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
The Investor Update I Stopped Sending Weekly
Three years of weekly investor updates. Reply rate dropped to single digits by month four. Switching to monthly doubled it.
Don't Take the Acquisition Meeting
The corp dev intro sounds like flattery. It's calibration. The buyer learns what you'd sell for, not to buy, and you pay for that in the next negotiation.
When the Co-Founder Email Wins
A six-week cofounder standoff, three failed coffees, then a five-paragraph email that ended it in an afternoon. Why writing beats talking it out.
More on founder decisions
- The Conversation Postponed for a Year
- The board update I should have sent was three paragraphs
- Why I Cancelled the Offsite
- Cofounder Equity, Three Years Later
- 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