On IT Nightmares, host Justin Esgar hears true tales of IT terror from MSPs, sysadmins, and integrators—stories of outages, breaches, and tech disasters that still haunt the people who survived them.
Enter if you dare.
An office move is a tough time for the IT lead to disappear. Add a new job, an unfamiliar network and an unexpected trip to intensive care, and suddenly business continuity becomes a very personal concern.
In this episode of IT Nightmares, Justin Esgar talks with Andres Plaza, CEO of OneconnectionIT, about the ruptured appendix that put him in the hospital for two weeks just as he was learning a new employer's environment and preparing for an office move. With Plaza barely able to communicate, a trusted MSP stepped in to keep the work moving. His experience offers a hard-earned lesson about documenting what you know, building strong relationships between internal IT and service providers and making sure someone else can carry on when you unexpectedly cannot.
2 Oct 2026
#008 - The Patent Trap | Guest Nathaniel Smith
A big idea can launch a business. It can also launch a nightmare when protecting it turns into a fight you never budgeted for.
In this episode of IT Nightmares, Justin Esgar talks with Nathaniel Smith, founder and CEO of Blue Nova Technology, about what Smith describes as a yearslong struggle to defend his mobile payment invention against much larger technology companies. What began with a patent application and plans to bring an idea to market became an ongoing battle over intellectual property, legal costs and the limits of protection on paper. For MSPs developing their own software and services, his experience offers a cautionary tale about sharing ideas, planning ahead and understanding what it takes to defend what you build.
4 Sept 2026
#007 - Seven Paths to Nowhere | Guest Sean Maguire
In IT, few things are more unnerving than a problem that disappears whenever you try to diagnose it. One minute, customers cannot access critical systems. The next, everything works again, and every provider involved insists the trouble must be somewhere else.
In this episode of IT Nightmares, Justin Esgar talks with Sean Maguire, president and founder of Synivate, about an MSP's ill-fated venture into private-cloud hosting. Despite redundant infrastructure and seven supposed paths into the data center, intermittent connectivity problems left customers frustrated and Synivate trapped in a finger-pointing nightmare. Their experience offers a hard-earned lesson about vendor accountability, customer communication and knowing when critical infrastructure is better left to someone else.
7 Aug 2026
#006 - The Price of No | Guest Dr. Jared Knisley
In IT, there is only so long you can warn a client before "we'll think about it" turns into "how did this happen?" Old firewalls, outdated systems, weak security controls — the risks can pile up quickly when every recommendation sounds like an upsell.
In this episode of IT Nightmares, Justin Esgar talks with Dr. Jared Knisley, managing director of managed IT and cybersecurity at XDuce, about a client that spent years resisting security upgrades before ransomware finally struck. The attack became a painful lesson in trust, liability, and knowing when an MSP should be willing to walk away.
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10 Jul 2026
#005 - Reboot of Doom | Guest Matt Rose
In IT, few words are more deceptively harmless than "just reboot it." Most of the time, that is the beginning and end of the fix. Other times, it is the first creak of the floorboard in a much bigger horror story.
In this episode of IT Nightmares, Justin Esgar talks with Matt Rose, chief experience officer at Tech Rage IT, about a new-client onboarding that started with a routine server reboot and quickly became a lesson in when to stop troubleshooting and start recovering.
9 Jul 2026
#004 - The Handoff Horror | Guest Eric Weast
In IT, the scariest moments are not always when something breaks. Sometimes, they happen in between — between vendors, between contracts, between "we've got this" and "wait, who's responsible for that?"
In this episode of IT Nightmares, Justin Esgar talks with Eric Weast, president of ECW Network & Solutions, about an offboarding that went from routine to ransomware.
9 Jul 2026
#003 – Municipal Mayhem | Guest Norbert Doeberlein
The biggest IT horrors aren't always ransomware or failed hardware. Sometimes, it's walking into an environment wrecked by bad processes, poor communication, and MSPs pretending to be experts. In this episode of IT Nightmares, Justin Esgar talks with Netzbahn CEO Norbert Doeberlein about the terrifying reality of municipal IT, why most MSPs approach it completely wrong, and the business-first mindset needed to survive in one of the industry's toughest environments.
9 Jul 2026
#002 – RMM Gone Rogue | Guest James Wroten
It started with a single call on a quiet Sunday afternoon… then another… and another. In this episode of IT Nightmares, host Justin Esgar sits down with James Wroten to relive the moment a trusted RMM tool became the attack vector. Unleashing a fast-moving ransomware event that encrypted two-thirds of his clients in minutes, what followed was weeks of exhaustion, recovery, and survival in a nightmare where the tools meant to protect you become the threat.
9 Jul 2026
#001 – Mouse Unseen | Guest Justin Lewis
Sometimes the scariest IT problems aren't catastrophic server crashes—they're the tiny things that vanish without a trace. In this episode of IT Nightmares, host Justin Esgar welcomes IT consultant Justin Lewis to recount a haunting help desk call from the dial-up era, where a simple missing mouse pointer turned into a patience-testing tech horror story. In a world before screen sharing, finding that little arrow became a nightmare all its own.
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