Five Years as a Startup CTO: How, Why, and Was It Worth It?

Summary

I can’t believe it’s been five years since my last post… Five years since I decided to join an early stage startup as the CTO / “the tech guy”. Five years since I took my last train to the office in Manhattan. It feels like the whole world changed multiple times over – first with the lockdown during the global COVID-19 pandemic, then again with the start of the war in Ukraine, followed by the war in the Middle East. All of that spiced up by the great divide of the country, influx of the new money and resulting inflation, vaccination cards, Messi finally winning the World Cup, presidential elections circus and massive advancements in the blockchain and AI technology. Wow, after re-reading the above just making it to today feels like an achievement. When I was initially approached by one of the founders there was no product and no team, just a half backed tangled messed built on the Salesforce platform by one of the top consulting firms (yes, it wasn’t cheap). As it often happens in the “done for you” engagements the business requirements have evolved shortly after technical specifications were done and passed to the development teams… When the product was finally delivered, it was pretty much useless to the target customers. Sounds familiar? That’s where I stepped in. Yeah, right. In all honesty it was more like this: Do think you can fix this, Sergey? These were the words I’ve heard after about an hour of the first meeting with the founder where we desperately tried to connect all of the missing business dots. I can’t exactly recall what I was thinking at the time, but I’ve heard myself saying something along the lines of “No promises, but I’ll give it a shot”. It’s always fun to tinker with another software project, right? Well, I’ll tell you what, based on my experience these are the situations that push you to the new heights (or take you down from the fantasy land, haha). You take a plunge into unknown, step out of your comfort zone and make you best effort not ...