Lenny's Podcast

Josh Woodward, head of Google Labs, the Gemini app, and AI Studio (home of NotebookLM, Project Genie, and Flow), argues every company now needs to operate like a labs team: generating ideas, running experiments, and, just as importantly, knowing when to quit. He walks through the 'almost possible' framework for picking bets, recognizing genuine product-market fit early, which skills are rising in value in the AI era, and why roles are not actually blurring into one universal builder role. For consultants: a practical blueprint for the experiment-driven operating model many clients say they want, from someone running one at scale.

Tibo Sottiaux, who leads ChatGPT and Codex at OpenAI, recorded at DevDay hours after shipping 20-plus products including the Dots personal agent platform. He argues most actions on the internet will soon be taken by agents, that hand-tuned agent workflows (loops, graphs, fine-tuning) are a passing phase, and maps which skills are trending up and down. For consultants: the vendor-side view of the agent era your clients' operating models are about to meet.

Molly Graham returns to argue her famous give-away-your-Legos career advice no longer holds in an AI world, and names the grief, loneliness and burnout sweeping tech as team structures collapse. Includes why delegating to AI is fundamentally different from delegating to a human, and which Legos you should never hand to AI. For consultants: one of the sharpest current takes on what AI does to team structure and identity at work.

Peter Sellis was Snapchat's first product manager and later Head of Product at Discord, and having left that role he speaks with unusual candor: nothing to promote, no PR, no comms team. He covers why he designs teams like terrorist organizations, what it was really like to manage Nikita Bier, why the median PM is so bad, why Snapchat's ads business never reached its potential, why growth almost always comes from the core product, and his three 'oxymorons' of great product management.

Roman Ugarte, who previously led Growth at Cursor as it scaled from 15 people to over 1,000, helped incubate Grok Bot, the knowledge-work agent from SpaceXAI: a small, isolated team took it from first line of code to a working internal product in four weeks. He explains the decision to build it from scratch rather than add it to Cursor, why the team personally onboarded nearly 300 of its first users, and their 'colleague-pilled' product philosophy.

Anish Acharya, General Partner at a16z focused on consumer investing, argues that company building will now involve creating a series of loops, and that you do not have to worry about becoming part of the 'permanent underclass.' He surveys what is happening in consumer right now, why the biggest opportunity is '/loop, make me happier,' and his thinking on moats.

Tara Seshan leads product for Codex and ChatGPT Work at OpenAI, after six-plus years at Stripe and a product leadership run at Watershed. She describes AI's third era, persistent AI coworkers, and the shift from 'rowing' to 'steering': human judgment and ambition become the differentiators as AI takes on execution, while OpenAI builds for model capabilities two to three months out. For consultants: the rowing-to-steering frame is a compact way to describe how roles change when execution gets delegated.

Jen Abel breaks down enterprise sales as a 15-step process, not the five-stage pipeline most CRM software sells you. She walks the full cycle step by step: the "pincer model" to land both the exec and the N-minus-one simultaneously, how to extract intelligence before showing a demo, structuring a two-to-three-day pilot, and navigating the procurement gauntlet without losing momentum, all illustrated through her SpaceX legal tech deal. The real game is orchestrating multiple stakeholders and jointly defining what success looks like before the pilot even kicks off. For consultants: Enterprise sales reveals organizational design in real time: you're mapping where authority actually lives in a buyer organization, learning whether power flows through delegation or consensus, and discovering what trust infrastructure needs to be built before a contract closes.