The 229 Podcast

July 24, 2026: Dr. Jen McKay spent 20-plus years as an internal medicine hospitalist in rural South Dakota before becoming CMIO at a major Midwest health system, and now she's the Senior Clinical Specialist at Google for Health. Jen explains why so many AI governance efforts stall out, and it usually comes down to one missing ingredient: clinical leadership at the table from day one. She unpacks why physicians serve as the real "API" between fragmented healthcare data inputs, whether AI will ever replace doctors, and what she'd tell a CMIO whose organization is adopting AI faster than policy can keep up with.

Key Points:

• 03:16 Where Governance Fails

• 05:12 Humans Are the API

• 06:17 Will AI Replace Doctors?

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July 23, 2026: Liz Scott is the co-executive director of Alex's Lemonade Stand Foundation, founded by her daughter, Alex, a four-year-old cancer patient who promised to raise money for kids "like her." What started as a single lemonade stand has grown into a movement with over 15,700 community fundraisers and hundreds of research grants funded every year. Bill Russell and Sarah Richardson sit down with Liz to explore how a pure, tragic story became a national movement, what a $100 donation actually funds a decade later, and why she still hasn't burned out after 20 years of building something bigger than grief.

Key Points:

• 01:56 Alex Story Spark

• 12:06 Super Sibs Support

• 20:01 Research And Grants

• 25:10 Leadership And Future

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July 22, 2026: Clay Maddux, Healthcare Horizon Practice Director at CrowdStrike, joins Drex DeFord to preview a free, live webinar on August 13th that tackles one of the fastest-growing threats in healthcare security: adversary-in-the-middle attacks on SaaS applications. Clay shares a preview of what's coming, including real cases of "payroll pirates" hijacking Workday accounts and rerouting employee paychecks, plus a live demo of browser-in-browser phishing in action. Open to the entire healthcare security community, no CrowdStrike account required. Register now and bring your team.

Register for the Defending Against AiTM Attacks in Healthcare Webinar: https://go.crowdstrike.com/2026-08-aitm-healthcare.html?utm_campaign=stop_ai_accelerated_adversaries&utm_medium=evt&utm_source=prtn&utm_language=en-us

Key Points:

• 01:10 Webinar Invitation

• 02:37 What Attendees Learn

• 04:31 Phishing And Browser Attacks

• 05:07 Live Demo And Token Theft

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In 2022, a furious insider leaked more than 300,000 internal messages from Conti, one of the most notorious ransomware gangs on the planet, and it read like the group chat from hell.

Buried in the gossip and office politics was a message that stopped Drex cold, a gang member pushing to attack hundreds of American hospitals and laughing about who might die. But not everyone inside Conti agreed with him.

What happened next in Ireland shows just how thin the line is between catastrophe and survival, and why you can never build a security program on the hope that the person attacking you has a conscience.

Remember, stay a little paranoid.

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July 20, 2026: A new Nature of Medicine study claims general-purpose LLMs outperform specialized clinical AI, but is that the right benchmark to begin with? Bill and Drex are joined by Yaw Fellin, General Manager of UpToDate at Wolters Kluwer, and Matt Troup, Clinical Strategy Principal at Abridge, to break down what those benchmarks actually measure, why shadow AI is already spreading through health systems, and what "clinical grade" really means. Plus: the first-ever look at UpToDate's new drug dosing feature in Expert AI, and why automaticity bias may be the next liability crisis hiding in plain sight.

Key Points:

• 03:18 Nature Study Breakdown

• 10:25 Shadow AI Reality Check

• 18:37 Transparency and Provenance

• 23:40 Human in the Loop Wrap

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Sebastian Estades, Senior Account Executive for Enterprise Platforms and Devices at Google, brings 15 years of healthcare software experience to a conversation that starts with a hard question: do you actually know what AI tools your clinicians are using? Drex DeFord sits down with Sebastian to dig into where health system browser security is quietly breaking down, why shadow AI usage is the gap most organizations can't even see yet, and how enterprise browser is building a real financial case against VDI infrastructure costs.

Key Points:

• 02:30 AI Blind Spots in the Browser

• 04:56 The Shadow AI Question

• 06:19 Quick Start Enrollment Steps

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July 16, 2026: Dr. Everett Weiss, Medical Director, Health Informatics at Rochester Regional Health, has been a clinician, a vendor, and a health system informatics leader -- and that full arc is exactly what makes this conversation different. In this episode of Flourish, Sarah Richardson sits down with Dr. Everett to unpack why clinician burnout is a systemic problem long before it's a technology problem, what a holistic wellness program looks like when it's built by someone who's lived on every side of the equation, and what really happens when a provider looks up from a keyboard for the first time in years.

Keep up to date on the latest in health IT:

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Key Points:

• 04:01 Wellness Beyond HR

• 08:27 Power of No

• 10:47 AI With Purpose

• 17:59 Closing Advice and Wrap

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July 15, 2026: Adam Hawkins, EVP, Healthcare and Life Sciences at Cyderes, has spent more than 20 years at the intersection of clinical operations and cybersecurity, from co-founding a clinical decision support startup in college to building Cyderes's healthcare vertical from the ground up. Drex DeFord and Adam cover what the sprint to AI actually looks like from the security side, why most health systems are building guardrails while the car is already on the freeway, and the emerging concept of "blast radius", understanding not just what's vulnerable, but what actually breaks when something goes down. The conversation ends with a clear-eyed look at the next five years: machines versus machines, and what that shift means for healthcare security leadership.

Key Points:

• 01:22 Adam’s Early Healthcare Start

• 05:10 Lessons from Robert Hershebeck

• 07:30 Today’s Biggest CISO Challenge

• 09:49 Security Context and Blast Radius

• 13:03 Machines vs Machines Future

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Drex and Sarah join to discuss how board members are quietly using personal AI tools to review confidential health system materials, and most organizations have no policy for it. From there, the conversation gets personal. Sarah shares how she uses her AI agent as a real-time wellness coach, adjusting nutrition and habits on the fly. Drex unpacks his experience with WHOOP and asks the question every wearable user should be asking: when you clicked accept, who actually owns your data? Then the conversation shifts to Epic's Su Mi, his decision to step away, and what it reveals about identity, purpose, and the cost of never stopping

Key Points: 

• 02:38 Secure Tools and Training

• 06:56 Wellness Coach in Your Pocket

• 12:02 Epic Leadership Shift

• 17:15 Purpose and Closing Thoughts

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A threat researcher at Sysdig was picking through the logs of a recent breach when something stopped him cold. The attacker moved too fast. No pauses, no fumbles, no fatigue. Over 600 payloads fired in sequence. When one failed, it read the error and adjusted. One time, from a failed login to a working fix in thirty-one seconds. No human does that.

Buried in the attacker's code were comments -- the kind a chatbot writes when it's reasoning through a problem. No person was at the keyboard. An AI agent had run the entire heist: reconnaissance, credential theft, lateral movement, persistence, and finally locking up 1,300 configurations before leaving a ransom note. Sysdig calls it Jade Puffer, and they believe it's the first ransomware attack ever run end-to-end by an AI.

The entry point was a vulnerable open-source AI tool sitting on the internet with cloud credentials right behind it. Health systems are bolting AI onto every workflow right now. Every one of those tools is a new door. The skill floor for running a full ransomware operation just dropped to the cost of an agent subscription. Drex has a few questions for your next leadership meeting.

Remember, Stay a Little Paranoid

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