How Isaac Saul Built Tangle Into a Million-Dollar Newsletter

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The first time I talked with Isaac Saul, in August 2020, he predicted the future of his American political newsletter, Tangle.

“Tangle is special,” he told me via email back then. “I know most people probably think that about their newsletters. But I truly believe I’m sitting on one of the next seven-figure giants in the industry.”

At the time, he had 7,000 readers, including 1,000 subscribers who paid $50 per year. Isaac had been building Tangle for a little less than a year while still working full-time at A Plus, a now-shuttered news site co-founded by Ashton Kutcher. Tangle then was bringing in about $50,000 a year in revenue, so predicting that he’d one day hit a million dollars in revenue was bold.

But Isaac was right.

Tangle is a daily newsletter that goes in-depth on one big news topic per day. While other newsletters try to package the news into a quick read, Isaac’s gone a different route: The main section covers topics like immigration or international elections and frequently runs more than 3,000 words, highlighting how the political left and right in the U.S. react to that topic, followed by Isaac’s analysis. 

The format has resonated: Tangle now has 100,000 readers and more than 16,000 paying members, who pay $59 per year. (Subscribers from the early days of Tangle are grandfathered in at a rate of $50 per year, while a few hundred others pay either $199 or $499 as “thank you” or “founding” members.) Isaac’s added additional revenue streams — advertising, a tip jar, and merch — and is closing in on $1 million per year in annual revenue.

Tangle’s team has also grown. Isaac has since hired Magdalena Bokowa, head of ad operations and social media; Ari Weitzman, Tangle’s managing editor; Will Kaback, their editor and communications lead; and Jon Lall, executive producer for YouTube and podcasts.

I spoke with Isaac in early June to learn more about how he made his prediction come true. In our conversation, we talked about when it’s time to go full-time with your side project, his friendly tone in marketing messages and membership-related emails, how his team produces such an in-depth daily newsletter, why cross-promotion is an important growth lever for him, and possibly expanding Tangle to other markets.

(This interview has been condensed and edited.)

You started Tangle as a side project. Now, it’s a full-time business that employs multiple people and is closing in on a million dollars in revenue. How do you know when it’s time to take a side project and turn it into a full-time thing?

I surveyed my readers. I think I had about 4,000 or 5,000 free subscribers on the mailing list at the time. I said, “How many of you would pay for this product if I offered, say, one new newsletter a week that was behind a paywall?” I got a positive response: 300 or 400 people [said]  that they would pay for the newsletter. The moment I saw roughly 15% of the people on my mailing list saying that they would pay, I decided that I was going to leave my job and pursue this full-time. That was a strong sign of a lot of energy behind it. 

I used the survey, the metrics, and the math. Let’s say 80% of these people say they will pay. How much money is that? Can I survive on that? For me, it was a no-brainer.

I kept my full-time job [at A Plus] when I turned on paid subscriptions, which I think was smart. When we turned on the paid subscriptions, the conversion rate was above 15%. We got more people than even the survey indicated. I was like, “All right, there is a huge chunk of this organic readership that’s willing to pay.” The money that came in accounted for about 70% of my previous salary. I went to my job and said, “Hey, I’m gonna leave here in about three months, and I want to make the transition as smooth as possible. This is my plan.” Then I used that three months working hard but also saving a bunch of money that I didn’t previously have. I gave myself some runway.

That was how I did it. My advice to people [thinking about going full-time] would be: Actually ask your readers first, run the numbers and make sure that you’re comfortable with the financial situation.

Usually, I tell newsletter operators that if you have a paid subscription product and 3% to 5% of your audience converts, that’s good. Your conversion rate is exceptionally high, at 15-16%. Why do you think that is? 

I think there’s a personal nature to the way that we deliver the news. In the political news space, having that personal nature is pretty different. 

Every edition has my take. I go out of my way to give little personal anecdotes and updates in the newsletter when it feels appropriate. If I’m taking a day off, I explain why. If there’s a political story that’s tied to something that’s happened in my life, I make sure to mention it. I respond to reader emails and build relationships with people that way. 

One of the key things is that when I request people to jump to the paid subscription, I’m just honest, and I ask for money in the voice that my newsletter lives in.

I don’t send people something that is going to look like a Wall Street Journal or New York Times request for a subscription. I say stuff like, “Listen, I’m not asking for this money because we’re going to change the world and reshape the political alignment in America. I’m asking for this money because I want to hire two people, and this is what the money’s gonna go to.” Or I say, “We’re competing with Fox News or CNN, who get millions of viewers a night. We have 100,000 people on our mailing list, which is awesome, but we’re still a small fish in a big sea. The only way we can compete is with paying subscribers, so I need your help.” I make people feel invested in the project and give them a realistic reason for subscribing. 

