Jack Rhysider is a security veteran and host of the Darknet Diaries podcast. He’s also an accomplished storyteller who knows how to build an audience from scratch. 

I talked to Jack about cybersecurity trends, advice for anyone creating content, and the three major problems every podcaster faces. 

Listen to my interview with Jack or scroll down to read a lightly edited transcript of our conversation.

Mike: So, Jack, what makes for a good security podcast story?

Jack: I think a good story in general has twists and turns, like you expected one thing to happen, but then something else happens entirely differently, and throws you off. And I’m looking for stories like that, which have at least one big turn or twist, and two would be even better, right? So if you’re trying to accomplish one thing, but something else happens instead, and it puts you on a new course — that’s a twist, and that’s what I’m looking for.

Now, does that usually come during your research or as you’re having the conversation?

One thing is that a lot of the stories I cover, they seem to be exciting just by default because we’re talking about breaking into something, hacking into something, stealing something.

I like those stories just by themselves. But if something goes terribly wrong, that’s even better, right? So if you’re trying to break into a building and hack something or whatever and then the cops show up, OK, well that totally throws off your plan. So, that’s part of it, but if the cops don’t show up, it’s still exciting because how did you successfully get in and get out without getting captured? So, yeah, I just think that there’s some sort of element that these stories have that just make them exciting by default as well.

What advice do you have for anyone creating content around cybersecurity?

There are a lot of different formats to this, right? So you can do news, you can do interviews with people in the industry to talk about different technologies and experts in this field. And then there’s storytelling like I do. Another show is “Malicious Life,” which does something similar to me too. There are a few shows like that.

So there are different formats, and trying to figure out what your format is going to be is the first step. And then, just trying to pack it with as much value as you can. You have to figure out what you want your listeners to get out of your show, and then just start with that and keep delivering that throughout.

So if you want them to be educated on the latest news, then make sure you have some good solid news stories in there that are well researched. And if you want them to hear what other experts are saying, get some really good people on the show as guests, so you can hear what they have to say.

I’ve listened to some interview-type podcasts like that where I’ve listened to the same episode three or four times because it was just so educational to me, and when something is just, slam packed with education, it’s OK to listen to it multiple times and soak it all up. So yeah, those can sometimes be really valuable.

And what major trends or stories in cybersecurity are you most interested in right now?

I like the stories where there are nation-state hackers, right, so governments hacking other governments. These are always fascinating to me because it’s kind of like the top-tier hackers out there, the professionals, the World Series of hacking, if you will. There’s no one who’s going to be better than governments at hacking, so it’s very exciting to see what the upper limits are of the capabilities of those kinds of hackers in the world. And, yeah, it’s pretty scary what they’re capable of, so I’m always really interested in that sort of stuff.

So with COVID, how has it affected what you talk about, and how you approach those stories?

So, I’m a slow news kind of storyteller, right? So I’ve revisited stories that are 10 years old and gone back and said, OK, what have we learned in the last 10 years? Well, we’ve learned a lot. We’ve actually captured the person, and they put them in prison, and then this was the after effect of it all.

So I wait until all that’s done before I really cover the story. So with COVID hitting, I think it’s still too new for me to cover those stories, and I’m waiting for — OK, yep there’ve been some COVID ransomware attacks and some other COVID-related attacks, but we don’t know who did it, and how much damage they caused or all these things, so I’m waiting for that second piece to land and maybe the third piece and the fourth piece before I cover those.

So, as far as content goes, it really hasn’t changed me; I’m always a laggard in that way. But it definitely has impacted my daily routine.

That’s an interesting take. I agree that some of these stories have yet to be told and unfold, but I think there’s some good ones out there — I’m sure you’ll find them.


What separates the most helpful sources and guests from the least helpful sources and guests in your experience?

I always like a good talker, right? Somebody who’s got just a boring way of talking, and doesn’t really like to expand on what I’m asking — that’s not really good for audio, right? I’ve got to really draw out the stuff that’s there.

But the people who can kind of laugh at what they did and have stories about it, even though it’s a horrible experience, that’s fun. I interviewed one guy who was getting arrested and the police were surrounding him, and they draw their weapons and they say put your hands up. And I was like, well what did you do? Did you put your hands up? He’s like, well yeah, what else could you do? I’m not gonna pull out a weapon and start firing back. Of course I put my hands up.

So he had a really funny response to that, so it was a comical moment in the middle of a very serious experience so I do like when people have a sense of humor about it.

It’s also really fun when people just have a good story to tell, because some people have stories that aren’t quite related to my show, and they have good stories to tell. And I can’t really fit those in, but they’re still good. But yeah, I like it when they’re very tech oriented and those are my favorite.

And so, what would you say is the difference between a story that’s a good fit for Darknet Diaries versus one that one that more mainstream media or mainstream business media might publish or tell?

