Darknet Diaries is a gripping podcast that mixes human dramas with the dark world of cybercrime, malware, cryptography, and internet privacy. Jack Rhysider is the investigative voice behind it.
The show has been on the air since October 2017 and combines storytelling with cybersecurity knowledge. Jack Rhysider researches, writes, edits, and puts together each episode with great care, building a loyal following and turning real-world digital threats into interesting audio stories. Before he started podcasting, Jack worked as a network security engineer, where he tracked threats and protected networks. This experience helped him develop his unique storytelling style. His work connects the hidden, often invisible world of cybercrime with the ears of everyday people, making the dark side of the web both easy to find and hard to forget.
1. You started as a network security engineer in a Fortune 500 SOC—what was the defining moment that led you to blend that expertise with storytelling in the form of a podcast?
I went to defcon and learned how we are vulnerable in 100 ways. I tried to get a meeting together with my team and explain to my boss how we need to really improve our security. But the boss seemed unmoved by my efforts of telling him how vulnerable we are. I realized I needed to improve my pitch to convey the importance of security better. And I can do that through storytelling. While I wasn’t able to get my boss to take security more seriously, I have been told that bosses in a lot of other companies have listened to my stories and have taken big steps to improve the security of their department. So I’m glad I had an impact.
2. You launched Darknet Diaries because you couldn’t find your ideal cybersecurity story podcast. What was it lacking, and how did that inspire you to create it yourself?
The podcasts I was listening to at the time were either interviewing people in the cybersecurity field, or news. Both of which were dry and technical. You needed to be a cybersecurity nerd to understand any of it. Which I was and that was fine. But I was also listening to wonderful podcasts that were stories. Such as This American Life and Radiolab. And I wondered why there’s not a podcast that combines the two, cybersecurity + storytelling. That’s what I couldn’t find. And I knew that so many cybersecurity stories have high drama moments to them that they’d make amazing stories. So that’s what I set forth to make. Something both a geek could like, and someone who just likes good stories.
3. Building a podcast from scratch is daunting. How did you balance your day job with launching the show in 2017?
I’m a pretty driven person! When I get the notion to do something, I have been known to cancel my weekend plans and stay up all night working on stuff. Even today I feel like I have so much to make and not enough time to make it all!
4. You self-taught audio storytelling by listening to This American Life and studying books like Out on the Wire—how did that shape your narrative voice?
My voice took a long time to find. At first I wanted to sound like the narrator in Mr. Robot. But I learned that his voice sounded like he was an insomniac and sleep deprived. So I tried staying up until 3am to record an episode. And that didn’t go well. I didn’t get the voice I wanted and made a lot of mistakes. So then I tried on a lot of other voices to see if I liked them better. Such as Ira Glass, Malcom Gladwell, Rod Serling, Paul Harvey, Jab Abumrod, Aaron Mahnke, etc. I would try to write like them and deliver the lines like them. Some where incredibly hard, yet sounded amazing, others didn’t sound good at all. After doing this for a few dozen episodes I finally found a voice and writing style I felt comfortable with as being my own. Honestly all I’m shooting for is just having a voice like I’m a close friend of yours and I’m telling you this story at a bar or on some walk. And to get there I sometimes had to pick up a phone and act like I’m telling the story to a friend over the phone. I actually pictured that I was on the call with a specific close friend telling it to them. And that worked really well! My narration came off very natural.
5. For the first 40 episodes, you handled every task—from research to editing and marketing—on your own. What did you learn from that challenge?
A lot of people ask me for advice on how to get started. And my advice is kind of boring. It’s just to start making stuff. Just go build. Don’t let me guide you, guide yourself. In the process of making and building you learn so much that nobody would be able to teach you. I learned journalism, storytelling, audio engineering, how to address a mic, how to sound proof the room, how to write with suspense and drama, how to end stories in a great way when there’s no good ending, how to market, how to grow, how others are running their podcasts. It was a magnificent time of growth and learning.
6. As the show grew beyond episode 40 and profits allowed you to expand your team, how did your creative process evolve?
My voice became closer to how i naturally speak. Which seemed to upset some people. But it’s just a testament of how close my audience and I are. They can spot difference in my inflection, and I feel more comfortable to use my normal voice more. It’s fascinating.
7. Darknet Diaries now attracts over 300,000 downloads per episode. What marketing strategies did you focus on in the early days to reach that level?
The early days was all about making something so good that as soon as someone listens to it, they immediately have to tell someone else to go listen to this. Word of mouth is king and I estimate is how 80-90% of my audience found me. So instead of trying to find new listeners, I’ve always focused on surprising my current listeners with more and more stuff they love. But besides that, I was all over socials, active in every corner there was chats about cybersecurity, and spreading stickers at conferences, and being a guest on dozens of other podcasts, and doing promo swaps with other shows.
