Pessimists Archive: The Ultimate Podcast for Techno-Liberitarians

All great podcasts have to start somewhere. Many of the behemoths of today began in someone’s closet and with just a handful of friends for listeners. So, what changes that? How does a little, independent podcast spread, ultimately growing to reach an audience of millions? Today we unpack just such a story, and who knows, maybe you’ll find a nugget of wisdom that sends your own project into the stratosphere.

Pessimists Archive bills itself as “a history of why we resist new things.” It’s about nay-sayers throughout history who opposed innovation, and, in retrospect, look pretty silly now. We’re talking about people who were vehemently opposed to horrifying abominations like… the umbrella, elevators, bicycles, refrigerators, and yes, even teddy bears and birthdays. The idea is to look at why these things seemed so scary when they were new, and, now that we know they’re not so scary, perhaps calm down about the innovations we’re freaking out about today. The podcast currently averages 50,000 listeners per episode and has reached millions over its lifetime, but it certainly wasn’t born into these kinds of numbers.

Jason Feifer writes, produces, and hosts the Pessimists Archive podcast. When not working on the podcast, he does his “day job” as editor-in-chief of Entrepreneur Magazine, and before that he was an editor for Fast Company. (Disclosure: I wrote a couple articles for Jason in his FastCo days, and I currently do voiceovers for the Pessimists Archive podcast purely because I enjoy it.)

Pessimists Archive began in 2015 as a Twitter feed run by a British web designer named Louis Anslow. It existed for much the same purpose that the podcast does. Anslow would dig up historical apoplexies about things that now seem commonplace, much to the delight of modern audiences. The feed first came onto Feifer’s radar a year later. For years, he had been interested in the idea of repetitive fears and had been writing about it for Fast Company, so the Twitter feed felt like something he might have thought up.

Feifer reached out to Anslow, said he loved his work, and wondered if he might be interested in collaborating. Anslow did some research into Feifer, saw some videos he’d produced, and asked if he would like to make a podcast together. Feifer, who had already been yearning to get into podcasting, said yes, and the rest is history. Well, sort of.

“We had no idea what we were doing,” Feifer tells me. “Or whether or not it was going to resonate, or whether it was a project we even wanted to continue on. The first episode took three months to make. I mean, I had to get a microphone and teach myself audio editing.” They had a suspicion that there was an audience who would be hungry for the podcast, though, because the Twitter account already had about 20,000 followers, and some of them were big names in tech.

When Feifer and Anslow did finally put the first episode out in September of 2016, it got to 5,000 listens fairly quickly. “We had heard that that was a big marker of success for podcasts,” Feifer said. “And we were like, ‘Oh, well, if we hit that on the first one, then I guess maybe it’s worth doing more of them.” 

To get to the next level, though, the two hosts would have to completely change the way their show was made. After a handful of episodes, it was becoming clear that their styles of working weren’t particularly compatible. Episodes were still taking far too long to make, and sending bits and pieces of each episode back and forth was not only frustrating both of them, it was making it tougher to put the show together in a cohesive way. Eventually, the two agreed that they should just focus on their strengths. Feifer would produce the podcast and Anslow would continue to dig through archives to provide research and run the still-popular Twitter feed.

These kinds of internal restructurings are frequently make-or-break moments for podcasts. “It was stressful,” Feifer says. “But I think that you have to constantly be revising your process and just have open communication about that.” Fortunately, they both emerged unscathed, and the podcast became stronger for it.

The podcast grew in the first year, but because episodes were coming out three months apart, that growth wasn’t exactly linear or easy to track. “One day we would see a spike,” Feifer says. “Like suddenly there was a thousand people who listened to it all one day, which was a huge number back in the early days. And we were like, ‘What is that? How did that happen?’ We’d scramble around, and the answer was something like ‘we were referenced on some random other podcasts.’ Somebody said our name. That’s not searchable so it’s really hard to figure out what that moment was.”

The big breakthrough moment for growth, though, was when they won a grant from the Charles Koch Foundation. Feifer was able to hire someone to edit the audio, which would usually take him at least 10 hours an episode. He could now walk into a studio to record the voice-over rather than mucking around with his own equipment. Because of that, they were finally able to put episodes out every month. Notably, he now also had a bit of a marketing budget, which meant he could spend some money on ads, and the returns were massive. The podcast went from a total of less than 200,000 listens across everything to over 1 million in that year alone. 

