
Howard Holton
15
APPEARANCES
8
PODCASTS
024
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Oct 23, 2026
AI Isn't Software: Rethinking Cybersecurity for a New Era
H
21:59Howard HoltonGUEST
I know it's been out for a few years and it feels like a massive acceleration, and it is.
H
22:03Howard HoltonGUEST
It's moving faster than anything else, but it's not improving as fast as it's changing.
H
22:14Howard HoltonGUEST
One I just discovered the other day, like I'd been hinting around it, but I started a project and because I've been working with AI for a while and I'm noticing that I get some different results and I'm working with AI my way and you can never see inside someone else's head.
H
22:25Howard HoltonGUEST
So I asked AI to write an article about working with me from its perspective.
19 MINS LATER
Why Do We Keep Complaining About the Same Issues in Cybersecurity?
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7:17David SparkHOST
I'm going to assume, Howard, you've talked to many businesses, and they've said many of these lines as their selling point, and you're like, "All right, guys, we gotta right the ship here." Has that happened? Yes?
H
7:30Howard HoltonGUEST
Almost every call that I have, even one where I'm there to advise, and they know what the setup is, and they're familiar with me, and I have yelled at them before, they still lean into a trope, or two, or three, or four.
H
7:49Howard HoltonGUEST
There are pieces of compliance that absolutely are, but compliance is the assurance that you are following the required regulations that apply to your organization.
15 MINS LATER
Hacking Microsegmentation for Machine Workloads
H
8:41Howard HoltonGUEST
But as to the last one, it can't both behave as a proper process and be malicious at the same time.
H
8:52Howard HoltonGUEST
The question has a logical fallacy contained within it on that last question.
H
8:57Howard HoltonGUEST
If I've authorized a host to communicate to this service over this port, which is what I want to do with microsegmentation, then it's an authorized service acting over that port and communicating with that service.
10 MINS LATER
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19:03Galeal ZinoGUEST
So secure by design was like the term, Howard, that first came to my mind when I saw that question.
BONUS EPISODE: Super Cyber Friday Express - Hacking Vendor Selection
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9:59Howard HoltonGUEST
It's helpful to have more employees, but also as a CISO, I'm an, an executive in a company that's political, 'cause most companies are political.
H
10:07Howard HoltonGUEST
My political power is derived directly from the number of people in the org that report to me.
H
10:12Howard HoltonGUEST
I'm not going to get more influence in the organization by cutting my headcount from 80 to eight.
BONUS EPISODE: Super Cyber Friday Express - Hacking Vendor Selection
H
9:46Howard HoltonGUEST
Yeah, especially when you talk to like the words that are actually being said.
D
10:59David SparkHOST
And I think that's always a good angle, but rather than trying to be all things for all things, because then you're nothing for anybody.
You Can’t Govern AI Like Software with Howard Holton
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13:38JayHOST
Or is it
H
13:45Howard HoltonGUEST
I know we're all exhausted by AI, but the AI governance conversation at Black Hat was insane.
H
13:53Howard HoltonGUEST
Like the AI SOC thing, you could almost measure that as like a heartbeat because it was constant and it was just like thrum.
11 MINS LATER
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25:26JayHOST
We can start to slow it down.
Hacking Vendor Selection
H
8:30Howard HoltonGUEST
Yeah, especially when you talk to like the words that are actually being said.
D
9:43David SparkHOST
And I think that's always a good angle, but rather than trying to be all things for all things, because then you're nothing for anybody.
Proving Resilience with Gambit Security
8:49
H
1:13Howard HoltonGUEST
I, I've been through it a few times, where we think everything is good, we go to reco- restore after some sort of failure, only to find all of our assumptions were wrong.
H
1:23Howard HoltonGUEST
And they're not necessarily 100% wrong, but we didn't have a clue what we were doing in recovery, and I've never had a board more interested in what I'm doing as a CIO or a CTO or a CISO than when I'm in recovery.
H
1:38Howard HoltonGUEST
It, it's effectively an all-hands-on-deck type of situation, and the fewer people I involve, the less thorough I am, the less everyone knows what their job is, the less I'm able to actually certify that this works, if I don't have people to contest, if I don't have proper procedures, if I don't have any of this stuff done.
H
1:54Howard HoltonGUEST
And you really kinda have to do it a lot more than once, otherwise it's never a muscle, right? And we don't need to do it 10,000 times or do a Malcolm Gladwell 10,000 hours sorta thing, but we do need to do it enough that everybody knows what their role is, everybody knows what the goals are, and we can actually certify that this stuff works.
7 MINS LATER

Curtis SimpsonGUEST
So we're looking at the actual recovery time frames compared to your business targets, defining the action plans for those applications, and enabling you to proactively prepare for that event, as opposed to orchestrating the recovery from the event itself.
