Isaac Saul on Building a Truly Independent Tangle

This week, I spoke with Isaac Saul, the founder of Tangle, a political media company that looks to tackle issues with analysis from both sides.

Special thanks to SEBPO, for making this episode possible.

Jacob Cohen Donnelly: Let’s start at the very beginning. What is Tangle, and how and why did you find yourself launching this brand?

Isaac Saul: Yes, great question. I started Tangle for two reasons. I think one was a response to what I was seeing in the media industry, specifically how political news is being covered across the space. The other was a response to what I was seeing in my personal life, which is basically that people who disagree politically have a hard time being in the same room together anymore.

I grew up in Bucks County, Pennsylvania, which is part of my genesis story. I talk about it a lot. It’s a bellwether county and a bellwether state. Very politically divided. Lots of class divisions. In my high school, my friends growing up, across my family, they’re just people who have really different political beliefs. When I came into the media world, I got my start in journalism at the Huffington Post, a notorious left-leaning news outlet. I saw how the sausage was made, I think, and the way in which people played to their audience a little bit in that space.

From there forward in my media career, I think I got a lot better at spotting some of the signals news outlets were sending out to appeal to specific readers or viewers or listeners. This is, of course, not just true on the left, it’s true on the right too. I was keen to the news bubble thing, I think, before it became really popularized and well-known. In 2012, 2013, it was very obvious to me from Facebook and Twitter that people were operating in a very insulated manner. Now everybody knows this, that your feed gives you more of what you like, and so news outlets try and give red meat to the base.

I wanted to build something where people from across the political spectrum could come together. I started this Substack newsletter where we’d tackle one big political debate every day, and we would explicitly share opinions from the left and the right about that debate. If you read our newsletter from top to bottom, you would have a really holistic understanding of how different political parties and different political minds from across the spectrum, from the lefty Bernie Sanders to the establishment Democrat, to the never-Trump Republican, to the far-right Trump intellectual types, were thinking about the issue. Then I share a little bit of my take too in every newsletter.

We’ve been building an audience that I think is representative of what we’re doing that is made up of people from a lot of different political backgrounds.

Jacob: I have an inherent bias against political content just because I think, like most people, we’re tired of it. My belief, I’ve had debates with friends about this, that the only way to make money in political media is to take an intense slant. You are obviously proof against that. What is the audience telling you that makes you believe that there is a space for this center or both sides debate?

Isaac: Yes. First of all, I think it’s important to talk about why I think a lot of those media companies fail that try and walk this line. I think it’s literally because it’s boring. I think news is walking the line of entertainment. When news outlets try and do this, either very neutral language or just a all sides or flip side type, here’s what the left’s saying, here’s what the right’s saying, there’s something that happens there that I think is a little bit dry for a lot of readers. That, I guess, suppresses a level of engagement that the more partisan news outlets have that I think is really important.

What we’ve done as a way to address that is I share my own take, which is, A, an act of transparency, in my opinion, because it’s telling the readers, here’s the person who’s providing your information, how they actually feel about the arguments that we’re sharing. It’s me saying, all my cards on the table and you can take it or leave it. B, it creates a space for a little bit of controversy and a little bit of engagement and something for the readers to say, oh, I didn’t like how you said that and have a little bit of the dialogue and the back and forth.

I think that makes the whole newsletter just a lot more interesting. It makes the podcast a lot more interesting that there’s this one person who’s behind it versus a unaccountable media brand that doesn’t really reply to you at all. I think that’s part of why we’ve done so well organically. What I hear from readers and listeners is basically two things. One, they feel a personal attachment to me. I get that a lot. If my view changes on an issue and I write about why it’s changed, people will say, it’s been so interesting to watch you evolve here, and I feel like I’ve been along for the journey, et cetera.

