The Hindsight Game

There are all kinds of strategies for evaluating startup ideas - investors talk about having a “prepared mind,” others build market maps, I like to think about toys, and we could go on. What everyone wants to do is predict the future. That’s honestly impossible. But we can pretend a bit and use hindsight as a framework to find the kinds of opportunities that are worth working on.

We’re living through an example of how this could works thanks to generative AI.  Roll the clock back five years and ask…just about anyone where they expected AI to have its first big impact. I’d imagine (at least I imagined at the time) most people would have said that AI would rise first in technical fields. We’d see leaps in biotech as computer minds outpaced human ones on drug design and discovery. We’d see vehicles capable of navigating themselves. We’d witness new materials and devices churned out by intuitively leaping machines. We wanted these things to be true because they’d be cool and also would produce huge financial returns.

But we all knew, as we’d been told by countless works of fiction, that the creation of art would be the last realm to be conquered, that it would be the thing after AGI emerged because of how important the creative spark is to novel artistic endeavors. The patterns there don’t matter, we told ourselves; the soul is the thing.


In hindsight, of course the first truly breakthrough moments of AI came roaring out of creative fields - from art and from writing. The patterns were there, even if we pretended they weren’t. Look at a great photograph. It is not great at random. It is great because of the placement of elements in the frame, because of the balance of light and shadow, of negative and used space. Compare a photo from Henri Cartier-Bresson to the average selfie and your brain knows that one is great and one is bad even though you don’t know why. But feed a gazillion images to an AI and it will find those patterns once it can process enough of them. And then it can spit those patterns back out.

The key to figuring this out, at least for an observer (and ok an investor and probably a founder thinking about what to do) is the hindsight bit. The English idiom has it that “Hindsight is 20/20” meaning that all the mistakes are only ever obvious when you’re looking backward. But we’re not looking for mistakes, we’re trying to figure out the next big thing.

I don’t think anyone can accurately predict the future, but I think of this…hindsight game as the startup version of Albert Einstein’s Gedankenxperiments - his thought experiments that started with an impossible thing like “imagine you are riding a beam of light.” It’s a simple tool that most people will simply fail to either use or have enough imagination to find useful. It will also, probably, throw out lots of false positives.

For thinking about technology and businesses, I find that the hindsight game looks a little something like this: take an idea that’s been presented to you. Rather than find all the things wrong with it, or the ways in which it will obviously be interesting but not huge, ask a simple question “what if everything about this is true, but only more so?” That’s the first part of the game. It requires you to imagine the future with one big change - don’t try to change everything, that’s too hard.

Now, once you have that in your head, the next question is “ok, so what else is possible?” That’s the fascinating bit to me, not just what happens if X is true, but what Y exists only because X is true?

It is fun to play this game with AI because of how fast the field is moving. So let’s work through a round of our game - let’s pretend that AI’s generative and analytical ability only gets better such that, in 5 - or 2 or 10 or 20 - years, it becomes painfully clear that there’s no such thing as a public market investor with an edge. The data is all public, the AI can analyze the data and run all kinds of scenarios and understand the relationship between all the assets and consider your needs and what’s logical and probabilistic and then spit out an ideal trade for you. But even that doesn’t matter much because there’s no alpha to any trade since the AIs are so fast and everyone has them.

So what’s the point of active trading? Where do all the hedge funds go? Maybe they go poof and the real value accrues to the exchanges that figure out how to serve the AI trading mechanic and are now ludicrously valuable because stocks and bonds still need to trade. And then there’s a different kind of exchange because people like to gamble - but that exchange has an AI referee that looks for any unfair “edge” the way Call of Duty looks for cheaters. This could be totally wrong, but it’s coherent!

Now you have hindsight. You have a model of how the world looks 5 years from now, looking back. What should you do now, knowing what’s to come? There’s no one answer to it, but it sure does open a lot of ideas on which to make some huge bets.

This is fun! Try it with a different set of conditions in a different market. Use it to evaluate the startup idea you have - if you’re right, do you destroy your own market or create and own a new one? Is your idea as big of an opportunity as you think, or is it bigger?

We’re all guessing what will work when we try to build or invest in something new. There’s no one version that works, but I like having different games and frameworks to think about ideas. Sometimes you just need to think about the founders and sometimes you need to think about markets. And, sometimes, you just need to pretend you’re already living in the future.