“I started to run these little experiments where I would pay for ads on certain podcasts and some would hit really well and just drive a ton of traffic, and then some would do nothing,” Feifer told me.

“And the podcasts that I was buying on were like the same size. So, what was happening? Well, what was happening is I was learning about my audience. I was discovering that ads on tech podcasts, for example, do really well, but ads on history podcasts don’t really do well.

And that made me start to think of things like, ‘I always thought about this as a history show, but maybe it’s not a history show.’ Or ‘maybe I should stop talking about it like a history show because my audience isn’t history people.’”

Overall, though, Feifer isn’t really into checking numbers. He comes from print magazines where you never get numbers. “So, I’ve never been acclimated to having numbers, and I just kind of hate numbers.”

Instead he feels that you should focus on making the best product that you can and engaging directly with the people who consume it.

As for whether there has been a single tipping point for the show, he’s not exactly sure. “I mean, the thing about tipping moments is [that] a tipping moment also means that success is somehow defined,” he says, “and I don’t know what success looks like yet for the show” But he did note that the past year or so has had a number of smaller tipping points, such as the sheer number of very high-profile people (including entrepreneur Marc Andreessen and psychologist and author Steven Pinker) liking and talking about the show completely on their own. He was also featured on both Radiolab and Reason Magazine’s podcast, which sent their numbers skyrocketing for a month.

Thanks to a new budget via the Koch Foundation grant , the hosts are planning to hire a consulting firm that specializes in audience development. There’s only so much you can learn about your audience from watching who is following you on Twitter and anecdotally collecting those who are engaging with you, Feifer says. This consulting firm will be able to directly survey the podcast’s audience, giving thema more definitive understanding of why followers of the show like it so much. 

This is exciting from an audience-building perspective, but Feifer also sees how it could turn into a trap of preaching to the choir. For example, one of the things they already know about the show is that it’s popular with fans of technology, and also with libertarians.He says libertarians tend to buy in on the concept from the get-go because they are very pro-innovation, and they see Pessimists Archive as a sort of pushback against the forces that limit innovation.  “It’s not how I thought of it, but I get it,” Feifer told me.

“But I don’t want to give into that and make this a show that’s just for libertarians, because then it’s not impacting anybody. Right? Then it’s just giving a set of people who like this what they want, and what I want to do is—I want to challenge people, and I want people to say, ‘Oh, this changed the way that I think.’ And I am seeing people say that on social media. That’s extremely gratifying,” he says.

“So, I don’t want to pivot too hard into my audience, but I do think that it’s important to understand who your audience is so that you can grow, and so that maybe you can figure out who adjacent audiences are so that you could, you could expand it to there.”

Feifer is careful to note, though, that he does encourage audience members to reach out with their ideas, not only because he’s interested in how people respond to the show, but because if they have valid points then he wants to build them in. Over the last few years, he has incorporated some ideas for topics as well as for the overarching tone of the series, and the show has been made better for it.

Feifer wasn’t shy about admitting that his goals for Pessimists Archive aren’t necessarily confined to the worlds of podcasting and Twitter: “You know, to me, the ultimate tipping point would be if I could do this as a full-time job, or if it could lead to some kind of massive new thing like a TV show, or I’ve been exploring a book on the subject, but haven’t done it yet.I don’t know what the show’s starring role is yet, but I’m very encouraged that every time we release an episode, I get a better sense of that.”

He sees Pessimists Archive almost as the beginning of a thought movement, and as a potent argument for something that’s critical now, which is understanding change and, hopefully, being a force for positive change. Whether that manifests through TV, or books, or partnering with an organization focused on innovation, almost doesn’t matter, as long as the product continues to grow and become more influential. Or, as Feifer himself put it, “I’m constantly curious and exploring ways in which it can be as much as it can possibly be.”

At this point, none of those lofty goals feel unattainable. Through learning about his listeners and building his understanding of what it is about his show that hooks people, Feifer has managed to draw many more people in. His audience is now a platform he can stand on, build from, and continue to reach for those higher aspirations. It’s amazing what a little research can do.