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
Three Emails Beat Fifty-Two
A CEO who emails every Monday trains the team to skim. Three emails a year that name the CEO's own bad call get read, and they cost the CEO something.
The Reference Check I Stopped Skipping
Five senior hires, three reference calls done. Two flagged concerns the panel never saw. After a third failed hire, references stopped being optional.
Why a Founder's Job Description Has to Change Every Year
The job that closed your first ten customers is not the job that scales the next hundred. Keep doing it at year three and the company stalls there.
More on founder decisions
- When the Best Hire Quit
- Why I Stopped Saying Yes to Coffees
- When the CEO Should Stop Hiring
- What I Told the New CFO First
- The Investor Update I Stopped Sending Weekly
- Don't Take the Acquisition Meeting
- When the Co-Founder Email Wins
- 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