67: Host File with Jack Rhysider

This episode has been automatically transcribed by AI, please excuse any typos or grammatical errors.

Chris: I’m here with Jack Rhysider, a linchpin in the security industry and creator/ host of the extremely successful Darknet Diaries podcast. Jack, welcome to BarCode.

Jack: Ah, thanks for having me.

Chris: Yeah, absolutely man. So this is actually the first time that you and I have had the opportunity to converse one on one.

Chris: So I’d like to start at the root of your legacy. Many of us know you or recognize you as the voice of Darknet Diaries, although your cybersecurity career actually spawned within a knock. So would you mind just talking us through that time and what caused you to reroute your career to security?

Jack: Yeah, so I got a degree, a bachelor’s degree in computer engineering, but it was very general, right?

Jack: So it was like one of every technology was part of the curriculum and I didn’t feel like specialized and I had trouble finding a job out of college. So I did odd and ends odds and ends stuff for a while, but then I was like, Oh, I gotta get back into tech. That’s where my heart is. So I got. CCNA certifications, Cisco Networking associate, and that got me a job at a knock network operation center.

Jack: So from there I was watching networks up, down status troubleshooting. And, and, you know, escalating where it need to be. And I just kept going. I was like, Well, let me get my CCNP, you know, the professional level cert. And so I just started testing for that and I was like the only one in the knock that had that level cert.

Jack: So they’re like, You need to get outta here. You need to go to the engineering role. Where you know more professionals. Are doing stuff. So I was like, Yeah, I’d love to, let’s go. They said, Well, we don’t have any like, you know, route switch positions open, but there is a security position open. And at the time I didn’t even know like how to do some basic commands on a firewall.

Jack: And so I was like, Oh yeah, I want any engineer job. I don’t really care what it is. So I applied and they liked me and, and took me on. So from. I went crazy into security just getting all my security certifications and stuff like that. But what I realized was this is where I’ve always meant to be because in security you need to know a little bit about everything.

Jack: You need to know, a little about coding, a little about CS admin, a little about. Networking to really understand the whole picture of why an attack happens and how to secure, like systems holistically. And so having that degree really helped me just get in the game mentally and understand the whole like ecosystem of how everything works and comes together.

Jack: And I just, I just sort, I just love security and I spent 10 years as a network security engineer. Even built out a, a sock, a security operation center, which was an enhancement to our knock. And yeah. And at some point I was like, Oh, where are the podcasts that are, that are really into like high drama storytelling shows that talk about hacks and cybersecurity, you know, stories from the trenches at time where it was like the worst day of your life at work.

Jack: Let’s hear that story. Let’s hear how you, you know, got through that and or what happened when you attacked, you know, a network, whatever. And so I didn’t hear, I couldn’t find those show that those podcasts and I really was into podcasts. I was like, Oh, shoot, maybe I gotta try and make this myself. And that’s where I got the idea of L all right, let’s make Dark Net diaries.

Jack: And that was so successful that I just ended up switching over to that and do that full time now.

Chris: Nice. So what type of podcast were you into at that point? Were you into Tech podcasts? Was it True Crime podcasts? You know, I’m just curious what genre had your interest at that point.

Jack: Yeah, there was A lot of ’em.

Jack: So I think Serial was something that really got me back into podcasts. I think before that I had tuned in a little and was just like, Ah, there’s a couple guys talking. I don’t really care about some of this stuff. Right? It was hard to find good stuff. But then when Serial showed up, I was like, Oh, this is amazing.

Jack: And then of course I’m like, Oh yeah, of course this American Life is here. And Radiolab, I love that. And you know, 99% invisible. All these. All these really popular shows. I was like, Oh wow, I can listen to these, like the whole back catalog. This is great cuz it, you know, this used to be just on the radio and you’d only, you know, get the last 10 minutes and you’re like, ah, I wish I that was here for the whole show.

Jack: So, you know, going back and being able to listen to all these was great. And so that’s, you know, what I was into, but at the same time I was learning as much as I could about security, right? So I was listening to down the security rabbit hole, Paul’s Security Weekly, and then you know, Risky Business. All these like news security shows and, and interviews type security shows. And, and a couple of them actually did have some good stories. I remember when Paul Security Weekly interviewed John McAfee. I was so glued to this whole story because this is a guy who’s been on the run and accused of murder and all this kind of stuff, and I’m just like, What?

Jack: I’m so, I’m so glued to this story. What is happening here? This is the craziest InfoSec story ever. And so, you know, those kind of things made me think like, Oh man, there is such. Space here for having a really interesting a, a security hacker story that can just glue you the whole time and get you into it.

Jack: And, you know, we’re in this age of like, everyone knows about hackers today. You know, you’re Barbara, your 10, it doesn’t matter who’s out there, they all are talking about hacks and security. So it seems to be something the masses could appreciate too.

