# Jake Bernstein

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EP 213: The Group Writing the Rules for AI Trust

Would you know if the AI tools your team is buying are actually trustworthy to use? Who gets to decide what trustworthy AI even means? Let's find out with our guest Jim Reavis, CEO of the Cloud Security Alliance, the group that helped the world learn to trust the cloud and is now building the stand…

Soderbergh Ep. 35: The Laundromat (2019) with Luke Savage

FOR IMMEDIATE RELEASE: our episode on Soderbergh's 2019 Panama Papers infotainment film THE LAUNDROMAT. Joining us to parse this deeply odd "comedic" "look" into the mysterious world of offshore finance is co-host of the Michael & Us podcast and author of The Dead Center: Reflections on Liberalism …

EP 214: AI Agents Don't Behave Like Humans

Your cybersecurity tools were built for people: a login, a single sign-on, an email address. But the AI agents now showing up inside your company don't work that way, and most of them slip right past your controls. So how do you find the "Shadow AI" already running in your business, and get a handl…

EP 215: Is Your AI Strategy a Risk Decision in Disguise?

There's a popular new playbook for running an "AI-native" company. Record everything, put all your data in one place, and let an AI agent reach all of it. The productivity story is real. New hires ramp up in days, and the whole company can ask questions it never could before. But the same moves tha…

EP 216: When Reasonable Beats Bankrupt

After a breach, you either pay the fine, or fight the regulator and lose. There's a third path. It comes down to one word: reasonable. A method called DoCRA turns that question into something a court can use. DoCRA is short for Duty of Care Risk Analysis. Our guest Chris Cronin of HALOCK Security L…

EP 217: When Hospital Systems Go Down, Who Keeps Patients Safe?

When a hospital's systems go down, care does not stop. It goes back to pen and paper, and the first sign is quiet, because the alerts stop. Physician and CISSP Mark Yoffe explains clinical compensating controls: the steps clinicians take to keep patients safe during downtime. He covers who owns the…

EP 219: Why Gears Don't Guess

Every system you've ever governed is a gear. Same input, same output. AI is the first system that guesses back, and that's why your management instincts misfire on it. Kip's new book, Gears Don't Guess, is out Sept 28th. Jake interviews him on why he wrote it, who it's for (the CFO, the general cou…

EP 220: Every AI Agent Needs Its Own Name

Your firewalls, access rules, and least privilege all assume software behaves the same way every time. AI models don't. So what still works, what breaks, and what should you build next? Our guest Dan Stocker, Principal Cybersecurity Architect at JPMorgan Chase and a Cloud Security Alliance contribu…