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

• (0:00): Intro to Dialectic
• (2:55): Brick laying vs. capital allocating
• (6:04): Acid Story: Trying so hard to be a somebody
• (9:20): Planning, judgement, elasticity, and abundance
• (11:28): Ambition and Trusting your future self
• (14:20): Fear; Confidence is the memory of success
• (18:46): Compounding psychology of risk taking
• (21:30): Do you get what you deserve?
• (22:32): Playing life on hard mode
• (27:22): Agency, Taking Accountability, and becoming essential
• (35:58): Consulting and Independent Contracting
• (39:52): Ambition and “Manhattan Project” Appeal
• (42:30): What are you motivated by?
• (44:36): Challenge runs and side quests
• (46:39): How to be prolific
• (53:46): Mastery, complex games, and creative fingerprints
• (57:47): Programming, animation, and style vs. cohesion
• (1:07:56): Jason only writes with his voice--with some LLM help
• (1:12:47): Flooding the airwaves with content
• (1:14:10): Twitter growth: simple math
• (1:19:49): Using the “sawdust”
• (1:23:30): ELI5 RAG (Retrieval augmented generation)
• (1:27:39): A final rant against couches

References

• Losing My Hands by Jason
• Advice to Young People, The Lies I Tell Myself by Jason
• A Critique on Couches by Jason
• Things you're allowed to do by Milan Cvitkovic
• Duolingo founder Luis Von Ahn on engagement vs. education