The Operating Letter · Vol. VI
The Operating Letter
A weekly briefing on decision quality, written for the founders and operators running companies past $10M ARR.
Since 2019, one letter has gone out every Tuesday morning at 6:14 a.m. Pacific — read by 24,300 founders, COOs, and operating partners across 41 countries. It is not a newsletter. It is a sustained argument about how good companies make hard decisions under pressure, told across roughly 1,400 words at a time. This page is the archive of that argument, grouped by year, going back to the first issue.
There are no sponsors, no sponsored sections, no popovers, and no tracking pixels. The only call to action is at the bottom of this page, and it has been the same one since issue No. 1.
On these letters
A short editorial header, and a few sentences about what this publication is — and what it deliberately refuses to be.
The Operating Letter is a single weekly brief written for the operator who already knows their company is good and is now worried it might not stay that way. It assumes the reader can read a P&L, has sat through at least one painful all-hands, and has stopped believing in playbooks that begin with the words "at our stage."
Each issue picks one operating decision — how to sequence a board meeting, when to fire a VP, how to think about headcount as a function of gross margin, why a quarterly OKR is a worse instrument than most founders think — and works the argument for 1,400 words. There are no interviews, no roundups, no "five things I learned this week." If a piece does not say something specific, it does not ship.
The letters do not sell anything. They are not a content funnel. They are not a top-of-funnel for the practice. They are the practice, in writing — the same arguments I make inside a Clarity Sprint, delivered once a week to people who may never hire me and whose reading I am quietly grateful for. Subscribe if the archive moves you; ignore it if it does not. The writing is the only thing on offer here.
The Archive
Three years of letters, newest first. The full index runs to 312 issues; the selections below are the ones readers most often forward to a co-founder.
2024
52 issues · one selected below2023
51 issues · two selected below- 19 September 2023 · Issue No. 241 Decision quality is not decision speed A working distinction between the two, and why confusing them is the single most expensive mistake a $30M company can make.
- 14 March 2023 · Issue No. 209 Operating Leverage Index, version three The 2023 revision of the index, with three new variables and a worked example from a 47-person Series B that found its margin hiding in plain sight.
The full back catalogue — every issue since No. 1, March 2019 — is available to subscribers at the foot of each Tuesday's letter. The selections above rotate quarterly.
The job of an operator is not to move faster. It is to be wrong, on purpose, for shorter and shorter stretches of time — until the gap between a decision and its correction is smaller than the gap between a decision and its consequences.
— From Issue No. 184, "On the geometry of correction"
If the writing has been useful
The next step is not another letter. It is ninety minutes inside the operating system the letters describe.
A Clarity Sprint is a paid 90-minute diagnostic with me, designed for founders between $10M and $120M ARR whose playbook has stopped working and who want one decisive quarter instead of another eighteen months of drift. Fourteen slots a year. Roughly 70% of inbound is declined by design.
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