1: Jason Liu - The Freedom in Being Nobody
Jason Liu (Website, X, Github, Newsletter) is a technologist, consultant, teacher, and friend. He spent the first part of his career as a machine learning engineer, mostly at Stitchfix, only to run into a wall: a hand injury that prevented him from being able to write any software for over a year. Fortunately, he's not so one-dimensional, and spent time reclaiming somatic experience in learning to free-dive, train Jiu-Jitsu, and return to the pottery practice he developed in art school, all while reckoning with big questions of ambition, purpose, and self-fulfillment. Since then, he's built a consulting practice helping modern AI companies better implement RAG (retrieval-augmented generation), avoid system design mistakes, hire elite talent, and build for an LLM-centric world. He maintains a large structured output library called Instructor with about 1m downloads per month, writes prolifically (which he does entirely via voice input with LLM editing, as we discuss), tweets semi-manically (he's grown to 30K followers on X with the simplest strategy I've ever heard anyone articulate—tweeting 30K times), and teaches courses on RAG and online consulting. Finally, my man can yap. He was a perfect first guest because he has no shortage of ideas but comes at nearly everything with a beginner's mindset. Timestamps
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Speaker A: Hey, I'm Jackson Dahl, and I'm excited to share episode 1 of a new interview podcast, Dialectic. I'll have conversations with the sharpest, most creative, and original people I know, or want to know, and it will be wide-ranging, probably covering the stuff I care about most: ideas, ambition, tech, startups, business, art, culture, philosophy, taste. But also it will really be about people. There's an idea from Kevin Kelly I love, which is that the goal of life should be to have become yourself by the time you're on your deathbed. Put another way, you shouldn't aim to be the best, but to be the only.
I called the show Dialectic because it's fun to say, and because if I've been told I'm good at anything, it's sparring with people about their ideas, pushing them to click down one level deeper. I hope this show will feel like watching a great tennis rally, seeing some sparks fly, but ultimately trying to get closer to truth, to lessons, to wisdom. Into really, again, what makes people tick. I think this is going to be a tough balance to strike with an interview show, but as the show progresses, I really hope to push my guests in creative ways.
Episode 1 is with Jason Liu. He's a technologist, machine learning and AI expert, consultant, teacher, and among other things, a guy who can talk. He spent the early part of his career as a software engineer, primarily in machine learning and AI at a company called Stitch Fix. And then he ran into this weird wall where he had a hand injury that prevented him from being able to write code. And it caused him to go off on a number of side quests from jiu-jitsu and freediving and pottery to kind of like reckoning with his ambition in his career, if he couldn't do what he had done for his entire career.
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