Chris: Yeah. And it’s ironic that you mentioned the John McAfee interview because now you have running with the Devil on Netflix, Right? Which is, is looking through those interviews of John McAfee. Mm-hmm. Which is, which is insane. So yeah, as a security engineer I believe at that time you were also, you were also writing articles online, right? So do you feel like. Creative outlet that you were doing then ultimately led you into the podcasting realm, or do you feel like podcasting was something that you had already had your sites set on?

Jack: Yeah, I, I do think it was kind of like a stair, a staircase, right? So jumping into podcast is not like your first step and just maybe online creating. So yeah, what I was doing before that was blogging for seven years, I was throwing out random YouTube videos, like, Here’s how to do this.

Jack: Here’s how to use this tool. Here’s how to, you know, sometimes I’d give a talk somewhere. And a presentation maybe to my team, maybe at a conference, and then I’d record that and put it on YouTube. You know, like things like this. I was just kind of producing little bits of content out in the world. And so, you know, I’m building a brand, I’m building a name, I’m, I’ve got social media started, you know, I’ve got all this stuff that was already in gear before making the podcast.

Jack: And I think it did pave the way in many ways, especially blogging. And presenting stories, right? So in my mind, that first episode was, this is a presentation that I’m doing, but I’m trying to make it as entertaining as possible, right? And, and so that’s, that’s kind of the basis where I started from is, I don’t know how to make a documentary.

Jack: I don’t know how to be a journalist, right? But I do know how to present to my team at work when I have some, you know technology I want to teach them or something I learned at a conference. So I, I, I just. Wore that. In fact, my first episode I made a PowerPoint presentation and you just don’t see it.

Jack: Right? Cuz it’s a, it’s a podcast. But I’m, I’m kind of flipping through the slides as I’m, as I’m telling the story. , because that’s what I knew. Yeah. So yeah, I think coming from like, and especially like blogging because that, that was like you know, Troubleshooting in, in these blog posts, right?

Jack: If you get this problem, here’s how to solve it, kind of thing. But what that taught me was, well, we’ve got this really complex problem and there’s this really complex solution. How do I make this as easy as possible? What, what are some of the complexities I can get rid of? What are, what’s the base problem here?

Jack: Right? So I’m, I’m kind of pushing away all the other. You know, stuff that isn’t really even part of this problem. To be able to just explain these complex topics as simple as I can. Sometimes I’m explaining what a VPN is and how to like build it from scratch. And so what are the core parts there and how, what does this mean, a hash and what does this mean?

Jack: Encryption and Diffie Hellman and all this kind like stuff, and do I need to explain it and stuff. So just kind of walking through like how to explain things to the world in a way that is just what they need and not too much or not too little. And I just think seven years of practicing that was really helpful as.

Chris: I love that because in our field it can get very technical and a lot of times it is hard to, to segment that technology from communication and being able to talk through that and properly communicate it, is a huge skill.

Jack: Yeah. I think listening to podcasts kind of built helped me build the language as well.

Jack: You know, I, I’d listen for a long time security podcast and then talk to my customers and be able to use some of this flowery language, you know, of like adversary and threat actor and all this kind of stuff where, yeah, you know, before you didn’t, you didn’t maybe hear that stuff because you’re not in that space.

Jack: You don’t have your team that’s talking like that and stuff like that. So, yeah, I think podcast just really taught me a lot as well.

Chris: Now I would like to ask you about an aspect that I’ve noticed about you that by the way, I have the utmost respect for, which is the, the anonymity aspect and your decision to mask your own identity.

Chris: And I’m just curious, is this because you are, you know, a, a practicing privacy advocate, or would you say there’s a dangerous side to what you do where. You feel as though you need to conceal your identity for safety concerns.

Jack: Mm-hmm. When I was in high school, I had bought something on eBay and the guy canceled the listing and was like, Oh, I still have the item, but can you want Western Union me the money?

Jack: And I was like, Okay. And you know, I went back and forth. I was like, Right, this is fishy and stuff. But eventually I was convinced and so I sent the money and never got it. And so this is kind of a life lesson of like, Oh, the internet can scam you and you can like, Burned in, like, so you learn like how to like step back and be like, Okay, I can’t trust everyone out here.

Jack: And another one of these kind of life lessons was when I was, you know, before I was podcasting, I was putting these YouTube channel YouTube videos out. And one of ’em was, I don’t know, it was just me setting up like a solar panel or something like that. And the, there was a fan who just loved it so much and loved my delivery and what was in the background and like the scene set up and all this kind of stuff that he, he tried.

Jack: Messaging me on YouTube, but I didn’t respond, I didn’t see it, whatever. So then he was like, Okay, well where is this filmed? Right? So there’s a back, a mountain there. Oh, is that a street sign? Okay. So they’re like finding things in the background of the video and then pinpointing like, where I filmed this, which was my house, and then looking up the county records of who owned that house, finding my name, and then looking up where I work, and then emailing me at work.

Jack: Geez. Yeah. And I was like, Wait, what? Who are you? And they’re like, Oh, I’m your biggest fan. I just wanna say hi. And if you’re ever in my neighborhood, we could hang out. And I’m just like, Whoa. And, and so I had them explain to me how they found me, and yeah, that was kind of one of these, Oh my gosh. Do I want this as a creator?

