The Grind and Growth: A Podcaster's Journey With Jack Rhysider From Darknet Diaries

Ever wonder why some shows last for years while others fade before episode seven? We sit down with Jack from Darknet Diaries to unpack the systems, mindset, and storytelling choices that keep a podcast resilient without burning out the host. Instead of chasing viral spikes, Jack lays out a playbook for steady growth: batch recording, rest cycles, and that deceptively powerful one percent month-over-month target. It’s practical, humane, and it works.

We dig into his editorial compass with three distinct tracks: personal obsessions, proven crowd favorites, and bold forays into new communities like crypto and gaming. Jack explains why listeners often prefer penetration test stories over higher-stakes CIA operations, and what it takes to earn trust from niche audiences by learning their culture first. The curtain pulls back on hard-to-book guests, silent PR walls, and the rare times a source vanishes after recording—plus the elusive thrill of chasing “ghost” hackers who should never speak on record.

From there, the conversation turns to craft. Jack’s background as a network security engineer sharpened his ability to explain complex topics simply. He shares how layered explanations let beginners and veterans both feel seen, why command line beats screenshot soup, and how relentless revision turns knowledge into clarity. We also tackle AI and cybersecurity with nuance: not as job eraser, but capability amplifier. Think better triage, secure-by-default coding, and an arms race where defenders and attackers wield similar tools—and the edge comes from better questions and stronger priorities.

Beyond the studio, Jack talks health, music, language learning, and swing dance, and how a wetware mindset—designing stories to trigger empathy and memory—guides every episode. If you care about making work that lasts, telling stories that land, and adopting AI without losing the plot, this conversation is a masterclass in sustainable creativity and modern security. Subscribe, share with a friend who needs a morale boost, and leave a review with the one tactic you’ll try next.

Darknet Diaries: https://www.youtube.com/jackrhysider

Chapters

• 1:46 Staying Past Episode Seven
• 3:49 Sustainable Growth And Motivation
• 6:06 Three Lenses For Episode Selection
• 10:10 The CIA Story And Stakes
• 13:13 Agencies, Gatekeeping, And A Career Detour
• 17:12 Safe Houses, Testing, And Revoked Referrals
• 22:13 Vanishing Guests And Silent Phones
• 25:11 Intelligence Communities That Won’t Talk
• 28:33 Dream Guests And Missed Legends
• 32:05 Editing Less, Explaining More
• 36:05 From Firewalls To Clear Teaching
• 42:14 Writing For Beginners And Experts
• 46:35 Documentation, Detail, And Drift

Transcript

SPEAKER_01: 0:53

How's it going, Jack? It's it's great to get you back on the podcast. You know, it's been it's been three or four years at this point. And one, I can't even believe that my podcast has stayed around for that long. There's so many podcasts out there that, you know, stop recording and stop posting and everything. And I think that's a good thing.

SPEAKER_00: 1:11

Yeah, congrats to you for staying around that long. Cause I think the average podcast quits before seven episodes. And so people always ask me, like, what's a good goal for when I start my podcast? I'm like, just get past episode seven. If you could do that, you're more you're better than half the podcasts out there. And now, how many years have you been doing this? Uh, it's coming up on five. That's amazing. Yeah, congrats to that.

SPEAKER_01: 1:32

Yeah, five, five years of weekly uploads, you know. I mean, weekly, wow. Yeah. Weekly interviews. I like I like doing it because at least that way I can stack them. So I'll go a couple weeks and I'll do a whole bunch of recording, you know, and then release it throughout the next couple months, take those months off to kind of recharge, focus on other things that I've been procrastinating about. But I looked at that same stat that that you mentioned, right? And I'm all about trying to figure out ways of, I don't know, like fooling, fooling my mind or keeping myself going. And so as soon as I see a stat like, oh, if you make it to episode seven, you're above 98% of the podcasts on the planet, right? It's like, oh, I just gotta get to seven. I could do seven, you know, like yeah, and I just keep on going off of that. So it's it's interesting.

SPEAKER_00: 2:22

Yeah, exactly. I don't like to hope for like huge number success, like end of the game kind of stuff. I just want the next step in my growth journey. Episode seven was was one of my first goals. But then after that, it was can I just grow by one percent from this month to the next month? Right. It wasn't this huge leap to I want a million downloads or something. It was just like growth is better than no growth. Growth is is is living while you know declining is dying or whatever. Like that that's all it was. So one percent growth was it. And if you're at like a a hundred downloads per episode, that's just another listener. So it's like I need one more listener this month. How do I find one listener? And that's doable when you're starting out.

SPEAKER_01: 3:00

Yeah, yeah. It's the journey has been quite a grind, to be honest with you. You know, I mean, I'm I'm sure you're obviously well well aware of it, well acquainted with the grind. But like, it's hard to get yourself motivated when you know you recorded an episode, you thought it was great, you had a great guest, great conversation, and you get like a hundred downloads. It's like, okay, what did I like, what am I doing this for then? You know? And it's not like it's not about the downloads, but it's like the validation of your hard work. Those that's what those downloads are. That's at least how I view it, you know?

