The 229 Podcast

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 should stop you 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.

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

Keep up to date on the latest in health IT:
https://thisweekhealth.com/news/
X: This Week Health
LinkedIn: This Week Health
Donate: Alex’s Lemonade Stand: Foundation for Childhood Cancer

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

Keep up to date on the latest in health IT:
https://thisweekhealth.com/news/
X: This Week Health
LinkedIn: This Week Health
Donate: Alex’s Lemonade Stand: Foundation for Childhood Cancer

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:
https://thisweekhealth.com/news/
Key Points:
04:01 Wellness Beyond HR

08:27 Power of No

10:47 AI With Purpose

17:59 Closing Advice and Wrap

X: This Week Health
LinkedIn: This Week Health
Donate: Alex’s Lemonade Stand: Foundation for Childhood Cancer

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

Keep up to date on the latest in health IT:
https://thisweekhealth.com/news/
X: This Week Health
LinkedIn: This Week Health
Donate: Alex’s Lemonade Stand: Foundation for Childhood Cancer