Jack: Yeah. That everyone, anyone and anyone can just find where I work, find like my location, find where I live, all this kind of stuff. No, no, no. So I took that video down and I just kind of scrubbed myself from the internet. And like really took it a lot more seriously at that point. There was a book that I really appreciated by Mike Bezel called Extreme Privacy, How What it Takes to Disappear.

Jack: Yeah. And yeah, it’s kind of step by step like here’s how to set up your computer, your phone, your mailing, you know, system, all this kind stuff so that it is harder for people to find you online. And so, yes, I am a big privacy ex you know, proponent and I love. Like just practicing it as well. And I, I get scared when I see people oversharing online.

Jack: You know, here’s my, I got my first driver’s license. Yay. Or look at my kids, or first day of school how excited they are. And, you know, we’re on a trip somewhere. It’s like, well, you’re obviously not home and someone could rob you. You know, like there’s just so many red flags I see online on social media that.

Jack: I’m just like, Okay, I’m definitely happy I’m taking this more back. You know, you gotta pull back from the internet. You can’t overshare, you can’t share what’s going on in your family or where your location is or what your picture of you is and stuff like that. To, to keep this privacy. But I think it’s important and worth it.

Chris: Yeah, that’s understandable. I mean, I think as a security professional, you know, paranoia runs through my veins as well, and, and there’s been many times where I’m just. I need to go off the grid. I need to go off the grid. And then when I talk to people that I see, you know, willingly posting information, you know, it feels like it’s my responsibility to, you know, say something and, and educate them.

Chris: So I definitely get where you’re coming from.

Jack: Yeah, the best, the best time to do it is when you’re gonna move and you can put like your new address and all that kind of stuff into. Like a different identity. Yeah. Right. Because a lot of times when your, your, your current location is sort of permanently burned and it’s in too many databases and it’s connected to your name in too many ways.

Jack: So that I think is the best time. If you ever feel like, Okay, I need, I really need to do it when you’re moving, like, look it up, like extreme privacy is the book that, that I recommend.

Chris: Awesome. So, yeah, you’ve become, you know, exceptional at the artist storytelling, and you know, in my opinion, listening to your show, you continue to sharpen that skill, you know, with each episode that you release.

Chris: And you mentioned this a little bit before with the YouTube videos that you produced and the, and the content that you’ve developed over time. As you look back, do you feel like you’ve always had a natural ability for storytelling? Maybe just in a d. Method or is that something that you had to research and a skill that you had to develop over time to get you to the pinnacle of where you are now?

Jack: Yeah, it was definitely a skill that I’ve researched and fine tuned. It started with me reading the book out on the wire and this is one where they interview people like Ira Glass Roman, Mars, Ja, Arod storytellers in the, in the podcast and radio. That are kind of kings of storyteller. And so.

Jack: You hear how they break it down and you hear how they think about a story. Like for instance, they use a formula. Sometimes I think iron glass uses a formula. This is a story about X, but Y happens instead. And you start plugging in these, these pieces. And the thing is here is you want the story to go in a certain trajectory, but then it’s going to take a wild.

Jack: Right, and that’s what it means. But this is a story about X. You think you’re going in this direction, but Y happens instead. It takes this crazy turn. And so you have to kind of think about, okay, what direction are we going to go in to start? Instead of, let’s just go straight into the craziest part that happened, right?

Jack: And so you want kind of the, this, you know, this unexpected turn and stuff. So there’s a lot of different formulas like that and ideas. And, you know, the craziest thing to me is that it actually changes the chemicals of your brain in certain ways. Like if there’s a cliff hanger that gives you this sense of.

Jack: Oh, something, something is gonna happen and I, and I’ve gotta get tuned in. Right? And there’s, and there’s certain chemicals in your brain. I, I don’t remember exactly what, maybe it’s oxytocin. You know, when I, when I say a joke, then there’s dopamine that comes into your brain. Right? And like, it’s just wild to me that I can say something on a microphone and it can trigger chemicals in your brain to be secreted and you can feel certain.

Jack: Feelings and emotions and stuff like that. And I’m just like, this is the most amazing, powerful thing I, I know of to be able to, to give people this like chemical cocktail to as they’re listening. And yeah, I mean, let’s do it. Let’s have fun there. I mean, this has gotta be a wild thing that we can do together.

Jack: So, yeah, I mean, that’s kind of how I approach it is like, well, Let’s see how let’s see how glued I can get the listener if I can make them levitate, right? They’re on the edge of their seat. They, they can’t wait for the next moment. They’re disappeared from their world, whatever it is. Like, I really want them to get into it.

Jack: So, yeah, I’ve taken it seriously and I’ve, I’ve also, like, I think there’s a Khan Academy class that partnered with Pixar called Pixar in a Box, and they teach the art of storytelling and you know, how character development works and all this kind of stuff. And so I’m always just. More interested in how other shows are doing it and how, you know, some of the best storytellers in the world are doing it.

