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 board update I should have sent was three paragraphs
The midnight update ran twenty-two pages and six charts. The update I should have sent was three paragraphs.
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Why I Cancelled the Offsite
Three days, a venue in the Berkshires, an agenda with seventeen sessions. Nine days before it was scheduled, I cancelled it. The team thanked me twice.
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Cofounder Equity, Three Years Later
Sixty-forty in year one, each cofounder doing half the work. The forty-percent cofounder noticed in year three, and the relationship never recovered.
More on founder decisions
- Four articles in, the press stopped working
- The first time you lied to the board
- Name your successor before the bus does
- The strategy doc you never wrote down
- The first ten employees who carried the wrong values
- The roadmap you couldn't defend
- The 'no' you wish you'd said in year one
- The mentor who was actually a fan
- The therapist you should have started seeing in year two
- The board seat you gave away too cheap
- The vacation you didn't take for three years
- The customer call you stopped doing
- The pivot you delayed by a year
- The acquisition offer you didn't take seriously enough
- The investor you took money from for the brand