungoverned adoption at scale is. A bootstrap-trained CTO's view on measuring return, not usage.

The product decision I didn't make in 2014 because I couldn't afford to be right — and what it taught me about conviction, financial autonomy, and the invisible cost of having no choice.