The earnout years

A deadline changes the work

An earnout gives a transition a clock. Expectations are explicit, but the finish line can distort a decision if it becomes the only date that matters.

Two timelines remain in view. One belongs to the agreement. The other belongs to the product, team and customers, who do not organise themselves around transaction documents.

The incentives were not shameful. Pretending they were not affecting a decision would have been the problem.

From owner to steward

The cap table changes immediately. The sense of responsibility usually does not. Ownership and responsibility, which can feel like the same thing before a sale, are suddenly separate.

Sometimes the work still needs the founder to lead. Sometimes it needs them to transfer context, support successors and become less central. Staying indispensable makes the transition worse, not better.

The least glamorous part is taking knowledge held by individuals and putting it into decisions, systems and teams that can continue without them.

Leave without disappearing

Leaving requires clear ownership, honest succession and enough space for new leaders to make decisions differently. If everything still depends on the departing founder, the transition is not finished.

There is a personal transition too. A founder has to work out who they are when the company is no longer the main answer. Rushing into another startup can postpone that work.