Lenny's Podcast: Product | Career | Growth
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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An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison
<p>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. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—...
From skeptic to true believer: How OpenClaw changed my life | Claire Vo
<p>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.</p><p></p><p>We discuss:</p><p>1. The exact step-by-step process to install and...
The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
<p>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.</p><p></p><p>We discuss:</p><p>1. Why great ideas often don’t get buy-in</p><p>2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much</p><p>3. Why executives are usually op...
The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
<p>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.</p><p></p><p>We discuss:</p><p>1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump</p><p>2. Why Jacob sees 40% average movement when negotiations are run well</p><p>3. Whe...
How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky
<p>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 stresses me out, and the scar...
The most successful AI company you’ve never heard of | Qasar Younis
<p>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.</p><p></p><p>We discuss:</p><p>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</p><p>2. Why Qasar intentionally stayed under the radar for nearly a de...
The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)
<p>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.</p><p>—</p><p>We discuss:</p><p>1. Why the classic discovery → mock → iterate design process is becoming obsolete</p><p>2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack</p><p>3. Whether AI will eventually surpass humans in taste and judgment</p><p>4. Why Jenny left a director role at Figma to ret...
AI is critical for humanity’s survival: Cisco president on the AI revolution | Jeetu Patel
<p>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.</p><p></p><p>We discuss:</p><p>1. How Cisco went AI-first across 90,000 employees</p><p>2. His six-part framework for building great companies: timing, market, team, product, brand, distribution</p><p>3. Why...
Head of Claude Code: What happens after coding is solved | Boris Cherny
<p>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.</p><p></p><p>We discuss:</p><p>1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month</p><p>2. The counterintuitive product principles that drove Claude Code’s success</p><p>3. Why Boris believes coding is “solved”</p><p>4. The latent demand that shaped Claude Code and Cowork</p><p>5. Practical tips f...
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)
<p>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.</p><p></p><p>We discuss:</p><p>1. His LOCKS framework for evaluating founders</p><p>2. Why you should build your team like the 2004 Red Sox</p><p>3. Why hiring “spicy” candidates beats consensus picks</p><p>4. Why enterprise sales will be the last white-collar job AI replaces</p><p>5. Some of my favorite “Halliganisms”</p><p>—</p><p>Brought to you by:</p><p>Sentry—Code breaks, fix it faster: http://sentry.io/lenny</p><p>Datadog—Now...