You’ve made conscious choices about incorporating that voice into the regular newsletter as well as things like your renewal emails. How do you think about these touchpoints with the audience?

Every time a news organization — or a service similar to what we offer — does something I hate, I note it. I put it in a note on my phone or in a Google Doc, and then I’ll scour the things that we’re doing and think about ways to counterpunch that. 

This renewal email is a great example. This was born out of the fact that I was doing my taxes, and I saw, like, eight subscriptions for news that I didn’t read anymore that were going to my spam folder and that I got no notice about the fact that were re-upping my subscription. On Substack, they let you kind of customize that message, and there was nothing in it that felt personal. [Tangle started on Substack but has since moved over to Ghost.] It was very clearly an automated message. I saw low-hanging fruit there where I could spend 20 minutes and write a message that’s like, “This is why we still need you to subscribe. Here’s why I’m sending this notice. Here’s what I hope you do with it.” 

I get a reply to that email all the time. That’s one of the highest response rates of any automated email we send. People are just like, “Dude, thanks for sending this. People never do this. I love Tangle, and I’m so happy to keep supporting what you’re doing.”

When people write back to say, “Hey, I don’t have much money right now. I lost my job, I need to cancel,” then I can gift them a subscription and do something to build that brand loyalty. Similarly, we track our corrections at the top of newsletters and podcasts, and that was born out of my experience reading articles in the New York Times or the Washington Post or Wall Street Journal and seeing tiny little footnotes about very significant corrections at the bottom of stories, and thinking, “This isn’t how this should be done. I hate when news outlets do this — how can I do something a little different?”

As you’ve gone from 100 readers to 100,000 readers, you likely can’t reply to readers one-to-one the same way as you used to. How has your relationship with the audience changed? 

Yeah, the responses and interactions in our inbox have changed the most. The first 50 or 100 readers were mostly friends, colleagues and family members. But many of the first 1,000 readers were random people from the internet who found us early on through the network effect. Those people are the ones who, I think, have the hardest time with scaling.

Early on, I’d have ten emails, so I’d spend an hour a day or two hours a day writing 1,000-word emails to readers who were writing about my political views. We’d have these rich, robust exchanges. Now I’m writing back one-sentence responses, or I’m not replying at all, because there are a lot of new readers coming in to whom I want to give those responses. It’s just a time management thing, and I think that’s been hard — more for those people who had that relationship that’s gotten narrowed, but it also sucks for me because I wish I had more hours in the day to give people that kind of attention. 

The other way I think it’s changed is recognizing that you’re gonna get a much wider spectrum of feedback because the audience is so much bigger. [I’ve had to get] comfortable with the fact that one email, especially because of the content and the stuff we write, is going to piss off some people on the far-left spectrum and piss off some people on the far-right spectrum at the same time. 

There was a long period when our audience was so small that many of the responses were kind of homogeneous. It was obvious early on if a newsletter resonated because 95% of the emails would be positive. Now, I will never hit that satisfaction rate because we’re covering divisive political issues, and the audience is so big that you’re bound to upset people. I’ve had to allow some criticism to roll off my back a bit more.

Tell me about how you’ve incorporated reader questions and polls into the newsletter. To me, that is a way of engaging with the audience, even if it’s not you, Isaac, writing back to each reader personally with a note. 

Early on, someone would write in with a follow-up question about something we wrote. Then, the next day, I would include that as a reader question in the newsletter. Now, because we’ve grown so much, I have a form where people can submit questions, and we monitor that form.

I think a general frustration people have with the news is they don’t see themselves in it. They don’t feel like they’re being heard. We want people to feel like they write in and have a decent shot of having something published or a question answered in the newsletter. It’s also a great tool for understanding what stories are resonating with our audience. Like, if I get ten questions about Joe Biden’s age in a day, I know that there’s some story that came out that is making a bunch of people think about that story. That surfaces news for us that we might be missing, which is helpful and interesting. 

I also get opportunities to clarify my own positions or even issue corrections. A lot of times, the reader is scratching at something they didn’t like about our take, or maybe our take wasn’t clear, and we get to clarify or update our position a little bit. It keeps the conversation going. 

The polls were shepherded by my managing editor, Ari, who I hired when we got to a certain level where I could do that. He wanted to get day-to-day glimpses of how our readers process certain political issues. We realized that we were just taking those polls and keeping them internally. Then we were, like, “Oh, this is awesome content, we should show this back to the readers.” We started publishing the results of the polls the next day, which I know a lot of other newsletters do. But it took us a little while for that to totally click. 