Jack: And, and yeah, this was something that I just dove into and spent maybe the first 20 to 40 episodes just kind of practicing and doing different things and, you know, editing different ways and moving stuff around where, Okay, instead of saying that at the beginning, let’s put that way at the end. Let’s hold off on the, you know, this, or let’s put that early, or, you know, all this kind of just mechanics.

Jack: Of how it works and yeah, I think it, I think it’s a lot of fun to do. I don’t know if I can, maybe I come natural at it cuz I, I’m working with other people who don’t quite get it, but it’s maybe my style as well that that’s how I

Chris: do it. Nah, I love it, man. And, and it’s seeing that reaction that you bring, not only from the entertainment side, but also that high of just knowing that you are solely providing that, that mental vision for people.

Jack: It’s a theater of the mind, I call it sometimes.

Chris: Yeah, absolutely. So I saw a tweet from you the other day, and it, I think you posted, you know, your highest download episodes, right? Your or your, the numbers, your metrics there. And I think the highest downloaded episode was just over 850,000.

Chris: If I remember correctly, man. And that’s just, that’s fucking incredible, man. , you know, I can’t, I can’t fathom that at this point. But other than time itself, what do you feel has helped contribute to such a high listener count and download count? And even more importantly, you know, what do you feel is the key to continuing to scale that?

Jack: Yeah, I mean, when, when this kind of came around, I was really, you know, chomping at the bit, like, I need to make something, I need to do something. Right. I’ve always, ever since 1999, I’ve been like, Oh, I need to be an online entrepreneur. Right? Some sort of, let’s make a website, let’s make a something as a service.

Jack: Let’s make something. I’m ready. And like, so, you know, 20 years of just being so ready when I finally had something to. Let’s go, let’s market this. I had already like, you know, studied entrepreneurship and marketing and all this kind of stuff. Seth, Seth Go is probably one of my favorite marketers. Gary Vayner.

Jack: Chuck really kicked me in the butt to like, go, go, go. So like, all this kind of stuff just kind of came like, okay, let’s just, let’s, this is ready. Like, you know, I’m 10 episodes in and I’m just. You know, the, the audience is like, We want more. We want more. I’ve listened to every episode twice. Where’s the next episode?

Jack: Come on, gimme more. And I, I kind of get that wind of, Oh my gosh, this, this could be big. And so I was just like, Let’s go, let’s just throw as much fuel on this fire as I can. So that’s kind of when I quit my job and I was like, Alright, let’s just market this like crazy. So social media has been like, just a big thing, like just being present there, being part of the community.

Jack: I think being part of the community goes a long way, right? It’s like, Oh, you’re one of us. We’re con we’re having conversations together. You’re reachable. You’re, you’re here. You know, if you’re in. If you’re in a community and then someone’s trying to come from the outside, like, Hey, listen to my stuff or something, you’re like, I don’t know who you are.

Jack: But if, if somebody in your community is like, Hey, I started this thing, and other people in the community are like, Oh, it’s good. You should definitely listen to it. Then it, then it works. Yeah. Right. So, you know, I was, I was speaking at conferences already. I had a blog already, you know, so I, I had like some sort of community involvement just in InfoSec Twitter and on Reddit and this kind of,

Jack: So, yeah, I mean, that’s where I think things started mostly on Twitter. Just getting crazy on social media, just posting like crazy. Not always about podcasts, but jokes or stories or news articles or how to, or look at this malware that is out there. It just being part yeah, I, I, I could go on and on forever about marketing, but I think the, probably the biggest thing is word of.

Jack: Probably spread the, spread it the most. So getting a listener to share it with another person. And so I heard so many stories and this is what I asked at the end of a lot of episodes. It’s like, look, the thing that will help me the most right now is not for you to subscribe or, or spend money, send money, or whatever the case is, is just to tell one other person that they should check out this show.

Jack: Text someone right now, Tell your friends at work, tell your family whatever it is. Just please bring someone else here as a listener. And that’s what I would ask. And you know, you put it all in that way, then they’re like, Okay, I think I can help Jack out. So you’d hear, I’d hear stories about it. Like, you know, we went on a drive and I had my whole family listen to it on the, on the car ride or I went to work and I, I made my whole team listen to it at work.

Jack: And now we have like, you know, Tuesday. Or Tuesday afternoon, you know, listening parties or something. Cuz I like to publish every other Tuesday. So, yeah, I mean that was, that was, I think, spread the most is word of mouth. Yeah,

Chris: that’s, that’s great advice. Especially about just, you know, tell someone else, just tell one person to listen to my show and, and see.

Chris: And then also having that cred, you know, having that cred in the security industry. But then, then once it took off, you know, you’re reaching entirely outside of the security industry. , do you get, you know, hit up often from those listeners outside of security and how you’re affecting them?

Jack: Yeah, definitely.