SPEAKER_00: 3:38

Yeah, I think as a creator, I I kind of I mean, there's there's a certain lens that all the episodes have to go through like a certain filter in order to make it on the show for me. But there are there are kind of three tracks in my mind of what kind of episode this is. It's either an episode that I love so much, and it's just for me, because this is the kind of stuff that I just am so into, or it's an episode that's for like the it's a crowd favorite, right? And for me, crowd favorites are pen test stories. People love hearing all the gear and the tactics and stuff pen testers use. And then the other one is to sort of go outside my comfort zone and grab something, a whole audience that I I'm not serving now and go into an area that I don't know. And and so historically, that's been video games or cryptocurrencies or something like that, right? When I do a a hacking story about one of these things, I've got to learn a lot about that culture. There was a music one I did, and I didn't know that much about that kind of music, right? And so I had to really play those games and get in that space and buy the cryptocurrency just to see what it is like to use this app and all this sort of thing and to be in with those guys screaming about all this stuff. And then I I feel like I understand the culture and then I can I can present it properly. And so it's either a personal favorite, a crowd favorite, or drum up like a whole new audience out of this. And and when you go deep into something, you know, if somebody's really into crypto and that's all they think about all the time, and then you show them a story that they've never heard, they love that. That's value to them because they're like, wow, I didn't, I didn't even know about this, and I've got my finger on the pulse on this every day. What what else is this guy teaching me? And so they become a listener, like they they come in, like, wow, this guy's valuable and in other ways. He is teaching me about crypto, but he's also teaching me about all this other stuff. So I love bringing in those brand new audiences, and that's that's one of my favorites, is when suddenly there's a whole group of people that I've I've never interacted before in my Discord. I'm like, oh boy, let's see where this goes.

SPEAKER_01: 5:32

Yeah, no, that's that's really interesting. I remember I think it was last year. I I don't think the I don't think your episode went live last year, but the episode that I heard of yours with Jim Lawler was just so fascinating to me because that's a world that I tried for years to get into. I mean, literally you wanted to get in the CIA. Yeah, I really wanted to get into any agency with the end goal being that agency. And I I mean like Oh yeah, because you're ex-military, aren't you? No, no. So I'll give you I'll give you a little bit of that background on me, right? So, you know, in in high school, I was tempted to go into the military, but I knew if I went into the military at that point in time, it would be just about doing the minimum, getting out, going and getting a free degree, right? And I didn't want it to be about that. If I wanted to go in, I really wanted to like spend my life in that area. So I went to college and you know, in college, I had the full intent of like, hey, I'm gonna get this degree, I'm gonna go into the federal agencies and make my career there. I think it was like my second year in college, my sister developed kidney disease, so I ended up donating my kidney to her. And uh, you know, towards the end of my college degree, my bachelor's, I figured, okay, well, like, let's give the military a try. It might be a quick way to get in with, you know, different agencies. Military would not take me. I applied to every single branch, interviewed with a couple of them, you know, started going down that process. And as soon as they found out I donated my kidney, they're like, nope, you're disqualified, you're done. So I started to focus on the agencies, and the agencies were fine with it. They were like, no, that shows more, you know, to your towards your character and integrity. You know, that's what we want above and beyond anything else. And so I started going down that path. And I mean, you know, I I I went through the interview process and uh for for the FBI and I can actually talk about this, but they uh, you know, they sent me to like what looked like a safe house almost where you know to like do a computer test. Their computer assessments are like really, really interesting. So like they just give you this address and they tell you to show up at this time. And I showed up, I parked in the driveway. It's just a just a random house in in the suburbs, right? Suburbs of Chicago. And I'm like, man, I'm at the wrong place. Like I triple check this address and everything. So I was like, you know what? Like, whatever. Let's just go up to the door and get turned away just to be sure, you know. And I knock on the door and someone opens the door and they're like, what are you here for? And I told them, you know, my test or whatever, and they were like, All right, come in, go all the way to the back, right? Like, that was the weirdest thing. So I passed, I passed like all of their tests, and the year before I started this journey, the process had changed where it used to be where if the field office liked you, they could just refer you and send you to the academy, right? Like, as long as you pass all of their tests and everything, the field office was like kind of that final say. Well, they changed it to where if you pass all of the tests, the field office then refers you to DC, and a board that you've never talked to, never seen, or anything like that recommends you to go to the to the academy, or they revoke you. So they actually revoked me, and my recruiter called the board personally, and she's like, You don't understand? I've been talking to this guy since you know he was in college, he's worked at this every single day for the last four or five years. I'm personally recommending him as well as like, you know, the special agent in charge of the Chicago division. And they were like, Yeah, we don't care. He has to wait until he's 30. And they said, Well, that was the first time that they ever heard anything like that was that someone has to wait until a specific age to go in. And so I said, Okay, well, maybe that's an maybe that's an FBI thing, right? So I went just straight down the list, went to all the agencies, every single one told me I had to wait till I'm 30. And my reply was, guys, you do understand, like, I'm 22 right now. You could drop me off in Afghanistan and say, Don't come back until this date, and I'll be totally fine. Like, I will enjoy it, I'll love the challenge. That's what I'm signing up for, right? But when I'm 30, I might have kids, I'm probably gonna be making a whole lot more than what you would be paying me right now. Like, why would I join? And their reply was you have to wait till you're 30. They didn't give me anything else. So, like, getting to talk to you know, Jim Lawler is just it's fascinating for me because like I I understand that world as much as I possibly can without ever being in it, you know?

SPEAKER_00: 10:15

Yeah, it's it's interesting you have a personal uh connection to that one. That that's episode 116 called Mad Dog. And we're talking about Darknet Diaries here. I uh you haven't mentioned that. That's what I uh that's what I make. But in case anybody's not in tune here, I'm Jack, I make the show Darknet Diaries. But episode 116, Mad Dog, is a CIA agent named Jim Law or Lawler who goes to foreign countries and gets information, like uh, you know, information that country doesn't want the the U.S. to have. And he does it in various ways. And it's to me, it is like a penetration test story, but it's not monopoly money anymore. It's real stakes. Life is on the line. Like he could go to prison because espionage is illegal and this is what he's doing. And so it's he's not it's not allowed to do this. This is against the law in in any country. So it's it's like serious stakes at hand here. But but to me, it's like that's I like that sort of thing that's the high stakes we're in uh we're we're in a life and death situation. But my my audience loves, no, we like penetration tests more. We like the guys who are who have the whole kit of gear and are paid to go and and break into a building because those are good stories. And I'm like, but what about this one? This one is like way higher stakes, like everything is on the line here, and it's not as much of a fan favorite compared to just a regular uh penetration test story. And that's always surprised me because I'm like, this is the real deal. Yeah.

