Letters to a Founder at Series C

There is a particular loneliness to the middle of a company's life. The early scrappiness is over; the institutional grandeur has not arrived. The founder who was celebrated for doing everything is now the bottleneck for everything. This is the Series C problem, and almost no one names it out loud.

The instinct that built the company — control, intensity, personal involvement in every decision — becomes the thing that limits it. The hardest transition in a founder's life is not raising the round. It is learning to be less necessary.

"Early on you are paid to do the work. Later you are paid to build the people who do it."

What a founder must let go of is not ambition but proximity — the comfort of being in every room. The companies that make the leap are led by people who replaced their reflex to intervene with the patience to develop others, and who learned that delegation is not abdication but the highest form of leverage a leader has.