What if your biggest career advantage didn't come from your wins, but from the projects that didn't go as planned? Missy Krasner's career includes some of the boldest bets in healthcare: Google Health, Amazon Care, Box's healthcare vision. None went the way she originally envisioned. And she wouldn't change any of it. Because what she extracted from those experiences—being inside big tech's most ambitious healthcare ventures—gave her something more valuable than a conventional win: a clear understanding of what it actually takes to make change stick in the most regulated, fragmented industry in America. Now, as co-founder of Penguin AI, Missy is applying those hard-won insights to tackle the trillion-dollar administrative burden crushing healthcare. But this isn't another AI hype story. Missy has been at the forefront of healthcare innovation for over 20 years. She was building Google Health before meaningful use existed. She was evangelizing platform thinking when electronic health records were still competing with manila folders. She's witnessed three watershed moments transform the industry: meaningful use driving EHR adoption, COVID accelerating telehealth adoption, and now AI. And she believes this moment is fundamentally different. Why Missy's experiences at Google, Amazon, and Box taught her more about healthcare transformation than conventional success ever could What's really happening with the trillion-dollar administrative burden and how AI can finally address it at scale Why the current political and economic disruption will accelerate consumer-driven healthcare innovation Missy's candid assessment of the headwinds facing women leaders right now and what it means for advancement Why "nobody's coming to save us" and what that means for how women need to show up in leadership What fuels Missy after decades of innovation and her advice for anyone trying to push through when it's hard About the Guest: Missy Krasner brings 35+ years of healthcare experience spanning big tech (Amazon, Google, Box), government (helped launch the Office of the National Coordinator for Health IT), venture capital (Canvas Ventures, Redesign Health), and now as co-founder of Penguin AI, which recently closed a $30 million Series A. She serves on multiple digital health boards including Uplift, Overalls, and Syntax, and holds degrees from Stanford (M.A.) and UCLA (B.A.). Chapters 00:00 - Introduction at Health Conference 01:14 - Journey Through Google, Box, and Amazon 02:53 - Three Watershed Moments in Healthcare 06:59 - Penguin AI and the Trillion-Dollar Administrative Burden 10:34 - Women Healthcare Leaders for Progress Reflection 14:15 - Finding Innovation Opportunities in Chaos 16:45 - Advancing Women in Leadership 22:13 - Learning from Failure and What Drives Success Guest & Host Links Connect with Laurie McGraw on LinkedIn Connect with Missy Krasner on LinkedIn Connect with Inspiring Women Browse Episodes | LinkedIn | Instagram | Apple | Spotify