Episodes
Five years of tape. Every episode is checked claim by claim and playable.
45 episodes in 2026
🎙LENNY'S PODCAST
1h 22m How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)
In this in-depth conversation, Lenny Rachitsky interviews Roman Ugarte, product lead for GrokBot at SpaceXAI, exploring how a small autonomous team built and launched a breakout AI colleague…
51 statements 16 featured 3 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 19m Why companies are becoming a series of loops | Anish Acharya (a16z)
Lenny Rachitsky interviews Andreessen Horowitz General Partner Anish Acharya on how artificial intelligence is reorganizing companies into automated agentic loops while amplifying human agen…
43 statements 11 featured 5 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 21m AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)
OpenAI Product Lead Tara Seshan discusses the transition into AI's third era—collaborating with persistent AI coworkers—and explains how product teams must discard static strategy documents …
33 statements 6 featured 3 assessments
🎙LENNY'S PODCAST
1h 24m 84 minutes of enterprise sales alpha | Jen Abel
In this tactical masterclass, enterprise sales strategist Jen Abel breaks down a granular 15-step enterprise sales cycle, providing founders and sales leaders with practical frameworks for e…
29 statements 8 featured 1 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 12m Chatbots are not the final interface: OpenAI’s Head of Design on what’s next | Ian Silber
In this in-depth conversation, Lenny Rachitsky interviews OpenAI Head of Product Design Ian Silber about the evolving landscape of AI interface design, addressing workforce anxiety, and why …
17 statements 6 featured 1 assessments
🎙LENNY'S PODCAST
1h 30m The playbook for building high talent density teams | Adam Ward, Head of Talent at Cursor
Adam Ward, Head of Talent at Cursor, breaks down the tactical playbook for building high talent density teams, arguing against traditional volume-based hiring funnels in favor of rigorous se…
34 statements 9 featured 1 assessments
🎙LENNY'S PODCAST
1h 24m This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)
In this in-depth interview, Whatnot Chief Product Officer Tom Verrilli joins Lenny Rachitsky to deconstruct conventional tech organizational structures, advocating for lean, hands-on product…
34 statements 10 featured 2 assessments
🎙LENNY'S PODCAST
1h 33m Why AI is going vertical (again) | Dianne Penn (Anthropic)
Anthropic's Head of Product for AI Research and Labs, Dianne Penn, joins Lenny Rachitsky to discuss how frontier models, purpose-built harnesses like Claude Code, and eval-driven product man…
26 statements 9 featured 2 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 12m Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)
In this in-depth interview, Netflix Chief Product and Technology Officer Elizabeth Stone joins Lenny Rachitsky to discuss how generative AI is reshaping organizational structure, championing…
23 statements 7 featured 1 assessments
🎙LENNY'S PODCAST
1h 36m Why the AI’s honeymoon is ending (and tech workers are feeling it) | Noam Segal
Host Lenny Rachitsky and research executive Noam Segal analyze findings from a 6,000-person tech worker sentiment survey, exploring how artificial intelligence is driving unprecedented burno…
40 statements 14 featured 24 assessments
🎙LENNY'S PODCAST
1h 8m The rise of taste, human authenticity and judgment in an AI world | Adam Mosseri (Head of IG)
In this in-depth conversation, Head of Instagram Adam Mosseri joins Lenny Rachitsky to discuss the future of product development, organizational restructuring into small pods, algorithmic re…
24 statements 8 featured 2 assessments
🎙LENNY'S PODCAST
1h 9m Why OpenAI is merging Codex and ChatGPT and the future of knowledge work | Andrew Ambrosino
Lenny Rachitsky interviews OpenAI's Andrew Ambrosino to discuss how AI inverts software product development, why Codex is transforming into a universal desktop platform for knowledge work, a…
27 statements 11 featured 1 assessments
🎙LENNY'S PODCAST
1h 38m What happens after coding is solved? | Fiona Fung (Claude Code & Cowork)
Anthropic engineering leader Fiona Fung explores how AI tools like Claude Code and Cowork are eliminating raw coding bottlenecks, transforming engineering management, blurring traditional te…
25 statements 10 featured 1 assessments
🎙LENNY'S PODCAST
1h 39m The hidden pattern behind successful products | Mark Pincus (FarmVille, Words with Friends, & more)
In this in-depth interview with Lenny Rachitsky, Zynga founder Mark Pincus breaks down his 'Proven, Better, New' framework, the discipline of killing unviable products, and how to build brea…
36 statements 9 featured 4 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 35m Tony Fadell: How to build real taste (and why AI makes it matter more)
In this masterclass on product leadership, iPod and Nest co-creator Tony Fadell joins Lenny Rachitsky to explain why human taste, disciplined storytelling, and opinion-driven decision-making…