Jack: And a lot of people are getting. Into security because of it. They’re like, Oh, I’ve always liked computers and, and hacking and stuff. I just didn’t know there was a whole place that I could be part of to like be part of like, do that. I’m quitting my job as a painter and I’m switching over to InfoSec. But yeah, I get a lot of I get a lot of like, yeah, non-security people who, who message me and say they’re into it.

Jack: It’s really wild. But I think, you know, the core audience I want to reach is that security community cuz I want them to have this sort of fun. Feel drawn into the story and be like, Eh, I’m part of this. Like, this is my career. This is what I’m doing. And you know, like, like you connect with them in a, in a way that’s profound.

Jack: And, and they’re gonna, they’re gonna, yeah, they’re gonna take you and share your stories with their family. And now, you know, you know, people are like, Oh, my, my spouse never could understand what I do. But now, after listening to this episode, they now understand. And they can’t stop listening now. Yeah.

Jack: They wanna hear all this stuff. So, yeah, it is really fun to see it expand out, which I’ve always been kind of on the fence of like, who should I really make the show for? And I, and I never really landed on either side. I want it to be accessible for everyone, but I also wanted to be not boring for the InfoSec community and just as fun and, and exciting to listen to.

Chris: What’s one aspect that Darknet Diaries has provided you that you didn’t expect? Was it the, the pure success that you didn’t see coming? Was it the knowledge that you gained from conducting interviews or was it, you know, relationship building as well? What, what’s something that, you know, as you’re playing this out, sort of just took you off on a side road?

Jack: Yeah, I think the gratitude I’ve gotten from fans is something I did not expect or know how it was gonna affect me. You know, I, I had in my head like, this could make me some money and I could quit my job and do this. And you, you’re thinking like that, right? Like, how can this, how can this make me money so I can just do this all the time?

Jack: This is fun, but, When you see people send you letters of how the show has totally changed their life or saved their butt, or it got their, got them a job, like, you know, mentioning that they listened to the show in, in a job interview, or this is what they base their you know, report off of in high school or something like that.

Jack: It’s like remarkable to me, and it makes me feel a, a way that I’ve never felt in my life to kind of put your artwork out there in the world as I feel like it is a piece of art. I’ve got like all kinds of songs in there and there’s storytelling, crafting, and all this kind of stuff. So to put like your own thing out in the world and then for someone to just pick that up and love that and take that to make their own meaning of life.

Jack: And I, no, that, that’s just like a feeling that I’ve never had before. Just it’s so profound and it, it gives you, gives me a high that it’s just wonderful that it’s clean and pure too. Right? So it’s, yeah, that’s just something that every time I’m step back and like, I can’t believe people like it this much.

Jack: And I don’t really know what to do with that, but it’s just such a, a wonderful feeling to be able to help people in the world or give them that kind of entertainment or whatever it is in that way. Yeah, that’s, I did not expect that to kind of carry me through some of the downs as well, Right?

Jack: Cause when you’re like, Ah, I’m just worn out, I don’t wanna do it, and stuff like that. And then you see this email of somebody who’s like, Oh my gosh, this is such a helpful show. Please don’t ever stop. And you’re like, Okay, like I guess I, I’ll pick up the mic and go again, .

Chris: No, that’s amazing, man. And, and you’re changing and, and altering lives and perspectives by the masses at this point, so.

Chris: Mm-hmm. . Now if you could go back to a point in time where you started Dark Net Diaries and was that 2017 I believe? I think so, yeah. Okay. Around that timeframe. So if you could go back to that point and, Talk to yourself or provide yourself with one piece of advice to maybe, you know, cut corners that you couldn’t cut at the time, what would that be?

Jack: Oh, we’re getting philosophical here. I love it. . So the problem with this question is like, I feel like I had to go through all the problems in order to get to where I am. Right. And if I didn’t go through those problems, I wouldn’t be who I am. And so I feel like I wouldn’t wanna give myself any advice cuz I needed to get through it.

Jack: It’s hard. Like I, I’ve surely I hit many mistakes, but they’re just kind of mistakes that I’m like, Okay, I’ll just fix that for next time and keep going. Right. So It’s, it’s really hard to, to go, to, go back and give myself advice. I have a tough time with that one. No. And I like your perspective on knowing that you’re going to make mistakes.

Chris: You had to make those mistakes, or you had to go through that failure point to make yourself stronger.

Jack: So one of the, one of the other things I did was just really just jump into the podcast world and I was going to podcaster meetups and I was calling up other podcasters and in podcast mastermind groups and just talking to podcasters as much as I can.

Jack: And this gave me like new connections and like mentorship and ways that I never, ever expected to get mentorship. And yeah, I mean like I was getting fed like tons of advice from really important people out there and helpful people. And so it was just kind of like, I’m sure there was lots of advice that came to me that I was just like, I don’t know what to do with this.

Jack: I don’t understand what you’re saying, kind of thing. And or just I don’t care. You, you, it’s just kind of out of context advice that you don’t know what to do with, but it’s the advice that I had that under I understood at the right time and helped me at that time. That was really the most profound and.

