Lenny's Podcast: Product | Career | Growth - podcast cover

Lenny's Podcast: Product | Career | Growth

Lenny Rachitskywww.lennysnewsletter.com
Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.
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Episodes

Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell

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 a...

Jun 07, 20261 hr 35 min

A rational conversation on where AI is actually going | Benedict Evans

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...

May 31, 20261 hr 20 min

The AI paradox: More automation, more humans, more work | Dan Shipper

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...

May 24, 20261 hr 34 min

Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)

Hardware veteran Caitlin Kalinowski delves into the unexpected evolution of VR technology, explaining how its innovations became foundational for modern robotics and physical AI. She explores the complex challenges of developing and scaling hardware, including critical supply chain bottlenecks, memory price shocks, and the geopolitical implications of manufacturing. Kalinowski also shares insights from her time at Apple, Meta, and OpenAI, detailing principles for hardware excellence, the future of AI in engineering, and why humanoid robots aren't always the solution for industrial applications.

May 17, 20261 hr 39 min

How to build a company that withstands any era | Eric Ries, Lean Startup author

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. Th...

May 10, 20261 hr 39 min

Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)

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 ...

May 03, 20261 hr 27 min

Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel

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...

Apr 26, 20261 hr 10 min

How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)

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...

Apr 23, 20261 hr 26 min

Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)

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...

Apr 19, 20261 hr 35 min

Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

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...

Apr 12, 20261 hr 23 min

Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare

Amol Avasare, Head of Growth at Anthropic, shares insights into navigating unprecedented hypergrowth from $1B to $19B ARR in 14 months, highlighting how AI automates growth experiments and reshapes PM and engineering roles. He also delves into Anthropic's strategic focus on AI coding and B2B, its unique mission-driven culture balancing growth with safety, and offers advice for thriving in an AI-first future. Amol also shares personal stories of overcoming a startup failure and a traumatic brain injury.

Apr 05, 20261 hr 53 min

An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison

Simon Willison, co-creator of Django, provides an AI state of the union, explaining how coding agents have passed an inflection point, enabling "dark factories" where AI handles most code. He discusses the mental exhaustion of working with AI, the shifting value of human code, and the critical importance of adapting skills. Willison also delves into the lethal trifecta of prompt injection, emphasizing the unresolved security risks and the surprising demand for tools like OpenClaw.

Apr 02, 20261 hr 40 min

From skeptic to true believer: How OpenClaw changed my life | Claire Vo

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...

Mar 29, 20261 hr 47 min

The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

Jessica Fain, a product leader at Webflow and former Chief of Staff at Slack, discusses the art and science of influencing executives. She reveals common misunderstandings about how leaders make decisions, emphasizing the importance of empathy, understanding incentives, and tailored communication. Jessica highlights why influence is an indispensable skill, especially in the age of AI, and offers tactical advice for presenting ideas, building trust, and growing into senior roles.

Mar 22, 20261 hr 34 min

The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)

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’...

Mar 15, 20261 hr 55 min

How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky

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 ...

Mar 12, 20261 hr 7 min

The most successful AI company you’ve never heard of | Qasar Younis

Qasar Younis, co-founder and CEO of Applied Intuition, reveals how his $15 billion AI company quietly empowers vehicles in sectors like mining and farming, predicting AI's imminent role in creating abundance and addressing labor shortages. He challenges fears about AI's impact on jobs and offers a nuanced perspective on China's AI advancements. Younis also delves into Applied Intuition's unique culture, stressing the importance of early traction, radical pragmatism, continuous learning from diverse sources, and the art of decisive leadership.

Mar 08, 20261 hr 24 min

The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)

Jenny Wen shares her perspective on the demise of the traditional design process, explaining how AI's rapid development necessitates a new approach focused on supporting implementation and establishing short-term vision. She details her daily life as a designer at Anthropic, highlighting the shift towards direct coding, continuous feedback, and building trust through speed. The discussion also covers the future of design roles, the importance of adaptability, and unique hiring archetypes for the evolving landscape.

Mar 01, 20261 hr 17 min

AI is critical for humanity’s survival: Cisco president on the AI revolution | Jeetu Patel

Jeetu Patel, Cisco President and CPO, shares insights from an AI summit, detailing Cisco's cultural shift to become AI-first and its crucial role in AI infrastructure. He outlines frameworks for strategy and leadership, including his unique approach to public critique, and emphasizes the importance of human connection and selecting impactful career paths in the age of AI. The discussion also covers the future of AI, parenting in the AI era, and a six-part framework for building great companies.

Feb 26, 20261 hr 27 min

Head of Claude Code: What happens after coding is solved | Boris Cherny

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...

Feb 19, 20261 hr 28 min

Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach. We discuss: 1. His LOCKS framework for evaluating founders 2. Why you should build your team like the 2004 Red Sox 3. Why hiring “spicy” candidates beats consensus picks 4. Why enterprise sales will be the last white-collar job AI replaces 5. Some of my favorite “Halliganisms” — Brought to you by: Sentry —Code breaks, fix it faster: http://sentry.io...

Feb 15, 20261 hr 15 min

“Engineers are becoming sorcerers” | The future of software development with OpenAI’s Sherwin Wu

Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents. We discuss: 1. What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes 2. How AI is changing the role of managers 3. Why the productivity gap between AI power users and everyone else is widening 4. Why “models will eat your scaffolding for breakfast” 5. Why the next 12 to 24 months are a rare window where engineers can leap...

Feb 12, 20261 hr 20 min

The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder)

Lazar Jovanovic, a professional vibe coder, details his innovative approach to building software using AI, highlighting how a non-technical background can be an advantage. He outlines a rigorous workflow focused on 80% planning, dynamic context windows, and parallel prototyping to achieve clarity and "world-class" output. The discussion covers practical tips, debugging strategies, and insights into how AI is converging traditional tech roles, making emotional intelligence and design skills paramount for the future.

Feb 08, 20261 hr 43 min

A child psychologist’s guide to working with difficult adults | Dr. Becky Kennedy

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside , and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dy...

Feb 01, 20261 hr 32 min

Marc Andreessen: The real AI boom hasn’t even started yet

Marc Andreessen discusses why AI is arriving at a critical moment to counter demographic decline and boost productivity. He shares insights on how to prepare kids for an AI-driven world, debunks job loss fears, and explains the shifting dynamics within tech roles. The conversation also delves into the future of companies, the unpredictability of AI moats, and the concept of AGI surpassing human capabilities, concluding with Marc's personal media and product recommendations.

Jan 29, 20261 hr 45 min

5 questions to ask when your product stops growing | Jason Cohen (2x unicorn founder)

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team. We discuss: 1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market 2. A small tweak that’ll double response rates on...

Jan 25, 20261 hr 46 min

The non-technical PM’s guide to building with Cursor | Zevi Arnovitz (Meta)

Zevi Arnovitz, a non-technical PM at Meta, shares his complete AI workflow using Cursor and Claude to build sophisticated products. He demonstrates how to leverage multiple AI models for planning, execution, and a unique peer review process where AIs critique each other's code. Zevi also discusses AI's transformative impact on the PM role and how to maintain high-quality outputs.

Jan 18, 20261 hr 15 min

How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and ...

Jan 15, 20261 hr 27 min

Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering. We discuss: 1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they ...

Jan 11, 20261 hr 26 min

The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth. We discuss: 1. “Give away your Legos”: a framework for scaling yourself as a leader 2. “J-curves vs. stairs”: the two ...

Jan 04, 20261 hr 32 min
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