Lenny's Podcast

“I like being scared”: Molly Graham’s frameworks for rapid career growth | Molly Graham

We replaced our sales team with 20 AI agents—here’s what happened next | Jason Lemkin (SaaStr)

10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

In this episode of Lenny's Podcast, Lenny Rachitsky interviews Matt MacInnis, Chief Product Officer at Rippling, about achieving extraordinary results through extraordinary efforts. Matt shares insights on leadership, including the importance of understaffing projects, escalating issues, and maintaining intensity withi...

Why securing AI is harder than anyone expected and guardrails are failing | HackAPrompt CEO

The AI security industry faces critical vulnerabilities, particularly regarding prompt injection and jailbreaking, which can lead to serious real-world consequences as AI agents and robotics become more prevalent. Sander Schulhoff, an AI researcher, highlights the ineffectiveness of AI guardrails, noting that they offe...

The new AI growth playbook for 2026 | How Lovable hit $200M ARR in one year

In this episode of Lenny's Podcast, Elena Verna, Head of Growth at Lovable, discusses the unique growth strategies employed by the company, which has seen unprecedented success in its first year. Elena shares how traditional growth playbooks have been largely discarded in favor of innovation, building in public, and pr...

Inside OpenAI: 2026 is the year of agents, AI’s biggest bottleneck, and why compute isn’t the issue

In this episode of Lenny's Podcast, Lenny Rachitsky interviews Alexander Embiricos, product lead for Codex at OpenAI, about the development and future of Codex, OpenAI's coding agent. Embiricos discusses Codex's explosive growth, its architecture, and its role as a software engineering teammate, emphasizing its potenti...

The $1B Al company training ChatGPT, Claude & Gemini on the path to responsible AGI | Edwin Chen

In this episode of Lenny's Podcast, Lenny Rachitsky interviews Edwin Chen, the founder and CEO of Surge AI, about Surge's extraordinary success as a bootstrapped AI data company that reached $1 billion in revenue in under four years with a small team. Edwin shares his contrarian views on company building, emphasizing t...

The end of product managers? Why LinkedIn is turning PMs into AI-powered “full stack builders”

In this episode of Lenny's Podcast, Tomer Cohen, Chief Product Officer at LinkedIn, discusses the Full Stack Builder model, a new approach to product development designed to empower individuals to take products from idea to launch, regardless of their role. Cohen explains how traditional product development processes h...

What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google)

In this episode of Lenny's Podcast, Lenny interviews Jeanne Grosser, COO at Vercel and former CPO at Stripe, about building world-class go-to-market teams. Jeanne defines go-to-market as any function touching a customer or making revenue, including marketing, sales, customer success, and partnerships. She discusses the...

A guide to difficult conversations, building high-trust teams, and designing a life you love

In this episode of Lenny's Podcast, Lenny Rachitsky interviews Rachel Lockett, an executive coach, about leadership, coaching, avoiding burnout, and building strong co-founder relationships. Lockett shares actionable strategies for leaders to coach effectively, emphasizing active listening and asking powerful questions...

Mental models for building products people love ft. Stewart Butterfield

In this interview, Stewart Butterfield, the founder of Flickr and Slack, discusses product development, leadership, and company building with Lenny Rachitsky. Butterfield shares insights on utility curves, the importance of taste and craftsmanship, and the concept of "hyper-realistic work-like activities." He emphasize...

The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li

In this episode of Lenny's Podcast, Lenny interviews Dr. Fei-Fei Li, often called the "godmother of AI," about the history, present, and future of artificial intelligence. Dr. Li discusses the early days of AI, the AI winter, and her work creating ImageNet, which provided the data needed to advance AI. She shares her p...

“Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (co-founder)

In this episode of Lenny's Podcast, host Lenny Rachitsky interviews Grant Lee, CEO and co-founder of Gamma, an AI-powered presentation and website design tool that has reached $100M ARR in just over two years. Grant shares the story of Gamma's founding, including an early investor's harsh criticism and how that motivat...

"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

Scaling from $1M to $10M ARR requires a strategic shift toward enterprise-focused sales that prioritize vision-casting over traditional problem-solving. Startups should target tier-one logos early, as these industry leaders act as early adopters seeking a competitive edge. Rather than pursuing ill-defined mid-market se...

The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins

In this interview, Lenny interviews Melanie Perkins, the CEO and co-founder of Canva, about her journey building the company. Melanie shares insights into Canva's success, which she attributes to "column B thinking"—envisioning a desired future and working backward to create it. She discusses the importance of setting ...

How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

In this episode of Lenny's Podcast, Lenny interviews Dhanji Prasanna, CTO at Block, about Block's AI-native transformation. Dhanji discusses the company's internal open-source AI agent, Goose, which saves employees significant work time by automating tasks and enabling non-technical teams to build their own software to...

Al Engineering 101 with Chip Huyen (Nvidia, Stanford, Netflix)

In this episode of Lenny's Podcast, Chip Huyen, an AI expert, discusses key concepts in AI, including pre-training, post-training, fine-tuning, RAG (Retrieval Augmented Generation), and RLHF (Reinforcement Learning from Human Feedback). She shares insights on building successful AI applications, emphasizing the importa...

How to measure AI developer productivity in 2025 | Nicole Forsgren

In this episode of Lenny's Podcast, Lenny interviews Nicole Forsgren about measuring and improving developer productivity in the age of AI. They discuss the concept of DevEx (developer experience), the importance of flow state, and the challenges of measuring productivity gains with AI. Nicole shares insights from her ...

Figma’s CEO: Why AI makes design, craft, and quality the new moat for startups | Dylan Field

In this interview podcast, Lenny interviews Dylan Field, the CEO and co-founder of Figma, about Figma's journey, culture, and products. Dylan shares insights on maintaining focus and motivation after a deal fell through, keeping a startup pace, Figma's culture, and his leadership style. He discusses counterintuitive de...

Inside Google's AI turnaround: AI Mode, AI Overviews, and vision for AI-powered search | Robby Stein

In this episode of Lenny's Podcast, Lenny interviews Robby Stein, VP of Product for Google Search, about the recent success of Google Gemini, the evolution of Google Search with AI, and lessons learned from building successful consumer products. Stein discusses Google's focus on delivering great products quickly, the e...