Roughly 18 months ago I took the jump of leaving my CTO job managing 600 engineers to start Echoes HQ, my first company as a founder. This post is a personal reflection of what I've learned and what surprised me in that transition, in no particular order.
Managing a large team inevitably involves a daily dose of bad news. Each day may bring a key person's resignation, a major production incident, or that budget cut you're going to have to handle.
Startups, especially at their early stage, are way bigger rollercoasters. But despite the frequency and relative amplitude of events being stronger, I feel like my time as CTO was a great preparation for it. One of the most important skill I gained is the ability to separate how I may feel about a particular event and how I'm going to act on it. That doesn't mean you should bury emotions, we're humans!, but that you should not react on emotions.
Startups are built on learnings and every event, good and bad, is an opportunity to learn. Be disappointed, upset, sad even about that customer you lost, but accept that fact and don't let emotions cloud your analysis of the situation.
I believe a founder at an early stage startup has more room, but also more duty, to be transparent about their feelings.
Your doubts as a CTO can be detrimental to your organization's success. Teams tend to mimic and through their size amplify the sentiment of their leaders. This can in some cases turn into self-fulfilling prophecies, when for example that project you say might get cancelled inevitably loses steam.
Startups on the other hand cannot succeed without embracing their doubts. The whole journey is a thug of war between the confidence in your vision and the reality of what works and doesn't (which in the beginning is roughly everything).
This cognitive dissonance is uncomfortable but healthy, and isolating the founding team from it is not doing anyone a favor. Early startup employees have a different aversion to risk than members of large organizations: doubt mustn't be an issue.
Setting goals is something that most CTOs would be very familiar with. I soon realized how different an exercise that was for an early stage startup, as our first attempts felt very much like wishful thinking. Indeed, while you may now be in full control of your goals, being pre-product market fit means that you have much less ability to predict their outcomes.
This required doing the opposite of what goal setting typically looks like in a mature company. Instead of setting goals on outcomes and largely leaving the solution space open, I was left setting goals on outputs. For example a revenue target becomes a number of demos, and an increase in conversion rate becomes a number of shipped experiments.
What was most unexpected to me in this transition is how founder (and even solo founder in my particular case) feels surprisingly less lonely than CTO.
Part of the reason is tied to the previous section on doubts: running a large organization forces you to constantly censor your thoughts, and you may not always have room to share things transparently.
Part of the reason is that while communities of CTO do exist, I personally find the ones I participated in to be quite mechanical. What I mean by that is that conversations are very much practical: discussing processes, organizations, tools, etc. That doesn't make them useless, but I can't say I've met many friends in these places (again, my personal experience!).
There's something very unintuitive here, but I believe that the little practical overlap between early stage startups makes for deeper conversations between founders. We each play such different games that there's little to discuss about practicalities: the personal journey is where we have the most overlap. It's been heart-warming to discover how other founders genuinely want to help, and have mostly no issues being vulnerable in conversations.
We had the chance with Echoes to be part of YCombinator S21 batch, which put us from day 1 in one the best communities we could hope for.
My time as a CTO taught me (sometimes painfully) that problems don't fix themselves but only tend to get worse. I've therefore developed a habit of doing what I hated most first, which proved very useful as a founder.
There are so many aspects to the role that some of them will inevitably suck, although different people will naturally have an aversion to different things. For me, it's administrative work (surprise!), such as legal and accounting. And I've been doing it flawlessly, because I know that if I don't do it immediately I'm only going to get a double dose of it.