"Security's Fuckin' Weird" with Dan Tentler
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Why does the host say “security is weird” and what does that mean for the industry?
Security's fucking weird, man. The problem becomes, I don't know, you think about any other major profession, and to this point I think both security and data are becoming very major professions. Most of them have rules. I like to go to medicine a lot because I did a talk for ColonelCon one year. I called it Who Wants to Fire Some Missiles? Because ColonelCon is in the same city that US CentCom is in, like Central Command. Literally, the button to fire the nukes is in this city, and a bunch of those people and incidentally SenseCom is also where the Space Force is and at the con there were dudes walking around in fucking military barpat fatigues that said space force and I'm like, why do you need camouflage in space?
Explain the show.
Like that's like what are you talking
about? Two. Yeah, you're floating around in space with like green and black, like good job. But the reason I titled the talk that way was because the whole concept was how to fake it into a position of power using these techniques, in large, very large part standing on the shoulder of Harun Mir's talk, because my talk was about how you as an individual can do the same thing that you can to defraud security, like Haroon described. So Haroon described you can buy these awards and you can buy influence and you can lie to investors. And this is how we've seen it done, and all this other stuff. And I was like, okay, cool. I'm gonna take that concept and say, here's how you do it as a person. Here's how you can fake getting a CISSP.
Here's how you hire an Indian guy to do your OSCP and OSCE for you. Here's a company that will pretend to be a reference. You give them a bunch of names if somebody asks you for references. This is a company that literally you give them a script and tell them what you want them to say, and when some place calls in for your reference. they will just feed them whatever you want them fed and they just charge a fee for that. There's resume services that'll and now you can just use GPT, but this was you know twenty twenty, I think. Twenty twenty twenty. And you can just buy all this shit. You don't need to have any experience. You don't need to have done anything. If you have like ten grand burning a hole in your pocket, you can buy everything.
The C I SSP boot camp is seven grand. You pay the seven grand and they let you take the test over and over and over again until you get the C I SSP. Now you have a C I SSP. So what fucking good is how common? What good are these things when you just buy them? How common is that
what I mean? You said the name of it. OSCP? Now that that I knew a little bit about the OSCP because my brother sat for it and we had a lot of conversations. And I was actually really impressed because we don't have something like the OSCP for data. And it looks like assuming you don't cheat, it seems like there is no real way to pass it without knowing something about what you're doing. It's not like a university exam. Exactly where you can just kind of
I took it in 2009. Yeah. I took it in two thousand nine. And back then when it first came out, it was literally the gold standard of if you want a job in security and you have an OSCP that basically earns you a title of somewhere between junior and mid. You know enough to be dangerous. You have some experience with a debugger. You have a bunch of like it's essentially a classic. Like the OSCP, last time I touched it, 2009, Jesus fuck, like 15 years ago. I'm old. The last time I touched it, the easiest way to wrap your head around what it was is essentially it's a training course. It's an obstacle course that trains you how to use Metasploit. It trains you how to do stuff by hand in Python and Bash if you don't have Metasploit available.
It teaches you the basics of how shells work. It makes a lot of assumptions that you know the basics of how computers work. You have some basic understanding of the command prompts that you have to be able to get around on in a Linux shell. You need to understand the very basics. basics of networking, like what a firewall is and the basics of how packets work and things like that.
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Chapters
8 chapters
1
Why does the host say “security is weird” and what does that mean for the industry?
0:00–8:24
2
How can someone fake security credentials like OSCP or CISSP and why does it happen?
8:24–16:17
3
What was the “obstacle‑course” training the host created for aspiring security engineers?
16:17–24:37
4
How did a real‑world outage at a financial firm reveal a memory‑leak bug in the switches?
24:37–33:17
5
Why does the host prefer using grep over Excel for large log analysis?
33:17–43:28
6
What’s the difference between compliance check‑lists and true security testing?
43:28–54:50
7
What red‑flags should you look for when hiring a security vendor or consultant?
54:50–1:04:06
8
What practical advice does the host give to people wanting to break into security?
1:04:06–1:11:40