VP of Engineering at Shopify.
Previously VP of Engineering at Stitch Fix, SVP of Product at Pet360, and Director of Engineering at LivingSocial.
From Silver Spring, MD.
This year I read 30 books (just 2 in Spanish).
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I’ve got a story to tell.
It’s been 14 years, so I think we’re past the statute of limitations on this one. I’m also pretty sure nothing here qualifies as proprietary anymore.
One disclaimer: I’m working from 14-year-old memories, so I might get some of the details wrong, but I’m pretty sure I’ve got most of the story right.
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A friend of mine leads an internal data team for hospital group.
They recently received the updated 2025 ICD-10 codes which is a coding system of ~74,000 codes that are used by healthcare providers and insurance companies for billing, tracking public health trends, and medical recordkeeping.
Basically, they got handed a plain text file with 74,260 lines and were asked to annotate the data with various additional bits of information. For example, they want to record whether each ICD code represents an infection:
A200 Bubonic plague is an infectionY9366 Activity, soccer is not an infectionAnnotating more than 74,000 lines is tedious and time consuming1, so he hit up the group chat asking about how to script an LLM to do this.
This seemed like a fun toy problem to try out some stuff I personally hadn’t done yet, so I decided to see how well I could use LLMs as a binary classifier for “infection/not infection”
They did some quick napkin math that it would take ~300 hours of labor from a documentation nurse to do this which would cost ~$18,000. ↩
Looking back, I noticed a couple of themes in my reading this year. One was biographies of people who had achieved success and then figured out how to change so that the drive that propelled their success didn’t eat them from the inside (Becoming Steve Jobs, Pep Guardiola)
Another theme was books that prompted some reflection that I would read (or listen to) in the morning as I got the kids ready for school (What We Owe The Future, Not The End Of The World, A Decent Life)
And then there is my normal mix of trying to better understand the world and pick up additional tools for functioning in it (The Laws of Trading, Thinking in Systems, Sludge, Noise, Stories that Stick). I’m happy with those books if I take away one mental model or skill that I can use.
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I read 18 books in 2023. Including 5 in Spanish. Here they are.
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