Pillar
Founder decisions
The calls only the operator can make — about energy, ego, focus, and the costs of being in charge.
Some calls only the operator can make. The raise that solved the wrong problem. The cofounder conversation postponed through Christmas. The acquisition meeting it would have been better not to take. The board update that bought six more months versus the one that triggered a search.
The founder decisions that compound are not the ones in the deck. They are the small calls about energy, ego, focus, and the cost of being in charge — the ones the operator makes alone, often at eleven at night, often with the wrong information and the right intuition.
These essays are about those calls. The skip-level you stopped doing. The forecast meeting you stopped trusting. The senior hire you were right about and didn't act on. The conversation you postponed until it postponed you.
Start here
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The hire you made because you couldn't find anyone else
The role had been open for four months. The pipeline was empty. You hired the one candidate who said yes. They left in nine weeks.
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The email you drafted at 11pm and shouldn't have sent
It was clear, direct, and absolutely correct. It also cost you the relationship. Being right at midnight is the most expensive form of being right.
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The board update that buried the bad news
Page nine, paragraph three, fourth sentence in. The number that mattered most was hidden where nobody would ask about it.
More on founder decisions
- The advisor you only call after you've already decided
- The cofounder conversation you keep postponing
- The founder who couldn't be on vacation
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