Second Order

From Scrubs to Startups: Why Doctors Choose to Build

In this episode, Dr. Derek Paul, physician-turned-founder and CEO of Glass Health, joins Elsa to discuss the mindset shift from medicine to entrepreneurship—and how clinical reasoning can shape the way we build AI. Backed by Y Combinator and Breyer Capital, Glass Health began as a digital notebook for doctors and evolved into a leading platform for AI-powered clinical decision support. Derek explains how physicians’ structured approach to diagnosis—testing hypotheses, managing uncertainty, and learning from feedback—translates directly into effective product design and company building. He shares how Glass ensures medical accuracy and safety, what it means to train AI models with physician expertise, and how startups can navigate FDA frameworks, EHR integrations, and data compliance while maintaining speed and innovation. From leaving the clinic to leading an AI company, Derek reflects on the cognitive frameworks that drive both good medicine and good startups—and why mastering uncertainty is the core skill behind both.

From Code to Care: How AI Is Transforming Modern Medicine

In this episode, we sit down with Dr. Matt Lungren, Chief Scientific Officer at Microsoft Health & Life Sciences and former Stanford radiologist, to explore how AI is truly reshaping healthcare—beyond the buzzwords. We discuss how Microsoft’s new multi-agent orchestration frameworks could change the game for hospitals—turning tools like Teams into intelligent ecosystems where agents collaborate across radiology, pathology, and clinical trials. Matt breaks down why integration now matters more than innovation, how startups can avoid building “features” instead of products, and what it really takes to cross the “last mile” into hospital deployment. The conversation goes deep on AI governance, compliance, and the future of agentic systems, while offering blunt, practical advice for entrepreneurs: why raising capital isn’t a milestone, why distribution is everything, and how to know if you’ve built something users can’t live without. From wearables and precision medicine to personalized therapies and real-time data, this episode reveals where the next decade of healthcare AI is headed—and how founders, clinicians, and technologists can shape it.

Building in Clusters: Elad Gil on Career Strategy, the role of a CEO, and AI's Next Frontier

What separates careers that plateau from those that keep accelerating? Elad Gil has some surprising answers. Today's guest is Elad Gil, serial entrepreneur, investor, and author who's been at the center of Silicon Valley's biggest shifts for over two decades. We explore why location and industry clusters matter more than most people realize, how the best CEOs adapt their leadership as companies scale, and which emerging technology sector could be poised for a major breakthrough. Elad shares why some of his best investments defied conventional wisdom, what trips up even experienced founders as they grow their companies, and how regulatory challenges in one industry offer unexpected lessons for another. We also discuss the balance between following themes and staying open to opportunities you didn't see coming. Whether you're building a company or just trying to make smarter career moves, this episode offers practical frameworks you can use right away.

Sketching Your Tomorrow with James Landay

What does Stanford’s James Landay believe will be the next paradigm of computing? You’ll have to listen in to find out 👀 Today’s guest is Professor James Landay, Stanford Computer Science faculty and co-director of the Stanford Institute for Human-Centered AI. In this episode, we explore how sharp UX and smart data drive entrepreneurial wins. From early-stage validation to spatial computing, storytelling interfaces, and AI-native design, James shares frameworks, failures, and future predictions that every founder should hear.

How To Train Your Founder: Keegan Cooke on Systems Frameworks

What do mud-powered science kits, Stanford's Startup Garage, and systems thinking have in common? Keegan Cooke. In this episode, we sit down with the Director of Stanford Ecopreneurship to unpack what it really takes to train future founders. From turning microbial fuel cells into an educational startup to mentoring students through the chaos of early-stage ventures, Keegan shares the mental models, frameworks, and lived experiences that shape how Stanford teaches entrepreneurship. We talk about second- and third-order effects, global customer discovery, and why great mentors know when to step back. If you’ve ever wondered how to build ventures that think two steps ahead, this episode is for you.