The 229 Podcast

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.
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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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