Then they also say that what we’re doing and what we’re providing is turning the temperature down. They feel less crazy when they read our newsletter or listen to our podcast because they’re not just getting one side saying the world’s on fire, the other side’s evil. They’re getting an actual holistic look at the arguments, which I think whenever you do that, not whenever, but most of the time you do that, you’re going to come to the conclusion that there’s some nuance about the debate that’s happening. There’s a reason it’s a debate because it’s probably not as simple and black and white as some people want to make it seem.

We definitely hear from folks who feel like they have a little bit more level-headed news consumption diet with us in it. I’m personally really proud of that because I think there’s far too much sensationalism and exaggeration and scare tactics and fear in the media space right now.

Jacob: How do you avoid falling into the trap of false balance or both-side-ism?

Isaac: This is one of the questions we get probably most often, or maybe I should say one of the accusations we get most often. There’s a couple of different ways we think about how we select the stories or the opinions that we’re going to share. The general construct of the newsletter is we’ll introduce a topic in the most, I guess you could say, neutral language possible. Maybe how it would look in a place like Reuters or The Hill or something like that, where it’s a very bland explanation of the hopefully non-debatable facts. Then we share arguments from the left, then we share arguments from the right.

When we pick those arguments, we’re looking for a combination of arguments that are representative of what we think the mood of the political tribes are. If there’s an issue like Israel and what’s happening in Gaza, where the left is really divided, we’re not going to just say that everybody on the left is saying that we should force Israel to pull out of Gaza or whatever, because a lot of people on the left don’t feel that way. There are a lot of Democrats who are very pro-Israel. We’ll share a mixed bag on the left and we’ll try and make it representative. That’s primarily our goal, is to show you what people are actually thinking and believing from the two predominant political tribes.

After that, we start looking for arguments that are maybe dissenting opinions from the tribes. We look for arguments that we personally, as a staff, find really compelling. Things that just stuck out as being a really cogent or well-rounded argument or something that brought a fresh take to the one side of the other’s perspective on the issue.

A lot of people will say, how would you cover an issue like climate change or something like that, where there’s going to be a lot of voices on the right who maybe are doubting whether climate change is actually real or not, and you’re going to weigh both those things equally? The answer is, we don’t, A, because I have my take section every day where I get to call some balls and strikes. That is my way of saying like, here’s what I think about this argument that this side’s making that strikes me as a crappy argument. B, we make it clear, as is true with most issues, that everybody on the left and right isn’t totally in unison. They don’t agree, or maybe they agree, but they don’t agree for the same reason.

I usually get this question from people who are oriented more politically to the left who will say, how are you going to give both sides to claims of the election being stolen or something? I just say, look, we’re going to share opinions from the right of people saying that the election wasn’t stolen, because a lot of people on the right feel that way. I’m going to say, I don’t think the election was stolen, because I don’t think it was. Then everybody on the left is going to say that. Maybe you get five opinions saying that it’s clear the election wasn’t stolen and two saying it was. You just have to live with those two and actually engage the argument in an honest, open-minded way.

It’s a really difficult balance to strike, but that’s part of the challenge of our work. It’s something we try and navigate every day.

Jacob: Let’s jump right into the business model then. You describe on the website the publication as a subscriber-supported newsletter read by over 90,000 people in 55-plus countries around the world. What percentage of the revenue comes from paid subscribers?

Isaac: Over 90%. We only introduced advertising into the newsletter in Q4 of 2023. It’s actually a fairly new venture for us to have paid ad slots. They show only to free subscribers. We now have a freemium model where the free readers will see the advertisements, but the paid subscribers will not. We have, I think, about 15,000 paid subscribers now. We make a little bit of money off of merch sales and a little bit of money off of donations and a little bit of money off some of the events that we’ve done, but over 90%, maybe even 93% or 94% of our revenue comes directly from paying subscribers.

In exchange for that subscription, those subscribers get Friday editions, which are typically exclusive, more unique, original, deep dive-type content. Sometimes it’s works of journalism that I’ve been working on, original reporting. Sometimes it’s just transcriptions of interviews I do with people. Sometimes it’s a personal opinion piece or a deep dive on an issue that’s maybe more aggregated and less reported. It’s generally just premium-esque content.

