2026-09-12 · Retro
From Lecturer to Founder: A Retro on Judgement
I've held four roles: university lecturer, Fortune 500, investor, founder. Looking back, they didn't teach me four skills. They taught me four price tags on the same thing — a judgement, priced anywhere from nothing to everything you have.
From a lectern, judgement costs nothing
When I taught, a call I made about a theory cost me, at worst, a sharp question from a student or a disagreement with a colleague. The cost of being wrong approached zero, which made it easy to mistake "thought it through" for "got it right." That's a dangerous illusion: a judgement with no price attached looks smarter than it is.
Inside a large company, process absorbs the error
The corporate years taught me that what's valuable isn't one person's brilliance, it's a system's ability to average mistakes down. Process, review, sign-off authority — all of it is insurance on judgement. What I learned there was translating "I think" into "the data says" and "the process permits."
In investing, judgement starts charging tuition
Investing put a price on being wrong for the first time: right, the account goes up; wrong, it goes down. Nobody absorbs it and no process carries it for you. That forced a rule I still keep — every view has to be writable as "if X, then Y; otherwise Z." A call you can't write down isn't a call, it's a wish.
In founding, you're all in
Founding pushes the price to the limit: a bad call costs money, but also the team's time, your reputation and the options you didn't take. So my framework for deciding now grows backwards — check whether I can survive the worst tail first, then talk about the upside. It's the same muscle as sizing a position from its downside.
The retro in one line
What the four roles taught me isn't how to be more accurate. It's to attach a price to every judgement, then decide how much to bet on it. The more expensive the judgement, the more it has to be written down, leave a trace, and survive being reviewed later. That's also why this site exists: once a judgement is written, it stops being noise in your head and becomes something you can revisit, correct and re-use.