SPEAKER_01: 11:38

I mean, that's really that's fascinating why that wouldn't like resonate with your fans, with your listeners, you know?

SPEAKER_00: 11:46

Yeah, I mean people liked it. It's it's been one of the one of the top 20 best, but it's it's not it's not the thing that they clamor for every time. Like more penetration tests is what they ask for. Never more CIA agents.

SPEAKER_01: 11:58

Have you have you ever interviewed someone that you know worked for a government and then they just like disappear off the internet?

SPEAKER_00: 12:07

Worked for the government and then disappeared off the internet.

SPEAKER_01: 12:09

Yeah.

SPEAKER_00: 12:09

People disappear all the time because they're like quitting Twitter and quitting everything and I mean yeah, lose them and then they come back around.

SPEAKER_01: 12:17

I mean, I'll I'll give you an example, right? So a couple years ago, I interviewed someone that is a cyber warfare officer, at least he was at the time, for the NSA. And the only reason why I was able to corroborate him like actually being in it and doing it, was because during the podcast, he gave me like details about the training and the process and everything else like that. And I ran it by people that I know are familiar with that area, and their response was, yeah, he never should have been on your podcast. And yes, all of that is accurate, right? So like I know that the guy was real, but and he had a presence before coming on the podcast, and then he comes on the podcast, we record the episode, it wasn't live or anything like that. Then he just he disappears. He basically messages me, tells me, Hey, it's highly recommended that you do not post that episode. You have to wait, you know, several years, five plus years before you post it. You shouldn't post it tomorrow, which I didn't tell anyone that I was posting it tomorrow. It was scheduled to go live in my in my stuff for tomorrow for the next day. And then he just disappears. Like Twitter's gone, like everything that he had was gone. His email, all of it gone.

SPEAKER_00: 13:32

Wow.

SPEAKER_01: 13:32

And I'm like, man, this guy like completely ghosted me, like to the max.

SPEAKER_00: 13:37

Yeah, yeah. Wow. That yeah, I don't think I I mean I've had people disappear on me, but not like uh that.

SPEAKER_01: 13:43

Yeah, it was the weirdest thing because like it was scheduled to go live literally the next day, and then he sends me this message was like, hey, do not post it. You can't post it for five years, you know. I'm like, okay, like that's fine. I don't feel like having the FBI show up at my door, like it's it's not a good look in my neighborhood, you know? Like, yeah, that's not something I want, so I won't post it, and then he just disappears because I was looking for him even recently, because I was like, Oh, it'd be cool to have him back on, like as like a part two almost, you know.

SPEAKER_00: 14:16

I can't find the guy. How fascinating. I did every now and then I'll get like a very strange call, you know, someone will message me on Signal and be like, hey, I want to do a quick call with you, and then like they don't tell me anything, and then they work for some intelligence agency, and they're like, you know, that last episode or something was spot on, but you've you didn't you didn't ask this one question, and maybe you should ask it next time. And and they tell me something to look at, and I'm like, oh, okay. What more do you know about that? I can't I can't talk about it and they hang up or something, but it's really fascinating because I don't know who these people are, but they'll call me every now and then and give me some strange trail to follow.

SPEAKER_01: 14:51

They just like randomly call you, just like look you up in the NSA database and get your number that way.

SPEAKER_00: 14:57

Yeah, I mean, I've interviewed uh CyberCom NSA, I've interviewed well, I guess a few four NSA agents now. Someone from the CIA, someone from an Israeli intelligence, and that's it. But it would but like Canada will never speak. Canada's intelligence agencies and UK's intelligence agencies will never speak. Of course, Cozy Bear and Panda and all these guys, Russia and China will never speak. But it would be fun to interview the APTs from around the world. Yeah.

SPEAKER_01: 15:27

It's interesting that they won't speak, but then like Israel, because I've had so many people on from the 8200 group. I mean, it's almost boring to me, you know, because it's like they give you the same, the same sort of stuff, you know, same rough outline, and then it's like I can't talk about any malware that I reverse engineered. Uh-huh. Okay, well, thanks. You know, like it's it's interesting.

SPEAKER_00: 15:50

Yeah, I get the the the a lot of CEOs message me or or their PR people and they're like, hey, I'd like you the CEO to be on your show. And I'm like, hmm, with a name like that, and your company based in Israel, I'm pretty sure your CEO went through 8200. I would love to talk about all the stuff they did in 8200. And they're like, Yes, absolutely, he went to 8200, but he can't talk about that at all. I'm like, okay, well then we'll we'll wait.

SPEAKER_01: 16:14

Yeah, no, it's it's uh it's a weird world. And then what was it? I mean, I I doubt that you know this, but I had Jim, I had Jim on this summer, right after the US bombed Iran and or bombed the Iran, you know, nuclear facilities. And so I had him on, and that's all that we talked about for like an hour. And uh he told me, he goes, you know, I actually got read into it like a month ago that this was being planned and thought through and everything, and they were asking for my opinion, and he said, Yeah, we should absolutely do it. And that was like essentially factored into the overall decision to actually do it. And then the day before they launched, he got read in and said, Yeah, we're gonna launch at this time. And he said that he was like getting near real-time updates the whole time. And he's like, I've been retired for you know X amount of years, right? Like they don't have to do that, but it was a nice courtesy because he had like so much, you know, he had close operations in that region and whatnot.