Then on Sundays, we have a newly launched Sunday newsletter that’s also part of the paid subscriptions. That’s like our take on the Sunday time. It’s comics and a puzzle we created and some quotes of the week and some roundups of our coverage and that stuff. So far, people seem to really like that. We didn’t really know how that was going to go, but it’s been pretty successful so far.

We are subscription first. In my opinion, that is the most sustainable way to build a media company right now. I think it is also the one that has the least dangerous incentives for people who are on the content side. I am super excited because I’ve worked in this space for 10 years, and this is the first time I’ve ever been at a company that relied on subscription revenue. It’s my company and it feels really good to be there because I’m not looking at the clock on Friday every week hoping that I don’t get a layoff email before five o’clock basically.

Jacob: Roughly, 90,000 people, 15,000 paid subscribers, so about a 16% conversion rate. What tactics have you found work particularly well to get people from the free list to the paid list? Because 16% is a pretty strong conversion rate.

Isaac: Yes, we’re super proud of that. It’s one of my favorite metrics to tell people about our content and a super low churn rate too. I think less than 1% or something. 90% of those subscribers are on yearly subscriptions. It’s a really consistent, reliable revenue stream. We do a few things. The one that has always worked the best for me is a really personal, honest, just ask, like a dedicated email. We do about two of them a year where I just write to everybody on the free list. The subject line often will say something very direct and cheeky like, I’m asking for your money or this is an email asking for your money or something like that.

I say explicitly just a lot of news organizations beat around the bush. I’m not going to beat around the bush. I’m writing to you because I want you to give me a subscription. Here are the things you get when you subscribe. Here are the five reasons it’s really important for us that you subscribe. If you’re not ready or you just signed up, I understand, but let me know what would make it more compelling for you to jump on board and then read some of those emails. We usually get hundreds of subscribers from that.

The second thing that’s really, really effective for us is in our welcome email flow, we just immediately offer people a 20% discount right after they subscribe. It’s similarly a personalized email. It’s a picture of me with a note about why I started Tangle and it’s a welcome page that just says, this is an offer. When you exit out, it’s going to disappear, which actually isn’t true. We just say that. Theoretically, they could find the URL again if they wanted to. Same deal. Here’s a 20% off offer and here’s why this subscription is important. Put a little bit of urgency behind it and people tend to respond well to that.

Then the third really big one for us is we give previews of the Friday editions. That’s a button I’m more hesitant to push. People don’t love running into a paywall in their inbox, which I totally understand. I don’t love it either. When I publish a piece that’s a little bit controversial maybe or something that I think has some juice behind it and we send the first third of it to the email list and we put a paywall in, we’ll get 10 emails from those 95,000, 100,000 people saying, or whatever, 90,000 free subscribers, saying, this sucks that you did this and it’s really annoying to run into a paywall, but 150 of them will get paid subscriptions. That’s a trade-off for me that’s worth it.

While I don’t love the little subtle looping in there that’s necessary, it’s also necessary for me to pay my team and keep the lights on. It’s something we have to do.

Jacob: Just so I understand the tactic, you will send an email to the paid list with a partial post. Then it’s just basically like if you want to read the full thing, you got to become a member.

Isaac: The free list. Yes, exactly. It’ll be the first quarter or third of an edition. Oftentimes, I’ll put a note at the top that just says– I publish on Ghost, and they have a feature that allows you to include a piece of text that only shows for free subscribers. You send it to the full list and you put a little preview bar in there that creates a button that encourages people to subscribe. At the top, I’ll say, just a heads up, this email is going to have a paywall about halfway through or whatever it is. You’ll be asked to subscribe to read the whole thing. Yes, if the topic is interesting, that converts really well usually.

Jacob: You said that the whole list gets four newsletters and then the paid list gets two additional newsletters. How did you find that balance between free and paid? Why did you decide that was the way to do it?

