Evaluating IPO Window Assumptions and the Risk of Leaving Vested Equity

Jason Lemkin discusses the trend of executives leaving millions in vested stock options to join mid-to-late stage startups, reflecting an implicit belief in an endless IPO window for SaaS companies. He argues this behavior mirrors dot-com era thinking and questions the prevailing venture capital consensus that SaaS companies can IPO anytime they reach $80-100M ARR with growth, regardless of public market conditions.