Securing the Open Source Supply Chain with ActiveState
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1:46Rich StroffolinoHOST
The exploitability in the open source supply chain, why is all of a sudden this the topic of the day?
H
1:52Howard HoltonGUEST
So I think there's probably three things at work here, right? The first is open source is public.
H
2:01Howard HoltonGUEST
What it means is it's more public when anything happens and anyone can fork an open source project, inject malicious code.
H
2:09Howard HoltonGUEST
And if you're not paying attention, it's really, really easy to kind of get compromised.
H
2:22Howard HoltonGUEST
And the velocity is on both sides, right? The velocity is the velocity of the malicious attacker or the malintentioned to compromise open source projects, but also the velocity within software development has increased.
7 MINS LATER
The Department of Know: PeopleSoft exploit, Ford brings back gray beards, LLM vetting
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41:17Howard HoltonGUEST
Transparency can be, you know, this thing occurred on May 27th, right? There's a f- there was a 14-day 12- dwell period where 300 PeopleSoft instances at 100-plus organizations were compromised, right? At that point, this is effectively public.
H
41:37Howard HoltonGUEST
It's, it's June 10th before Oracle issues the emergency out-of-band patch, which is 14 days after the exploitation began, right? On the 11th, Google Mandiant published the attribution.
H
41:54Howard HoltonGUEST
During that period, right, um, the University of Nottingham published on June 5th that they were compromised a- and the records were published as proof from, um, from ShinyHunters on June 5th, right? What is that, roughly 10 days after the, after the hack began? Um, that's a very long time, during which time t- organizations continue to get compromised and Oracle's not acting as a partner.
H
42:21Howard HoltonGUEST
That's my biggest problem, right? It's okay to go, for Oracle to go, "We're gonna notify everyone that could be affected by this.
Elevating the SOC with Prophet Security
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1:28Rich StroffolinoHOST
Is that just massively increasing the signal and, and causing even more overload?
H
1:38Howard HoltonGUEST
While I appreciate the potential that AI brings, AI brings the infinite problem to both sides of the equation, right? As long as whatever tool you're using to speed up your own efficiency is able to be used by the attackers, it ends up being kind of an infinite game.
DtSR Episode 705 - Idiocracy or Star Trek
H
4:29Howard HoltonGUEST
So, so one of the reasons I became an analyst was I used to spend a lot of time talking to sales teams about how to sell me, because they'd come into my office and they'd be like, "All right, Howard, we got this great C-level presentation for you.
H
4:41Howard HoltonGUEST
We know C- CIOs don't wanna hear about speeds and feeds, so we're gonna mix it up for you.
H
4:46Howard HoltonGUEST
We're gonna be really CEO-focused, and we're gonna give you, you know, feeds and speeds instead." No speeds and feeds, it's just feeds and speeds, right? And I'd go, "Guys, like I don't care about any of the things you talked about.
H
5:01Howard HoltonGUEST
I have to assume if you got into my office, your feature set is liked by my analysts, is liked by my engineers, is liked by my architects.
15 MINS LATER
DtSR Episode 704 - Market Saturation, Innovation and Procurement
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11:28Rafal LosHOST
I'm not gonna go spend money on something new that does just that." Does that make sense?
H
11:33Howard HoltonGUEST
Y- yeah, I mean, we- w- we're, as an industry we are all about the white space.
H
11:37Howard HoltonGUEST
Like the entire tech industry is about the white space, right? Can I find enough elbow room between the vendor to the left and the vendor to the right of this problem that I can wedge myself in there? A- and, and that is a fine strategy, again, when the acquisition cycle is high.
H
11:53Howard HoltonGUEST
M- the problem I think comes back to, you know, I was having a conversation with somebody.
H
11:58Howard HoltonGUEST
I really liked their tech, and I was like, "Cool, so what are you displacing?" And they're like, "No, no, we're net new." Okay, cool.
H
12:05Howard HoltonGUEST
Like no one's gonna buy that.Right? I don't have enough money to solve the problems that I have today.
7 MINS LATER
Department of Know: Autonomous AI cyberattack, CISOs back to work, bus kill switches
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27:38Rich StroffolinoHOST
Someone on their staff asked someone to read the manual and they used AI to tell them.
H
27:42Howard HoltonGUEST
Yeah, no, they stumbled into some dark place in AI, and AI went, hey, by the way, your buses can be remotely detonated.
H
27:48Howard HoltonGUEST
And they went, I don't understand, we have buses? And then lost the whole investigative committee.
H
27:58Howard HoltonGUEST
The story of a friend of mine who was a pilot in Vietnam, and they were initially using sensors attached to their planes that would smell for the presence of Viet Cong.
8 MINS LATER


