#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, Jus…
#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 Old firewalls, outdated systems, weak security controls — the risks can pile up quickly when every recommendation sounds like an upsell.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…
#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 experienc…
#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 …
#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 terrif…
#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…
#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 …
Can Your MSP Land Big Deals Without Compliance? | EP182
Most MSP owners talk a big game about cybersecurity and compliance, yet operate their own businesses with zero formal governance. You try selling $10k/month agreements or pitching enterprise-level clients, but as soon as an RFP asks for a SOC 2 report, you’re instantly disqualified. Running an MSP …
#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 d…
Two Dudes and an Analyst: The Real Status of AI in MSPs | EP183
Running an MSP is ridiculous, especially when everyone is screaming that AI will make you a millionaire overnight while nobody shows you how to actually bill for it. In this episode, Justin Esgar and Eric Anthony sit down with industry analyst Dave Sobel (Business of Tech) to cut through the hype, …
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