Rollover

Rollover — redeploying the proceeds of a liquidity event into the next operating asset (a second business, a holdco acquisition) rather than rotating into the diversified portfolio. It’s how serial entrepreneurs compound faster than the U-turn’s default path — and how some ride concentration over the top twice. The course’s framing: a rollover is pattern #4’s move and a legitimate choice made deliberately, with chips still taken off the table; drifting into one because selling felt like betrayal is failure mode #1 wearing ambition’s clothes.

First used in: 5.8 · Your composite path