SPEAKER_00: 17:12

Yeah, that's fascinating.

SPEAKER_01: 17:13

It's an interesting, it's an interesting world for sure. Is there anyone that you haven't been able to get on that you know you really want to get on still after all these years? Yeah. Yeah.

SPEAKER_00: 17:29

I mean, I think by default or by design, I suppose, I want those hard to get interviews. And so it's always it's always a lot of you know, shoulder tapping that not even knows. It's just it's just ignor ignor ignoring me, right? And uh yeah, I mean, like I said, uh Russia's hacking team or Chinese hacking team, that'd be really cool. But it's like they're not gonna ever come on. They'd be killed if they came on. So it's chasing ghosts in a lot of ways, right? There's um some of the high profile hacks that have happened that we don't know who it was, like I don't know, Goosefer or or whoever hacked what is it, hacking team in Italy? Just some of the stuff that's that's happened, like, ooh, somebody somebody came and hacked this and we don't know who, or like it'd be fun to to get those those people because those people should never come to on my show, right? And so that's kind of what I'm looking for is the people who wouldn't would never and should never come on my show to tell me that. And and yeah, I've chased lots of different things. Uh I mean uh so I had one of the early people that was really surprising to me that was just such a good storyteller was John McAfee. And I heard him talk about how crazy some of the adventures that he went on on the some other podcast. And I was like, wow, I'm glued to his story. How am I glued to this? And it was just so fascinating to hear him run from the cops and people are chasing him through the streets with guns and stuff. And so I was like, wow, that's that's such a good story. So I I reached out to him and I said, Hey, do you want to tell this stuff? He said, Yeah. But I realized like two things. Number one, he was getting crazy into like conspiracy theories and stuff. And I was gonna be, I was listening to some of his other interviews at that time, and he just any question just goes right off the rails into conspiracy land. And I'm like, man, I don't know how I'd get this guy back on the track. And then number two is you know, some documentaries were made about him about like how he killed his neighbor's dog or whatever. I don't, I don't know all the details. And and he would like absolutely hate talking about certain aspects that he thinks, you know, make him look bad or or he did something wrong and stuff like that. And those were those were kind of the questions that I'd like to go to of like, hey, did you kill your neighbor's dog? Did this happen? Like, why are you on the run for real? Not just your thoughts, about like what did you actually do? And so I I just thought it would be impossible to have him on. And then when he passed away, I felt really bad that I didn't have him on, just to kind of capture just the craziness of what what his world was. And so yeah, that that one is it's always hard. That's another thing is there's like uh you know a dozen people that I wish I had on before they passed away, but they but I wasn't able to get them on. And some of them I was I was in chats with or talking to. And I just missed the miss the moment.

SPEAKER_01: 20:06

Yeah, that is that's the challenge with like running this sort of show, right? Because like life happens and you never know, you know, you never know if you'll you'll be able to get them on ever, right? Like that's why I always I I mean, I probably come off as pushy to a lot of people, right? But that's why like I always push for at least a yes or a no. Like, hey, if I'm asking for you to come on or you know, do whatever, if you don't want to do it, just tell me no, you know, and like I'll go away, I'll leave you alone or whatever. But if you say yes, that's exciting to me. That's like, okay, you said yes, you're gonna come on. That's someone that I didn't have on before, you know. Like it's an exciting story, it's a very interesting story. How much when you're working on an episode, how much from your recordings actually makes it into the episode? Good question.

SPEAKER_00: 20:51

I think it depends on how. Much I research this person first, right? So sometimes we we hop on the call and I don't know their stories at all. And and because of that, I've got to feel out the edges of the stories and we go down, you know, random streets and be like, all right, is there is there anything to this like you know, you said that you is your f is your you brought this thing along or something, and is there what what was the why did you do that and all this? And I and I'm fishing for something interesting there, and it's just there's nothing interesting there. And so there's a lot of you know tape I've got to edit out there. But if it's a story that I can research really well beforehand because there's court records or news reports or something, then I can be really prepared with what streets I want to go down and we because I'll get like exactly what I'm looking for, and there's a lot less editing, but still I'll probably chop out 10 or 20 percent even there.

SPEAKER_01: 21:41

Hmm. Yeah, I I try to take out nothing mostly because of my my my workload right now. I just I try to do as little editing as possible, right? But something that I feel like you do really well, that I try to become better at myself is being able to tell a very technical story or even explaining a very technical topic in a way that captures both sides of the audience, the audience that may not understand it and the people that like understand it inside and out, like that's what they do every day. How did you get so good at doing that? Do you like I I don't know. I don't know how you would even get that good at it, you know? So because you, I mean, you captivate me, man.

