Lessons from a failed startup
Roles can be fluid, but they must be defined

Thursday 28 July 2022 at 18:00 CEST

In failing to build a company, I have learned many things. Core to all of them is that a company is not a product. Ideas change, products change, people change. We “pivot”, rapidly, relentlessly, sometimes ruthlessly.

Managed well, change is a catalyst. Managed badly, it can be catastrophic.

In this series, I try to explain the various ways in which I failed to understand this, and how I would endeavour to do better next time. You may notice that the style of these posts is more instructive than usual. Remember that these are mostly addressed to my future self, and as such, I am telling myself what to do; you, my dear knowledge aggregator, can do whatever you want.

When you start a company, the first thing you do is give yourself a ridiculously overblown job title. “Chief Technology Officer”, you call yourself, ignoring the fact that you’re a chief of 1 person—yourself, you don’t know what your technology is yet, and you don’t have the first clue about being any kind of company “officer”.

The title is important, because you’re communicating to the outside world that you, in fact, represent the company; you don’t just work there.

However, this is an external-facing title. Internally, roles are more nebulous. Perhaps one day, you’re the programmer, and the next, you’re the accountant. Congratulations: you’re now a generalist. This is an incredibly valuable set of skills you’re learning; rejoice!

Of course, you won’t stay the accountant for long. You’ll probably outsource that work anyway, but it makes sense to do it first so you can understand the job.

Some roles aren’t so clear-cut. Who decides the roadmap? Well, you're the CTO; surely this is your job?

However, this can go badly. What if the CEO expected to have final say over what comes next? After all, they're the one talking to potential customers… probably.

Roles are fluid, but they’re also a source of pride and privilege for the people taking them on. We don’t expect them to change without our knowledge. You signed up to start a company because we thought it was intriguing, challenging, joyful, purposeful… if you wanted to be told what to do and receive a high salary for doing it, you'd go get a regular job.

Just like everything else, the key to a harmonious relationship is to regularly have open conversations about roles and responsibilities, explicitly recognise changes, and write them down. This includes roles that no one is taking on right now: if you need a website but no one has time to make one, make sure everyone is aware of that.

An unmentioned change is still a change, except that it’s going to cause havoc when you least expect it.

More in the series

1. Introduction
2. Focus on the problem, not the solution
3. If the company goals change, the company should probably change too
4. "Do research" is not a corporate strategy
5. Your corporate values transcend your product vision
6. Trust your gut, understand your heart, and open your mind
7. Go to therapy with your co-founders
8. Explore the terrain first
9. Unless someone cares, don't waste your time
10. Code is a liability; ship without coding, if possible
11. Do less, and do it better
12. Agile methods are tools to try more ideas in less time
13. Until you have traction, money is a trap
14. If you don’t know how to do it, that’s your biggest problem
15. Roles can be fluid, but they must be defined
16. Camaraderie is helpful, but no substitute for working together