I have been chatting with folks quite a bit lately about side projects.

A theme that keeps coming up that I don’t think is particularly obvious is that both of my successful projects spent a long time being not particularly successful.

Neither Buttondown nor Spoonbill had particularly meteoric launches. Both sported around a hundred signups in their first week; Buttondown had a grand total of, if I recall correctly, two paying users for the first month or so, whereas Spoonbill spent three years without a single paying customer (and, to be clear, this was because I didn’t offer paid functionality.)

This is perfectly fine. They were still successful by my metrics at the time: they were tools that I liked and were proud of; I learned something from having built them.

Most importantly, though, they were cheap to maintain. I was not hedging my livelihood on their success; I did not have investors who were requiring exponential growth. I could afford (morally and financially) to let them sit and grow slowly, collecting new users and functionality like a stone collects moss.

Scoping something as a small project lends you two powerful advantages in this vein:

  • You can pick and choose target markets whose size would otherwise be prohibitively small. “Metadata sync engine between Etsy and Mailchimp” is the genre of business that has a total addressable market size insufficient to sustain a business of a handful of employees, but it’s certainly large enough to pay for your groceries every month.
  • You can play the long game. “We are going to sit and collect DNS registration data for four years” is a difficult prospectus when you need to figure out where rent is coming from next month: it is trivial when you are looking for a way to spend a few evenings every month. 1

If you are going to find a project, I encourage you to find something particularly small and particularly durable (which is to say, does not require constant or near-constant attention), so that you give yourself the ability to take a break from the project for weeks or months while it accumulates interest.

  1. Speaking personally, one of the things I was dismayed about when launching Buttondown was how many similar projects were getting spun up that received press traction whereas I was marooned in the tar pits of word-of-mouth growth. I delight in the fact that the three other tools in my cohort of “email projects that launched in 2017” have all since shut down or pivoted entirely. 

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