I think it’s a nice way to show the audience what other Tangle readers are thinking and give people this micro-look into this community and how they process the news. Oftentimes, it reinforces the fact that we have a diverse political audience. We see how the responses come in; the breakdown of our audience, being conservative, liberal and independent, is pretty representative of the country.

You’ve got a newsletter that goes out four days a week to all readers. There’s the Friday edition just for paying subscribers, and now there’s a Sunday edition for paying subscribers. These are not short emails. You have the read time at the top of every email, and it’s often a 10- or 15-minute commitment. Tell me about how you produce Tangle and how you stay organized with a daily newsletter.

I will say I take pride in the read-time stuff because I think we’ve zigged when many other places have zagged. The short-form, bullet point newsletter is being done well by so many people. I read Axios every day, I read Morning Brew every day. I don’t want to compete with those guys. We very intentionally offer a deep dive with more detail and nuance that is going to take you a little bit longer to read. We’re trying to be unique in that sense in the political space. 

The production side has changed a lot now that I have a team. But the general thrust is we try to decide the topic 48 hours before we cover it. It gives us a bunch of time to do the research. I have one person who heads the research now, who goes out and scours 100 different news sources and collects the most interesting articles they can find from a wide range of pundits from the far left all the way to the far right. Then, he summarizes the arguments that are being made in each article, podcast, or YouTube video he can find. While he does that, two other members of our editorial team are doing our own independent personal research, where we’re reading a bunch about the topic, consuming as much about it as we can, and seeing if independently we come to some similar understandings of how the partisan breakdown is happening. Then, it all meets in an email thread where we share the results of our research. 

I write the introduction to the newsletter, and then my managing editor and I split the “questions answered” part of the newsletter. This is something I’m trying to change long term. I want the daily newsletter to be able to happen without me. Obviously, the “my take” thing is pretty important. But I think we need to get to a place where if I’m sick for a day or I want to take a couple of days off, there’s a team that can produce the daily newsletter without me.

We start a Google Doc, and everybody drops their elements in it. Then you edit the parts of the newsletter that aren’t yours, which is fun. It is an insane amount of content and it’s hard to keep up with — that’s one of the big problems that I’m solving for. What we’re doing is kind of absurd. 

For the Sunday newsletter, Ari, who’s the managing editor, owns that completely. It’s the only Tangle product that I just don’t touch, which is super fun. I get it every Sunday without knowing what’s gonna be in it. We have a Slack channel where everybody shares ideas for stuff that goes in there.

You told A Media Operator that more than 90% of your revenue comes from membership. You started running ads in Q4 of last year, have a tip jar, and sell merchandise. How important is it to you to grow those additional revenue streams?

I would say the advertising revenue stream is important. The tip jar revenue stream is usually based on how good our content is. We see a huge influx of tips when we publish something that is clearly well done. I can almost predict now when those bumps are going to happen because I can see the newsletter and feel like, “Oh, we nailed this today.”

The advertising revenue is something we want to scale within the confines of what I hope to do. I don’t want obtrusive ads, and I won’t do any advertising with explicitly partisan political groups. I want the products or services we’re advertising to be quality. If it’s a newsletter that wants to advertise with us, I’m going to read the newsletter for a couple of days, and I’m not going to put it in if I think that it sucks. I think that is what makes our advertising so powerful because our readers trust us. 

One of the big things is that we don’t show ads to our paid subscribers. That devalues the ad space a little bit because advertisers aren’t getting the people who are apparently most willing to pay. That’s a downside. The upside is our free subscribers are still super engaged. We get 48-50% open rates, even on the free subs, so we know they’re clicking through. We recently did a cross-promotion with The Hustle, a newsletter that is probably 10 to 20 times our audience size. We got almost the same amount of clicks in our newsletter as they did for us in theirs, which is proof that our audience is super engaged. They trust us with the advertisers we put in front of them, and most of our advertisers who have worked with us come back for more. 

I think as we get more proof of concept and as we can show over and over again how engaged our audience is, we can make those ad spots a little bit more premium and push the prices up a little bit more. The last few months, we’ve been doing something like $8,000 or $9,000 a month in advertising revenue, which is over $100,000 a year. That’s a salary or two if we are hiring someone fresh out of college. That’s important money for us. I want to keep growing that, but my focus is always going to be on the paying subscribers and making sure that they’re getting what they want.

What is the open rate that you see for the paying audience compared to the free audience?

We’ll see open rates between 70 and 80% every week on the Friday editions that we just send to paying subscribers. I know the open rate data is kind of fudged and it’s hard to know what’s what. On the full daily newsletters, we see 58-62% open rates daily. Most of our engaged subscribers read two to three newsletters we send weekly. Then there’s the superfan 10% of our paid subscribers who open every single email and read it top to bottom.

