IT Horror Stories

In the spine-tingling finale of IT Horror Stories , host Jonathan Crowe is joined by a fearless lineup of IT veterans who have stared into the digital void and lived to tell the tale. Guests Kallum Kyle, Senior Sysadmin at Storable; Josh Adcock, Director of Client Services at The Tech Doctor; and Adam Walter, Founder of Humanize IT, recount their most harrowing experiences from the trenches of tec...

IT isn’t just wires and widgets. It’s a minefield of lurking disasters waiting to strike. Few know that better than Mark Settle, 7-time CIO and author, who’s survived more operational horrors than most dare imagine. In this episode, Mark takes us into the shadowy corners of enterprise IT, where outdated processes haunt progress, bad news festers in silence, and AI ignorance prowls like a predator...

Negotiating with cybercriminals is no walk in the park. Shelley Ma, incident response lead for Coalition Incident Response, highlights the human element of cybersecurity: dealing with both clients in crisis and the criminals themselves. ------ Guest bio: Shelley Ma is an incident response lead for Coalition Incident Response, where she assists businesses in managing the response and remediation of...

Things are bound to go sideways in the world of IT and security, but there are certain three-letter government organizations that you never want to hear from. In this episode, long-time security veteran and Chief Security Officer at Vetcor, Andrew Wilder, joins us to unpack several harrowing encounters with bad actors and local law enforcement – ranging from chasing down unknowing internal payment...

When a huge cloud platform migration stalls out mid-flight with no hope of changing course, panic lunges to take the wheel. In this episode, Mahesh Guruswamy, CPTO at Kickstarter and author of How to Deliver Bad News and Get Away with It, recounts the night he took down production and had no other choice but to push through. Tune in for the blow-by-blow — from anxiously watching the clock as queri...

When blueprints start to smolder, true leaders draft new ones on the fly. In this episode, former architect turned Wawa CIO & SVP John Collier reveals how his background in design thinking has helped him make split-second judgments when even the most unforeseeable crises hit. From war-room gut-checks made in the dark to culture-defining decisions that outlast the chaos, John shares hard-won tactic...

In this episode, Wyatt Hansen, Vice President of Information Technology Services at LeaderOne Financial, sits down with host Jonathan Crowe to discuss an IT horror story that he experienced early on in his career while working at an MSP. He unpacks how a back of house server going down turns into a massive nightmare for one of his biggest retail clients, shuttering POS systems and leading to busin...

In this episode, Dr. Chase Cunningham, aka DrZeroTrust, joins us to shed light on what a horror story looks like from an adversarial perspective. In drawing on his extensive red teaming and NSA background, he explores why doing the basics and applying them intelligently does matter, why people should abandon the notion of perfect security, and what controls and practices organizations can adopt an...

When COVID lockdowns loom in early 2020, it’s up to Matthews team to prepare hundreds of laptops for an employee base that’s about to start working from home. Matthew Schuster, Information Security Analyst at a major sports team, describes the inevitability of IT problems, and the importance of learning how to solve them. His stance is that no questions or problems should be left unresolved. Matth...

In this episode, Mike Anderson, CIO & CDO at Netskope, joins Jonathan to discuss several IT horror stories that have stuck with him throughout his career – including a fire suppression test gone wrong, how he helped his organization quickly recover from a ransomware attack in his first tenure as CIO, and now as a more seasoned CIO, how he thinks about taking calculated risks, investing in people,...

When a corrupted virus definition file was distributed by a centralized management server, it was up to Jay Abbott to find a fix for the company-wide blue screen of death. Jay describes how the emergency escalated, how he mobilized an all-hands-on-deck response, and how he diagnosed the issue. Tune in for a masterclass in incident response and disaster recovery as Jay, Director of Corporate IT at...

Nick Colisto, CIO of Avery-Dennison, describes the IT disaster he faced during Hurricane Sandy. When the storm caused a major power outage and a fuel shortage, his company’s primary data center had to rely on generator power. Tune in to hear how Nick prepared, adapted, and fought through the emergency. Avery-Dennison is a global materials science and digital identification solutions company with l...

IT problems are a nightmare. And you’re not alone in losing sleep over them. If you’ve worked in IT, you’ve probably got a few ghost stories. This show is dedicated to those stories and the IT heroes who survived to tell the tale.  Join your host Jonathan Crowe, and some of the world’s top IT leaders, as they recount the most harrowing experiences of their careers. They’ll share how they found the...