Isaac: Truly in the beginning, I was publishing five days a week to everybody. I did that almost for the entire first year until I got to maybe 5,000 people on the mailing list. I turned on paid subscriptions as a just support us type ask. We converted something like 20% of that initial batch of subscribers, which I was thrilled about because I was told to expect maybe 3% to 5%. That was a signal to me that people were just genuinely interested in supporting the work and there was a mission-oriented nature of it.

In response, my sense was that audience was big enough that they should get something that’s special and specific and outside the normal offering. We just started paywalling the Friday editions. They were just normal versions of the newsletter, but just behind a paywall on Fridays. Then I iterated from that into, God, I would love a little bit of space to just write about whatever I want outside the Daily Tangle format. That’s what the Friday editions turned into.

The Sunday newsletter is pretty much brand new. I think it’s maybe three months old. That was a product of two things. One, people who are unsubscribing, the number one reason they unsubscribed was they said it was too many emails. They would get behind. They’d have 8, 10 unread emails in their inbox from Tangle and it would really stress them out. We were thinking, let’s create a churn bust email for that where we can say, hey, don’t unsubscribe. We’ll push you to a Sunday once a week newsletter where we’ll just send you summaries of what we covered that week, and you’ll only get it once a week.

Our initial idea was just this churn busting newsletter. Then as we started thinking about the Sunday edition, we were like, oh, we should put some other cool features in here besides the roundup. Then we were like, maybe this is a premium type product that we can launch as something that’s actually an incentive for people to pay. Even the people who are unsubscribing because there’s too many emails, maybe they’ll pay just to get access to this once a week roundup.

This all was happening around a time that we were thinking about raising our prices a bit. What we settled on was, let’s pair a bump in our subscription price with the launch of this product. We’ll tell our audience, prices have gone up. Cost is going up everywhere. We’re going to bump our prices up, but we don’t want to do without offering something new. We’re adding this additional feature to the paid package. That in the end was how it came out.

Jacob: You mentioned that you’ve started exploring and introducing some advertising. What have been the products and what types of advertisers have you been working with?

Isaac: I think a lot of the ones that you probably see around the newsletter space. We get everything from supplement-type stuff that we have to do some more than usual vetting to other newsletters. I think today we advertise Masterworks, which is like an investment-type arm. You’d probably know better than I would. We get hearing aids. People want to advertise that in our newsletter, I suppose, because email audiences maybe skew a little bit older. We’ve advertised Babbel. We’ve advertised other political news outlets like Dispatch. All sorts of different stuff comes across our desk.

We do have an advertising policy around not taking any ad revenue from anybody that has political affiliations, basically, because of the work that we do. Not just political campaigns, but any advocacy group or special interest group, we’re not going to take any revenue from.

I know there’s a lot of money in getting advertising from a Comcast or ExxonMobil or whatever. I see those ads all over Axios and Punchbowl and other really big dominant politics newsletters. That feels very icky to me personally, and I think is damaging to our brand. Because we have so much subscription revenue, I think we sacrifice that and we say we’re not going to take that money. It’s hard sometimes, I have to admit, because I’d love to have really big, expensive premium advertisements with obscene amounts of money that those groups throw around, but I think from a brand perspective, it’s smarter for us long term not to.

Maybe I think our consumers are more conscious than they are, but given what we’re trying to build, it’s just one of the ways that we’re trying to be a little bit different.

Jacob: How much revenue does Tangle generate in total, and is the business itself profitable?

Isaac: The business is profitable. It’s been profitable since it started because– I actually launched it when I had another job, and I quit my day job the moment the revenue surpassed what my salary was, which was a really good feeling. Ever since then, we’ve been even or in the green. We are coming up on a total $1 million annual recurring revenue this year. I hope that’ll happen in the next couple of months. I think right now, our subscription revenue alone is something like mid-800s or something like that. We get another 70 or 80 grand a year from the ad revenue.

