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 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

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In this episode, Mark takes us into the shadowy corners of enterprise IT, where outdated processes haunt progress, bad news festers in silence, and AI ignorance prowls like a predator in the dark.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

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

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

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