IT Horror Stories

NinjaOne
  • 5.0 (4)
  • TECHNOLOGY
  • UPDATED BIWEEKLY

If you’ve worked in IT, you’ve probably got a few good ghost stories. This show is dedicated to those stories and the IT heroes who survived to tell the tale. Join some of the world’s top IT leaders as they recount the most harrowing experiences of their careers. They’ll share how they found themselves in hot water, managed to escape disaster, and their best advice for making sure you don’t end up in the sequel. This is IT Horror Stories, where the call is coming from inside the office. Brought to you by NinjaOne, the leader in automated endpoint management.

  1. ITOops

    08/05/2025

    ITOops

    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 tech. They relive moments when end users were their only hope, when vulnerable software lurked like ghosts on forgotten networks, and when automation backfired so badly it cost them their jobs. These stories aren’t just frightening—they’re all true! Timestamps: 01:46 - Kallum's tale 14:36 - Josh's horror story 24:54 - Adam's woeful experience Links:Find Kallum on LinkedIn Find Adam on LinkedIn Find Josh on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne

    42 min
  2. Human Error

    07/22/2025

    Human Error

    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 In this episode, Mark takes us into the shadowy corners of enterprise IT, where outdated processes haunt progress, bad news festers in silence, and AI ignorance prowls like a predator in the dark. He shares battle-tested wisdom from a career spent defusing digital disasters and building resilient, process-driven teams that can take a punch. --------- Time stamps:01:23 - About Mark 12:28 - Oh, the horror! 16:36 - What happens after the big mistake? 29:19 - Looking at IT trends 36:56 - Don’t be in the sequel --------- Links:Find Mark on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne Subscribe on Apple Podcasts Subscribe on Spotify

    38 min
  3. Bitcoin and Brown Paper Bags

    07/08/2025

    Bitcoin and Brown Paper Bags

    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 cyber breaches. Shelley specializes in ransomware cases and ransomware negotiations, with a high success rate in reducing ransom amounts. As an EnCE-certified examiner, the depth of her experience lies within complex breach investigations, computer forensics, and incident response. Since 2014, Shelley has analyzed, responded to, and investigated thousands of incident cases. She specializes in network intrusion investigations, litigation forensics, intellectual property theft, and related crimes. --------- Time stamps:01:22 - Shelley’s journey 03:20 - IT’s crisis role 12:20 - Oh, the Horror! 26:00 - The cost of cybersecurity 27:54 - Don’t be in the sequel --------- Find Shelley on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne

    34 min
  4. The Nightmare Phone Call

    06/24/2025

    The Nightmare Phone Call

    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 payments to known hackers and cracking down on vulnerable vendors. Andrew explores why establishing relationships with your local law enforcement before bad things happen is key in a world where so much often goes awry, and how to translate risks into opportunities for growth. --------- Time stamps:01:21 - About Andrew 05:56 - Oh, the horror! 17:48 - Oh, the horror! Part 2 23:17 - How to promote cybersecurity in your business 34:38 - Don’t be in the sequel --------- Links:Find Andrew on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne Learn more about Cyber Up

    37 min
  5. Point of No Rollback

    06/10/2025

    Point of No Rollback

    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 queries time-out to the tightrope walk of breaking bad news without breaking trust. You'll leave with the brutally simple playbook Mahesh now swears by to make sure your next migration doesn’t become an IT horror sequel. --------- Time stamps:00:59 - About Mahesh 03:08 - The incident 21:18 - Don’t be in the sequel 26:46 - More lessons learned 31:34 - How to equip yourself --------- Links:Find Mahesh on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne

    34 min
  6. Crisis Clarity

    05/27/2025

    Crisis Clarity

    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 tactics for IT leaders who want a real seat at the table — and who want to be ready when all eyes turn to them. At Wawa, John is responsible for establishing the strategic direction for Wawa’s expanding technology and business services. He leads technology strategy, development, implementation and ongoing operations for Wawa, Inc. Guest Bio: John Collier is the SVP and CIO at Wawa, Inc., a chain of more than 1,000 convenience stores located in 8 states across the eastern US and the District of Columbia. John came to Wawa in October 2017 as the VP and CIO, to lead Wawa’s information technology team. At Wawa, John is responsible for establishing the overall strategic direction for the company's expanding technology and business services. Prior to joining Wawa, John worked as CIO for TracFone Wireless, Inc. And before TracFone, John spent 5 years with Walmart Stores, Inc. in positions as Global Chief Architect and Intellectual Property Management and Monetization. Time stamps: 01:06 - About John 06:00 - Oh the horror! 20:56 - Don’t be in the sequel 23:24 - Building cross-functional communication 31:08 - How to embrace design Links:Find John on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne

    34 min
  7. POS SOS

    05/13/2025

    POS SOS

    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 business chaos. He also explores the upsides of having a nontraditional career path, learning on the job and having room to fail, and why clear communication and documentation are the best ways to counteract crisis. Wyatt Hansen is the VP of Information Technology Services at LeaderOne Financial, a leader in mortgage banking. He was born in Alaska, raised in South Dakota, and now resides in Kansas with his wife and their beloved Corgi, Luna. He attended the University of South Dakota, where he graduated with a BFA in Theatre in 2019 while working part time with Erickson Solutions Group LLC (where he got his start in remote technical support!). When he’s not working, he can be found whipping up brunch, breaking out a board game, or catching up with friends on Helldivers 2. Time stamps:00:26 - About Wyatt01:41 - Let’s set the scene06:48 - Oh the Horror!36:05 - Don’t Be in the Sequel36:25 - The big take awaysLinks:Find Wyatt on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne Subscribe on Apple Podcasts Subscribe on Spotify

    33 min
  8. Confessions of an Adversary

    04/29/2025

    Confessions of an Adversary

    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 and follow to make it a bad day for bad actors. --------- Key Quotes:“ It's called a best practice for a reason. It's not because somebody woke up and was like, how can I just, you know, put things on a piece of paper? It's a best practice because it's a practice that's best.” “ I think people should abandon the idea of perfect security because it doesn't exist. You know, you think if you're if you're postured up and you've spent enough money and you've got the right things in place that you're not going to have a breach. The odds of you not having a breach are really, really slim. It's just a matter of time. That doesn't mean that you stop trying, but it just means to be aware of when things go wrong, what is your plan, how will you isolate, how will you minimize the damage, how do you move or how do you stop lateral movement, etc.” “There are some people that you just have to say like, Look, man, I gotta put some additional controls around you because you're, you're prone to clicking, bro. Like I don't know what to tell you, man, but I got to do something about you. And it's not because I don't like you and I don't like your hair color or whatever else, but you're a risk to my business.” --------- Time stamps:02:26 - About Chase 03:58 - What’s a classic attacker horror story? 08:49 - Red teamer incidents 12:35 - Lessons learned 26:00 - Advice for security leaders --------- Links:Find Chase on LinkedIn Find Jonathan on LinkedIn Learn more about NinjaOne

    30 min
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Ratings & Reviews

5
out of 5
4 Ratings

About

If you’ve worked in IT, you’ve probably got a few good ghost stories. This show is dedicated to those stories and the IT heroes who survived to tell the tale. Join some of the world’s top IT leaders as they recount the most harrowing experiences of their careers. They’ll share how they found themselves in hot water, managed to escape disaster, and their best advice for making sure you don’t end up in the sequel. This is IT Horror Stories, where the call is coming from inside the office. Brought to you by NinjaOne, the leader in automated endpoint management.

Information

  • Creator
    NinjaOne
  • Years Active
    2K
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © NinjaOne
  • Show Website
    IT Horror Stories