We have a team of five people, five full time employees, myself included. We have some part-time editors. We have some interns. The majority of our expenses are that. It’s payroll. We’re all remote. I have an office space here that I’m talking to you from. Most of the team is remote or in some shared office space. We put a ton of money back into all the subscription services we pay for to read all the news, which is actually a huge expense, website maintenance, things like that.

We are definitely profitable. We put away a couple hundred grand last year, which felt really good for me because this is the first time I’ve had a full team under me. This last year, we hired three people, three other full time people. I had before that just a team of part time folks. I really wanted the safety net of like if we have a few bad months of growth or things go south or there’s some major economic disruption that it’s not going to be layoffs for everyone type situation.

We’ve got our rainy day fun put away now, which feels good. Going forward, I want to invest as much of that cash that I can into just growth, into finding new readers and advertising our newsletter in other platforms. I’m hopeful that we can do that. Right now, there’s some headwinds. I think people are generally a little bit exhausted by the politics news space. That’s something we’re definitely running into.

Jacob: I want to come back to that in a second. You had 5,000 people, now you’re over 90,000. We’ve talked about your conversion from free to paid. The vast majority of your readers are still unpaid. How are you growing that top of funnel? What tactics have you found work to grow the free list? Yes.

Isaac: The one that is the least consistent but the most tried and true is just generating great content and going viral. That is the lightning-in-the-bottle stuff that you can’t really teach. I think there isn’t a formula to it.

I think last year, one of our biggest weeks of growth was basically I posted a version of my take from the newsletter onto Twitter in their long form new tweets that they allow. It was literally a copy and paste from my take in the newsletter about the initial attacks in Israel on October 7th. That tweet got, I don’t know, 30 or 40 million views. Elon Musk replied to it. The president of TED Talks retweeted it. There was all this stuff. We just saw in a matter of days that our newsletter list grew by 5,000 people and 20% of them came in as paid subscribers. All of a sudden, you’re looking at a $ 50,000-a-year bump in annual revenue that happens in a few days, and it snowballs.

Then I got invited on MSNBC and I went on some podcasts. Every one of those appearances gives you that long tail. A lot of people up and coming asked me about, what are the best ways to grow the newsletter? I really do think the answer is and will always be content is king. You produce something that’s new, that’s fresh, that people genuinely want. You’re going to win. If you try and copy what exists out there that a bunch of people are already doing, it’s going to be really hard. You have to do it really, really well, better than they’re doing it.

We advertise in other newsletters, obviously. I think a lot of people who get their news from emails, that’s the prototypical customer that we want because the newsletter is our core product. I go out and if I see a newsletter I really like or there feels like there’s an audience that might overlap with us, I’ll inquire about what their advertising costs are and do some plugs. We have a share button in every newsletter right in the middle of it and an ask for readers to spread the word. We see ourselves in the auto-generated email when they click the button so we can see how many people are using it. Every day, there’s still people who are sending those emails and passing the word on about us.

I think a lot of stuff that is already out there, my view is, there’s no need to reinvent the wheel. I am trying to experiment a bit more with social ad spends. I generally think that it’s a money pit and it’s a little bit dangerous, but I think there are some really smart people out there who know how to run those campaigns, and I’m trying to find them and use them. Aside from that, it’s leaning on the network that the readers have and getting them to push stuff out for you and forward the email to five friends or whatever it is. Then knowing and having a sense of when you have a really good piece of content.

Then the last thing I’ll just say is we’re hitting other channels. We launched a YouTube channel this year. We’ve had a couple of nice little hits there, videos that got 30 or 40 thousand views, which in the YouTube space is nothing, but for us, it’s 30,000, 40,000 people who have never seen our brand before.

We’ve seen a little spike. We put the URL to our website in the episode description or whatever, and we’ll see a little spike on the newsletter mailing list when we have a video do really well on YouTube because people are trying to learn more about us and they find our website and they sign up for our newsletter. That’s going to be the next frontier, I think, is expanding outside the newsletter website space and focusing a lot more on our podcast and our YouTube channel.