8. You’ve referred to your podcast’s growth as a ‘flywheel’—with word of mouth as its core. How did you encourage sharing among listeners?
There’s a lot I do for that! Since it is 80% or more of how my listeners find me, I want to help that any way I can. So I want to have attractive artwork for listeners to share, I want to have a great link preview for when people post it to socials the card that pops up looks great. I want to be on every podcast platform to make it easy for people to find, I want to be on every social platform, to make it easy for people to tag me. And if they tag me then I can help guide them to the show easier with links and good looking branding. Here’s how I think of it, my listeners are doing me a solid, a HUGE favor by telling someone else about my show. But what they are doing is handing it off to me, and I’ve got to finalize the deal. The show should have the copy and images that sells the new listener to get them to subscribe or hit play. So I’ve always looked at word of mouth like a dance I’m doing with my listeners that I want to be in lock step with them to help them get me new listeners.
9. When did you decide it was time to monetize the show, and what surprised you most about the response to your paid membership model?
I think it was around 20,000 downloads per episode that I thought it is probably worth it to start putting in ads. I just put in some affiliate ads at first. Like sign up for this VPN and I get $5 for each signup sort of thing. Which worked well as the income grew as the episodes grew. I didn’t have or even like Patreon at the time, but then I went to a conference and one fan was so thankful for my show he forced me to take $20 from him. He said to me that he tried to give it to me online but couldn’t find a way to do it so he had to meet me in person to give me money. And it was then when I realized having a paid membership was not just helpful to me, but it’s what my listeners wanted. So I started a Patreon and it did very well. People ask me when is it the right time to start something like Patreon, and I say wait until 3 people ask you how they can donate to the show or show thanks, and then you know it’s ripe for it.
10. Some episodes have had tangible real-world effects—for example, “Finn” was adapted by Snap Judgment, and “The Carder” aided a criminal investigation. What did it feel like when your stories transcended the podcast?
I’ve always hoped for some of the stories to make a bigger impact in the world. Like some of these absolutely should be making big waves and rippling through social media and news cycles. But I’ve learned podcasts rarely have that effect. They almost never go viral. But I’m still on a mission to make one that resonates strong enough that it triggers a bunch of news articles to be written and things change because of it.
11. You maintain strict journalistic standards—fact-checking, ethical sourcing, objectivity. Can you walk us through your process for ensuring accuracy and integrity?
First is my familiarity with the subject, cybersecurity. That goes a long way when I know a lot of details about a lot of stories, I can tell when something doesn’t add up or sounds wrong. Not only that but I have a lot of connections in this industry so I can ask experts who would be familiar with stories. And I rely a lot on court records and criminal records to fact check. My favorite experience is to listen to someone’s story and go “no way…” but then they show me their indictment and I’m like, “holy cow…” But I also read a lot of news stories, recreate scenarios myself, and talk to others familiar with the story.
12. Among the many stories you’ve covered—from malware to botnets to cryptography—what recurring misconceptions about cybersecurity have you encountered?
Companies aren’t keeping your data safe. Security isn’t their top priority. If you want proof just listen to the 160 episodes I’ve done. This is why I don’t trust companies with my data and I will give them fake names, burner credit card numbers, burner phone numbers etc. Because I know they are going to lose it or expose it in a breach or give it to the government.
13. With over 160 episodes now in the archive and a strong audience foundation, what new directions are you considering—branded content, investigative collaborations, or multimedia expansions?
Good question. Getting it off the ground was hard. But equally as hard is building a team that can keep it afloat. That’s what I’m still working on. Keep listening to see what’s next!
14. Reflecting on your journey—from cybersecurity engineer to indie podcaster—what advice would you give to other tech professionals who want to step into storytelling or a side project that ignites passion and impact?
Just start! Chase your passion. I started this late in my career. It’s not too late for you to start. And this has defined my career now. But I’ve got so much more to offer, that I hope Darknet Diaries goes down as my starting point, and not what I am only known for.
Throughout this insight into the Journey of Jack Rhysider, it’s clear that he is a driven and passionate candidate for chasing your dreams, in his case, Cybersecurity Podcasts. However, many issues have also been highlighted through this interview. Our data is not as safe as we once thought, emphasising the importance of keeping your data safe and maintaining strict controls on what we accept online may be the first steps to ensure privacy. It’s important that the public is privvy to information like this to put pressure on Corporations to make sure we know where are data is.
Once again, I thank Jack for taking time out of his schedule to do this interview with Cybaplug.net. Make sure to stay tuned for more interviews like this!
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