My friends and I bought five software businesses last year, on the thesis that:

  1. despite the recent uptick of interest in the space, it was still a fairly undervalued class of asset;
  2. it would be kind of fun and neat.

We purchased these businesses after around eight months of sourcing and searching; we've been operating them for a little less than half a year.

A lot of people have asked a lot of questions about almost every part of the process: sourcing, negotiating, closing, operating. Rather than actually be useful and write a two-thousand word screed on our tactics in finding and closing deals that we liked, I thought it would be more interesting to jot down a list of answers to the following question:

What do we know now that you didn't know a year ago?

(Thank you to Colin and Harrison for — well, for many things, but in particular for reading and improving this essay.)

If you have any questions — or are interested in selling us your software business — feel free to reach out at

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