Don’t be a desperate dreamer

During my startup journey was that I was never sure what was not working — the idea or me. It takes a couple of years before a good idea to flower or for a bad idea to really stink, says John Collison of Stripe. The only way to call it a day without heartburn is to put in the hours. And doing exactly this turned out to be the hardest thing.

I remember the day when the core thesis around Trackmemo took shape in my head. I had felt something lacking in my conversations at work — every meeting felt like wandering in a labyrinth and stumbling upon the same stone. What I felt was lacking was a common context that bound together the different conversations that happened around a project across meeting rooms and SaaS tools. It was a problem I was excited about. I had faced the problem, and my guess was that I wasn’t remotely alone.

I was so enamored by the big picture that I often lost track of the present. The final product we launched tried to solve too many things — but did not solve anything better than everyone else. I had tried to force fit my entire vision of the future into a product in the very first iteration. It was almost like the I was presenting my idea to the world, and not solving a real problem for a real user.

But if I had shut myself in and been entirely guided by the idea it would have been easier to put in the hours. But we did not. We started measuring our success and failure by how much money we had raised or how much press coverage we got versus the startup of the day. These comparisons gave an immediate boost but very soon led me into a torpor that got harder to climb as time went by. And this affected not just me but the entire team.

So here I was, spending inordinate amounts of time on something minor decision, checking if it aligned with the overall idea while keeping both eyes on what everyone else was upto. I was spending more and more time as a desperate dreamer. And neither my mind nor my eyes were on my actual users in that period.

By being a desperate dreamer I closed myself. Every piece of feedback seemed like criticism from someone who obviously hadn’t thought about the product, talked to customers or worried the problem enough. And since by definition I was the only guy doing all of this not listening to others seemed the right thing to do.

Again which is ok, if the startup was cashflow positive and I was making enough to take care of myself and the team. But I was not. I dreaded every funding conversation. Not because of the rejection — that was par for the course. But because of the advice I would invariably get.

Starting up is like running blind folded on the edge of a cliff. Stop for a moment, and you lose your bearings. Your next step might be your very last. And this was the hardest thing about being desperate dreamer — it froze me up. Made me incapable of moving fast. And this more than anything else, made it really hard for me to put in the hours.