SPEAKER_00: 22:28

Somebody told I was so before up, I was a podcaster, I was a network security engineer. I was mostly working on Cisco firewalls. And somebody told me in that role, hey, if you can explain complex topics simply, there's money in it. I'm like, what are you talking about? Like how I'm just troubleshooting a firewall. But then I started to uh, you know, get on phone calls with clients or customers or something. And I'm like, hey, you you know, here's what happened, and they're like, yeah, well, we're not gonna care about that or do that or do anything. And I'm like, whoa, whoa, whoa, I have to explain to you why you need to make a change here, why we need to authorize this change or make, you know, adjust this and fix this, whatever. Obviously, I didn't do it. And so I would try and it wouldn't get across, right? So that's that's number one is I'm not communicating effectively to someone who needs this information in order to make a change to secure their network better. But then I started thinking, you know, the only people in my who know I'm any good at this are like my coworkers, my customers. And I think that's it, right? There's no if I were to like quit that firewall job, man, it would be hard to like show that I'm good at firewalls to someone else. They're gonna be like, I don't know, can you show me your stuff? And I'd have to start from square one with like my reputation. So I thought, why don't I make a goal? It was a New Year's resolution goal, probably in 2007 or eight, where I said, I want to teach more people more things. And the the whole point was to not just teach my coworkers how to do things because I was I was always trying to teach people stuff. And so that's where I started a blog. And the blog is called tunnelsup.com. I haven't updated it in a decade, but but the blog was where I started saying, okay, here's if you if you have a VPN that you're troubleshooting on a firewall, there's a lot that could go wrong. Here's uh here's the troubleshooting steps. And now I'm explaining a complex topic. And I'm like, okay, that's that's draft one, great. And then I'd look at it like three months later because I'm troubleshooting it. And I'm like, what is this gibberish on the screen? I don't even understand my own like notes. And so I'd revise it and I'd make it better. And then a year goes by. I remember it clearly once that I was really sick. I had a terrible cold, but I somehow I still showed up to work and I was trying to troubleshoot a firewall. And I looked at my blog post on troubleshooting firewall, and I was like, this is such trash. Just I have got this clear vision on how this blog post should look. And I deleted it all and I rewrote it, and that's all I spent all day that day doing. I didn't do any other troubleshooting. I was just like, here's how to troubleshoot a firewall. And this now had graphics and and and terms, and it and it went down the list very clearly on how what's the best approach to this. And it was amazing that a cold is what got me there because I could not think deeply anymore. I needed the information just immediately and it wasn't there on the page. And I was like, all right, my mental blockage is making me realize that this post is not very good. And so it was this years and years. I probably spent seven or eight years just on the blog revising posts and making posts and all this sort of stuff. And it became this thing where now my goal is to make this not just a post on how to do this, but the best post on how to do this. This is the clearest way to handle this sort of thing, the most helpful thing. And that, you know, I I just, you know, did again and again in order to get better at that. And not only that, but I was giving presentations at work and stuff. We did lunch and learns to explain topics to people. And it was really helpful to just get these sort of things out. And I saw the power of it, especially with the blog, because then the blog started saying, I, you know, people were saying, Hey, can I hire you for a weekend? I'm troubleshooting a data center upgrade and I need or you know, I'm doing this and I need your your help. Would you mind doing it? I'm like, wow, this is cool. I'm getting like job offers basically from from these blog posts. And then other people would know it. And and and when I'd meet them at a meetup or something, they're like, wow, you're the guy who writes that blog that blog. Yes. And so it was really nice having that. Well, now more people know that I'm good at this and not just my coworks and stuff. And so when I started the podcast, it was this idea of, well, I want this topic to be explained in a way that is going to cater to both the person who's been doing this for 10 years and the person who knows nothing about this topic. And that is such a hard line to walk. And so that was the challenge of make it exciting to both people. And so the idea is quickly give you a summary of what this is, but then give you like one or two sentences of of the beat, the dirt and meat and potatoes of like what it really is, right? And so you can hear the first two sentences or hear the second two sentences, but I it's rare that somebody hears all four, right? Because they're like bored with the first two and they're just like, Yeah, yeah, I know this. But then as soon as I hit that third or fourth sentence, they're like, whoa, I didn't realize that. Or they'll hit the first two and they're like, wow, that's crazy. And now they're thinking about it, and they miss the second two, right? So I kind of expect people to process it in that way.

SPEAKER_01: 27:03

Yeah, it's a it's a really difficult skill to get, but it I always call it or or you know, describe it as like something that sets you apart from the rest of the market, right? Because like we're all smart, we're all really smart. We can all do basically the same, the same work when you're a special.

SPEAKER_00: 27:21

Honestly, that's the thing that I start with is I know my listener is smart. I'm not gonna talk to them like they're stupid or they're a fifth grader or they don't know anything about computers. And even my dad, who says that he's the dumbest person when it comes to computers, which he is, he's he's awful at computers, he even understands what I'm saying. And I know that that just gives everyone more credit, or people should give themselves more credit than what they give themselves because they they they are very smart. And yeah, talk to people like they're adults and it goes a long way.

SPEAKER_01: 27:46

Right. Yeah, I I remember early on in my career, I think it was like the first job out of college, I convinced them to like give me, you know, for me to own basically all of the, you know, military and federal agency contracts that we had. And this one place I went to in the middle of nowhere, West Virginia, in the middle of the mountains, I was there to do an upgrade, troubleshoot, kind of like move them along in their implementation process. And they hired a technical writer to come in and literally document every single thing that I did. And it kind of like reframed how I take notes because I saw it and they're like, Well, we want this to be so detailed to where if someone that knows nothing about this system is handed this piece of paper and said, do this work, they can do it start to finish, no issues. And that like kind of took it to a different level, right? Because like I went there with an upgrade guide of like two or three pages. And when I walked away, that upgrade guide was like 25 pages long, right? Because they literally went through every command, every result, every troubleshooting technique, every single thing. They documented, took screenshots, described it, everything, you know. So like now I kind of like carry that forward to some extent in the work that I'm doing.

SPEAKER_00: 29:01

Interesting. Yeah, this is why I like command line more because command line is very summarized or it's it's very uh short version of like all the things you've done, as opposed to 30,000 screenshots of well, I went to this screen and then clicked this button, and then it's it's in it's an awful documentation process compared to here's the two commands, type those in, you're done.

SPEAKER_01: 29:24

Yeah. Yeah. No, it's uh and for me, it was like never, oh, here's the 10 commands that you need to run. It's like because I would run into the most random issues, you know, of just things not working properly, and I'm in, you know, a pretty harsh environment where I can't call people, I can't open up my laptop and use Google, you know, I don't even have a phone on me. It's just me and my brain figuring out how this stuff actually works.