When does it make sense for you to do cross-promotional free swaps with another newsletter versus advertising in another newsletter?

I’ll do the cross-promotions when I feel like we’re tapping an audience that I’m not 100% sure is going to be interested in our products, and I want to test the waters. If we do the cross-promotion and it goes well, I’m like, “Okay, let’s buy an advertising spot for a couple months from now, since I know you guys have an audience interested in us.” 1440 is a newsletter that advertises itself as being unbiased, non-partisan, down the middle — they use tons of the same language we do, and they’re way bigger, so an advertising placement with them makes a lot of sense. We see their readers are sticky, and a lot of them convert to paid subscribers. They love our content because it’s a nice complement to the kind of short-form 1440 stuff. 

What is the overlap between the podcast and the newsletter?

I started the podcast purely out of audience demand. I was getting a ton of emails from people that were like, “Dude, I love your newsletter. I don’t have time to read it every day. If I could listen to this while I was doing the dishes, it would make a huge difference, and I would listen to it every day.” I started with this rudimentary version of a podcast where it was just me reading the newsletter and riffing and then publishing it as a podcast. Over time, it’s become more sophisticated. I have co-hosts who read some of the newsletter. We interview people on the podcast, so we have unique content that exists in the podcast but doesn’t necessarily exist in the newsletter. 

When I set out to do this, I thought, “Oh, this will be a discovery funnel for the newsletter,” which is not how it works. What basically happens is that people start reading the newsletter, realize we have a podcast, and say, “Oh, I prefer that. I’m gonna go listen to the podcast.” Then, they either leave the newsletter or mostly get their content from the podcast. 

Growing a podcast is so much harder than growing a newsletter has been. I very rarely get people who start at the podcast and then find out we have a newsletter. If I could go back and do it again, I would have started our YouTube channel three years ago when I started the podcast. We just started a YouTube channel in the last year, and it’s already bigger, gets more traffic than our podcast does, and already has a better top-of-funnel because YouTube’s made for discovery. [For those not in the marketing space: Top-of-funnel refers to the broad entry points through which someone first interacts with your product.] I regret that a little bit, but the upshot is I’m giving our most loyal readers something they want. It takes me 30 minutes to record the podcast, and then I ship it to an editor who publishes it. It’s low-hanging fruit for my work day. It costs a lot of money, obviously. But I think when it’s big enough, if we can advertise against it, we can paywall some podcast content, we can squeeze more juice out of it in order to get close to breaking even [in terms of costs], it’s worth it.

Are you surprised that someone hasn’t tried to take the Tangle format and build their own version in a country like France, Brazil, or Australia? Do you think it’s possible that someone could do that? 

I’m a little surprised I haven’t seen it pop up. I think, long term, that’s a potential growth strategy for us: franchising the brand out to different countries or into different beats. I want to make a Tangle Sports or a Tangle Culture or something like that, where we’re covering debates that exist in different areas. 

I think it hasn’t happened because what we’re doing is hard. It takes a unique set of circumstances — I had a full-time job and enough free time to get Tangle off the ground. I started it during the Democratic primary season in 2019, going into one of the most-watched elections in U.S. history, so the timing was good. We have, in my opinion, very good content, which is hard to produce. In some ways, I’m surprised that it hasn’t popped up in other countries. In another sense, I know how much work it requires. Without seed money or a flexible, full-time job, it’d be hard for one person to take it on. 

But long-term, I hope that we get to a point where I can take $100,000, hire somebody to be the French version of me, try to reproduce Tangle somewhere else, and then share in the revenue with them. I think that’s an interesting model. 

I’ve seen little bits of what we’re doing pop up in different places. Like the New York Times in The Morning [their flagship daily newsletter] the other day, I saw them literally say, “What’s the left saying about this thing, and what’s the right saying?” which kind of sends a chill down your spine. I had very informal conversations with [Semafor co-founder] Ben Smith early on about working with them or them buying Tangle, which didn’t work out. But they very generously told me, “We don’t have the money to buy you at the value that you should sell for, so you shouldn’t sell Tangle to us.” But then they created a Semafor format that is similar to ours. I’m not saying they’re copying us. But there’s something there that I think was almost definitely inspired by the kind of work we’re doing, where they give the reporter a stake in a very specific section or voice disagreement. 

Those competitors are popping up. But I think there’s something unique about our voice, how personal it is, and how many different topics we cover in our format that makes it hard to replicate.

Correction: The original version of this interview said that Tangle has a “forum” to collect reader questions — it’s actually just a “form.“ (Autocorrect strikes again!)

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