How to tell it’s time
The signals that actually mean something, and the ones founders mistake for them.
A letter for founder-owners thinking about what comes next — what an advisor actually does, what buyers really look at, and how to tell whether it’s time. Plain language, no jargon, no pitch.
One piece at a time, written for someone who has never sold a company and shouldn’t have to pretend otherwise. Unsubscribe whenever you like.
The letter starts shortly. These are the questions it opens with — the ones that come up in nearly every first conversation.
The signals that actually mean something, and the ones founders mistake for them.
The unglamorous version, stage by stage, and where the value genuinely comes from.
Customer concentration, owner dependence, and the three numbers that move a multiple.
What to fix before you go to market, when waiting is worth considerably more than selling now.
Diligence fatigue, quiet re-trades, and how a process protects you from both.
Who needs to know, when, and how to protect people you’ve worked beside for years.