SPEAKER_00: 29:47

Yeah. It's funny too if someone's taking notes because it's like, oh, you typed that? Okay, cool. But but I hold on, I had to undo that because that wasn't the right command. I I made a mistake. You've got to delete that. And let me just screw around for a little while to find what it is I'm trying to do here. Stop writing everything down. Okay, this was this was how I configured it. It wasn't uh it took me a long way to get there. And still you might be missing a step because you didn't realize, oh, you yeah, it was this that you had to enable before that works as well. It's still tricky.

SPEAKER_01: 30:15

Yeah, yeah, absolutely. Where where do you think InfoSec is going with with all this AI stuff, right? I I feel like one side of the camp is like, oh, it's gonna eliminate all of those jobs. Like InfoSec won't even be a thing, it won't be a thing, coding won't be a thing. And then, you know, we go and look at like the AWS outage. And conveniently, like two months ago, you know, the CEO said that like something like 75% of their code is all written by AI, and then they have a massive outage, you know, a little bit later, right? So to me, the skeptic in me is saying, yeah, but there's a whole lot of other variables that that AI model would have to figure out, you know, to be able to do my work. And on the other side, right, the the the stuff I'm researching with my PhD might be a little bit closer than I want to admit. So where where do you fall in it?

SPEAKER_00: 31:10

Well, I like to I like to try to, whenever we we talk about AI, it's like this new technology. And I like to try to unwind the technology and see where we'd be comfortable as security people, right? And you know, me looking at firewall logs, there's too much, there's too much happening. Me looking at Netflow logs, there's too much happening, me looking at packet capture, there is too much happening for my human eyes and brain to find what's in this. I need technology to help me, right? I need a sim, I need a logger, I need some sort of analytics tool to parse through this and read it for me, because I can't do it. And then I need some sort of tool to set up for alerts. Say, hey, if you see this in the logs, set the look for it. And so this is a this is a huge step into cybersecurity already, which is here's a computer that can charge, chug through millions of syslogs and netflow and packet capture data a second and handle it just fine. And it can see all the stuff going on. And I say, okay, great. Yeah, I can't do that on my own. And so does that mean, you know, we've just eliminated a million jobs because there it would take a million people to look through these million logs a second, right? Like it's it's it doesn't quite equal that. In my head, it's more like, oh, now we have functionality and capability we've never had before. Now we're able to secure the place in a way that we've never been able to secure before because of these tools. And I look at that as as a net positive. This is great. And suddenly I now I have total visibility into what something I could never been able to do before. I mean, we could even look at it as our own selves. Like we've we used to study sleep in humans, right? How do how do humans sleep historically, like in the 70s and and before, trying to you you can we could put up sensors on your brain, but trying to log all that sensors typically went to like a printout and a sheet of paper. And then you'd have stacks and stacks of paper, and you'd have all these like waves and and and and metrics on your sleep. A human would try to have to go through that. And it's just like, this is a very expensive sleep study. But now we have like watch that can just like you strap it on your wrist and it's like, well, now I can watch your sleep and I have infinite like you know data storage to just store logs and stuff. And so this is fantastic that we have these abilities to process so much more information than we ever had before. And now it's like, okay, well, I'm the one who has to tell you how to make sense of this information computer. Like you, I'm looking, I'm telling you to look for this sort of thing because you don't know that sort of thing. And but now we're saying, hey, wait, the AI has these ideas where it's like, you know what? If I were looking for a threat, this is where I would be looking. And it's got its own ideas of how to hide things, how to obfuscate, and then how to discover those things and detect it. And if and if it it can give us things that we never thought of, like I think we're in, we're gonna go through like a zero knowledge phase. I don't know if that's a that's a term or not. But the idea is we think we know what we're trying to accomplish. But I think there's gonna be some tools that come out that are gonna say, that's not what you're trying to accomplish. Go back to not square one, but square zero. And we're going to solve a different problem, but it's going to have a way better outcome than what we wanted from what you were trying to do. And this is going to have just a revolutionary different approach to securing things and building and all this sort of thing. The building thing is not what you're asking, though. You're not saying, hey, what about building with AI? You're saying, what about security with AI? And I think having these tools at our disposal is incredible, incredibly powerful to do it. And and like when Copilot first came out, I'm thinking get GitHub's Copilot of like, hey, we can we've got this tool that can help you build. And I'm thinking, my first thought was, no, I don't want it to help me build. I want it to help me be secure. And if we can have these tools check for buffer overflows or check for insecure credentials or something like that, and 100% just like start with the unit testing and make sure that these 5,000 things check, go through the OAS pop 10 first and foremost on my code and only always prioritize that before giving me any other suggestions. I think there is a possibility that we can get to a building phase that, you know, building apps and stuff that are secure by design that don't even have the option of a human making an error and making it insecure, which will be fantastic, but that's not what co-pilot's doing. It's giving you all kinds of recommendations. I'm like, here's how to build this for loop and all this sort of stuff. And I'm like, that's not what I want. I want you to be secure. So it's cool that these tools exist to help us build, but I but I really want their focus to be on making it more secure. And I think with that, there's huge potential and and possibility here.

SPEAKER_01: 35:48

Yeah, I view it as something that will be disruptive in the very beginning, you know, like right now, I guess. But people will shift their view of it into, you know, using this AI to help me be more productive, to help me cut through, you know, all that manual process work that I would have to normally go through to achieve the same goal.

SPEAKER_00: 36:11

But again, it's a manual process that we weren't doing to begin with. We weren't looking at one million packets and trying to figure out what was happening. We we just we never even tried that challenge. We were giving computers that challenge from the beginning. So when you say this manual process, what are what process are you thinking we're doing manually now that isn't going to just be like that's a process, like three years from now, we're doing processes with AI. I don't think we were doing today, is what I'm saying. I don't think we're we're do we're doing it.

