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Every episode
Lenny's Podcast: Product | Career | Growth
30 episodes
OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber
Aug 16, 2026 · 1 hr 12 min
Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of ho…
The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor
Aug 9, 2026 · 1 hr 31 min
Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech. In our in-depth conversation,…
This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)
Aug 2, 2026 · 1 hr 25 min
Tom Verrilli is the chief product officer at Whatnot, a live shopping platform that’s become the fastest-growing U.S. marketplace business in history, with over $8 billion in GMV. Before joining Whatnot, Tom was CPO at Twitch and director of product growth at Twitter (during one of the most turbulent periods in the company’s history). In our in-depth conversation, we discuss: 1. Why Whatnot’s product team was founded on the premise “we regret that product management exists” 2. How AI is reshapin…
Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn
Jul 26, 2026 · 1 hr 34 min
Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase. In our in-depth conversation, we discus…
Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)
Jul 19, 2026 · 1 hr 12 min
Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch. In our in-depth conversat…
How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)
Jul 12, 2026 · 1 hr 36 min
Noam Segal is a longtime research leader across Airbnb, Meta, Twitter, Zapier, Intercom, and Figma, a certified coach, AI builder, and my community research lead. Together, we run the annual Tech Worker Sentiment Survey, now in its second year and one of the largest of its kind: a quantitative study of how people in tech actually feel about their jobs, AI, burnout, and the future of their careers. This year’s survey captured responses from thousands of workers across product, engineering, design…
Adam Mosseri: AI is a tailwind for authenticity
Jul 9, 2026 · 1 hr 8 min
Adam Mosseri is the Head of Instagram, where he oversees an app used by over 3 billion people. He also leads the team building Threads. Adam has run Instagram for longer than its founders did, after taking over from Kevin Systrom and Mike Krieger in 2018. A designer by training, he spent over 15 years at Meta, starting as a designer on Facebook’s mobile app, rising to lead Facebook’s News Feed, and eventually chosen to lead Instagram. During his tenure, Instagram’s user base has more than triple…
OpenAI Codex lead on the new shape of product work | Andrew Ambrosino
Jun 28, 2026 · 1 hr 10 min
Andrew Ambrosino leads development of the Codex desktop app at OpenAI. Nearly 100% of OpenAI employees—not just engineers—now use Codex weekly. A lifelong builder with a background spanning engineering, design, product management, and founding companies, he is now responsible for turning the Codex desktop experience into what he calls “the best desktop app that has ever existed, full stop.” In our in-depth conversation, we discuss: 1. Why AI has completely flipped the product development process…
What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams)
Jun 21, 2026 · 1 hr 39 min
Fiona Fung leads the teams behind Claude Code and Cowork at Anthropic (overseeing Boris Cherny and the entire engineering and PM team). Before Anthropic, she spent 11 years at Microsoft building Visual Studio and TypeScript and then moved to Meta, where she started Facebook Marketplace (now generating over $100 billion in GMV annually), worked on Meta’s first smart glasses and AR glasses, and led infrastructure, growth, integrity, and safety teams at Instagram. She’s been an engineer for over 25…
The hidden pattern behind successful products | Mark Pincus (founder of Zynga)
Jun 14, 2026 · 1 hr 39 min
Mark Pincus founded Zynga—the company behind Words With Friends, FarmVille, and Zynga Poker—and has arguably created more hit consumer products than anyone in history. At Zynga, eight of 10 major game launches became massive hits, reaching over a billion players. Over the past five years, Mark has been synthesizing everything he’s learned about building successful consumer products and turning it into a book, Life at the Speed of Play, which comes out on June 23. This is the first interview he’s…
Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell
Jun 7, 2026 · 1 hr 35 min
Tony Fadell created the iPod, co-created the iPhone, and founded Nest (which he sold to Google for $3.2 billion). He’s co-authored over 300 patents, was part of the legendary team at General Magic, and wrote one of the most important and inspiring books for builders, called Build. In our in-depth conversation, we discuss: 1. The heated internal debates about whether the iPhone should have a physical keyboard 2. Why opinion-based decisions are essential for v1 products 3. Why marketing matters as…
A rational conversation on where AI is actually going | Benedict Evans
May 31, 2026 · 1 hr 20 min
Benedict Evans is an independent analyst and former partner at Andreessen Horowitz, where he spent years as their in-house “thinker” tracking the most important technology trends. For the past six years, he’s been publishing deeply researched presentations on where tech is heading, most recently focused on AI’s transformation of the economy. His work is read by founders, investors, and operators trying to make sense of a noisy field. His most controversial opinion: AI is as big a deal as the int…
The AI paradox: More automation, more humans, more work | Dan Shipper
May 24, 2026 · 1 hr 34 min
Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another…
Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)
May 17, 2026 · 1 hr 39 min
