1.
"Free forever" isn't a moat. When you refuse revenue, you can't invest in evolution. Craigslist's minimalism was a feature in 2005, a fatal bug by 2018.
2.
Anonymity flips from feature to bug. What felt authentic in 1995 felt dangerous by 2010. Safety and trust became the new competitive advantage.
3.
Specialists beat generalists when markets mature. Being okay at everything loses to companies doing one thing exceptionally well—Indeed for jobs, Zillow for housing, Facebook for peer-to-peer.