Startups are not a game of chess

One of the really hard things to do as a founder is not overengineer your problem-solving. I’ve found it is one of the first things I talk to early-stage entrepreneurs about, and it is something I struggle with myself.

There are two big reasons for this, the first is that as founders we have the entire business in our head. Having so much in your head makes it noisy in there as you think through strategic directions for the company: “should we focus on mobile or web?” “how is this going to scale?” “what if my vp sales leaves” “how would we deal with that competitor if they did this?” We build pro and con columns for dozens of ideas because, ultimately, we are going to be directing our team down a path. We play constant games of scenario analysis, because we are thinking about our businesses more than anyone.

The second big reason is that we talk to new investors, new customers, and new entrepreneurs every week about our business, layering on new questions and decisions to make. Constant new inputs to the system brings up constant new points that hadn’t been illuminated, and the natural desire is to resolve the questions put in front of us.

A lot of times, unfortunately, this ends up feeling like a game of chess, thinking a few moves ahead and trying to maintain optionality. While this might sound fine, it can be disastrous in many startup situations. A startup is a resource constrained environment, the truth is we don’t really have enough “pieces” to be playing chess. Even more importantly, it’s hard to think four steps ahead when the rules of the game are constantly changing.

At an earlier startup I cofounded called Conduit Labs, we were one of the first players in the Facebook ecosystem and launched a product that achieved immediate growth. But I was very worried about the end game with Facebook, playing out scenarios of them owning my customer and revenue stream. So we moved off Facebook, and built products on the web so we could control our destiny. Those products had great retention, but without Facebook they really struggled to grow.

It took us years to finally get back to Facebook and grow again, and at that time the ecosystem was quite different. What did we do wrong? We were thinking strategically, trying to stay two steps ahead, and ironically many of my reservations about the Facebook ecosystem turned out to be correct! But, at that time, we failed to make the simple choice to optimize for the #1 question,”given a great product, where will you best get users.” The answer, unequivocally, at that time was Facebook, and everything else was just overthinking the problem.

Instead of thinking of a startup like playing chess, the anology I’ve started using is football. In football you don’t think about the touchdown when you are on your own 20 yard line, the first step is just moving the chains, getting one first down at a time. You can’t answer all your questions simultaneously, as satisfying as it can be to try and let your brain do it. In early stage startups there is simply too much optionality.

How can you help control this?

Start by trying to list out all the questions your business is trying to answer right now. ie “Will people want to keep using my service?” “Do want green or blue on the homepage?” “Will they pay?” “How do we protect if google/microsoft/facebook come at us?” It’s fine to have a really long list, it could take you years to get to all of them.

Then, the key thing is to get ruthless about which of these questions you are trying to answer now, and which you are pushing off.

If done well, you’ll find your team suddenly knows what to do (“I don’t care about CPA optimization right now, just get me a small enough sample of users to prove if it works!”) and it’s a great way to focus the board of directors as well (“Very good point, we’ll solve for that after we’ve finished answering how to make curation better.”).

Try picking just one thing. Try making sure you will knock out of the park in the next 1, 2, or 3 months. It’s incredibly hard. But we all intuitively know it virtually never “all comes together” — it happens by simply, clearly, solving things one move at a time.