The startup CTO dilemma


About 10 years ago I took my first job as CTO but I wasn’t a CTO, I just had the title. I was a developer with ambition. I made mistakes, very expensive mistakes, mistakes that contributed to the failure of the startup. Since then I have learned and grown a lot and although there’s still a lot for me to learn, there are some things I understand reasonably well. One of those is how to be the CTO of an early and not so early stage startup.

With this experience, though, my salary went up. I’m more expensive now than I was 10 years ago and I didn’t know what I was doing. Because of this, I tend to evaluate working for a startup not on day 1, but on day 700 or later, when they have some traction, revenue, etc. The problem is that a lot of those startups are deep in problems that are very hard or impossible to fix by that point. It’s very painful for me to see expenses that cost hundreds of thousands of dollars because someone didn’t do 30 minutes of work 5 years ago (this is a real example).

So, the dilemma is this:

  • If a startup hires an experienced CTO from day 1, they are wasting money because they might only be spending 5% or 10% CTOing and the rest coding, doing IT, etc. which can be done by a less experienced developer.
  • If a startup doesn’t hire an experienced CTO from day 1, they are likely to make very expensive mistakes that may literally kill the startup in year 3 or it may slow it down a lot.

 I’ve been thinking about this for a while, how can this be solved?

One of my ideas was being a sort of CTO enhancer, to be the voice of experience for a less experienced co-founding CTO, helping them a few hours a week for a few months up to a couple of years. What do you think? Does this sound valuable? Useful?

I might be thinking a lot about this lately since I’m leaving my current job and searching for the next thing to do.

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