Creator Insights

How Jack Rhysider turned listener support into loyal subscribers

Jack Rhysider was a podcast fan looking for a show about the culture around hacking, but he couldn’t find one that kept him entertained. So, in October 2017, he launched Darknet Diaries, a show that explores “true stories of the dark side of the Internet” covering hacking, data breaches, and cybercrime. By the end of 2021, Darknet Diaries amassed 22.9 million downloads for the year

In addition to working with Apple Podcasts, doing more cross-promotional swaps with other shows, and tinkering with his marketing budget, Jack joined the Apple Podcasters Program to launch Darknet Diaries+. This offered listeners a way to financially support his work and receive audio benefits like ad-free episodes and bonus content.

Jack initially chronicled the first 45 days of launching his subscription on Apple Podcasts back in August 2021. Apple Podcasts checked in with Jack to explore more about how he set up his podcast for subscription success and what podcasters could learn from his efforts.

Meet the voice behind Darknet Diaries: Jack Rhysider.


“How can I support you?”

Jack’s desire to provide a premium experience for his listeners came out of a request from engaging with his fanbase.

“I think at first, I was very hesitant to hold my hand out and ask for anything,” he explained. “Just thinking there were other ways to make money at [podcasting]. But over time, there were people that got so much value out of the show that they were asking me, ‘How can I donate? How can I support you? What can I do to give directly to you?’ And I was like, ‘I don’t have the system, just keep listening and share it.’”

“But once five people reached out and were asking me, ‘How do I give money to you?’ I was like, ‘OK, I gotta set something up here... I’ll give that a shot.’ And that’s kind of how it started.”


Jack looked around at other podcasters to get an idea of what his premium offerings could look like and noticed that ad-free content and bonus episodes were the two most popular benefits. While he experimented with a few other distribution platforms, he was drawn to the simplicity of subscriptions on Apple Podcasts.

“I think what’s nice about Apple Podcasts Subscriptions is the whole experience is just all in-app and easier to use. With [other platforms], you’ve got to go to this other website and subscribe, create an account, pay some money, get your credit card out, and all these kind of things. But with Apple, it’s all integrated... it’s just much more seamless and easier on the listener.”

Revamping show art to maximize platform presence

After Jack set up his plan for subscriber audio and crafted premium content offerings, he realized it was time to revamp the Darknet Diaries visual branding. Jack wanted to continue to engage existing show listeners and draw in new prospective fans who would discover it on Apple Podcasts.

Jack was used to creating his own show artwork and episode-specific art for promotions on social media as well as the show’s website. However, in order to raise awareness of his premium offerings, he enlisted the help of designers to craft eye-catching illustrations for his podcast, including promotional platform artwork using the Show Page Tall and Subscription Wide templates on Apple Podcasts.

“Because there’s so much just endless scrolling on social media and in your apps you’re looking at, you want to get people to stop.”
Darknet Diaries host Jack Rhysider

“After I realized that this show has some legs, and it’s going somewhere, I decided to rebrand the entire thing by hiring some professional artists to redesign what’s going on there and rebrand it,” he said. “You know, a specific color theme and a specific style. All this stuff was really important to me at the time.”

An example of Darknet Diaries’ Show Page Tall artwork.

“Because there’s so much just endless scrolling on social media and in your apps you’re looking at, you want to get people to stop.” Jack also noted that the extra work put into making great art for a show can turn into a new revenue stream. “I decided, ‘OK let’s turn some of this into some shirts, and some stickers and stuff.’ So it becomes the second sort of stream of income because there’s all this extra artwork made, we can use it on other things.”

An example of Darknet Diaries’ Subscription Wide artwork.

Price advice

When it came to pricing out his premium experience for fans, Jack settled on $4.99 a month instead of other competitive price points on the platform. “I think it’s easier to start higher and go down versus start lower and go up.” 

Getting the word out

With the subscription offerings set up and the new brand art in place, it was time to let the Darknet Diaries listeners know there were benefits to go along with their financial support. And for listeners exploring those benefits on Apple Podcasts, Jack got right to the point with the in-app messaging.

