James’s Newsletter

Hi, I’m James (in some circles better known as Mackey). In my career, I am a software engineer that likes working in startups. I regularly write about the things that I am working on, but this is my first time posting publicly.

This article is about my journey starting my own company, selling it a year later, and what I learned along the way. I hope that it’s useful for anyone thinking about how to build products or start companies.

Career choices while you’re in your 20s should be optimizing for learning. Before LawStar, I worked in engineering management at a high growth startup. It was a thrill, but in my last year there, I wasn’t learning much new. So I began exploring a dream of mine - starting a company. I believed I had enough experience to be successful and could re-accelerate my learning curve. 

My first instinct was starting a classic VC-backed tech startup, and with the trajectory that LLMs were on when I started researching, I thought legal tech was a good place to start given the volume of text involved in the law. I started pitching some ideas to my friends in law. What I heard a few times was, “that idea sucks - what you should really look at is bluebooking.” Honestly, I’d never heard of bluebooking before, but decided to find out more.

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