SPEAKER_01: 36:39

I think, you know, so I I look at a lot of you know people's environments in the cloud and whatnot, and there's a lot of customers of of Wiz, for instance, that they have Wiz, they plugged it in, right? Or whatever CSPM solution they have, and they don't know what to do with it, right? Because the solution is great. It has all of the findings, it has everything in it that you need to pull all the information together. It even categorizes it, but it doesn't prioritize anything. Should I prioritize this medium that gets people access to my environment that I'm not suspecting, or should I prioritize this critical that's already within the network that isn't really a critical in terms of access and ability for people to exploit it? So I think that that's where it'll, you know, kind of come in and assist, so to speak. Yeah. At least that's my opinion.

SPEAKER_00: 37:29

I just imagine if we had like extra capabilities that we've never had before, that is a that is a special feature. Not so much, oh, we're we're taking these 10 people and taking it down to one because this just does it more efficiently. But no, we're we're able to do things we've never done before. And that's by making sense of the data in new ways that like like making new rules, looking for new kinds of threats. Yeah. It's I mean, the attackers have the and and this has always been an arms race in cybersecurity, right? The attackers get this new exploit, they get this new attack tool, and then we have to figure out a way to defend it. We make signatures, we make detection rules, whatever, and spot it. And it's it's been a cat and mouse game. And it's gonna be like that with AI as well, where the AI gives the attackers new ways to do things, change voices, uh, clone emails, whatever. It's gonna be new tax surfaces that we may not have expected as well. And that we have the tools as well to like, okay, hey AI, you're used, you're being used to uh make these sort of attacks. What would you do to detect those sort of attacks, right? And so it's nice that we have sort of the the equal, equal playing ground for these kind of you know, attacks and defense thing that we have to do. And if you think about some sort of historically as well, is there might have been some nation-state level actors that have access to maybe some kinds of technology similar to this that we didn't have commercially because it just was out of, we we didn't have the budget to research it and stuff. And now it's kind of exciting to see these commercial companies building these. I probably imagine that this some of this AI stuff is way better than what the government can produce, right? And so I feel like the technology was asymmetric for a long time, where they had access to stuff that we didn't. And now I think it's like, nope, we've got the same tools as you. What are you gonna do now? And that is that is a whole new thing as well, I think, which is like an evil, even playing field.

SPEAKER_01: 39:21

Yeah, it's an interesting time that we're in because like so many things are are shifting at such a rapid pace, too.

SPEAKER_00: 39:28

Mm-hmm. Yeah, you and you, and I think it's important to keep your finger on the pulse whether you like it or not. Because if you say, you know what, I'm not going to adopt this, I'm not gonna care about this, whatever, the time is gonna change, the world's gonna change right right under your nose. And then you when you're ready to when you look up and you start to tune in, it's gonna feel so odd and strange and scary and magical. And I think that's a version of future shock, right? And so I think Socrates came up with this idea of if you were to go into the future and suddenly you don't recognize any of this technology and all this sort of stuff, you would you could you know have physical ill ailments in future shock and you'd feel feel sick and disoriented and everything would be strange. And and I think because the technology is changing so fast, it's easy to experience that future shock. And I've experienced it in small doses already with just like things like when Midjourney showed up or even ChatGPT, and suddenly this computer could talk and and it make images in ways that I didn't understand because I have a degree in computer engineering. And so I know how computers work. I know how the bits and bytes and all this sort of stuff happens. And I'm just like, I don't know how this app is talking to me like this. I don't know how this app is making images. This is crazy. And it gave me this sense of magic. Like I don't know what's happening. This is magic. There's no explanation for how it's able to do this. And I even took classes on TensorFlow and different PyTorts and stuff just to try to understand what is. This AI stuff everyone's talking about. And there is no connection between PyTorch and what ChatGPT is doing. I'm like, there is you guys are working on two different things here. This is not the same world at all. Because tensors are just like, I don't know, four or five-dimensional like bits of data. Where in the world is there words in there? There's not even words. So what is this happening? So it's just like it didn't match up in my head. And so I could not, for the longest time, didn't not understand how any of this AI stuff was working. And I tried and I tried and I tried and I couldn't. But what I what how I got there was instead of trying to like build it, like, okay, well, if I just build it, then I'll know how it works and it's not magic anymore and I won't feel this future shock. Instead of doing that, I decided to just try to become like a super user and use the tools over and over and over. And I actually made a thing where I was gonna be like, I'm gonna, I'm gonna do a hundred days of different AI tools and see and just try them all and see what happens. I think I got to day five before I hit mid-journey. And that was just such a cool tool that I was like, oh my gosh, I'm just gonna use this every day. This is the funnest thing. And I and I gave up on my my challenge. But did what it gave me this understanding of what AI has in its capabilities, right? And I and I again got to the world of like, okay, we're in this realm of what's possible because what AI did was it showed me obviously we're in I'm in a realm that I don't know what's possible anymore, right? And that's what Future Shock is. You don't know what what can be done and what can't be done. And you're you're just like you don't have a grip on reality because of that. And so now I got a grip on reality. I know what you're capable of. You're capable of doing these things and these things and these things. Great. And as I became like a bigger user of the tools, then that really lowered my fear of the tools. And I think it's important to just keep them going, keep aware of, be aware of what's uh capable out there and what tools are being used because you don't want to suddenly be in this world of like, I don't know what the world is capable of anymore. I don't know how people are doing any of this stuff. Everything's magic to me because that's a weird world to live in and it's scary.

SPEAKER_01: 42:43

That's a really good point. When uh when you did your AMA earlier in the year, I can't remember when it was. Were there any questions that you were hoping someone would ask you that didn't get asked that uh you might want to go down now?