Jack: So if I come back and I say, Oh, hey, you gotta read this book or something, right? You should read this book earlier than later. You’d found it too late. Maybe that book wouldn’t have fit in. You know, my worldview at the time where I’m just like, I’m not ready for this or this isn’t, you know, as helpful as I thought or something, cuz.

Jack: It wasn’t ready mentally. You read a book at some point in your life and you’re just like, Okay, that was nothing. But then you read again later and you’re just like, Whoa, this is so profound. What, what’s different about it is like, you’ve got some new experiences, you’ve got some new perspectives, and so yeah.

Jack: It’s a philosophical question that it confuses me sometimes.

Chris: Yeah. You never know. Right. As a top ranked podcaster, what underrated tool would you say is indispensable for you? And when I say tool, you know, that could mean tech, that could be data, that could be your mindset, you know? What do you feel is a weapon within your artillery that you use that you could never part with?

Jack: Hmm. That’s a good question. I mean, I have. Like if my laptop were to break or go stolen or missing or something, it would really put me back like a few weeks to get ready and go on again probably. So I would, I think my laptop probably is my most important tool. Okay.

Chris: And on that laptop, I’m sure there’s, you know, the tech, the data and the mindset, right?

Jack: Yeah. You know, and so, Maybe it’s not even that important cuz I think I could, everything’s backed up and I think I could restore pretty quickly, but, I think the mindset really, like you said, if that’s, if that’s an, if that’s an option for one of the tools I do have this kind of growth mindset that it’s, yeah, I, I don’t know how to do it now, but that’s not gonna stop me.

Jack: I’m gonna just like figure it out kind of mindset. And a lot of people, you know, they have this mindset where that’s not my job. It’s not my, I can’t, I don’t never been trained on this. I don’t know how to do that. And they just kind of give up. And so I don’t really have that mindset mind’s more resilience of, okay, I’ve hit a.

Jack: I have, you know, the ground is paved over. I can’t grow any trees here. But look at that. There’s a crack in the sidewalk and a weed is growing, and I want that kind of attitude of like, I don’t need to be you know, watered or fertilized. I can grow out of a crack and a sidewalk. And I, and that, to me, that is that one opportunity that you’re gonna give me.

Jack: I’m gonna take it and I’m gonna, I’m gonna go crazy from there, right? So, Every time I see a we a weed growing out of crack in the road or the sidewalk, I’m just like, you are my spirit out of right there, , because I wanna be that, that tenacious in life to just grow wherever and just flourish in the most unlikely place.

Jack: And you know, sure enough, if you give me a nice place to grow, I’m going to, you know, do even better. But this is, this is what you got.

Chris: I’m gonna look at weeds in the sidewalk from a completely different perspective now.

Jack: Yeah. I can’t believe they’re doing that. You know, you’re, you’re trying to grow like a, you know, vegetable in your back yard and it’s like, come on, it’s not working.

Jack: That keeps dying and all this kind of stuff. And then you go on the, in the front and they’re like, What? What? Why is there weed growing out of the sidewalk and I can’t even get this growing? Yep.

Chris: So you’ve done a lot of interviews. Out of all of the interviews that, that you’ve conducted, out of all the people that you’ve met, do you feel like there’s been a takeaway for you that supersedes other takeaways?

Chris: Like have, has there been a specific story or a specific action or maybe even a line that someone has said to you that has just heavily impacted you, you know, beyond your expectation?

Jack: I think one of the one of the episodes that really. Made me, I don’t know if it broke my brain, but it made me just kind of not know what to say, was when I interviewed the guy from the Pirate Bay. Oh yeah. And this is this is a guy who just has a totally different way of thinking about everything in the world and You, you ask him something like, Well, isn’t piloting illegal? And then he starts talking about, Well, you know, let’s talk about what country you’re talking about.

Jack: What’s legal? It’s illegal in and like, like he just short circuits. All of like, like if you, if you throw a punch, he’ll somehow redirect it so that you hit yourself in the face. You know, like, it’s not like a fight with him. He’s just like, he dis he disarms you in a way that’s, I don’t know. It, I just wasn’t prepared maybe.

Jack: And so, Yeah, this guy just really made me think about like, you know, he, he got arrested and was sent to jail, but then he’s like, Well, I didn’t wanna go. And so I thought it was an optional, so I just didn’t go to jail. . I’m like, Wait, it’s not an option. The cops are gonna come. And he is like, No, I don’t agree.

Jack: I think it is optional if you need to go or not. And I was like, No. And so, you know, we had this conversation of like, what, you know, everything was just so crazy.

Chris: Yeah. How do you reason with someone like. Maybe that’s just in their mind. That’s the way it’s gonna be.

Jack: Yeah. And, and this is, this is one of the things that I think is important to the way I tell the story is I don’t want to tell anyone’s story unless I understand their story.

Jack: And if I don’t understand why they did a certain thing, why, you know, say there’s someone who attacked their school and took down their school, like, well, that sounds like a jerky thing to do. Right? But I don’t wanna, I don. Feel that way at the end, I want to feel like, Oh, I completely understand it. I may have done the exact same thing myself because you were bullied all your life, or you had, you know, some issue with that teacher or something, whatever the case is.

