THE AWKWARD EXIT: $150M TO $300M ACQUISITIONS

Summary from the TLDR Founders newsletter

A $200M exit is often life-changing for a founder but a failure for a Series C investor. This "Grey Zone" creates boardroom deadlock. Early investors (Seed/Series A) are happy with a 5x return, while late-stage funds that underwrote a $1B outcome may block the sale to avoid a write-down. The solution: negotiate secondary sales during your growth rounds.