Behind the Headlines with Isaac Saul of Tangle: Running and Monetizing a Media Newsletter

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Isaac: We're at the point now where we're really focusing on putting some money back into the business and scaling it. I think we have a proof of product now. We have an incredible array of readers, a really diverse readership — something like 40%-45% who are liberal-leaning, left-leaning readers, 30%-35% conservative readers, and the rest who self-identify as independent or really far to the right or far to the left. So I think we've proved that we can build this coalition of readers and put them under one roof and that they trust our content.

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Welcome to the Become a Writer Today Podcast with Bryan Collins. Here, you’ll find practical advice and interviews for all kinds of writers.

(interview)

Bryan: My guest today is Isaac Saul. He is the Founder of Tangle. That's an independent, nonpartisan subscriber-supported newsletter, which boasts over 75,000 subscribers in 55 plus countries around the world. I wanted to talk to Isaac today because Isaac has built a thriving business as a journalist. Within the news and media sphere, it was harder than ever to do speaking to somebody who used to work as a journalist, granted not a very good one. It's very nice to talk to you today, Isaac.

Isaac: Yeah, thanks so much for having me on. I appreciate it.

Bryan: I can't wait to hear about the story behind Tangle. But before we get into that, could you give the listeners a flavor for your writing career and how you got into journalism?

Isaac: Yeah, sure. So I went to the University of Pittsburgh where I was a non-fiction writing major. I was actually the sports editor for the school newspaper. So that was kind of my first paid journalism job. I had done some media work when I was in high school, to interning at a radio station. We're helping run the local high school television station that sort of covered school news. But college was my first foray into real journalism, getting some chances to shadow reporters from the Pittsburgh Post-Gazette, and ESPN, and other kind of big names that were operating in Pittsburgh at the time.

After college, I lived in Israel for a little bit. Then I came home from Israel for my first job ever which was at the Huffington Post, which I am fond of telling people. It was not because I was just a bleeding-heart lib. But it was really because I applied to 50 other jobs, and they were the only place who offered me a job when I was out of college and getting journalism jobs were really hard. That was my entrance into the political reporting space, which I think had a big effect on me.

It's part of the reason why I ended up creating Tangle. It's because I got to see a little bit of how the sausage was made at a news publication that had a particular political slant. Obviously, the Huffington Post is left-leaning or further left, depending on who you ask. After that, I worked at a company called A Plus, which was founded by Ashton Kutcher, the actor and investor. I was one of the first full-time employees there. Throughout my career, I freelanced for a bunch of different places: Time Magazine and Vox. I've gone on CNN and done a bunch of hits like that for things around my reporting. But those are my two big full-time jobs before I started Tangle about four years ago now.

Bryan: I'm guessing when you wrote for The Huffington Post, that was a paid journalism gig rather than part of their free contributor program. I think I wrote several articles under that contributor program years ago.

Isaac: Yeah, it was a paid gig. It was sort of like being a factory worker in an assembly line where we were pumping out three or four articles a day. Basically, the Northstar was how to drive traffic to the website. I mean, this was back in 2013, 2014. At the time, I was actually part of a team that was like the viral ninjas of The Huffington Post, where our whole job was to find stories that we could package in a way that would drive traffic to the website and go viral, which in a lot of ways was honestly really good training. Because it sort of taught me things about what people are interested in, why they click, and why they share articles. While I was there, I started doing some of my first real political writing, which I did mostly after my day-to-day duties were done, through writing for the opinion section or doing my own individual reporting on a political story. That was my first big foray into politics.

Bryan: So where did the idea come from to transition from working as a journalist and a freelancer to running your own publication?

Isaac: I think one of the big origin stories is just that I grew up in Pennsylvania, in Bucks County, PA, which is a bellwether county and a bellwether state and, obviously, a really politically-divided place. So I grew up with a lot of friends and family who had varying political opinions and views from across the political spectrum, which I think in today's America, unfortunately, is pretty rare. A lot of people are in their own bubbles, maybe have one or two friends or family members who don't really agree with their political world views. But we've become very tribal in that way. So I have always felt particular empathy and sympathy for people on both sides of the political aisle in our country, which I think has made me a little bit more open-minded maybe as a politics reporter and commentator and somebody who — I feel very politically incongruent myself. I don't feel a particular allegiance to either the blue or red team these days. So that was a big start.