Caitlin Kalinowski was most recently at OpenAI helping build their robotics and hardware teams from scratch. Prior to that, she was head of AR glasses and VR hardware at Meta, where she led the teams building every generation of the Quest, Rift, and Orion, and was Meta’s first consumer electronics hire. Before this, she was technical lead on MacBook Air and Mac Pro at Apple, and helped engineer the original unibody MacBook Pro. She’s designed and engineered some of the hardest and most beloved c…
How to build a company that withstands any era | Eric Ries, Lean Startup author
May 10, 2026 · 1 hr 39 min
Eric Ries is the author of The Lean Startup, a book that reshaped how a generation of founders think about building companies. His new book, Incorruptible, explains how successful companies are destroyed by failing to protect what makes them valuable, and how to change it. In our in-depth conversation, we discuss: 1. Why 80% of venture-backed founders are ousted within three years of going public 2. The governance structures that protect companies like Anthropic, Costco, and Novo Nordisk 3. The…
Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)
May 3, 2026 · 1 hr 27 min
Max Schoening is head of product at Notion, where he’s been especially effective at getting designers and PMs to ship code, prototype in the terminal, and launch extremely successful AI products. He was previously a PM at Google, ran design at Heroku, was VP of Design (and a part-time engineer) at GitHub, and is a two-time founder. He’s one of the most AI-forward product leaders out there and one of the deepest thinkers on how AI changes how we build and use software. We discuss: 1. What’s most…
Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel
Apr 26, 2026 · 1 hr 10 min
Evan Spiegel, the co-founder and CEO of Snap, is one of the very few people in the world who has successfully built and scaled a lasting consumer social product. Snapchat has nearly 1 billion MAUs, and Evan and his team invented some of the most important consumer products and features, including Stories, AR glasses, swipe-based navigation, the camera as the primary UX, and a lot more. In our in-depth conversation, we discuss: 1. Why distribution is now the biggest challenge for creating a consu…
How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)
Apr 23, 2026 · 1 hr 26 min
Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break into AI—and seeing firsthand what separates those who thrive from those who fall behind. We discuss: 1. How Anthropic’s shipping cadence went from months to weeks to days 2. The emerging skills PMs need t…
Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)
Apr 19, 2026 · 1 hr 35 min
Nikhyl Singhal is the founder of The Skip, a community for senior product leaders; a former product exec at Meta, Google, and Credit Karma; and a many-time founder. He’s also one of the most honest, unfiltered voices on what’s actually happening in product management right now. In our in-depth conversation, we discuss: 1. Why the next two years will be the most chaotic period in product management history 2. Why half of current product managers are at risk, and what separates those who’ll do wel…
Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
Apr 12, 2026 · 1 hr 23 min
Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad). In our in-depth conversation, Keith shares: 1. The barrels vs. ammunition hiring framework (and how to spot barrels) 2. Why talking to cust…
Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare
Apr 5, 2026 · 1 hr 53 min
Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year. In…
An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison
Apr 2, 2026 · 1 hr 40 min
Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwi…
From skeptic to true believer: How OpenClaw changed my life | Claire Vo
Mar 29, 2026 · 1 hr 47 min
Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life. We discuss: 1. T…
The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
Mar 22, 2026 · 1 hr 34 min
Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process. We discuss: 1. Why great ideas often don’t get buy-in 2. Why executive calendars are “like strobe lights” and why the first 30 secon…
The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
Mar 15, 2026 · 1 hr 55 min
Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes. We discuss: 1. Why a simple “What’s the chance there’…
How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky
Mar 12, 2026 · 1 hr 7 min
People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what m…
The most successful AI company you’ve never heard of | Qasar Younis
Mar 8, 2026 · 1 hr 24 min
Qasar Younis is the co-founder and CEO of Applied Intuition, a $15 billion AI company that adds intelligence to cars, tractors, planes, submarines, and other vehicles—essentially, Tesla or Waymo without the hardware. He was previously COO of Y Combinator, started his career as an engineer at GM and Bosch, and was born on a farm in Pakistan. We discuss: 1. Why the biggest AI revolution will play out in mining, farming, construction, and trucking over the next 5 to 10 years, not in software 2. Why…
The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)
Mar 1, 2026 · 1 hr 17 min
Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify. — We discuss: 1. Why the classic discovery → mock → iterate design process is becoming obsolete 2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack 3. Whether AI will eventually surpass humans in taste and judgment 4. Why Jenny left a director…
AI is critical for humanity’s survival: Cisco president on the AI revolution | Jeetu Patel
Feb 26, 2026 · 1 hr 27 min
Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li. We discuss: 1. How Cisco went AI-first across 90,000 employees 2. His six-part framework f…
Head of Claude Code: What happens after coding is solved | Boris Cherny
Feb 19, 2026 · 1 hr 28 min
Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work. We discuss: 1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month 2. The counterintuitive product principles that drove Claude Code’s success 3. Why Boris believes coding is “solved” 4. The latent dema…
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