Hello friends,

For our third episode of Rough Draft, we had the pleasure of speaking with Judd Legum, founder and author of Popular Information, a leading political newsletter known for its focus on holding those in power accountable for their actions.

Judd has been writing on the internet for a long time and was one of the first political newsletters on Substack. We discuss how Judd built a large paid newsletter without a paywall, the importance of experimenting and constant improvement, and why the business side is essential to get right.

The most important thing I’ve learned is that the connection you form with your readers is the key to everything.

To me, not too dissimilar from Doomberg, Judd always struck me as someone who enjoyed the business side of the newsletter. But as you’ll see, it’s more that he understands the importance of building a durable business around his research, writing, and the impact of his newsletter — the things he truly enjoys.

Check out the full episode on Substack, Apple Podcasts, Spotify, or YouTube.

Let's dive into a few highlights from our conversation.

I first met Judd while working on Yem, a product that helped paid newsletters grow revenue through automated emails. Judd was the first writer to trust us. I was thrilled to work with him — until I realized he didn’t have a paywall. I wasn’t sure how we’d help him grow his revenue.

Judd then shared a Google doc filled with pages of pitches he’d tested to convert free readers into paid subscribers. Over time, he discovered something surprising: people weren’t paying for access. They wanted the opposite: to spread Judd’s reporting as far as possible and maximize its impact.

I realized early on that people weren’t just paying for more content; they were paying to support accountability journalism.

At Substack, we often pointed to Popular Information as proof that you don’t always need a paywall to build a paid newsletter. Don’t get me wrong — paywalls are very effective, especially in certain categories (e.g., Finance, Business, Technology, etc.). The point is that it’s important to deeply understand what your readers are paying for and to mold paid benefits around that value.

Taking care of business

In my discussions with Judd, he always seemed to enjoy the business side more than other writers. When I asked him about it, he clarified that he most enjoys writing and researching, but also understands that’s all predicated on the business doing well. For those trying to do this for a living, Judd stressed that no matter how passionate you are about writing, understanding how to run a newsletter as a business is essential.

You need to constantly be improving both the business side and the content side. Standing still means you’re falling behind.

It seems this view was informed by his experience at ThinkProgress, where he learned that if you start to backtrack, that can accumulate its own type of momentum. ThinkProgress also helped Judd experience the perverse incentives and the rollercoaster ride of depending on advertising revenue. He also learned about the risks of over-hiring and taking on higher fixed costs.

I think this is why Judd is so proactive in monitoring email list growth, free-to-paid conversion, and churn, and why he’s constantly experimenting and searching for ways to improve. Carving out a little time each week to focus on the business side allows Judd to continue focusing on what he loves — writing and reporting — without having to constantly worry about the business collapsing.

You can't wait until you've dropped 25% to start paying attention to your finances.

Start growing your audience with non-scalable ideas

While Judd benefited from having a large Twitter audience when he launched Popular Information, he also did a lot of tedious, time-consuming things to grow his newsletter. Right after his first post, Judd sent nearly 7,000 personalized emails to everyone in his contacts, generating nearly 1,000 subscribers — a solid foundation.

He also stressed the importance of collaboration: reaching out to writers with a similar target audience and exploring ways to work together. That could include:

Judd also talked about how each new topic represents an opportunity to create awareness with a new group of readers. For example, if Judd were to cover a local topic for a certain town in Oklahoma, he would reach out to reporters in the area that have written about the topic he’s covering, asking for insight and creating awareness.

If you’re just getting started, don’t discount how impactful non-scalable ideas can be, especially in building an important foundation. No matter what stage you’re at, finding ways to collaborate with fellow writers and creators can go a long way, as can a more editorial-centric approach to growth.

Thank you to Judd

A huge thank you to Judd for joining us and sharing an avalanche of wisdom.

We’d love to hear from you! What did you learn from our discussion with Judd?

We’ll be back in two weeks with another episode of Rough Draft — see you soon!

Thanks for reading & listening,
Reid