Jack: And now you had that crazy opportunity and you were curious and the principal really pissed you off that day. Whatever it is, I wanna know those reasons, right. You know, if I’m in a, if I’m in a situation where I just don’t understand anything of what this person’s saying yeah, it really does help me say, Okay, well let’s break down.

Jack: Let’s get down to something that we understand in common or something. We’ll keep going from there. And so I might have to just keep going backwards until we find a space that makes sense to me, and then we can step from there and say, Okay, that makes sense. That makes. And, you know, by the end of that episode, I was convinced like all this other stuff.

Jack: Like and, and that’s what’s fun is for the listener to get this new perspective of something that they had never thought of before or considered or challenged mentally. And, you know, and, and I love that. I love giving listeners just a whole new framework of thinking through things. And I think that one really nailed it of here’s a whole nother framework of how to think about piracy.

Chris: It’s such an unexpected perspective. As a podcast/ content creator, we strive to deliver product at an intensely fast frequency. I know you’re every two weeks. I’m every two weeks. I would love to do it more frequent. From your experience, what would you say is your. Favorite or most used productivity hack for entrepreneurial podcasters and other creators?

Jack: Yeah. I mean, I, I think at first you gotta, you gotta look at the, the frequency of how you want your stuff. And I think there’s kind of two, two schools of thought here. Someone like Gary Vayner, Chuck is saying something like, Hey, just get out like an episode a day or a video a day and just go crazy.

Jack: And if you’re doing that, do two a day, get, get even more stuff out there. The more stuff you have out there, the. People can listen and find you and find stuff they love and it’s better that way. Trust me. Just go, go, go. And then there’s the other school of thought, which is maybe more like the Dan Carlin idea.

Jack: He makes hardcore history. He creates one episode every three months. Right? . So, or, or one story every three months. It might be like a five part episode, but he’s just like, It’s done. When it’s done. Don’t rush me. I will have it done when I’m ready. And that’s that. I love that because his concept is I want everyone to be fully caught.

Jack: I want my listeners, my fans, to be fully caught up on my show and hanging on for the next one and wanting that next one. While there’s no one on the planet who has listened to all. 4,000 episodes of Gary Vayner Chuck’s episodes. Right. I mean, it’s very repetitive and it’s some of them are not as good as the other, so you kind of jump around and you, you just can’t listen to it all.

Jack: Yeah. And so, which, what, you know, you gotta start out as a creator. Like do I want them to listen to everything or just flood them with stuff so that there, there’s always something fresh and there there’s just ton of con content so that they can get. And I mean, that’s, that’s kind of square one, right?

Jack: And so now productivity hacks to get it, get it done. I maybe I’m just one of these like mutant that is just really high powered and getting tons of stuff done throughout the day. But yeah, I’m, I, I am one of these people who. Is like tenacious at just getting work done. And I’ll, I’ll take on the hardest stuff first, get it out of the way, and then all the, all the little things after that can just kind of be rapid fired, completed.

Jack: But yeah, I think you know, single. Single tasking helps a lot. Don’t try to multitask. Turn off everything else. My phone has been on silent for years now, ever since I started the podcast. It’s been mu muted, completely silent, and you know, I’ll turn off emails and everything else and just focus on whatever else I have.

Jack: To focus on. And yeah, there’s this concept of like, you know, kind of being in deep thought and getting in flow state. And those are my favorite parts of having like, no, no distractions, nothing’s messing me up, and I could just focus on this thing I’m working on, whether it’s writing a story or troubleshooting something or whatever.

Jack: There’s just no other like, distraction or even like, worry that I’m neglecting something else going on out there that I should be working on. You’re just in this and, and you’re feeling it and you’re in it. And yeah, I think that’s the way to, to get through like the important things in your life is to find that flow state and remove all other distractions.

Chris: Yeah, don’t underestimate the power of single tasking outside of Dark Net diaries. Do you still have time to listen to podcasts? And if you do, can you recommend three I should be listening to, and let’s say industry agnostic, right? It doesn’t need to be security, but what, what interests you and what do you think, you know, are some other podcasts that are just as high octane as yours?

Jack: Well I, I kind of like, I’m in this phase right now where I’m into sort of philosophical ones, make me think but also a little bit weird. Maybe a little bit funny. So there’s a podcast that I’ve been listening to right now called Futile Attempts at Surviving Tomorrow. And yeah, it’s a bit poetic, a bit philosophical and a bit weird.

Jack: And then I also like philosophies this, which is about philosophy and I like the Paris Review podcast, which is not about Paris, but has some really interesting archival interviews from some crazy people like Hunter Thompson or like old, really old poets or something like that.

Jack: And it’s just, it’s put together in a very. Mind bending way. That’s just really interesting. So yeah, I, I like these ones that kind of push the medium a bit too.