I had this idea that was born from that, of just creating a publication that people on both sides of the spectrum in my social group could read and trust, a place where conservatives and liberals and independents and everybody, from the far-right Trump supporters, to the diehard Bernie lefties could all read the same news publication and trust what it was publishing. I didn't believe that that existed. And so I had this idea for Tangle, which was essentially explaining a story in the most neutral language possible, sharing arguments from the left about the story, sharing arguments from the right about the story, and then being really transparent about what my own take was. I had had it written up in a notebook maybe five or six years ago.

Then when I was at A Plus, we started moving away from written content and towards video content. The company was acquired. It went through an acquisition. We were bought out. The writing was on the wall that we were going to go in a different direction that I didn't necessarily want to go in. And so, in my off hours — basically, mornings, lunch break, evenings after work — I started writing this newsletter on Substack every day, which was executing this idea of just one story. One controversial story in the political world, summarizing what the right was saying, summarize what the left was saying, and then sharing my take. That was the very beginning of Tangle.

Bryan: So this was four years ago. It would have been in the run up to the last election and also around the time. So Slack was becoming quite popular for journalists who were looking for a different way to communicate directly with their readers. For Substack, was that the reason why you started on that particular publication rather than setting up your own website?

Isaac: Yeah, so there were — first of all, yes to the timing of it which was more luck than anything else. I mean, I think there are a lot of intentional things I've done that have contributed to the success of Tangle. But I got really lucky too, which is that I started this basically right when the Democratic primary in 2019 was heating up. I got to report on the presidential election and all the happenings in U.S. politics, all the way through Biden's victory over Trump. There was just a tremendous amount of interest in U.S. politics at the time that I started which really helped build the foundational readership.

The reason I chose Substack was two-part. One, the platform is incredible. I mean, it's a really easy place to publish. Two, I was really taken by the idea that newsletters were the future. At this time, we were not yet in the newsletter boom quite yet. I was one of the first people for sure that was jumping into that wave as it was developing. And I'm really glad I did. I just simply love the idea of going directly to people's inboxes. I love the idea of not having to rely on social media for traffic. I love the idea of longer form, more intimate content, straight to readers.

I love just the way the whole publishing process went, just the way to build an article on Substack and how easy it was to send it. And it was free. Their model is that they don't make money unless the writers make money, which made me feel like they were very invested in what I was doing and what I was producing. I really respected that. I thought that was a really symbiotic relationship. It's, I think, one of the things about their model that really works. So it made sense for me at the time when I didn't have any money to pay for my own website and publish on my own site to start off by building this free mailing list with them.

Bryan: Interesting. Yeah, Substack is great for somebody who doesn't want to worry about the nuts and bolts of running their websites or, for example, learning WordPress, or managing domains, who just wants to start writing newsletters and have an easy way of attracting email subscribers. I'm curious, when you were covering the elections, did you write a cover all of the initial articles yourself? At what point did you start hiring other journalists and writers?

Isaac: Believe it or not, I have basically been doing this by myself up until this last year.

Bryan: Wow. I'm surprised.

Isaac: Yeah, I had one hire that I made about three or four months after I turned on paid subscriptions, which is a woman named Magdalena Mikova, who does all my social media and advertising. She runs the Instagram and Twitter and channels like that. She's just been my right hand on everything since the very beginning. I found her by basically paying to put an Indeed ad on the front page of Indeed for 24 hours and then interviewing 30 or 40 people, and picking her out of the bunch.

My dad was a volunteer editor for the first year or two, and basically just proofread the newsletters before I sent them out. Then about two years into it, a reader volunteered to do some copy editing. And so I brought them on and paid them for an hour or two of work a day. Then slowly and slowly, the team built. Today, actually, we have four full-time employees. One of them is a managing editor. One is a YouTube and podcast editor. One does all the communications and some of the research for the newsletter and guest booking and manages my schedule and things like that. Then Magdalena is still on the team running all the social accounts and a lot of the advertising business. So we've definitely built out. We still have some part-time people who help edit day to day and some interns you come through and things like that.

But yeah, for a long time, I was producing that content daily by myself, which was a grind. I'm still working 12 or 13 hours a day, which I'm trying to get down to 8 or 9 so I can have a life outside of the work. But for right now, to fight with some of the big guys and do the work we need to do, that's kind of the output that it takes.

