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Accidental CISO

@accidentalciso.net
5.8K followers 734 following 1.9K posts

I accidentally became the CISO. I didn't want this job, but the job chose me. I'm scared, and I want to go home. www.accidentalciso.net

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Accidental CISO @accidentalciso.net · 8h
If your CISO isn't interesting, you have the wrong person.
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Accidental CISO @accidentalciso.net · 23/09/2026
I recently joined the GRC Engineering Club and volunteered for a local leadership role to help build our chapter. If you are a GRC nerd and want to learn about GRC engineering, check it out.
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Accidental CISO @accidentalciso.net · 17/09/2026
My strategy is to make my living working on boring Cybersecurity problems.
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Accidental CISO @accidentalciso.net · 16/09/2026
Don't feel bad about reporting something that seems off. It isn't an inconvenience. It's our job to check it out.
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Accidental CISO @accidentalciso.net · 14/09/2026
Look, you pay me to be paranoid. If I'm not worried about this, you definitely shouldn't be.
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Accidental CISO @accidentalciso.net · 10/09/2026
I've been looking forward to Blue Team Con all year, and it's finally almost here! Hitting the road to Chicago in the morning!
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Accidental CISO @accidentalciso.net · 09/09/2026
While I was at defcon, I picked up some Meshtastic gear in the vendor hall. I finally climbed up on my roof to install the outdoor radio. 😎
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Accidental CISO @accidentalciso.net · 31/08/2026
You know you are doing something right when your client's HITRUST auditor says, "Thanks, that was the easiest audit I've done." 😎
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Accidental CISO @accidentalciso.net · 28/08/2026
I bet the Germans have a word for that feeling when it’s Friday morning and your to do list for the week actually only has a couple small items left.
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Accidental CISO @accidentalciso.net · 27/08/2026
I’ve been keeping my eye out for a used King 2B or 3B valve trombone in good condition. Just stumbled across one with both the valve and slide sections. It’s pristine and only an hour away from me. It is also twice what I was hoping to spend. 🎉😭
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Accidental CISO @accidentalciso.net · 26/08/2026
Potential channel partner requests a meeting. Great! Then reschedules. Ok? Then no shows. Sigh... Good to know you are serious, my dude.
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Accidental CISO @accidentalciso.net · 25/08/2026
Dynamic vendor risk questionnaires that get longer as you answer questions, but offer no way to save progress are evil. 🤬
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Accidental CISO @accidentalciso.net · 20/08/2026
Paying my daughter to break apart a couple thousand discount code cards for coffee from The Flaming Bean to give away at a conference soon. 😎 Podcast listeners get 10% off with code: TMBSS.
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Accidental CISO @accidentalciso.net · 20/08/2026
New episode of my podcast hits the feed tomorrow. This one is about organizational change and stakeholder mapping in AI implementation initiatives. Then we live stream the recording of next month’s episode about AI governance on Friday afternoon. Focivity dot com slash podcast.
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Accidental CISO @accidentalciso.net · 18/08/2026
This is another great episode! I highly recommend this podcast if you're looking for some creative inspiration or interested in becoming a creative professional.
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Accidental CISO @accidentalciso.net · 16/08/2026
The weather isn't looking good for our community band concert this evening. Outdoor performances are always a gamble. Out last one was rained out back in June.
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Accidental CISO @accidentalciso.net · 13/08/2026
Buying life insurance is weird. You're like, "I'll bet you $70/mo that I'm going to die, and if I'm right, you give my wife half a mil." And the insurance company is like "No dawg, not yet. We'll take that bet."
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Accidental CISO @accidentalciso.net · 12/08/2026
Tabletop exercises are so much fun when the client is fully engaged and excited to improve their capabilities.
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Accidental CISO @accidentalciso.net · 11/08/2026
Who am I going to see at Blue Team Con in Chicago next month?
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Accidental CISO @accidentalciso.net · 10/08/2026
Everyone keeps talking about AI harnesses, but nobody is talking about AI muzzles.
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Accidental CISO @accidentalciso.net · 10/08/2026
Just sat down to do some focus work, but yea, that’s not happening. 🤣😭
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Accidental CISO @accidentalciso.net · 10/08/2026
I kind of wish we could go back to BBSes and IRC.
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Accidental CISO @accidentalciso.net · 10/08/2026
My flight is delayed, but it’s OK. I bought some chocolate to feel better about it.
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Accidental CISO @accidentalciso.net · 10/08/2026
My defcon experience continued at the airport, chatting with another attendee at the bar in the terminal. 🤣🎉
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Accidental CISO @accidentalciso.net · 10/08/2026
"I'll just find a nice quiet spot at the Las Vegas airport to decompress before my flight." -No one. Ever.
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Accidental CISO @accidentalciso.net · 09/08/2026
I’ll be at defcon for another hour and a half or so. If we haven’t managed to connect yet and you want to say hello, I’ll be hanging out in the chill out lounge.
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Accidental CISO @accidentalciso.net · 08/08/2026
Just scored some little projects for my hacker daughter from RM Cyber. 🔥
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Accidental CISO @accidentalciso.net · 08/08/2026
Back at it again! If you see me wandering around defcon, I'm probably lost, so be sure to say hello!
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Accidental CISO @accidentalciso.net · 07/08/2026