Chris: Nice. I have to check those out. As an artist myself, I do need to ask you this as well. You know, the, the episode artwork is killer. Can you talk to me a little bit about that design process and, and what goes in that?

Jack: Yep. So I come up with all the ideas and a lot of times I’ve got like a Pinterest board of really cool concepts or artists that I love that just kind of. Speak to me in some way. Like it might be some interesting lines, just basic lines, but I can see maybe those are wires, right?

Jack: Maybe those are ethernet cables or you know, something. So I’m kind of always trying to see everyday objects as computer parts and. How can that be? Like a window could be a monitor or a screen or a tablet, right? And so how can we take that monitor, turn it into, or, you know, window and turn it into a tablet and put it on a house?

Jack: Like, you know, I’m always thinking in like these mashing up ideas. And then when I get something, I’ll sketch it out and that won’t work and I’ll sketch it out again, or I’ll try to mash it up with like pictures. That I see online that are similar, right? So I could take a house and then I could put a tablet on the window and be like, Look, there’s a tablet on the window.

Jack: You see how this works? And then I could give that to my artist and explain to them exactly what I’m going for here. Nice. And then they put it together and I see, No, no, no, that’s wrong. Perspective for something. Let’s do it again. But here are the, here are the notes to make it different. And so I work with another artist to bring my idea to life and.

Jack: Yeah, after a while they, they do, and we’ve got something and yeah, there are a new, a new piece of art for every episode. And then a lot of that stuff is turned into shirts as well, so it, it produces another revenue stream.

Chris: Nice man. So Jack, normally I localize this next question, but out of respect for the anonymity aspect, I’ll ask you, location aside, what’s the best bar you’ve ever been to?

Jack: Well, I can tell you about Vegas. So Vegas you know, we go to for Defcon and stuff and there’s this place called the chandelier Bar at the Cosmopolitan. And the thing is, is that they have one drink there that I’ve never been able to find anywhere else in the world.

Jack: And that’s why I consider it to be the best bar. And I don’t even know the drink. Maybe it’s called a Verbana. It’s got something in it called Sichuan. Have you heard of it?

Chris: I have, It’s the flower, correct?

Jack: Yeah. So it’s a, it’s just a flower, right? And it’s not like a psyche psychedelic flower or a psychotropic or anything.

Jack: It’s just it’s like a, a flower. And it has this weird experience where, You I think you take a drink of, of some of the drink and then you chew up the flour, you eat it, and then mash it around your mouth, get it just kind of spread out everywhere. And then when you take a drink again, the flavor is just completely different and the flour itself tastes like you’re eating Electricity. It’s really a weird experience, . And so after having that, you take the drink and it’s just like a wild drink that you just like, it’s not something you can just continue to having a conversation. You’re just like, Hold on a second. Something really is crazy happening in my mouth and I need to like figure out what in the, should I run to the bathroom?

Jack: Like what is happening here? It’s an experience. Yeah, it is really an experience and I’ve never been able to find a Shewan button anywhere else in the world or any other bar. And so. Yeah, the chandelier room, our bar at the Cosmo is my favorite.

Chris: Nice. Somebody’s told me about that drink and explained it to me just like you did.

Chris: Maybe not as in in depth as that, but when I was out in Defcon this last year, I fully intended on going there and I didn’t make it happen. Unfortunately, it is on my list. All right. Is on my list. So I just heard last call here. Do you have time for one? If you opened a cybersecurity themed bar, What would the name be and what would your signature drink be called?

Jack: Well, you know, I’ve got the Rhysider last name. I think cider is gonna have to be something in there. ? Yes, it has to be Jack’s rhyCider. I don’t know, something like that. I think. Yeah. So one of the things when I went to Vegas last time, I was asking for cider at a lot of places and they didn’t have it.

Jack: They did not have alcoholic cider in like every bar I went to. So, I really like ciders. So I think ciders would be somewhere on there. I went to I went to a trip to some apple orchard this summer and they had like 15 different ciders or more, and I was just like, just gimme all of ’em. And so they gave me a flight of ciders, , and it was such a great experience.

Jack: So I, I would like to redo that.

Chris: Yeah. There’s no bars that really focus solely on cider, so I, I, That could definitely be That could definitely be something new.

Jack: That one I went to, it was in Canada somewhere and it was in an apple orchard. So you were outside on a hill looking down over the valley and you just had this like, flight of ciders and it was, it was just beautiful.

Jack: So I think, you know, really good view of nature with some apple cider would be it.

Chris: Nice. Thanks again so much, man, for taking the time to speak with me. Outside of Darknet Diaries, where can our listeners connect with you online? I know you mentioned Twitter, but what are, you know, some of the other social media handles that you use?

Jack: Yeah, I mean, Twitter is where I’m most active, so Jack Rhysider on Twitter. But yeah, if you go to dark and diaries.com, you’ll see links to all of the places I’m at. So that’ll be the easiest way to get ahold of me.

Chris: Perfect. Jack, I wish you much continued success. Take care and be safe.

Jack: Thank you. Thanks for having me. This was a lot of fun.