Bryan: I can imagine, especially for something that involves political reporting. At what point did you decide to turn on subscriptions for your newsletter, or should I say paid subscriptions?

Isaac: Yeah, we did free newsletters for about eight months. That was basically at the recommendation of Substack. It was to sort of stretch it out as long as you could to build that reader relationship and the habit of people reading the newsletter, which I think was great advice. I thought that was one of the best pieces of advice I got in the beginning. It was to build that relationship first and not immediately go for the money.

When we turned on paid subscriptions, we did it slowly. I surveyed readers. I said, how many of you would pay for one additional newsletter a week that we were putting behind a paywall? And if you were to pay, how much would you pay? I gave them different options. Then I gamed out what was the best way to incentivize subscriptions, and what was a good price or cadence, things like that, in order to maximize the number of people who wanted to come in through this subscription base.

We ended up turning on paid subscriptions at a $5 a month, $50 a year tier. We had a $199 a year kind of founding membership. I think we had maybe 3,000 or 4,000 people on the mailing list when we turned on paid subscriptions in the beginning, and about 18%-20% of the people converted to paid subscriptions, which was incredible.

Bryan: It's very impressive.

Isaac: Yeah, Substack told me to expect maybe 5% to 8%. That was both, I think, a reflection of this community we were building and a lot of my friends and colleagues and family members who really wanted to support me. But also, I think a reflection that the product work. There was a desire for it. People wanted to support this kind of reporting. People wanted to support this kind of news. And so, once I saw that, I saw the subscriptions come in, that gave me the courage to quit my full-time job and go into doing Tangle full time. I did that a couple months after we turned on paid subscriptions. And ever since, I've been basically living off that money that's been coming in.

Bryan: That's fantastic. It must have been a great validation to see all your hard work pay off when so many subscribers converted. I've heard even lower rates of conversions. For example, 3%. So to get at 18%-19% is really good.

Then at some point, you decided to move from Substack to Ghost. And if people aren't familiar with Ghost, it's another newsletter tool which is similar to Substack. But the idea is that it's a bit more like WordPress in that you manage the website, and you manage pretty much everything rather than letting Substack do it for you. But what was the reason for moving away from the Substack model to something like Ghost?

Isaac: For me, it was almost entirely just a business decision and a financial one. As I mentioned at the top, one of the great things about Substack is that you can publish using their tools for free, and you can build their newsletter list for free. They only make money when you make money. But we got to a point growth-wise where I think we were doing maybe $200,000 a year in revenue. Substack takes 10%. So it was $20,000 that they were taking from the subscription revenue, which as somebody trying to build out a team and get help and all these things, I mean, $20,000 is enough money to pay a part-time person for almost a year of work. So when I looked at other options, places like Ghost, places like WordPress, to publish, the fees to pay to send those emails were maybe $1,000 or $2,000 a year. I just saw the savings, and that was basically what drove me to make the jump.

The interesting thing was, at that time, Substack didn't have a lot of the tools that they have now. I think they have the network tool which helps elevate different writers and bring people into the network, and you can grow internally among other Substack readers. They've introduced all sorts of customization tools for the websites, and for publishing podcasts, and doing a lot of stuff that I wanted to do back then.

If I were on Substack today, because migrations are such a hassle, I'm not 100% sure I would make the switch again. I think it's still a big enough savings. I probably would. But the other side of it was that Ghost, at that time, was a much more flexible publishing tool. There's just a lot more you can do, custom website designs. We were trying to drive people to the website, traffic more, expand out of just being a newsletter product. A lot of stuff we're still doing now that I think is probably easier to do on Ghost than Substack. But yeah, more than anything else, it was just a business decision. I mean, it was just about the fee and how much it costs to send emails.

Bryan: Yeah, I was on Substack for a while. I had a newsletter, and I migrated it to Ghost. Now I manage the newsletter with something else, ConvertKit. But the Ghost team actually took care of the migration for me. What I liked about Ghost was, it was quite fast compared to WordPress to use. Relatively intuitive. Maybe a slight bit more of a learning curve than Substack, but certainly not much. It probably doesn't have the discovery built into it that Substack has. For example, I've interviewed a few newsletter subscribers who said that they get a lot of their new readers from people recommending the publication within the Substack app, or from the Discover, or Chart section of Substack? Whereas if you’re on Ghost or your own website, you have to track all those readers yourself. So how are you currently growing Tangle at the moment? What's your current plan to grow the newsletter on the website?

