Crazy is a feature

During the time that I have been running ContentBoost, actually it spans back to when I left Customer.io and started TaxDog (which later became Taxify), I realized the importance of being crazy. Some call it playfulness (Snapchat brands it creating toys), other companies just term it “fun”. The core idea is to free people from taking themselves seriously and just “do stuff”.

To make your own path, and decide something needs to exist is an experience that is painstakingly bereft of normal. Many of the cases when I have started something, it’s not because there isn’t a way to get from A to B, it’s often because I consider a more optimal route to B. Communicating this, and finding an audience is what determines whether something succeeds or fails. It’s actually pretty hilarious that during the time when I created KeepTabs, I realized users could join the app and invite their peers and all that, but I lacked visibility into that onboarding journey. In my haste to find “a winner”, I used my experience of handling messaging to quickly create my own solution to receive notifications and nudge users to take more actions. At no point in that adventure, did I stop to consider the total addressable market for that solution, and if anyone would use it, let alone what alternatives even exist. I learnt a lot of course, to the point where I can argue forging ahead with less than optimal information led me to this moment of reflection. It was absolutely crazy that I created something without validation at all, but I learnt a different lesson than the one market research would have taught me. Some things appear naturally via experience, I guess.

All of this raises the key question, so when do you know you have enough information, and when do you start? To answer this accurately, the definition of “start” needs to be clear.

As software developers, the one thing we’ve found easiest to do is to code and see something immediately. So starting, naturally, has always been associated with the act of creating something the world can immediately access and find value in. But that’s often a step too far. Coming up with an idea, is almost starting but given it doesn’t produce an artifact, we can’t point to its existence. So having an idea alone, is not starting. Starting is doing something concrete about the idea. But how do you start, what signal says “go now”?

You just have to be crazy enough to take the leap.

You don’t learn backflipping or swimming by having just a theoretical understanding of the mechanics. The journey to that place of enlightenment is a mixture of both. Knowing something about the activity is helpful, but you can always work it backwards if you started without that knowledge. The journey might just be longer. So is someone else’s experience irrelevant? Not totally. That’s something one can use to know what not to do. Having some sense of the lay of the land is helpful, as a general map of where landmines could be, not to tell you where to go. That person isn’t you, and they definitely lack the unique value you have to solving even the same problem.

If you are not crazy enough to make the move without all “necessary” data, you will never know what the game is about.

Be crazy, bet on yourself and keep moving.