Leaving Deno Land

At the end of October 2022 I made the hard decision to leave Deno and started working for CTO Labs in the M&A due diligence practice. I had done consulting for many many years before joining Deno and in one way it was a return to my roots. Looking back at my time of Deno is for me, a story in following a passion project, both with upsides and downsides.

Goodbye, Denoland

The root of why I left Deno is a challenge of geography. I live in Australia and my nearest colleague was in Tokyo. Even then, the people I really needed to work with were in the East coast of the US or central Europe.

When I joined Deno in 2020, we were small, just five of us. I had experience in leading divisions of technology at scale, I had been a CTO, I had been doing big tech strategy work for several years. I knew when Deno started to grow there would be roles that would be able to leverage though skills, but initially it would be awesome to get back to the fundamentals of just cutting code on a product I was super passionate about.

And it was great. We started to grow, there was (and still is) a plan to do a huge amount of open source but have a commercially viable business that can be leveraged to support that investment in open source. It was cutting edge technology positioned to be a foundation of the next shift in how computing is handled.

There were challenges though. I am loud, I have opinions, but most of all I thrive in situations where there are few barriers to collaboration. There started to be situations where I was frustrated with some of the strategic decisions we were making. I tried really really hard to argue the point, but instead of being able to influence things, I just became increasingly frustrated that I wasn't really landing my point. I found myself up at 3AM my time checking messages, afraid that we would head down the wrong path. Certainly part of my inability to have the influence I wanted and felt I needed was down to who I am and my style, but the distance didn't help.

I became increasingly convinced that if I could be closer, even trivial to be in the same room with others on a regular basis, I would either be able to have the influence, or feel comfortable that my points had been heard and considered in the proper context. I've always had a problem with being overly emotionally connected to work, but working on something that was your passion from the very start, that you had invested over four years of your life into, but large parts of it you had to deal with at arms length, was taking a super huge emotional toll on me.

I had made the decision to leave in advance of our first company off-site. For the first time most of us would all be in the same room for an extended period of time. Ry and Bert said they still wanted me to come, I think in part hoping they could talk me out of my decision. The offsite was awesome. I got to spend time with people I had been working with for years, some for the first time in person. So much progress was made in aligning thoughts and vision for the company and understand how big we had grown and how much we had accomplished.

The time came for Ry and I to have a chat. While Ry had seen the offsite as confirmation that we had a great team assembled and I was a critical part of it, what I saw was only confirmation that I was banging my head against the wall. The offsite was awesome, but I knew I would go back to Australia, shift timezones, and be isolated again. I have a young kid and been with my partner for over 20 years. I moved to Australia in part to find a good work life balance. If I was younger, less established in my life, I would have easily moved to pursue the dream, but I can't and I couldn't live in frustration. Ry finally saw it from my point of view and conceded. He did say I would be back because I like building things.

Hello CTO Labs

Well, I do like building things, so Ry was partly right, but it doesn't have to be software. I joined CTO Labs. I had worked with one of the co-founders before, and the other co-founder and I shared a lot of connections. M&A tech due diligence did sound exciting to me, and it was a company focused on Australia and a bit of South-East Asia. What I have found is a lot more exciting.

I think like a lot of people, I suffer from a short attention span. I like to be in the thick of it. Tech due diligence satiates both for me. They are usually fairly short and contained pieces of work, where we get to dig in and root out any risks and evaluate the technology. In the over 9 months I have been on board, I have seen 10 tech organisations, big and small, up close. I get to draw on the years of experience I have had as well as the experience and knowledge of my colleagues.

I would almost be happy with that, but what has emerged is an opportunity to build and grow a business. We are specialist, niche and small, but we are good at what we do and that has spread organically by word of mouth, but working with the co-founders, I am starting to help lead the growth of the advisory part of our organisation. Shaping what and how we do what we do. A small organisation is great because things are fluid and we get to play to our strengths.

And beyond

I can see myself being happy for quite a while. It is a high bar to match at the moment. I'm emotionally attached to the people I work with for sure, but I have to say that is a lot easier then being emotionally tied to a piece of software. That software can't appreciate you back, can't talk to you. I was emotionally attached to the people I worked with, but in the end, there was this thing I had to put effort into and nature which kept me up at night when I was worried that bad things would happen to it. It is great being passionate about something like that, but I don't think I could let myself follow my passion again. I don't regret one moment I spent on Deno and working with the great people I got to work with. I learned a lot though, a lot about myself, that I will carry forward with me for ever.