Isaac: Yeah, it's good question. For us, we're at the point now where we're really focusing on putting some money back into the business and scaling it. I think we have a proof of product now. We have an incredible array of readers, a really diverse readership — something like 40%-45% who are liberal-leaning, left-leaning readers, 30%-35% conservative readers, and the rest who self-identify as independent or really far to the right or far to the left. So I think we've proved that we can build this coalition of readers and put them under one roof, and that they trust our content. And we've just seen, because of our work, we've seen some stuff organically. Pieces we've published go viral, or the newsletters get shared heavily. People in the industry, other media people, other journalists, other political pundits pointing to us as a place to get really fair and balanced news. So that has basically affirmed our view that we have something that's working. I think we've iterated to the point where we don't want to change much about the product right now.

Our biggest goal is, like, how do we get — we have 78,000 people on our mailing list or something like that. How do we get that to 100,000, 500,000, a million? So we're doing a few things. One is, we're advertising, which obviously is the most direct way to pick up new subscribers, which mostly involves buying ad space and other newsletters. The reason for that is if people are reading news and newsletters, then they're going to be comfortable reading our newsletter. So we want to just get in front of people and meet them where they are, people who are already kind of newsletter readers.

The other thing is, we launched a YouTube channel. That was one of the big investments we made in the last year. I hired a full-time YouTube editor, and we are publishing content on YouTube now. Then we clip that content. We put it on Instagram and TikTok. We're doing that mostly to try and grow a younger audience, but also function as a top funnel for the newsletter.

Then the third thing is just focusing on earned media, which is doing interviews like this, spreading the word about what Tangle is, how it was created and the kind of work we do. Then also making sure that anytime we publish something, that really seems to resonate, that we ride that wave a little bit. I'd get an interview out of it. Go on a network television to talk about a story I wrote, make sure people who are interested in that topic see it and maybe share the piece, those kinds of things. For us, that's kind of like the three-pronged strategy that we're really leaning into in the next year, and hoping to just pour some gasoline on the growth.

Bryan: Interesting. Maybe I misheard. But didn't you say that your last publication years ago because you're moving towards video?

Isaac: Yeah, it's funny. When I was at A Plus, they sort of did the, at the time, cliche pivot to video. For me, what that meant is I basically had to learn how to edit videos overnight and became a script writer and a video editor, which was not the work that I wanted to do. My real core passion is writing, and politics is just a big interest of mine. But once that happened, it became clear to me. I was, A, not a good video editor. And B, I didn't want to do it.

When we launched Tangle, I think one of the things we saw was, our mailing list was growing organically. We were seeing everything up into the right, which was awesome. But when we surveyed readers, we saw that a really good chunk of them are in the 50 and up age bracket, which is great. I want to talk to those people. But we're also trying to change how people consume political news. We're trying to shape the next generation of voters and the next generation of politics consumers, and teach them to be more open-minded and view arguments from across the spectrum and get out of that bubble that they're in.

There just aren't a lot of 18 or 16- to 30-year-olds who are reading emails every day to get their news. They're on YouTube. They're on TikTok. They're on Instagram. And so, building out those channels to bring in a younger audience was really the North Star for us in that decision. Now, fortunately, I don't have to edit these videos anymore. But it was a good experience learning a little bit of that craft before I did this, because it helped guide the early days of the YouTube channel.

Bryan: Yeah, video editing is really time consuming. I'm trying to grow our YouTube channel at present as well. I don't mind recording the videos. But the editing really is difficult, so I do invest in working with an editor. So for the website, are you able to get it in Google News with Ghost? Do you look at SEO, or are you focusing on what you mentioned previously, the owned and earned media?

Isaac: Yeah, the last time I checked, we were in Google News. It's weird. Sometimes you get in, and you get booted. I have not invested a ton in SEO, because I generally view it as a money pit. I mean, I think there are so many people who say that they're really good at building SEO traffic for news organizations. I've experimented with some of them, and the results have varied so widely that it has never struck me as a particularly strong way to grow an audience.

