A Military Satirist’s Successful Journey from Blog to Substack
How the Journalism Creators Program helped a former Marine build a subscription newsletter
by Elise Czajkowski
In the nine years since Paul Szoldra started his military parody site, Duffel Blog, the evolution of online media has led to new challenges and opportunities for independent journalists. So in 2020, he turned to the Entrepreneurial Journalism Creators Program at CUNY’s Newmark Graduate School of Journalism to re-launch Duffel Blog as a Substack newsletter.
Szoldra started Duffel Blog in 2012, two years after leaving the Marine Corps. He said he was inspired to launch the site because other satirical outlets like The Onion so often got things wrong in their military stories. “It makes it hard to enjoy the story for a lot of people,” said Szoldra. “Like, they just can’t get over it. And I was kind of one of those people.”
“So I thought, ‘Hey, I could do what The Onion does. Looks easy enough,’” he said, “which it was not.”
By 2018, Duffel Blog had about a million unique visitors per month. But as Facebook petered out as a referral source and ad revenue began to drop, the site became less sustainable. In November of 2020, Szoldra turned to Substack, launching the newsletter with a subscription model.
Paul Szoldra shifted his parody site Duffel Blog into a Substack newsletter and developed new relationships with his readers
“I was jumping off a cliff basically,” he said of this thought process at the time. “I did have ad revenue, I did have traffic. But I can kind of see the writing on the wall. This is okay, sustainable, for now. But maybe a few months from now, maybe a year from now somewhere, it’s going to go away. And I’ve got to figure something out.”
He says without the pressure of social media referrals or ad clicks, he’s been able to focus more on providing good content and converting his readers to subscribers. The world of digital media is very metrics-focused, he says, while Substack incentivizes high-quality content that gives loyal readers what they “really, really want.”
Outside of his side project, Szoldra is the editor-in-chief of Task & Purpose, a site covering military news and culture. He was drawn to the J-School’s Journalism Creators Program because he had never worked as a full-time freelancer, and wanted to learn about what being independent entailed.
“What I really got most out of this was the conversations and hearing where things are going, and getting exposed to people much smarter than I on these topics,” he said. “Talking about newsletters and where they’re going and what the next phase of media is, and where we end up.”
A particular highlight for him was a class with professor Jeff Jarvis about the history of media. “It just made me think about, this is a constant changing process,” Szoldra said. “We’re never stuck in, like, this is how you do the business of media.”
He says the current newsletter boom reminds him of the blogosphere that he started out in, where writers like Ezra Klein could draw enough attention to rocket them to mainstream success. He sees the next generation of Substack writers being hired — or having their newsletters bought out — by large media organizations who see the value of this direct connection to readers.
Switching to a newsletter format has allowed Szoldra to improve the quality of his work. With reader support, he is now able to pay his writers double what he could before.
His time in the Creators Program also helped to emphasize the importance of serving readers. He makes a point of talking to subscribers in the comments section and responding to all reader emails, whether they’re compliments or complaints.
“That’s something that was drilled in,” Szoldra said. “It’s a really important thing to do, to demonstrate — Hey, I’m right here, I am a human just like you, and I appreciate your feedback and your commentary.”
This thinking has permeated his work beyond Duffel Blog. In his day job at Task & Purpose, he has shifted his thinking about reader feedback away from avoiding criticism towards giving everyone the chance to voice their input.
“Especially now, there’s a big problem with trust in journalism, and lack of trust in reporters,” he explained. “Whether that’s founded or unfounded, it really doesn’t matter. It needs to be recognized. People are thinking it. It doesn’t really matter whether it’s true or false.”
“If our readers think it, it’s a problem for us. And so we have to do that stuff. We have to respond in good faith and try to get people to come over, back to our side.”
