The Calculus of IT

Nathan McBride & Michael Crispin
  • 5.0 (5)
  • TECHNOLOGY
  • UPDATED WEEKLY

An exploration into the intricacies of creating, leading, and surviving IT in a corporation.  Every week, Mike and I discuss new ways of thinking about the problems that impact IT Leaders.  Additionally, we will explore today's technological advances and keep it in a fun, easy-listening format while having a few cocktails with friends.  Stay current on all Calculus of IT happenings by visiting our website: www.thecoit.us. To watch the podcast recordings, visit our YouTube page at https://www.youtube.com/@thecalculusofit.

  1. FEB 25

    Calculus of IT - Season 3 Episode 11 - Shadow AI vs Shadow IT

    Newsflash: Shadow AI is just Shadow IT with better branding and worse consequences. We set out to compare Shadow AI (people using ChatGPT at home because you won't give them tools at work) versus Shadow IT (people using Smartsheet because your approved system doesn't meet their low quality standards), and discovered they're pretty much the exact same problem. BLUF: if you don't have governance, training, and approved options, you've already lost. Your employees are prompting away on personal accounts and there's nothing you can do about it except train them properly and give them legitimate alternatives. Nate revealed his company trains 100% of employees on GenAI within their first week, runs daily tests to see if Claude's LLM has been "whitewashed", and has a nine-level certification program where personas don't unlock until level six. We discussed the high probability that 80-90% of employees at most companies probably use personal AI accounts, suggested the solution is "lightweight guardrails" and multiple approved options. We also learned that Mike cooks frozen burritos (aka shit logs) in an air fryer and we agreed that TestiCoin might be our best option for a retirement plan. Beard Watch officially launched: Mike's two-week beard progress is "barely visible" and resembles dirt splashed on his face. Next week we're diving into CWP (Cakewalk Pro? Build-first culture? Both?) and why low-code/no-code is the newest (and lamest) Shadow IT. Listen at thecalculusofit.com • Join our Slack board at thecoit.us • Leave five stars • Invest in TestaCoin • Stop dry shaving while driving. —Nate & Mike Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    1h 57m

  2. FEB 17

    Calculus of IT - Season 3 Episode 10 - Training Our Elders (and Ourselves)

    The new episode is live, and special guest Kevin Dushney joined us to ask the question nobody wants to answer: at what point do people just stop learning technology, and what the hell do we do about it? We set out to explore whether IT should hire someone with 10 years of experience or someone who learned everything in the last two years via YouTube and GenAI, which spiraled into a debate about aptitude versus historical context, and whether we're designing systems for people we have or people we wish we had. The uncomfortable truth: we're in a race to train everyone as fast as possible, but the second we finish, everything changes and we have to start over, which means the only winning move might be to stop caring entirely and just tell retirement-age folks to click "yes" on everything (we're kidding, mostly). We also realized that nobody outside a tiny fraction of nerds gives a shit about token optimization or Opus pricing, that reviews written by AI are the corporate equivalent of outsourcing your soul, and that Nate once testified in court about a Nest cam recording of a drunk driver who tried to flee the scene with a tow truck. The breakthrough moment: maybe the elders aren't screwed - maybe they're the only ones who figured it out by refusing to engage with this madness at all. We also continued building out our IT Department of the future with our new roles including the Token Optimization Engineer (TOE), Pre-Prompt Engineer (PPE), all reporting to the omnipotent Chief Truth Officer, who reports to the Department of Generative AI Truth. Next week we're tackling Shadow AI vs Shadow IT, aka "the sequel is worse." Listen at thecalculusofit.com • Join our Slack board at thecoit.us • Leave five stars • Change your parents' router password from the default • Don't eat Whoppers while driving. —Nate, Mike & Kevin Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    2h 7m

  3. FEB 9

    Calculus of IT - Season 3 Episode 9 - PowerPoint Inc.

    In this episode, Mike and I put on the latex gloves and explored the uncomfortable reality that PowerPoint has ruled corporate communication since 1987, and somehow nothing has replaced it despite Prezi, Lucidchart, Google Slides, and Canva all existing and working perfectly fine. The thesis: PowerPoint persists because it's the ultimate crutch.  It's like eating a donut.  Relatively safe, expected, and nobody will question you for eating it, even though it forces you to cram complex ideas into six-by-five-inch boxes and encourages people to read slides word-for-word like they're performing at an elementary school talent show. We traced PowerPoint's origins back to overhead projectors and slide carousels, realized the military lives in PowerPoint because hierarchical briefings need slides apparently, and discovered that the name "PowerPoint" came to someone in the shower (omen: they saw a sign at an airport). Mike admitted he'd rather get a Word doc than sit through most presentations, Nate confessed he uses jellyfish backgrounds and white text on purpose so people can't read the slides and have to actually listen, and we both agreed the "appendix with 70 backup slides" move is corporate theater at its finest. The breakthrough: if you need slides to tell your story, you either don't know your material or you're presenting to people who should've just read the pre-read. We also announced a new spinoff podcast called "If Life Was a PowerPoint" where we'll grill each other on invisible slide decks, which is either genius or a cry for help. Next week we're tackling Training Our Elders, aka why your relatives are still on Yahoo Mail and Lenovo laptops from 2017. Listen at thecalculusofit.com • Join our Slack board at thecoit.us • Leave five stars • Stop reading slides word-for-word • PowerPoint is here to stay, sorry. —Nate & Mike Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    1h 53m

