How to Turn Your "Failed" Projects into your Biggest Career Advantage

What if your biggest career advantage didn't come from your wins, but from the projects that didn't go as planned?

Most people build their reputation on successes. Missy Krasner built hers on bold bets and invaluable lessons.

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.

What makes Missy's perspective distinctive is her pragmatic clarity about what's actually happening right now. The political landscape has shifted dramatically. DEI has gone from celebrated to contested. Women's health funding is trending in concerning directions. The buyer community, from employers to health systems, is being squeezed in ways that will fundamentally alter care delivery models. And Missy sees all of this disruption as the exact conditions that will finally enable the consumer-driven healthcare revolution big tech has been working toward for two decades.

But perhaps her most important message isn't about technology or market dynamics. It's about what women leaders need to do right now: Move faster. Be bolder. Stop waiting to be saved. Because nobody's coming. The networks and support systems that existed are evolving, which means women need to find their tribes, pull each other forward, and build businesses with such undeniable traction that gender becomes irrelevant.

This is the conversation for anyone who needs to hear that setbacks aren't the end of the story—they're the foundation for breakthrough thinking..

✔ Why Missy's "failures" at Google, Amazon, and Box taught her more about healthcare transformation than 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 chaos will accelerate consumer-driven healthcare innovation
✔ Missy's blunt 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

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