Building Great Teams in The Age of AI
In this episode, Jeremiah, Rishabh, and Jack trade stories as Jack prepares for his first baby, then workshop potential new names for the podcast. The group lands on the idea that the show lives in the one to a hundred territory, covering companies past the zero-to-one phase but before the hundred-million-dollar scale that a lot of podcasts focus on. Rishabh floats "The Adolescent Software Company" as a name, pulling from Dario's essay on the adolescence of software. Jack talks about wanting to build a community and website around the new brand. The group briefly touches on the TBPN acquisition by OpenAI, estimating it landed somewhere in the low hundreds of millions in OpenAI stock.
The conversation shifts to org structure and how hierarchy is breaking down. Rishabh walks through Jack Dorsey's essay on why reporting lines existed, how corporations took hierarchy from the military, and why information being available to everyone instantly removes the original purpose of that structure. At Fermat, Rishabh has flattened the entire org with all go-to-market reporting to him and all engineering reporting to his co-founder Shreyas. The output delta between the best and mid-tier engineers is now closer to 10x because the constraint moved from time to creativity, which means having a top engineer manage four people reduces total output. Rishabh lays out a framework of mentor, teach, coach, model, and argues modeling is the only one that works right now because leaders are learning at the same time as their teams. Jeremiah describes how his leaders have naturally shifted toward modeling and references Stuart Revo from Rivo shipping a hundred updates in three months with two engineers as one end of the adoption spectrum.
The group gets into how AI is changing day to day work. Jeremiah describes reframing AI for a team member who felt replaced by telling him to treat it like a junior employee. Rishabh describes using Claude to write his board doc by having it pull his last three board docs, cross-reference Slack, and evaluate whether he followed through on commitments. He compares using AI to using a calculator and talks about letting his four year old use AI to create books, pushing her creativity in ways he would not have expected. Rishabh shares a data point from Fermat showing that the difference in product browsing between Google and Meta traffic was much smaller than expected, the kind of insight that surfaces when you can cut data quickly and move through hypotheses without spending weeks on each one.
00:00 The Journey of Birth Experiences 02:31 Expectations and Pain Management in Labor 05:10 Podcast Name Change Discussion 08:05 Exploring Organizational Structures and Hierarchies 10:52 The Impact of AI on Organizational Design 13:35 Performance Management in Flat Organizations 16:32 Navigating Constraints as a CEO 24:37 The CEO's Unique Challenges 26:12 Adapting to Market Changes 27:29 Shifting Communication Strategies 30:37 Evolving Leadership Models 36:40 The Role of Player-Coaches 43:52 Navigating Uncertainty in Leadership 47:49 Leveraging AI for Enhanced Productivity