I remember sitting in crypto meetings around 2017 feeling genuinely lost.
Everyone spoke with total conviction about tokens, protocols, Layer 2s. I’d nod along and go home wondering if I was missing something obvious or if the emperor had no clothes. Thanks Noah Jessop for helping me learn quite a bit 😉
Turns out it was a bit of both. But in the moment, I couldn’t tell.
That feeling is back.
There’s a military concept called the fog of war – information is incomplete, the situation keeps changing, and you have to make irreversible decisions anyway. The commanders who succeed aren’t the ones who wait for clarity. They develop principles that work under uncertainty.
Investing in AI right now feels exactly like that.
Every week something shifts. A model drops that changes the competitive dynamics of three categories simultaneously. Deals move faster than I’ve ever seen – first meeting to term sheet in days. Inbound is up dramatically. And yet I keep asking myself: are we even seeing the right stuff? Will we know it when it walks in the door?
I passed on Hugging Face early. I didn’t fully understand what they were building or how big the platform could become.
The AI fog is harder than the crypto fog in one specific way. Back then the question was “is this real?” Now I believe it’s real. The question is which of it is real, for whom, and when.
In the same week I might look at deep domain AI for a regulated industry, a silicon chip innovation, and a company with a pricing model that didn’t exist two years ago. Each requires a completely different knowledge base.
You need both a PhD and a BS detector 😉 and they pull in opposite directions.
The PhD says: technically impressive. The BS detector asks: is it special? Does the founder actually understand their customer or are they just riding the wave?
I’ve been trying to anchor on things that don’t change when everything else does. The founder’s obsession with the problem, not with AI.
But the crypto experience taught me one thing: the people who felt most certain in those rooms in 2017 weren’t always the ones who ended up right.
Sometimes the confusion was the more honest signal.
I’m trying to hold onto that.