Jacob: You mentioned that you’re dealing with increasing headwinds with the audience with growth. There’s a lot to unpack there. Why do you think this is happening? What are these headwinds?

Isaac: I would say, if you looked at our chart, our growth chart, it’s up and to the right. I think over time, I switched platforms. I went from Substack to Go, so I don’t have a great linear from beginning to today graph of the subscriber growth. I would say over time, it’s probably pretty consistent with some periods of flatness.

I think right now, we are in a quiet time for a few reasons. One, the last year or two, we’ve been out of election season, which is a really natural growth time for us. I’m hopeful that over the next six or eight months, people are really going to start to tune in to what’s coming in 2024. That’ll help us a lot. Two, there’s tons of polling and media surveys and data from people who track website traffic and things like that. That interest in political news is down across the board. Washington Post, CNN, New York Times, Fox News, whatever, all their ratings and their traffic are all down. They’ve been down over the last year.

I think that is specific to us, just a reflection of the fact that there’s a ton of news fatigue out there. There’s so many people who are just like, I can’t have another space where I’m just getting political news thrown into my face. They don’t want it in their inbox. I get that. When people unsubscribe, they get an auto email from us asking why they unsubscribe. The multiple emails a week thing is one of the big reasons we get. The other one is I’m just exhausted and I can’t take reading about the news anymore.

I think that sentiment is spreading across the country. We’re trying to think about how to position ourselves advantageously for that by saying, all you need to do is spend 10 minutes with us a day. You don’t have to read anything else. We’ll cover it. We’ll filter out what’s important and show you that. I’m hoping that’s a message that resonates for the people that have a little bit of the news fatigue, but I don’t know. We’ll see. I think it’s going to be a battle. I think as people get more and more interested in what’s happening in the election, and as the 2024 election gets closer, I’m hoping and assuming that people are going to be interested enough to tune in. Right now that feels really prescient.

I would say the other thing is advertising across the newsletter space is struggling. I’ve seen that places like Morning Brew, they built the roadmap for the rest of us in a lot of ways. They’re laying people off, and their revenue’s down, and they’re having financial troubles. I think the whole ad industry in the news world is struggling. I think that is genuinely a product of the fact that they have a less engaged audience today than they did three or four years ago.

I don’t think that’s because their product’s worse. I think it’s just like the space is really saturated. There’s a lot of newsletters. There’s a lot of options to get your news. Tons of different people have popped up into the space. For us, it’s just we’re another competitor among a bunch of other people who are coming up behind us too.

When I started my newsletter, Substack was barely known by anyone. I was on top five politics newsletters on Substack for a while because there’s nobody else on there. Now, it’s like Substack is almost a household name. It’s amazing how much they’ve grown in terms of being mainstreamed. The brand is obviously taking some hits from some of the controversies and stuff they’ve had. I’m no longer on Substack, but there’s so many people who are running prominent newsletters there. They’re all people that folks can choose to read over me.

Yes, I think competition’s up. News fatigue is up. Saturation of the space is up. There’s a little bit less big money interest in supporting these kinds of news outfits because a lot of media companies are failing right now.

Jacob: I will do a slight fact check only because I was the publisher at Morning Brew. Business is fine. It’s certainly more competition. I don’t think there have been layoffs in a year.

Isaac: That long ago? A year?

Jacob: Yes, it’s been a while. Anyway, I won’t dig in any more deeper because former employer and all that.

Isaac: Hey, that’s a good fact check. My understanding from talking to people there was just that the rates for an advertisement placement or whatever had gone down. They actually started doing something that was interesting too, which was I wanted to advertise in Morning Brew and they’re not advertising other newsletters anymore, which I thought was super interesting. That was the reason they told me they wouldn’t take my money, which I didn’t feel like.

I thought that was pretty curious about where the space is that there’s a competitor posture that I think a lot of people are having because so many people are trying to copy what they’re doing. I feel like I’ve been around for a while now, after five years, but I was a new kid on the block to them at the time. Now there’s all these other people coming up behind me that I just think there’s so much competition. It’s changing the landscape a bit.