SPEAKER_00: 42:59

I mean, I don't just work on a podcast, right? I I've been working on guitar and piano quite a lot recently and swing dance. I like to do swing dance. And so, you know, I could go on and on. And and this year also I've been studying a lot of Spanish. And so personally, just like learning and growing and doing all that sort of stuff. I'm just like so invested in these things that I could I could go on and on about all that. I don't know if there's a question there, but these are my passions, right? And so when you say, what do I hope people talk about? I hope people talk about my what I'm passionate about. And of course, I'm passionate about dark nadaris and I love talking about cybersecurity. This this is a really um fascinating thing as well. But these are some of the other things that I'd just be like, oh my gosh, yes. Guitar and guitar music theory and making music and all this sort of stuff is is really fun.

SPEAKER_01: 43:48

Huh. Yeah, that is something that I feel like people always would forget to ask, right? What else do you do outside of Darknet Diaries, right? I mean, what does that look like? What's your hobbies look like? That's a very like it's a I don't know, it's a simple question, but I could see how people wouldn't even think to ask.

SPEAKER_00: 44:09

I I like to word it, how what are you what are you learning these days, right? Because that I think if it's not work stuff just on your own. Because if you're learning something on your own, then you've got some sort of passion there and it's fascinating to you. And I think that's uh that drums up lots of conversation. But the other thing is uh I've really been dialing up health as well, and it's going to the gym way more than I ever have in my life and eating healthier than I ever have in my life as well. And I have my my morning smoothie here with me to have this conversation with, and this is this is a crazy smoothie. There I put like 20 or 30 things in it. There's so much that I put in this smoothie because I just try to jam it full of nutrients and good stuff for the day.

SPEAKER_01: 44:49

Yeah, no, as as I get older, I definitely pay attention more to it. I had this will Yeah. When I I had to think through if I wanted to discuss it real quick, right? But because we're already over time. But when I with my two and a half year old, now she's two and a half year old, when she was born, I like had a doctor's appointment just right after the time that she got out of the NICU. And so the NICU is like extremely stressful for me, you know. Like my kid almost died two or three times. It's like the worst, the worst thing that you could go through as a new parent. And uh, I have this doctor's appointment, you know, the Monday after she comes home. And the doctor, you know, asked me a real simple question while his nurse was booking me a room in the hospital uh behind my back I didn't know about. He just asked me, Do you plan on being there when your daughter graduates high school? I said, Yeah, of course I'm gonna be here. And he's like, Well, do you plan on like walking her down the aisle and whatnot? I was like, Yeah. And he's like, Well, with what I'm seeing right now, you won't make it. Like, you won't make it to her eighth grade graduation. And so, like, that just like reshaped everything immediately for me. And now I'm down almost 40 pounds from where I was, you know, like working out, being very mindful with what I eat. I do intermittent fasting every single day. I'm like, I haven't even eaten today, right? Just doing everything I possibly can to be here for that little girl.

SPEAKER_00: 46:19

Yeah, it's amazing how completely changed me. Rechange your goals and priorities because they they definitely have that effect on you. It's like it's like almost hitting reset on yourself as well. Because when when you're like, oh, okay, we've got this little kid, you can also look at yourself of like, well, you know, if the kid is going to have to learn all this stuff, and maybe that's something I haven't learned myself, that gives me time to learn these things, right?

SPEAKER_01: 46:44

Yeah.

SPEAKER_00: 46:45

And so there's there's idea that comes to mind that like if you gave up on trying to learn cello or something, but you think your kid can learn cello in your lifetime, then you're like, well, obviously, then there's enough time for me to learn cello in my lifetime, right? So like it just reshapes the whole time span of of your life and and and resets a lot of stuff. It's really a powerful thing. The oxytocin, right? Yeah. Oxytocin is one of the things that I really try to deliver in my show. And I do that by getting you to connect with the guests and feel what they're feeling. And I think the more closer, like if the guest is vulnerable and has this kind of openness to them, you get this sort of oxytocin where you feel sympathetic towards them and sort of thing. And that oxytocin is, I think, a wonderful drug. It's it gives you these things of like empathy and calmness and happiness, and there's all sorts of really great feelings you get from oxytocin. And you can deliver it through storytelling. So I'm always researching oxytocin. And in fact, uh, to extrapolate that even further, you could just say that my operating system nowadays is wetware because that's the brain. And I used to work on operating systems like computers and stuff, but now I'm working on the brain because I'm a storyteller. And I have to try to get the thing, I have to try to get the story into your head in the most amazing way so that you enjoy it the best, but then also remember it and it impacts you and it changes you and inspires you. And in order to do that, I have to I have to know how your brain works to uh deliver it as best I can. Yeah, wetware is my it's my new thing.

SPEAKER_01: 48:17

Oh well, Jack, you know, we're we're already over time, unfortunately. This was fun, a lot of fun. Oh, I I really appreciate you taking the time to to come on, you know, to even respond to my email. Like it's it's always very appreciative, appreciated on my end. Yeah, keep doing it.

SPEAKER_00: 48:35

It's awesome.

SPEAKER_01: 48:36

Yeah, definitely. Well, Jack, before I let you go, how about you tell my audience if just in case they've been living under a rock where they could find your podcast and where they could find you if they wanted to reach out?

SPEAKER_00: 48:46

I I challenge them to put Darknet Diaries in any search engine and see if they can find it. If if they find a search engine that it doesn't show up on, let me know because I want to get it in there. Darknet Diaries, that's all you gotta type. Search engine of choice. Awesome.

SPEAKER_01: 48:59

Awesome. Well, thanks, Shaq, and thanks everyone for listening to this episode or watching it, whatever platform you're on. I really appreciate it. Thanks, everyone. Bye.