a triangle love story

“If he asks me, I will join” – I remember telling a friend, about joining a startup, in case the founder, who was someone I looked up to, ever calls me. I had no such indication that they might even need me. But that was a secret wish. Like those Malayalam movie dialogue sort of “avan vilichaal njaan irangi pokum” (“if he calls me, I will elope with him”). And like in such movies, I never asked if they would need me.

I had daydreams about starting a startup for a long time, making some very detailed plans as mental exercises – it was almost like a game I play or sort of entertaining myself. Or like a prisoner planning escape routes. But never had the courage enough to actually try even any baby steps towards any such ideas, to test if any of those had market potential or any such. Since this was like a fantasy world building, in whatever small ways I practiced how this might work out – like kids playing house. I used to think that anything I do, I run it like I am running my own business, not act like an employee, but act like I own all of it. At one time, along with a good friend, we did make something as an “Intrapreneur” took it a bit far, sold it couple of customers – eventually got absorbed by a big fish within the company, just got a brief thanks for it. And it continued like this for years.

Then everything accelerated and took some turns last year. There was a call for startup idea submissions to an internal incubator. Since this was like a fake ticket to the fantasy land, obviously I went for it. How could I not, after years of daydreaming? My excuse was that I am just checking things out, not expecting anything. In one night, detailed out one sketchy idea in about three or four hours, about how the industry would change with AI, how we might create a group that is like an “advanced scout” to discover that change and just before the final (extended) deadline, submitted it. One thing led to another and before I know it, I was getting into the final shortlist for selection. They wanted commitment that if selected, I will move full time into it and I said yes.

Now for the big twist. After all those years, the call that I wanted also came. Think about the timing. If it was just a month or two before, I wouldn’t have had to think much. But now there is a dilemma – would I want to pursue “play house” with “house money” in the safety of a large organization (which can be extremely frustrating also, that I knew, even though not to what extent – that story is to follow) or jump into “unknown” (even though they were established already, so it is not like a huge risk).

Now like the triangular love story, the first story was moving towards the “engagement function” and since it had come this far and now that I had “co founders” who I could not abandon yet, I went through the final pitch. My reasoning at that time was that, what is the big deal – I am replaceable, let the team win and if all works out, I pull out. Looking back, that might have been a mistake on my part – I should have taken the tough call then, that go on “auto pilot” or postpone the hard decision thinking there is still time. “Engagement” aka final pitch happened and they decided to fund us. Right next week, on cue, offer from the startup also came up. Now I can understand why some bride or groom run even the day before the wedding day – the indecision, fears, moral and ethical considerations, pain of breaking relationships, leaving comfort for unknown and many such calculations grind someone to inaction till it is time.

I told the first team that this is the dilemma and I would ideally like to join the second, since that was a long time wish. But they played the moral / conscience card – that it wasn’t “playing house”, serious commitments were made, I shouldn’t have played it if I wasn’t serious, I should have quit in some previous rounds itself so that someone else could have taken my place.

After a lot of mental anguish, I said no to the one I had dreamed about for years, even knowing the choice I am making may not be the best option. I justified it as the morally right thing to do, to honor the commitment made first, give it a year of my life.

It made me question hard about my deepest fears, whether what I say at the surface level is really the right reason, whether I should have been even more “proper” and “timely” in my decisions and commitments, whether my habit of postponing conflicts or hard conversations is causing harm.

Now that the decision is made, I went all in, as I would to anything I might do. It had been stressful, fun, learning, maddening year. A year of watching how an industry is starting to reshape during a generational technology change. It is not anywhere near done and by the time it settles, I think it will have had profound changes in society, jobs, politics, economy.

A blog friend’s last post was that a blog is like a “scent bottle” for the memories. I hope to leave those “scent drops” about this journey, to look back in a few years’ time. More to come about this journey in the last year, how it is unfolding and what I might be learning about myself and others in this wild ride.