IT Horror Stories with Jack Smith cover art

IT Horror Stories with Jack Smith

IT Horror Stories with Jack Smith

By: Jack Smith
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About this listen

We delve into the bizarre and often cringe-worthy world of IT mishaps, glitches, and the horror stories that come with it. With a sarcastic twist we recount the tales of those who somehow manage to create chaos out of the simplest tasks. We strike a balance between relatable frustration and dark humor that gets even the most cringe-inducing stories entertaining and you will find yourself laughing, cringing, and shaking their heads in disbelief as we take a wild ride through the chaotic world of IT, where every glitch is a ghost story waiting to be told.2024-2026 Economics Management Management & Leadership
Episodes
  • The Failover That Failed Successfully - Lessons from a Successfully Failed Disaster Recovery and Failover Test
    Apr 6 2026

    Conducted during a busy release weekend, the failover test exposed gaps not in the technology itself, but in coordination and communication. While production ultimately stayed unaffected, the situation quickly escalated as subcontractors weren't aligned, assumptions didn't match reality, and information didn't flow when it mattered most.

    We unpack how a well-intentioned test turned into a coordination challenge, where timing, dependencies, and unclear responsibilities created confusion across teams. It's a story about how resilience isn't just about systems and infrastructure, but also about people, processes, and making sure everyone is on the same page — especially when things are supposed to "just be a test."

    00:00 Welcome & Setup
    01:34 Corporate Environments
    03:30 Failover Planning
    07:19 Double Disaster
    09:08 Critical Failure
    13:20 Realization Moment
    15:28 Split Brain
    17:34 The Recovery
    21:13 Lessons Learned
    31:32 Conclusion

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    33 mins
  • Jack's Rants - IT Hiring Chaos – The Strange State of the Tech Job Market
    Mar 12 2026

    In this short episode, Jack takes a look at the current state of the IT hiring market — where job postings seem plentiful, but actual opportunities often feel strangely elusive. From "entry-level" roles asking for a decade of experience to companies searching for the mythical full-stack, cloud, DevOps, security expert all in one person, we discuss the growing gap between job descriptions and reality. With a bit of sarcasm and a lot of firsthand observation, we unpack what's going on in tech hiring right now and why so many professionals feel like the market has become a puzzle nobody quite understands.

    00:00 Introduction
    00:39 Market Struggles
    02:22 Hardware Shortages
    02:56 Merged Roles
    05:12 Interview Issues
    08:31 AI's Impact
    10:18 Conclusion

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    12 mins
  • Raspberry Mistery - 200 Techs Using A Single Raspberry Pi: The Temporary Server That Failed
    Mar 2 2026

    A few hundred field engineers. Real humans. With vans. And jobs. All coordinated by a device roughly the size of a coaster and powered by something suspiciously similar to a phone charger.


    For months, it runs slow but flawlessly. Tickets dispatched. Routes optimized. Managers happy. The tiny silicon hero hums along in its noble plastic case, bravely pretending it's not one 'apt upgrade' away from a crisis.


    Join us as we unravel the mystery, debate the true definition of "production-ready," and ask the question no one wanted to say out loud.

    00:00 Welcome Back
    01:23 Shadow IT Chaos
    05:18 Major Outage
    12:04 Data Center Discovery
    17:59 Where's the Server?
    19:58 Raspberry Pi Reveal
    25:13 Migration Success
    30:36 Closing Thoughts

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    32 mins
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