Lenny"s Podcast: Product | Career | Growth - Podcasts

99:10

Why we’re at the beginning of the AI hardware boom |...

Lenny"s Podcast: Product | Career | Growth ·

2026/05/17

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

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99:22

How to build a company that withstands any era | Eric...

Lenny"s Podcast: Product | Career | Growth ·

2026/05/10

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 public2. The governance structures that protect companies like Anthropic, Costco, and Novo Nordisk3. The simple

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87:22

Why cultivating agency matters more than cultivating...

Lenny"s Podcast: Product | Career | Growth ·

2026/05/03

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 worked

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70:24

Snapchat CEO: Why distribution has become the most...

Lenny"s Podcast: Product | Career | Growth ·

2026/04/26

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 consumer

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85:34

How Anthropic’s product team moves faster than anyone...

Lenny"s Podcast: Product | Career | Growth ·

2026/04/23

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 days2. The emerging skills PMs need to

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95:11

Why half of product managers are in trouble | Nikhyl...

Lenny"s Podcast: Product | Career | Growth ·

2026/04/19

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 history2. Why half of current product managers are at risk, and what separates those who’ll do well3. Why

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82:39

Hard truths about building in the AI era | Keith...

Lenny"s Podcast: Product | Career | Growth ·

2026/04/12

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 customers

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112:49

Head of Growth (Anthropic): “Claude is growing itself...

Lenny"s Podcast: Product | Career | Growth ·

2026/04/05

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 our

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99:51

An AI state of the union: We’ve passed the inflection...

Lenny"s Podcast: Product | Career | Growth ·

2026/04/02

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 worldwide

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106:35

From skeptic to true believer: How OpenClaw changed...

Lenny"s Podcast: Product | Career | Growth ·

2026/03/29

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. The

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93:33

The art of influence: The single most important skill...

Lenny"s Podcast: Product | Career | Growth ·

2026/03/22

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-in2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a

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114:54

The tactical playbook for getting 20-40% more comp...

Lenny"s Podcast: Product | Career | Growth ·

2026/03/15

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’s a

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66:53

How I built a 1M+ subscriber newsletter and top 10...

Lenny"s Podcast: Product | Career | Growth ·

2026/03/12

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 most

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84:23

The most successful AI company you’ve never heard of...

Lenny"s Podcast: Product | Career | Growth ·

2026/03/08

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 software2. Why Qasar

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77:25

The design process is dead. Here’s what’s replacing...

Lenny"s Podcast: Product | Career | Growth ·

2026/03/01

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 obsolete2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack3. Whether AI will eventually surpass humans in taste and judgment4. Why Jenny left a director role at

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87:23

AI is critical for humanity’s survival: Cisco...

Lenny"s Podcast: Product | Career | Growth ·

2026/02/26

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 employees2. His six-part framework for

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87:45

Head of Claude Code: What happens after coding is...

Lenny"s Podcast: Product | Career | Growth ·

2026/02/19

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 month2. The counterintuitive product principles that drove Claude Code’s success3. Why Boris believes coding is “solved”4. The latent demand that

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74:37

Sequoia CEO coach: Why it’s never been easier to...

Lenny"s Podcast: Product | Career | Growth ·

2026/02/15

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 founders2. Why you should build your team like the 2004 Red Sox3. Why hiring “spicy” candidates beats consensus picks4. Why enterprise sales will be the last white-collar job AI replaces5. Some of my favorite “Halliganisms”—Brought to you by:Sentry—Code breaks, fix it faster:

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79:39

“Engineers are becoming sorcerers” | The future of...

Lenny"s Podcast: Product | Career | Growth ·

2026/02/12

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 minutes2. How AI is changing the role of managers3. Why the productivity gap between AI power users and everyone else is widening4. Why “models will eat your scaffolding for breakfast”5. Why the next 12 to 24 months are a rare window where engineers can leap ahead

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102:30

The rise of the professional vibe coder (a new AI-era...

Lenny"s Podcast: Product | Career | Growth ·

2026/02/08

Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI.We discuss:1. Why having no coding background can be an advantage when building with AI2. Why most of your time should go to planning and chat mode, not prompting3. What to do

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Lenny"s Podcast: Product | Career | Growth

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