My Path to CTO, Part I

Learning the trade.

Introduction

Welcome to the paid newsletter for November 2025. This is the first ever paid article that I’ve written, so I’d like to thank you for being an early adopter of the paid subscription model. I hope you’ll find the content enlightening and engaging. I like to see it as the beginning of a conversation between us.

As I write more paid articles, I’d love to hear your feedback. I’ve opened the Subscriber Chat functionality on Substack so you can contact me directly. This way, you get the chance to shape the future of the newsletter.

We are going to start this month by diving into my story of how I ended up in a CTO role at a public company.

I think this might be interesting because it wasn’t always my intention. Rather, it was a random walk, to use a computer science term, following my interests, that got me here.

Additionally, CTO roles are very rarely advertised externally, so I’d like to give you some insight into how the world of executive headhunting works. If you’re interested in going down this path yourself, then I hope you’ll learn more about how to get involved.

It’s worth mentioning that everyone’s journey will be different. There is no one way to do this. So, consider this not a blueprint, but rather a map of the terrain that I’ve traversed. The easiest way to become CTO, after all, is to “just” start your own company.

What’s coming up

Since I wanted to use this opportunity to go deeper than usual in my writing, this newsletter is going to be split into two parts.

In part one, we’re going to cover the following:

• My original interest and desire to get a permanent position in academia, but how the economy, jobs market, and my desired life situation prevented me from going any further.

• How it was almost random that I got involved in a startup at the seed stage, but how curiosity, familiar faces, and a willingness to try anything in order to stay close to where I was living made it happen.

• How my managerial experience flourished when I realized that I had many interests and passions that were different from the engineers that I worked with, and how that set me apart and subsequently opened doors.

• How getting acquired showed me what I didn’t want my life to be like at work, and why trusting your gut is always underrated.

With that outlined, let’s get going. It might be worth getting a cup of tea for this one.

From academia to seed stage

I’ll briefly gloss over my early life, which is that I’ve always been incredibly interested in computers. I was a small kid playing with my sister’s ZX Spectrum and Amstrad CPC 464 as I grew up. When the initial internet wave came along in the 90s, and as I went from small child to teenager, I had a lot of fun messing around with HTML and PHP building websites, and of course, playing an unhealthy amount of online video games.

I felt at home when I was tinkering with technology, and I have fond memories of building computers, upgrading RAM and graphics cards, trying to hack games with a hex editor, and seeing the initial incarnation of the Web come to life via Yahoo!, AOL, Geocities, and later, Google.