23 statements 6 featured 3 assessments
🎙LENNY'S PODCAST
1h 19m The most rational take on AI you’ll hear this year
In this in-depth conversation, technology analyst Benedict Evans joins Lenny Rachitsky to deliver a rational, historically grounded perspective on artificial intelligence, enterprise value c…
23 statements 12 featured 5 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 34m AI predictions: Job markets, Codex beats Claude, and the death of org charts | Dan Shipper
Dan Shipper joins Lenny Rachitsky to deliver a comprehensive, contrarian forecast on how generative AI will reshape software, enterprise tooling, and knowledge work over the next year. Dispu…
31 statements 9 featured 1 assessments
🎙LENNY'S PODCAST
1h 39m Why the next AI boom is physical AI | Caitlin Kalinowski (ex-OpenAI, Meta, Apple)
In this in-depth conversation, hardware executive Caitlin Kalinowski breaks down why physical AI and robotics represent the next major technical frontier, sharing engineering principles, sup…
29 statements 9 featured 9 assessments
🎙LENNY'S PODCAST
1h 39m How Anthropic, Costco, and Patagonia all build incorruptible companies | Eric Ries
In this in-depth conversation with Lenny Rachitsky, author and entrepreneur Eric Ries discusses his book Incorruptible, explaining why successful companies succumb to short-term financial pr…
28 statements 8 featured 17 assessments 3 contradicted
🎙LENNY'S PODCAST
1h 27m AI era skills: Why cultivating agency matters more than job titles | Max Schoening (Notion)
Notion Head of Product Max Schoening and Lenny Rachitsky explore how artificial intelligence is transforming software creation, collapsing traditional role boundaries between designers and e…
40 statements 10 featured
🎙LENNY'S PODCAST
1h 10m How to win when software is not a moat | Evan Spiegel (Snapchat CEO)
Snap co-founder and CEO Evan Spiegel joins Lenny Rachitsky to discuss how consumer software companies can build defensible moats through distribution, hardware, and developer ecosystems when…
26 statements 10 featured 5 assessments
🎙LENNY'S PODCAST
1h 25m How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)
Anthropic Head of Product Cat Wu shares how her team achieves industry-leading shipping velocity, navigates the evolving role of AI product management, and designs agentic tools like Claude …
38 statements 11 featured 1 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 35m Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)
Veteran product executive Nikhyl Singhal and Lenny Rachitsky examine the profound shift transforming product management in the AI era. They analyze why administrative 'information movers' fa…
19 statements 6 featured
🎙LENNY'S PODCAST
1h 22m Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
In this in-depth interview with Lenny Rachitsky, veteran operator and Khosla Ventures Managing Director Keith Rabois shares contrarian frameworks on talent density, startup execution, and na…
40 statements 12 featured 3 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 52m Head of Growth (Anthropic): Anthropic is automating its own growth
Anthropic Head of Growth Amol Avasare reveals how the AI pioneer achieved historic hypergrowth by replacing standard playbooks with automated AI experimentation, exponential product bets, an…
26 statements 11 featured 3 assessments
🎙LENNY'S PODCAST
1h 39m An AI state of the union: We’ve passed the inflection point & dark factories are coming
Open-source pioneer Simon Willison joins Lenny Rachitsky to discuss the monumental inflection point in agentic software engineering, detailing practical architectural patterns, the cognitive…
46 statements 21 featured 7 assessments
🎙LENNY'S PODCAST
1h 46m From skeptic to true believer: How OpenClaw changed my life | Claire Vo
In this crossover interview, engineering leader and founder Claire Vo joins Lenny Rachitsky to demystify OpenClaw, explaining how she transitioned from an initial skeptic to orchestrating ni…
28 statements 10 featured 2 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 33m The art of influence: The single most important skill left that AI can’t replace | Jessica Fain
In this tactical masterclass, product executive Jessica Fain joins Lenny Rachitsky to unpack executive influence as the definitive, irreplaceable leadership skill for product builders in the…
25 statements 11 featured
🎙LENNY'S PODCAST
1h 54m He's negotiated $1B+ in executive compensation. Here's his playbook. | Jacob Warwick
Elite executive compensation advisor Jacob Warwick shares high-leverage negotiation strategies, behavioral psychology insights, and collaborative deal-structuring frameworks to help professi…
38 statements 13 featured 1 assessments
🎙LENNY'S PODCAST
1h 6m A behind-the-scenes interview with Lenny Rachitsky on building his newsletter and podcast
In a special format reversal, author and artist Michelle Rial interviews her husband, Lenny Rachitsky, exploring his journey from startup founder to top media creator, their creative workflo…