I'm wearing my avatar like a name tag. If you see me wandering around, please say hello!
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Accidental CISO @accidentalciso.net · 07/08/2026
I'm going to hang out in the nook at the back corner of the Blue Team Village until about 11:15 or so. If you are nearby, come say hi!
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Accidental CISO @accidentalciso.net · 07/08/2026
I'm just strolling around defcon looking around for folks I know, and realizing that I don't know what any of y'all look like.
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Accidental CISO @accidentalciso.net · 07/08/2026
Wheels down in Vegas!! Defcon, here I come!
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Accidental CISO @accidentalciso.net · 06/08/2026
Finally in the air. Next stop, Vegas!
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Accidental CISO @accidentalciso.net · 06/08/2026
Southwest managed to find a crew. My flight is now only delayed an hour. 🎉
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Accidental CISO @accidentalciso.net · 06/08/2026
Aaaaand my flight to Vegas is delayed by about 4 hours. 🤬
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Accidental CISO @accidentalciso.net · 06/08/2026
I've left the house. It's official. My trip to defcon has begun!
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Accidental CISO @accidentalciso.net · 05/08/2026
So many SMB “conferences” are super spammy. I’m looking for a community conference event for SMBs focused on topics like business fundamentals, finance, operations, supply chain, etc… with an eye to efficiency, risk management, resilience, and cybersecurity. Does this exist?
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Accidental CISO @accidentalciso.net · 31/07/2026
Someone submitted an anonymous AMA question on my blog to get my thoughts on how they might package up their services for a new vCISO practice for their smaller SMB customers (25-100 employees), and how they might account for onboarding vs ongoing operational work. Here are my thoughts. 👇
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Accidental CISO @accidentalciso.net · 31/07/2026
Someone submitted an anonymous AMA question on my blog to get my thoughts on how they might package up their services for a new vCISO practice for their smaller SMB customers (25-100 employees), and how they might account for onboarding vs ongoing operational work. Here are my thoughts. 👇
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Accidental CISO @accidentalciso.net · 29/07/2026
Who am I going to see at defcon next week? I’m finally making it out!
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Accidental CISO @accidentalciso.net · 24/07/2026
I need a firm but professional way to tell someone to “get over yourself”.
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Accidental CISO @accidentalciso.net · 22/07/2026
A good friend of mine has re-launched his UX/design consulting firm. If any of you know anyone building products or SaaS apps and that needs help with UX and UI design, he's great. Tons of experience with security products. agentuxlab.com
agentuxlab.com
Product strategy, UX design, and AI acceleration for startups.
We believe the future belongs to teams that can combine deep human insight with artificial intelligence. Our mission is to help businesses transform ideas into market-ready products faster and with…
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Accidental CISO @accidentalciso.net · 21/07/2026
Fundamentals, fundamentals, fundamentals.
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Accidental CISO @accidentalciso.net · 18/07/2026
Oh, look! Shel Silverstein predicted gen AI.
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Accidental CISO @accidentalciso.net · 08/07/2026
After three weeks of working from the RV in 7 different states, this Spacelink thing is pretty amazing. Yes, there are problems, but I think it is incredible from both an engineering and a UX perspective.
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The Mindful Business Security Show @mindfulsmbshow.com · 25/06/2026
Another new episode hit the feed this morning! This time, Zack Korman joins to discuss safely learning about AI in small businesses.
mindfulsmbshow.com
Experimenting and learning about AI safely in small businesses | The Mindful Business Security Show
The Mindful Business Security Show is a call-in radio style podcast for small business leaders. Join our hosts as they take questions from business leaders like you!   On this episode, Accidental CISO is joined by guest host Zack Korman. Zack is a business and cybersecurity leader with a background in law, finance, and tech startups. His love for building with AI has led him to launch his current startup, Embroidery, where he and his team are building an AI driven threat detection tool for AI agents. Join them as they discuss how organizations can learn about AI and experiment with it safely to build institutional knowledge.   You can find Zack and his hot takes on X: @ZackKorman   Are you struggling with how to deal with Cybersecurity, Information Security, or Risk Management in your organization? Be a caller on a future episode of the show! Visit our podcast page for more information about upcoming episodes. You can sign up to be a caller and guarantee yourself a Q&A session on the show!   Show Merch: https://shop.mindfulsmbshow.com/ Website: https://www.focivity.com/podcast Twitter: @mindfulsmbshow Hosted by: @AccidentalCISO Produced by: @Focivity Theme music by Michael Kobrin.
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Accidental CISO @accidentalciso.net · 20/06/2026
If you listen to podcasts, what are the formats of your favorite shows? Are there certain things that make the format work particularly well for each?
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Accidental CISO @accidentalciso.net · 19/06/2026
Ok folks, don’t forget! I’ll be live streaming the recording session of another episode of @mindfulsmbshow.com today at 3:00pm Eastern. We are talking about business drivers and goals for AI and taking “callers” from the audience. Tune in and call in!!
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Accidental CISO @accidentalciso.net · 19/06/2026
I have always wanted to do a series about what riding a motorcycle taught me about being a CISO. Now I’m thinking I also need to do a series on what being a CISO taught me about RVing. 🤣🤔
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Accidental CISO @accidentalciso.net · 17/06/2026
@tc.superteece.com and @medus4.com, We hit up Cathedral Caverns in your area today. Holy hell, it is incredible!!
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