At Techstars, my partners and I have been using the term “tricky pool shot” quite a bit lately. We’re seeing more and more startups that have to accomplish something difficult as an ante in order to get to the point where they’ll have the opportunity to do the thing they really want to do. The other type of tricky pool shot we’re seeing is when startups are trying to time a potential new market and be there when it emerges. In effect, they are trying to stay alive long enough to be relevant and be in the right place at the right time. They have to knock down multiple difficult goals in the right order to win.
Obviously (as in the video below), tricky pool shots are crowd pleasers and pay off enormously when they work. But the fail all the time too and they’re very high risk.
As investors, we don’t mind risk. We’ll occasionally invest in a tricky pool shot. But we’re very skeptical of them because they’re extra difficult. As in billiards, it helps if the first part of the “shot” puts you in a very good position even if you miss the second or third shot, so at least you get to shoot again because it’s still your turn.
For example, imagine that you believe in the future driverless cars. You’d probably be thinking back to when we used to call cars “horseless carriages” and thinking that perhaps this would be more of a change that people might imagine today. So you are building a company that imagines a world without the need for gasoline, and one in which the roads themselves will charge these futuristic cars. So you’re building infrastructure to enable these future cars to always be charging while driving, much like the trolly-bus system of San Francisco. This is a tricky pool shot indeed. Not only do we have to bet that most cars will be powered by electricity, but we also have to bet on when that will happen. And finally, you have to be on the mega-trend of autonomous vehicles as a driver for the change. You want to be there at just the right moment in time, and you’re starting right now. Investing in building out this expensive infrastructure before we know if any of those things are going to happen is quite a challenge. Perhaps there will be many electric vehicles but their range will be extended and there will be need to charge them so frequently. Perhaps solar will win. Perhaps we’ll all be flying around on drones instead of in cars at all. You only win if a certain tricky combination of possible futures come together. In this case, it’s several things to bet on with no great obvious intermediate states.
Of course, you might make the shot. And that would be rad.