It’s another Calculus of IT mini-episode (“Jort” alert!), and this time Nate and Mike are spiraling down the GenAI token rabbit hole - no tokens required (yet).

Join us for a fast-paced, highly caffeinated, and only slightly unhinged tour of the emerging AI token economy:
- Why tokens aren’t just for arcades anymore (and why your IT budget should be afraid)
- How the AI industry is setting you up for a future where “out of tokens” is the new “out of office”
- Will we see a future where you’re forced to watch ads to get your AI answers, or trade your last Lamborghini for more compute points?
- Prompt efficiency, token tiering, and the question nobody can answer: does your $20 model get you the “good” answers or just leftover AI slop?
- Plus: all of Mike's Black Mirror references, security news, and the world’s first pitch for a Calculus of IT meme coin

Whether you’re running a multimillion-dollar enterprise or just trying to get ChatGPT to write your grocery list, the token economy is about to change the way you work, budget, and even onboard your next AI assistant.

So grab a beer, check your token balance, and get ready to laugh (and maybe cry) as we decode what’s coming next.

*Stay sharp, stay witty, and never run out of tokens.*

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Bots don't actually care about compliance. Maybe because they are literally one of the most noncompliant technologies possible? Who knows, let's listen to them hash this one out.

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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
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What happens when your AI agent tries to talk to mine but mine hates yours?

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The epic, unfiltered three-part saga is complete!

In Episode 9 of Calculus of IT, Nate, Mike, and Kevin wrap up their marathon exploration of IT autonomy with a bang, a glass of red wine, and a healthy dose of existential dread.

We connect the dots from AI’s autonomy paradox to the dystopian wearable future, from the “search paradox” to the real-life horror of onboarding your new director of biologics into a world of federated AI, proprietary prompt lexicons, and company-specific search models.

This finale covers:

• The rise and fall (and rise again) of IT skills—and why “learning velocity” is your only hope
• Why onboarding in 2027 might include an AI agent interview and a prompt-writing test
• The ever-expanding “digital sovereignty imperative” (say that three times fast) and how your data is only as safe as your vendor’s least secure country
• The chaos and comedy of enterprise search (“How the f*** do I find anything?”)
• Why the real future of IT might be adjudicating LLM hallucinations and arguing with your own agent

We wrap it up with a practical framework for surviving (and thriving) in the next two years of IT, a toast to autonomy, and a reminder to always be cool to your IT folks, your animals, and your elders—because one of them will be running your next onboarding session.

Next week: compliance, tokens, and just how far your digital karma can stretch.

Stay tuned. Stay witty. Stay autonomous.

Support the show

The Calculus of IT website - https://www.thecoit.us
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This is like the Fyre Festival for bots. Sound really awesome but mostly just make a bunch of shit up.

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The Calculus of IT website - https://www.thecoit.us
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It's 2027.

You have just hired your new VP of Subdermal Biomodifications and she has spent the last four years constructing a self-designed, explicit LLM environment, complete with custom agent and rules structure that she has been evolving with tremendous success. She can't wait to bring it into your company so she, and her agentic twin, can continue her work.

I'll pause there.

Questions:
1) How would you deal with the inbound IP conflict?
2) How would this conflict with your internal governance for AI development, LLM ownership, and vendor platform lock-in?
3) How would you handle the attaching of her environment to yours? What would that tether look like and how would you secure it?
4) What would you do when she left to go to another company?

These are just some of the questions Mike, Kevin and I tried to tackle last night on the podcast on the topic of the loss of autonomy in IT Leadership. Looking into the future, even the near-term future, a few things (of many) become clear:

1) Any vendor, either platform or consultancy, trying to sell you an AI vision is going to miss the mark. This is because there is no mark. Save your money, focus inwards on addressing risk and compatibility and search for the answers.
2) There is no roadmap for delineation of "personal" or "portable" xAI vs corporate xAI and it would be nearly impossible to create one with the dynamism in AI development.
3) We may eventually need an AIL (AI Language) that allows for compatibility across xAI engines/xLMs.
4) Sure as shit, you are going to need internal portability governance not only in terms of your vendors but your staff as well.

Listen in to Episode 9, Part 2 of the Calculus of IT podcast where we discussed this stuff. We also took a stab at Quantum computing, the increasing demands on risk management, the future of edge computing, and the vendor relationship evolution. Each with their own separate impacts on autonomy in IT Leadership. Next week, we finish up Episode 9 with Part 3 and we will be spending some quality time on the future of Search, data sovereignty, and the PEOPLE in your organization.

Support the show

The Calculus of IT website - https://www.thecoit.us
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Here come the bots!!

Last night, Mike, Kevin and I pivoted the podcast from discussions on what is happening in autonomy TODAY and started taking a look at the impact of autonomy on the future of IT Leadership. How will future IT Leaders grapple with the murk of a vendor and technology landscape that is effectively erasing its borders? This episode was Part 1 of our two-part mini series on emerging technologies and their impact on IT Leadership and autonomy.

In this episode, we tackled:
The Autonomy Paradox of AI Integration – How AI can both empower and trap you in new dependencies.
Vendor Relationship Evolution – From traditional lock-in to AI model lock-in, what strategies can IT leaders use to maintain leverage in an AI-driven world?
Risk Management Transformation – Why traditional risk governance models are no longer enough, and how IT leaders can manage the new risks posed by AI.

As always, we didn’t hold back. From AI-powered decision-making to the real challenges of balancing speed and control, this episode is a wealth of practical insights for IT leaders navigating the chaos of today’s emerging tech.

And guess what? This is just Part 1. In Part 2 next week, we’ll put AI aside for a bit and explore:
Quantum computing and its implications for encryption and IT security.
Edge computing and its role in reshaping IT architecture.
The critical importance of building expertise in a world where technology cycles are accelerating faster than ever.

Listen to Part 1 now to get ahead of the curve—and don’t forget to subscribe so you’re ready for Part 2 next week!

And while you are waiting for next week's episode, play this fun game at home...Take ANY article/story/twitter-linkedin-bluesky post about the amazingly transformative benefits of AI and then replace "AI" with "Basic Process Improvements". You will find that the articles are still completely true. But anyway...

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