I think some of my stories would fit just fine in like Wired magazine or Motherboard and stuff like that. They do publish some long form journalism there.

That would work in those situations, but I think a lot of a lot of mainstream journalism is possibly shorter, and it’s the current news, right? So, this happened today or this week, or we’re just now finding out about it. Here’s the headline and here’s the one, two paragraphs of what we know so far. And that’s I think what mainstream journalism is doing.

And every now and then you get somebody who goes a little deeper and digs up some extra stuff on there but yeah I’d like to say, OK, hold on. I want to know everything. Like I said, I’m kind of a laggard with the news, I’m a slow news junkie. So let me wait until I have 5,000 words that I can say about this and all of them, they’re not just loosely related, like well I asked this security expert what his opinion is. No, I don’t want to go in those directions, I want to just cover the story and stick with it and not go on side roads or anything.

So I have to wait until there’s enough information that we can stick into it too. A lot of times we don’t know how the hacker got in or who the hacker was and all these things, and that’s why I have to just put that in my pocket for a while, until we figure those things out.

So what podcasts would you recommend to people working in cybersecurity PR or marketing? 

I don’t know about PR but I’m gonna pull up my podcast list and I’ll tell you about the other ones.

The cybersecurity news ones that I like are “Risky Business” and Cybereason. I also like listening to Down the Rabbit Hole.

And then when it comes to marketing, I’ve got a list of that, because this podcast is something I’ve wanted to do, and online entrepreneurism is something I’ve wanted to do for quite a while. So, when I finally had something worthy of marketing, I was really excited about it. And because I had actually absorbed a lot of marketing stuff in the past.

So, “Smart Passive Income” has a lot of good marketing techniques, tactics, tips. There’s some stuff on the Tim Ferriss podcast. I like the show “Everyone Hates Marketers” and the show “Indie Hackers,” and anything by Seth Godin. So Seth Godin has a “Startup School” podcast and also “Akimbo.” And I think that really helps me think outside the box as far as marketing goes. And then Gary Vaynerchuk has been influential. So, that’s kind of a quick rundown of some of the stuff that’s really impacted me.

What about advice for people starting podcasts. I mean, it can take time to build an audience. What advice do you have for people just starting out?

Well, I think you’re gonna hit three major problems as a podcaster. You’re gonna have a tough time making a great show. Good isn’t good enough anymore. People turn good stuff off to go listen to great stuff. So, getting to the point where your show’s great isn’t something you just pick up a mic and start making. You’ve got to really put a lot of focus into that.

A lot of people think, “oh, if I just had the equipment I should start making it,” and that’s kind of like if I just had musical instruments, I could make some music. Like no, it takes a lot of practice to make music, and it takes a lot of practice to make a great podcast. And so starting with that might take a year to get there, right?

And then the next problem is marketing it, and growing it, and the last problem is monetizing it. So these are the three bigger hurdles you’ve got to be ready to tackle.

So marketing it is more of a flywheel where you’re just kind of pushing it around and around and around slowly, or riding a bicycle across the country. There’s not one technique or tip for what’s the most effective, if you ask me; you just keep pedaling and pedaling and pedaling and pedaling to get to where you need to go.

So, being a guest on another podcast, getting guests on that have a big audience, emailing tons of people, anyone who has an audience: podcasters authors, journalists, YouTubers, other people who have newsletters. Get on their radar because they’re looking for content to talk about, and they might like your show and they might publish about it.

Going to conferences, being visible there, putting your stickers around, wearing your shirts, getting other people to wear shirts, talking at a conference. Wherever you can scoop up five or 10 new listeners, do it, because it’s worth it. You don’t know how much influence they can have.

And, yeah, if you have a great show, the point of it is, you’re going to get someone to listen, and then they’re going to love it, and then tell others. So if your show isn’t great, that’s where it comes back to problem number one. If it’s not great, you’re going to have a tough time getting that to spread, because your goal is to get people who really love it, and then they spread it for you. So that’s going to be the biggest thing that’s most effective for me in marketing is word of mouth. If that’s not there, you’re gonna have a really really hard time getting anywhere.

So what’s next for Darknet Diaries? What can we expect?

Episodes come out every two weeks, so I’m gonna keep doing that for as long as I can.

I’m working on a second podcast that’s kind of a longer form — each episode is already an hour long, but I think some of these things take five or 10 hours to explain. Like, for instance election hacking. That’s not one that can be wrapped up in an hour. There’s a lot to that. 

So, yeah, I’m exploring that, I’m exploring some other projects as well, some YouTube videos and things like that. Oh, and of course, I’ve always got some new shirts showing up in the shop. I’ve been designing a lot of stuff there and that’s a lot of fun. 

Jack, thanks again for taking the time today, it was great to talk to you. 

Cool, thanks very much.