Y Combinator Startup Podcast

For nearly two decades, Box co-founder and CEO Aaron Levie has been at the frontlines of how technology reshapes work—guiding the company through the rise of mobile, the cloud, and now the age of AI.In his fireside with YC General Partner David Lieb at AI Startup School, Aaron reflects on what it means to adapt a company over the long term, the hard lessons of staying relevant across multiple technology waves, and why he believes AI represents the most transformative shift yet.

Amjad Masad is the co-founder & CEO of Replit, now valued at $3B after a recent $250M Series C. He's spent nearly a decade making programming accessible to all—and with the rise of AI, that vision is closer than ever.In this talk from AI Startup School on June 17, 2025, Amjad traces the arc of computing from mainframes to personal computers to a future where AI agents can create software on demand. He predicts that the value of traditional software will approach zero, fundamentally reshaping how companies are built and how work gets done.

Bob McGrew helped build some of the most influential technologies of the past two decades. Bob was an early engineer at PayPal, an early executive at Palantir, and was recently Chief Research Officer at OpenAI - where he led the development of ChatGPT, GPT-4 and the o1 reasoning model.

During his time at Palantir, he was a pioneer of the Forward Deployed Engineer (FDE) model, a strategy that is at the heart of the AI boom today.

On this episode of The Lightcone, he explains how FDEs became central to today's startups, why "doing things that don't scale at scale" works, and where he sees the biggest opportunities for founders working in AI.

Michael Truell on June 17th, 2025 at AI Startup School in San Francisco.At 25, Michael Truell has already built Cursor into one of the fastest-growing companies in AI coding, hitting $100M ARR in just a year. In this fireside chat with YC General Partner Diana Hu, he shares the lessons that came from years of failed projects with his co-founders, why he believes programming is still essential even as AI changes how we code, and how Cursor is taking on GitHub Copilot with the conviction that all of software development will flow through models.

OpenAI recently released its first open-weights model since GPT-2, entering a field led by DeepSeek and Alibaba's Qwen.YC's Ankit Gupta breaks down everything you need to know about these top OSS models, including what sets them apart under the hood. He’ll compare their approaches to mixture-of-experts, long-context training, and post-training techniques that shape reasoning and alignment—and explore how different design choices lead to surprisingly similar performance.

In this episode of Founder Firesides, YC General Partner Gustaf Alströmer is joined by Max Junestrand, co-founder and CEO of Legora, one of the fastest-growing legal AI startups in the world. In just 13 months, Max and his team scaled from 10 to 100 people, raised $80M, and cracked the challenge of selling to one of the most skeptical industries. Max shares insights on building a successful vertical AI company, selling to conservative markets, and sheds light on what the future of legal tech looks like.

Navigating B2B sales for the first time can feel slow and overwhelming.Drawing from his experience founding Monzo and GoCardless, YC's Tom Blomfield shares his playbook for running a tight sales process that lands real, recurring revenue. He walks through each step—free and paid pilots, opt-out contracts, long-term deals—and shows how to prove value and close customers.

Dylan Field on June 17th, 2025 at AI Startup School in San Francisco.Dylan Field co-founded Figma to bring the design process online and make it multiplayer. From a meme maker built on WebGL to a design platform powering millions, Figma’s journey hit a major milestone with its IPO last week.In this conversation, Dylan shares the early challenges of building in the browser, the early risks and pivotal choices that shaped Figma’s growth, the principles that guided its product and community, and how he thinks about building tools that empower creativity at scale.

Brothers Chaz and Arnie Englander started Model ML after building and selling two YC companies.

What began as a tool to help them analyze deals has grown into a full AI-powered workspace purpose-built for financial services, empowering firms to create automations and workflows that reflect exactly how their teams operate. And it's already being used by 10% of the world's top investment banks and private equity firms to automate everything from client-ready PowerPoint decks to deep-dive research and due diligence—by orchestrating AI agents that work like expert team members.

In this conversation with YC Partner Gustaf Alstromer, they discuss going from internal tool to production platform, the power of perseverance, and their ambition to build a billion-dollar company with just ten people.

Jared Kaplan on June 16th, 2025 at AI Startup School in San Francisco.Jared Kaplan started out as a theoretical physicist chasing questions about the universe. Then he helped uncover one of AI’s most surprising truths: that intelligence scales in a predictable, almost physical way.That insight became foundational to the modern era of large language models—and led him to co-found Anthropic.In this talk, he walks through how that discovery reshaped the path to human-level AI, what it means for future models like Claude, and why even the dumbest questions can lead to the biggest breakthroughs. He reflects on memory, oversight, and what’s left to solve as models grow smarter—and longer-horizon tasks come within reach.