18 statements 6 featured 2 assessments
🎙LENNY'S PODCAST
1h 24m The real AI revolution isn’t software. It’s farms, mines, and trucks. | Qasar Younis
Applied Intuition co-founder and CEO Qasar Younis joins Lenny Rachitsky to discuss why the true AI revolution is unfolding in physical industries like farming, mining, and transportation, wh…
24 statements 8 featured 2 assessments
🎙LENNY'S PODCAST
1h 17m The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)
Jenny Wen, Head of Design for Claude Cowork at Anthropic, discusses how artificial intelligence has disrupted traditional product design processes, emphasizing rapid code-level prototyping, …
17 statements 6 featured
🎙LENNY'S PODCAST
1h 27m AI is critical for humanity’s survival: Cisco President on the AI revolution | Jeetu Patel
Cisco Chief Product Officer and President Jeetu Patel joins Lenny Rachitsky to discuss how Cisco powers modern AI infrastructure, why demographic decline makes AI vital for humanity's surviv…
20 statements 7 featured 2 assessments
🎙LENNY'S PODCAST
1h 27m Head of Claude Code: What happens after coding is solved | Boris Cherny
Anthropic's Head of Claude Code, Boris Cherny, explains how automated code generation and autonomous agentic workflows are eliminating manual syntax writing and transforming traditional soft…
46 statements 15 featured 6 assessments
🎙LENNY'S PODCAST
1h 14m How to be a CEO when AI breaks all the old playbooks | Sequoia CEO Coach Brian Halligan
Former HubSpot CEO and Sequoia Capital executive coach Brian Halligan joins Lenny Rachitsky to unpack modern startup scaling, executive hiring playbooks, AI-driven go-to-market shifts, and c…
36 statements 10 featured 3 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 19m OpenAI’s head of platform engineering on the next 12-24 months of AI | Sherwin Wu
Sherwin Wu, OpenAI's Head of Platform Engineering, joins Lenny Rachitsky to discuss how autonomous agent orchestration is transforming software engineering, the evolution of technical manage…
25 statements 5 featured 1 assessments
🎙LENNY'S PODCAST
1h 42m The rise of the professional vibe coder (a new AI-era job)
In this episode of Lenny's Podcast, host Lenny Rachitsky interviews Lazar Yovanovich, the first full-time vibe coding engineer at Lovable, exploring how non-technical builders leverage AI to…
33 statements 14 featured 2 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 31m A child psychologist’s guide to working with difficult adults | Dr. Becky Kennedy
In this episode, Lenny Rachitsky interviews clinical psychologist and Good Inside CEO Dr. Becky Kennedy on how foundational child psychology principles can be applied to corporate leadership…
29 statements 11 featured
🎙LENNY'S PODCAST
1h 44m Marc Andreessen: The real AI boom hasn’t even started yet
In this in-depth conversation with Lenny Rachitsky, venture capitalist Marc Andreessen explores how artificial intelligence serves as an essential economic counterweight to demographic colla…
32 statements 12 featured 2 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 46m The surprising advice from a founder who built 2 unicorns | Jason Cohen (WP Engine)
Serial entrepreneur and WP Engine founder Jason Cohen joins Lenny Rachitsky to break down a comprehensive five-step framework for diagnosing and reversing stalled product growth. Through tac…
23 statements 8 featured 4 assessments 1 contradicted
🎙LENNY'S PODCAST
1h 15m How a Meta PM ships products without ever writing code | Zevi Arnovitz
Meta Product Manager Zevi Arnovitz joins Lenny Rachitsky to break down his end-to-end workflow for building and shipping production software without writing code. Through live demonstrations…
15 statements 5 featured
🎙LENNY'S PODCAST
1h 26m How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook
Investor and operator Sam Lessin joins Lenny Rachitsky to demystify professional etiquette, offering startup founders a practical playbook for navigating high-stakes meetings, social dynamic…
20 statements 7 featured
🎙LENNY'S PODCAST
1h 26m Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google & Amazon
Lenny Rachitsky interviews AI practitioners Aishwarya Reganti and Kiriti Badam to unpack proven frameworks for building production AI products, emphasizing graduated autonomy, continuous eva…
37 statements 13 featured 2 assessments
🎙LENNY'S PODCAST
1h 31m “I like being scared”: Molly Graham’s frameworks for rapid career growth | Molly Graham
In this episode, tech operator and Glue Club founder Molly Graham shares essential leadership and career frameworks—including 'giving away your Legos,' J-curve career progression, the Waterl…
21 statements 6 featured
🎙LENNY'S PODCAST
1h 42m We replaced our sales team with 20 AI agents—here’s what happened next | Jason Lemkin (SaaStr)
SaaStr founder Jason Lemkin joins Lenny Rachitsky to explain how his organization replaced a ten-person sales team with twenty AI agents and a single human orchestrator. He shares practical …
45 statements 12 featured 5 assessments 1 contradicted