Scattered thoughts on buying software businesses

Two companies that I started following (with no small amount of envy) back in 2021: Hype (fka Pico) sold to an MMA-themed holdco earlier this year. Raised a $4.5m seed from Stripe and Bloomberg Beta and a $10m Series A; crossed the finish line at $200K ARR after eight years. Stir (which raised $16M from a16z at a $100M valuation) informally...

Hello! Lots of writing in October (what early parenthood takes away in terms of deep flow, it gives back in terms of twenty-minute pockets of time and thought): On the content front, I wrote about Monster Sanctuary (a delightful JRPG), The Anderson Tapes (a solid late-period Sean Connery heist), Trust (a rare postmodern novel that I disliked),...

Kevin Twohy has a list of heuristics for new projects/clients, and my favorite is simple: No Bozos. Simple policy. No exceptions. You know it when you see it. Every founder has a story about the time that they ignored the red flags and bent over backwards for a particularly standoffish or problematic customer/prospect/client/hire. It's easy to...

(Epistemic disclaimer: there are few Extremely Big Tech Companies to whom I feel apathy more vividly than Meta. I had a Facebook account in high school and college and got rid of it at some point post-graduation, though I'd be hard-pressed to tell you when exactly that was.) It was fun to listen to Acquired's six-hour episode on Meta. Ben and...

Lots of kind words poured in as a response to My approach to GTD and PKM, and one question was asked so frequently that I decided to write about it. Why is “Get mom a birthday present” a project and not a task? GTD is very orthodox in what a “project” is: it’s anything that: you think you’ll complete in the next year requires more than one step...