The Job Isn’t to Think Less. It’s to Act While the Picture Is Blurry.

13 years of investing, surely I should know the rubric by now?! Well … turns out it’s not that simple. I love frameworks like Thinking, Fast and Slow and Moneyball. The problem is the rules don’t seem to exist!

My biggest wins were domain insiders in unsexy, technical markets. Operators who lived a problem inside a regulated or infrastructure-heavy industry for years before they built anything.

Except some of my cleanest write-offs were the exact same profile. Deep, credentialed insiders, just in consumer and commoditized categories, where the moat evaporates no matter how real the founder’s scar tissue is.

Then it gets worse for the rule. Some of my best returns came from total outsiders, in categories so new no insider existed yet. Elite pedigree, the Ivy and the bank and the brand-name VC job, showed up in my write-offs about as often as my wins.

One of my earliest exits came out of central Canada. No elite schools, no Valley network. Exactly the founder a tidy screen filters out on sight.

When I had too little time with a founder, I couldn’t get to yes. When I had too much, I talked myself in, then out, then in again. Paralysis dressed up as diligence. There’s a narrow window in between where I actually invest well, and I still can’t fully draw its edges. My best checks were often the ones I made before I could overthink them.

So the rule was never a pattern. The lazy version of that is “stop thinking, move fast.” The job isn’t to think less. It’s to have the courage to act while the picture is still blurry, knowing it stays blurry.