  4. JAN 30

    Calculus of IT - Season 3 Episode 8 - IT aka the Pasty Anthropologist

    Mostly true but also possibly just purely theoretical fact: IT's real job is studying human behavior, not fixing computers. In this episode, Mike and I set out to explore why IT needs to think like anthropologists (e.g., observing how people actually work instead of how we think they should work) and discovered, as we tend to do in every episode, some uncomfortable truths along the way. It seems like the reality is that we design systems for idealized users, train people on features they'll never use, and then act shocked when they create workarounds or just Slack us instead of reading the wiki we spent weeks building. We realized that every workaround is a cry for help, every shadow IT solution is a prototype for what we failed to provide, and the shift-tab key is apparently still classified information in 2026. The conversation spiraled through: whether IT should be in every job interview (yes), whether we're designing for the people we have or the people we wish we had (wish), whether surveillance equals observation (it doesn't, but the line is thin), and why business analysts should've been behavioral scientists all along. We also mourned the death of CASBs, debated whether Mike's tolerance for "how do I use Outlook?" questions will last until 2030, and agreed that someday soon, not knowing how to write prompts will be a firing offense (Nate is banking on Q1'27). The breakthrough moment: if you could secretly watch how everyone uses your systems, you wouldn't be shocked by what they're doing wrong, you'd be shocked if they used them correctly at all. Next week we're tackling PowerPoint Incorporated, aka why the corporate world's only storytelling mechanism is a six-by-five-inch white rectangle and whether we'll ever escape it. Listen at thecalculusofit.com • Join our Slack board at thecoit.us • Leave five stars • Be nice to IT people • Stop the ethnic cleansing • Learn how to use Word, or at least shift-tab. —Nate & Mike Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    1h 56m

  5. JAN 27

    Calculus of IT - Season 3 Episode 7 - What Has Become of Chat?

    The new episode is live, and we went deep into the nostalgia mines before emerging with some uncomfortable truths about how we communicate now. Mike and I started by tracing our entire chat history from 1992 BBS systems (Nate had to mail his driver's license to Iowa to get approved for ISCA) through IRC, AIM, ICQ, Yahoo Messenger, MSN, Office Communicator, BBM (RIP that little red blinking light), and eventually Slack. Turns out we've been through dozens of chat platforms, and somehow we're worse at communicating than ever. The thesis: chat is supposed to be synchronous but we use it asynchronously, creating this weird hybrid where Nate will hate you if you don't respond in 7 minutes but his kids won't respond for days and think that's fine. We realized you could theoretically recreate chat using just Box notes and @ mentions (terrible idea, technically possible), proved that the core requirements for chat are absurdly simple (two people, one box to type in, a return key), and discovered that 58 different platforms at Nate's company all have chat functions now—meaning communication is fragmented across everything. Mike pointed out that Blackberry's universal inbox solved this problem 15 years ago and nobody's figured it out since. We also covered: why LinkedIn is now just pasta photos and fake job announcements, whether chatting with your network switches counts as early AI, Nate's refusal to read email for years (all goes to trash, works fine), the anxiety of contributing in chat, and why the "instant" in instant messaging was always branding b******t. Next week we're expanding this into IT as an Anthropologist—how we straddle old and new worlds while excavating ancient infrastructure with laser technology. Listen at thecalculusofit.com • Join our Slack board at thecoit.us • Leave five stars • Smash any flock cameras you see • Don't travel abroad with a phone you care about. —Nate & Mike Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    2h 8m

  6. JAN 17

    Calculus of IT - Season 3 Episode 6 - Slack as an OS

    So Mike and I set out to answer a simple question: What actually constitutes an operating system in 2026? Turns out, it depends on whether you're talking about computers or how people actually work. For a computer OS, you need hardware management and file I/O. For a business OS, you need the thing that, when it goes down, everyone goes home. By that definition, Slack is absolutely an operating system. Nobody in your company can tell you what OS version they're running, but everyone knows their Slack workspace name. The desktop is dead. Your actual "desktop" is just a browser, Slack, and some cloud storage shortcuts. For most users, you could swap Windows for Mac or Linux and they wouldn't even notice. The uncomfortable truth: if Slack is where you spend your entire workday, Slack IS your OS. The thing underneath it is just infrastructure. Mike thinks the computer OS should become invisible while the business OS (Slack, identity platforms, automation) becomes the focus. Nate thinks we're heading toward a world where everything runs in browsers and the OS is just a launcher, probably Linux-based, definitely not what we have now. We also proved you could recreate email using Box notes and @ mentions (terrible idea, technically possible), went full nostalgia on OS/2 and BeOS and Adium with the duck, and discovered Mike hasn't touched his Vision Pro in months but is still paying $29/month for AppleCare. Oh, and Nate will assume you hate him if you don't respond to Slack messages within 7 minutes. The autonomy problem looms: if Slack becomes your OS, you're locked in. Convenience breeds dependency. Next week we're diving into what has become of chat - the full timeline from IRC to Slack, and why instant messaging makes us hate each other.  Also, Flock is watching you.  Is that really ok? Listen at thecalculusofit.com • Join our Slack board at thecoit.us • Leave five stars • The OS doesn't matter, the work matters. —Nate & Mike Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    1h 45m

