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

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In this episode, Mark takes us into the shadowy corners of enterprise IT, where outdated processes haunt progress, bad news festers in silence, and AI ignorance prowls like a predator in the dark.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

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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

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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.

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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.

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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

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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.

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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

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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.

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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

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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.

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

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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.

• 00:26 - About Wyatt
• 01:41 - Let’s set the scene
• 06:48 - Oh the Horror!
• 36:05 - Don’t Be in the Sequel
• 36:25 - The big take aways

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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.

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“ 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.”

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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

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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.

Matthew Schuster has spent six years navigating the world of IT operations and information security within the fast-paced professional sports industry, steadily rising from an intern to various technician and analyst roles along the way. In addition to all things ITOps and security, he’s passionate about cars, motorcycles, baking, and 3D printing!

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“ During that time period where everyone was working from home, that gave us time to kind of think about and sit back of like, hey, we got through it.  If we had to do this again, which hopefully we don't, how can we make things better? Not only just adapting like that emergency plan. But also just improving  our day to day kind of stuff. And so, the changes that we made to that plan transitioned to our actual laptop refresh and desktop refresh strategy.”

“ We have a saying in the information security world of, you know, it's not if you get hacked, it's when you get hacked. So you got to be prepared for things and be proactive, but also learn how to fail and learn how to fail  quickly is the most important thing and learn from those mistakes.”

“A very, very common theme in IT is that at the end of the day, problems exist, and you gotta learn how to solve them. And, me personally, I don't like leaving a question or a problem unsolved. “

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00:59 - Matthew’s role

03:50 - Oh, the horror

09:29 - IT in a stadium

10:21 - Breaking down the tasks

15:57 - Don’t be in the sequel

21:05 - Matthew’s survival kit

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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, and depositing in relationship accounts to drive business forward.

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“ Security is everyone's responsibility in an organization. It's not just the CIO. It's not the CISO. It’s everyone in the organization, including the board of directors. And it's your job to make sure you're bringing forward the risks and having conversations about your risk appetite and how much you're willing to invest around the various controls you need to have and why certain controls are more important than others, depending on the business you're in and the risk if those business operations are disrupted.”

“ Things are going to happen. Things are going to go wrong. It's how you respond to it and how you recover. It's the resilience of your team.”

“ We have to make sure we're making calculated risks, but we also have to make sure we're creating a culture where people can experiment because that's how we're going to drive real innovation inside of our organizations.”

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01:08 - Meet Mike

02:58 - The shutdown disaster

05:38 - Managing risk

06:06 - First CIO cyber incident

15:17 - What we’ve learned

29:23 - The fiber catastrophe

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