“I toyed around with a lot of different ideas. I decided to just keep a very simple messaging. Like it says, bonus content and ad-free feed for subscribing.”

When it came to off-platform messaging, Jack initially admitted he’d “done nothing to convince or even tell my audience that they can get bonus content and ad-free episodes through Apple Podcasts Subscriptions. Which means 100 percent of these customers have discovered this on their own through the Apple Podcasts app. Which is huge.”

Since then, he’s worked on increasing the Darknet Diaries’ audience awareness of his premium offerings by including a mention of it during every episode of the podcast. Jack also added a page dedicated to promoting the bonus material on his website, in addition to a mention on the homepage.

Understanding listener behavior with Apple Podcasts Connect

After launch, Jack kept an eye on analytics and subscription reports within Apple Podcasts Connect to know how fans were engaging with the premium benefits and how his new efforts impacted his overall key performance indicators for the show.

“I think it’s good to just kind of check in every now and then to see if you get some additional information when people have decided to cancel the membership,” Jack said.

“The other thing inside Apple Podcasts Connect is the ability to see the listener retention on any episode,” he added about Analytics. “So just knowing, ‘OK, this episode really glued the audience through the whole thing to the end, versus this other one that I thought was more entertaining.’ You almost got a nice metric on what the audience feels and how they resonate with the show.”

It also helped him structure his editorial content. “Sometimes I go on rants or on tangents in the show. And I just was like, ‘Is anybody sticking around for this?’ And it’s just interesting to see that maybe I went too far out on a limb there. I see where I start losing people.” 


Impact and growth 

In January 2022, six months into exploring subscriptions, Darknet Diaries+ subscriber numbers grew to over 1,800 paying subscribers, up 168 percent from August 2021. “Which,” Jack noted, “at $4.99 a month is over $6,000 a month” from Apple Podcasts Subscriptions alone. At nearly a year in, that subscriber number now stands at over 2,200, up 228 percent from August 2021.

In the past, Jack has shared his overall download numbers and other stats on his site. Downloads for Darknet Diaries’ main feed — a metric used to sell advertising — also increased 66 percent on Apple Podcasts with 6.85 million downloads in 2021, up from 4.1 million from the previous year. 

Why share these podcast metrics publicly? “Once I get to a certain level of understanding, I feel like, ‘Oh, wow, there’s a lot of people that need this kind of information. I might as well share it with them,’” Jack explained. “So that’s why I blog and I answer questions, and just try to be helpful in the podcasting space.”

Since April, Jack has pulled back on his offering of bonus content, but he still offers his listeners the ad-free benefit, in part to give himself a little more bandwidth. 

“It’s kind of like that moment of how did your inbox get all these unread messages? At some point, I could only keep up with so many things,” Jack explained. “Marketing this and marketing that and trying to get new episodes out, and all this stuff. It’s not quite burnout, it’s just that I’m overcommitted on all these things.”

However, he believes the lack of additional content hasn’t impacted the audience sentiment about paying for his subscription because it all comes back to the initial question from his audience: “How can we support you?”

“There are 10 bonus episodes that I provide, as well as ad-free versions, I think that is an incentive for somebody who’s on the fence, like, ‘Oh, I see that there’s this extra thing, what do I get with that?’ And it’s ad-free, right? So we’re not going to waste the audience’s time with ads anymore. So maybe half of my audience was there for the ad-free version. And the other half is there just to support me.”

He has tied that direct support for him as a creator into messaging that promotes his subscription on Darknet Diaries. “Half the time I say, ‘It’s the people who support me that really allow me to keep this going. So thank you very much. If I’m bringing you value, then there are ways that you can support me such as subscribing on Apple Podcasts Subscriptions.’ And then the other thing is, ‘Hey, if you’re sick of the ads, I have an ad-free version you can get.’”

Looking back at the beginning of his subscription journey, the setup of ad-free content and bonus episodes required work, so Jack hired someone to help with uploading those subscriber benefits, knowing that a robust premium offering would be more enticing. “This is a genuine money-generating role. The monthly subscriptions revenue was more than what I was paying them,” he said. “Pay someone’s time and you get back more. It definitely is worth it.”