  7. JAN 12

    Calculus of IT - Season 3 Episode 5 - Who Speaks for IT Anyway?

    The new episode is live. As usual, we were topical af. The question: In an industry flooded with analysts, vendors, and LinkedIn thought leaders, who actually speaks for IT versus speaking to IT? Short answer: Gartner speaks TO IT (specifically to CIOs with budgets). The Register speaks FOR IT (with appropriate cynicism). Your Discord/Slack communities speak WITH IT (peer-to-peer, no b******t). Longer answer: IT spent decades being invisible. Now everyone’s asking what to do about AI, and suddenly we need spokespeople. Problem is, most IT people weren’t trained to articulate value or push back on bad ideas. We were trained to keep things running quietly. The shift from order-taker to value generator requires having a voice. And your voice is directly connected to your autonomy. If you can’t explain what you do, you won’t get authority to make decisions. Our Hot Takes Nate: “If you put all your chips in the Microsoft basket, you’re in for a rude awakening. Diversify or enjoy your web-only future.” Mike: “AI won’t kill all jobs. Companies will invest heavily, realize they need humans to verify everything, and create a whole verification economy. It’s regulatory job creation all over again.” Also Nate: “99% of enterprise data is garbage. Stop putting ‘confidential’ in document titles, you’re literally giving attackers the bread crumbs trail.” What We Actually Covered Why analyst firms talk to budget holders, not practitionersHow IT communities (like our Slack board) are the REAL peer support networkThe uncomfortable truth that nobody QCs anything anymoreWhy younger IT professionals will push transparency and voice furtherMike’s unused Vision Pro (eBay value: $2,500, bids: 0)Nate’s fantasy honeypot containing 200,000 PowerPoint decks with a hidden cipherNext week: Slack as an Operating System (e.g., when did your chat tool become your company’s nervous system?) Join our Slack board (vendor-free, occasionally unhinged): links in the footer. Leave five stars. We said we don’t care but we definitely care. And remember: 99% of your data is garbage. Focus on the 1%. —Nate & Mike P.S. We’re better than Gartner and we’ll let you in our Slack for free. Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    1h 20m

  8. 12/18/2025

    Calculus of IT - Season 3 Episode 4 - The Verification Economy (Part 2 of 2)

    In part two, we tackle who actually does all this verifying, what it costs, and the uncomfortable questions nobody's asking yet. IT is becoming the verification department whether you signed up for it or not. You're verifying employee identities, contractor credentials, AI agent authority, data provenance...basically everything, constantly. We explore the shift from proactive governance to reactive verification, the impossible tension between privacy and verification, and scenarios that keep you up at night: locked-out executives, disputed transactions, and verification systems that might be wrong. Big questions we couldn't fully answer: How do you verify AI agents? What gets verified - person, device, behavior, or all three? Can verification be continuous without becoming surveillance? Mike predicts 2-3 years before verification pressure really hits IT departments. New job titles emerging: Chief Truth Officer, Model Auditor, Verification Vigilante. We also accidentally invented a post-apocalyptic western about the last verification expert alive. It involves tape backup accidents and Mandalorian trust buoys. Don't ask. Next week: Who Speaks for IT Anymore? Support the show The Calculus of IT website - https://www.thecoit.us "The IT Autonomy Paradox" Book - https://www.longwalk.consulting/library "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 Slack - Invite Link Email - nate@thecoit.us Email - mike@thecoit.us

    2h 4m
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Ratings & Reviews

5
out of 5
5 Ratings

About

An exploration into the intricacies of creating, leading, and surviving IT in a corporation.  Every week, Mike and I discuss new ways of thinking about the problems that impact IT Leaders.  Additionally, we will explore today's technological advances and keep it in a fun, easy-listening format while having a few cocktails with friends.  Stay current on all Calculus of IT happenings by visiting our website: www.thecoit.us. To watch the podcast recordings, visit our YouTube page at https://www.youtube.com/@thecalculusofit.

Information

  • Creator
    Nathan McBride & Michael Crispin
  • Years Active
    2023 - 2026
  • Episodes
    106
  • Rating
    Explicit
  • Copyright
    © 2026 The Calculus of IT
  • Show Website
    The Calculus of IT