If there was a theme for the media industry in 2021, besides living in hell, it would be “The Great Substackening.” Last year, as the pandemic turned the erosion of the industry into a landslide, high-profile writers from all sides of the ideological spectrum exited positions at large media companies for Substack, the newsletter platform that has upended the industry since launching in 2017. Before the Substack pivot became a major industry trend, Judd Legum’s jump to the platform in 2018 felt monumental — and prophetic.
Over a decade after founding left-leaning political news site ThinkProgress, Legum stepped down as editor-in-chief of the 40-person staff to start Popular Information, a political newsletter that publishes four days a week. It was a giant leap, one that drew from his roots as a blogger in the 2000s, but it paid off. Since its first edition in July 2018, Popular Information has grown to reach over 125,000 free subscribers and over 10,000 paid subscribers, allowing Legum to hire a research assistant, Tesnim Zekeria, last June.
Popular Information has consistently broken through the now-cluttered newsletter space with its reporting. Last year, an investigation into the Darden company, which owns Olive Garden and other restaurants, led to the company extending paid sick leave for over 175,000 employees. This year, in the aftermath of the Capital coup attempt, Legum and Zekeria contacted 144 companies that had donated to Republican members of Congress who had objected to the certification of the Electoral College vote. Within a week, over two dozen major corporations suspended their donations.
Popular Information has shown the outsize impact that small, subscriber-based newsletters can have. After one sprawling interview with Legum in December ended in the horror of the audio file not saving (every reporter’s nightmare), I caught up with him again for a conversation about blogging versus newsletters, aggregated reporting, and the danger of Facebook sponsoring political newsletters.
This interview has been edited for length and clarity.
Study Hall: You started as a blogger in the early 2000s. What are some of the similarities and differences between Substack and traditional blogging?
Judd Legum: It taps back into the idea of the internet facilitating a lot of independent voices, which is really what blogging introduced. Prior to that, if you wanted to reach an audience, you had to either be part of a big media organization or convince someone who was to tell your story. Blogging changed that. [But] the thing about blogging was that it didn’t really have a good business model attached to it. To the extent that it did have a business model, it was advertising-driven, and that requires you to generate more and more content, which burned a lot of people out.
My conception of this [Substack migration] is it’s a return to more individual voices, but this time, attached to a business model that doesn’t just require ever-increasing content production. It enables you to extract some value out of deeper connections with readers. I do four [newsletters] a week, but even that is a much better pace than people who were operating their own blogs. If you ever had a day where you weren’t writing, it was costing you money, because it was all about your pageviews.
SH: You pointed out on Twitter that the DC political newsletters like Politico Playbook, Axios, and Punchbowl News all accept sponsorship money from Facebook and have run pro-Facebook content. One of Punchbowl’s founders also came directly from Facebook. What are the dangers of newsletters taking money from corporations with a history of corruption?
JL: I think it’s possible to produce good journalism while accepting sponsorships, but it certainly doesn’t make things easier. And, even if firewalls are maintained, it could have a subconscious impact on reporters who understand that relationships with sponsors are critical to keeping them employed. It’s even more difficult at a startup like Punchbowl where, by necessity, the reporters and the business people are the same people.
SH: You talked to Emily Atkin before she started HEATED, and talked to a few other writers who have since joined Substack. What were some of their concerns about leaving traditional media jobs and starting newsletters?
JL: The real hesitancy for a lot of people is stability and confidence that they’re going to have an income. If you go from having a paycheck to having your own little small business based on subscriptions, that exposes you to a lot of risks. If you can build a business around recurring subscriptions, that’s a good business. That’s why all of the tech companies want to do an [annual recurring revenue] business. Once you get up to a certain level, it is quite stable. Obviously, people subscribe and unsubscribe, but one person unsubscribing doesn’t become a big deal.
SH: How much time do you spend on original reporting versus aggregating other reporting?
JL: I don’t keep track, but I do four newsletters a week, so there are different kinds of newsletters. Some of them are a totally original idea I’ve had. Some of them are me taking an issue and trying to provide some analysis, but I’m not doing that much original reporting. Some of them are a combination. I’d say it’s probably about 50/50 between the reporting and the analysis.
SH: You also have a research assistant, Tesnim Zekeria, who you hired in June 2020 to help out.
JL: That helps a lot. She’s already working on stuff that I’m thinking ahead on. The four-a-week [schedule] puts a damper on your ability to work ahead sometimes, because you have to get the [newsletter] done for the next day.
SH: How often do you run into dead ends in your reporting? Does that stress you out, since you’re putting out so much content every week?
JL: It happens quite a bit. This year, I’ve done quite a few reports on the treatment of workers. A lot of people reach out to me or I’ll get tips, and then I’ll try to connect with people who work at that business. A lot of the time, it can be hard to connect with people. You just can’t get people to confirm your tip, or you’ll get someone to confirm but they’re worried about losing their job so they won’t send you the documentation you need to verify it.
I can’t really go just on somebody’s word. Maybe if I can find six or seven people who tell me that same thing, then I could feel more confident about it. But if it’s just a couple of sources, I want to get a piece of paper that I can go to the company with.
SH: What has been one of the most unexpected challenges of running the newsletter?
JL: There are ebbs and flows that I take quite personally, because it is so much “your thing.” The overall trajectory has been great, but you go through periods where, for two or three weeks, things slow down a little bit. I didn’t really think about it at the time, but you take that pretty personally. It can affect you more deeply than if you’re working for a publication and it’s going through a slow period. Now that I’m farther into it, it’s definitely easier for me, but in the first year, I didn’t have that experience. I was like, is this it? I had a good run for six months, and now nobody is interested in signing up anymore.
SH: Do you think there’s a future for bundling a pack of newsletters together under one subscription rate?
JL: I think it’s possible, [but] I think it makes it harder to succeed. The whole basis of [the newsletter model] is if you can get a thousand or two thousand subscribers and charge even a modest amount, that’s not a bad income. But if you’re no longer one or two people and you’re now six people, that means you have to get many more thousands to make a good income.
You’re also losing a little bit of control over what you’re selling. One of the things [about a newsletter] is you have total control over the product. That is a big advantage, and that helps you be successful. As soon as you start forming a league with other people, you’re selling 25% of you and 75% is other people who you’re not in control of.
There’s a widespread perception that I don’t really think is accurate, that so many people have reached subscription fatigue that you have to find something to reduce the number of subscriptions, and bundling is a solution for that. I think it misunderstands the scale at which these things can be successful.
SH: You really just need a core audience to subscribe who can keep your base rate of pay going.
JL: Yeah. People try to judge it by saying there’s polling about how much you’d be willing to pay on average for news subscriptions. They’re like, “Oh well it’s really quite limited. They would only do two or three.” I think what people don’t pick up is that it’s not about making sure your thing fits in with the average person. It’s about finding your audience. The scale of even wildly successful newsletters is much smaller than the numbers that people are talking about. You don’t have to become Netflix.