Also, because when people come in through Google searches, they're a lot more likely just to go to the website and bounce, or read the one thing that they came to read and then leave without really signing up. And if they don't become regular readers, if they don't give us an email address, or subscribe to the YouTube channel, or whatever, then it's a lot less of a value-add for us. So we actually have not done a ton of SEO work. We have a few articles that definitely pop up because of search results, just because they've gone viral in other places. But it hasn't been a big part of our business strategy. I can't say for sure whether that's a smart thing or not a smart thing. But I know that the results that I've had from investing in SEO have been pretty inconsistent, which kind of scared me off a little bit.

Bryan: I suppose I'm on a slightly different route. I have spent a good bit of time on SEO, but granted I'm not running a news website. So I'm currently more focusing on video for the same reasons that you mentioned there, Isaac.

One last area I wanted to touch on was your content production workflow. You're publishing news articles pretty much daily. You mentioned that you have a team. So could you get to give a high-level overview of what it takes to run Tangle each day in terms of content production?

Isaac: Yeah, so it used to be, again, I was basically just doing everything. And now with the team, I've had quite the burden lifted where I'm getting a lot of help in different areas. We are typically maybe two days ahead on the newsletters, or at least we know vaguely what story we're going to cover a couple of days in advance. We try and keep up with the news cycle, but we also don't want to be fast. We're not reactive. We really like to wait for things to clear up. Like for instance, the hospital bombing that happened in Gaza, the explosion last week, that was the story that broke on Saturday, or I guess it was just two weeks now. We could have covered it on Monday, but we waited a day just because it wasn't totally clear to us what was happening. And then push out a newsletter that I think was a lot more accurate and thorough and balanced than a lot of the initial reports that came out were.

But roughly speaking, it's a ton of research. I mean, it involves consuming an unthinkable amount of media content. We decide on what the main story is. We have to research that for the introduction and the explanation of that main story. Then we need to find three arguments from the right and three arguments from the left that specifically speak to that story. That part involves reading dozens and dozens of news articles, and listening to podcasts, and watching network news, and watching other political commentators on YouTube, and then deciding what three arguments we think are most representative of what the different sides are arguing and are also most compelling and are interesting fresh takes on what's happening so that we can give our readers a really wide spectrum of views.

Will, who helps out with the research and communications, he does a big chunk of that research now on the right-left arguments. Last night, Will sent me 30 articles he found for tomorrow's newsletter. I'll read through them, and we'll talk about which ones stick out to us and why. Then we'll slowly narrow it down. Then when we decide what six articles we want to include, then I have to decide where we're going to excerpt them and how we're going to excerpt them. Then I write my take, which is like a mini-editorial every day. That usually happens the morning the newsletter is going out. So I wait till the last minute to write that once I've read everything and seen all the different arguments. That's the last thing that happens.

Then we have a reader question we answer every day, which my managing editor now does the first draft of. And when he's editing my stuff, I edit what he wrote. Then there are some other smaller sections in the newsletter that are a smaller lift and a team effort. But yeah, I mean, it typically takes a full day or two to put together one of the newsletters, and maybe days or even weeks of reading and researching a topic before we feel like we're totally ready to cover it.

Bryan: Are you working with your team to Slack, or some sort of collaboration tool, or in-person?

Isaac: Yeah, we have a Slack channel. Right now, I'm in Philadelphia. I was in New York for about a decade, but I moved down to Philadelphia last year. Then a colleague in New York, a colleague in Vermont, a colleague in Oregon, and a colleague in Los Angeles. So we're very spread out. The vast majority of our contact happens through Slack or text messages sometimes, too. But Slack is the big tool that we use to organize and keep up with each other.

Bryan: Fantastic. Well, congrats on all the success with Tangle. Where should listeners go if they want to read it or hear more of your work?

Isaac: Yeah, please. You can find us at readtangle.com. You can sign up to the newsletter for free and read 80%, 90% of our content while you're on the free mailing list and decide if it's something you want to support. And if you're somebody who's interested in politics or even vaguely wants to learn a little more about politics, it's 10 minutes a day, I think, to get a really well-rounded look at some of the big issues people are discussing. We try to make sure we explain what's going on and share a lot of use out there about that topic, so I encourage everyone to check it out.

Bryan: We'll be sure to include the links in the show notes. Thank you again, Isaac.

Isaac: Thank you for the time I appreciate it.

(outro)

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