Jason Liu 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