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May 15, 2025 107 mins

It’s the regulation episode you didn’t know you needed - but absolutely do.

After three weeks swimming in the future of AI, quantum, and edge, Nate and Mike are back with a rundown of the one thing every IT leader loves to hate: compliance. From GDPR’s wake-up call to the alphabet soup of CCPA, DORA, and CPRA, we break down how the modern regulatory landscape is reshaping not just what you do—but how much freedom you have to do it.

In this episode:
- How to build compliance into your IT DNA (and why it’s not just “a legal thing” anymore)
- The autonomy-killing dangers of compliance fragmentation (and how to avoid them)
- Why “check the box” compliance is dead - and what replaces it
- Real-world stories: compliance councils, distributed champions, and the joy of deleting every trace of someone (on request)
- The new rules of “as-a-service” and why you can’t outsource your way out of an audit
- The secret to making compliance a competitive advantage (or at least less of a migraine)
- Strategic frameworks for balancing compliance, innovation, and your own sanity

Plus: philosophical debates on rope steak, cosplay, and the eternal question - what color pill do you *really* need to take to make all this go away?

Support the show

The Calculus of IT website - https://www.thecoit.us
"The New IT Leader's Survival Guide" Book - https://www.longwalk.consulting/library
"The Calculus of IT" Book - https://www.longwalk.consulting/library
The COIT Merchandise Store - https://thecoit.myspreadshop.com
Donate to Wikimedia - https://donate.wikimedia.org/wiki/Ways_to_Give
Buy us a Beer!! - https://www.buymeacoffee.com/thecalculusofit
Youtube - @thecalculusofit
Slack - Invite Link
Email - nate@thecoit.us
Email - mike@thecoit.us

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