Jacob: Do you think as the campaigns continue to go on and as the partisanship gets stronger, it looks like it’s going to be Trump versus Biden and it’s going to be like an absolute dogfight, do you think that is an advantage for you or do you have any concerns that the audience will disengage even more because you’re not feeding the angst and the tribalism?

Isaac: Great question. I think that eight years ago, maybe that would be a disadvantage for me. I think today it’s an advantage. I think part of the news fatigue is people are tired of that blue versus red, hate the other side setup. There’s a general angst about turning on the news and what you’re going to have to deal with and hear.

I think people are starting to realize, from where I’m sitting, there’s so many interesting things happening right now in that vein. Chris Cuomo sitting down with Tucker Carlson for an interview. This CNN, Fox News, ex-anchors shaking hands and trying to make a truce. Don Lemon interviewing Elon Musk. There’s these big players in the media space that I think are realizing these cross-partisan conversations are intriguing to people right now. We’ve been doing that for a while, but there’s a lot more of it that’s starting to happen. I think readers, listeners, viewers are getting more interested in that.

There’s a reason guys like Lex Fridman or Joe Rogan or whoever else they’re so popular and they have such a huge audience. It’s because they come to issues with a sense of humility and they give people open space to share their views. They interview people with a wide range of different perspectives. Audiences are clearly very interested in that right now.

My wish is that people are ready to step out of their partisan bubbles a little bit. In 2022, I made the rather audacious claim, I think, that partisanship might be hitting rock bottom in the US. I’m hoping we see a little bit of that bounce into 2024. Biden and Trump are going to do their best to stop it from happening, I’m sure, but I think people are tired of the pony show at this point.

Jacob: You’ve started to experiment with small-scale events. What’s the strategy here?

Isaac: First and foremost, I just really wanted to get an in-person taste of our community and see what they were all about. To me, there was just something really exciting about bringing what we do in the newsletter on stage and having people come out and experience it. We’ve done one live event in Philadelphia last summer and we have another one coming up in about a month, April 17th. The first event in Philly was– it was honestly magical for me. It was so cool to meet all these people, fill a room of 200 people. Some came from California, and Texas, and Virginia, people who were really invested in what we were doing and fell on the ground floor of this new media company.

That was super cool and the event went great. It went off without a hitch. We had a really interesting, I thought, moderated debate about the state of the Supreme Court, did some reader questions at the end, some audience questions at the end to mimic our reader questions. We just want to get people to walk the walk on this sort of open-mindedness and dialogue and experience it and do it in person. We’re going to see how this New York event goes. It’s already sold out, which is awesome. We still have some VIP tickets left for any New Yorkers who want to come check it out.

We generally are of the opinion that we can make a really creative and compelling evening of entertainment and experience by just bringing this sort of ethos and structure that we have in the newsletter and the podcast to the stage. I don’t know if we’ll make money on this event in New York. We had a great sponsor for the Philly event, so we actually did really well there. We’re still looking to secure a second sponsor for the New York event that I hope will put us over in the green. Whether we do or don’t, our goal is to bring this to a few other cities in the Northeast and then start expanding westward.

We want to hit the concentration centers where we have a high volume of readers, and especially paid subscribers who we think are the most likely to come out and see the event. We can use the newsletter, the mailing list, as a guidepost for a tangle tour. I don’t want to be on the road five months out of the year. That’s not something I’m interested in, but I think doing four or five events a year and having them grow and get bigger and bigger and walking the walk on this sort of open dialogue and debate and diverse audience politically and get people from across the political spectrum to come sit in the same room together and experience something like this together is good for the country and is probably a good way to make some money, too.

I think a lot of different media companies have proven that events are a lucrative path forward, so I would love for it to be a great business venture for us, too, as well as a really good experience.

Jacob: I know that you started on Substack, but what is the full technology stack that you use to power Tangle?

Isaac: We’re on Ghost now, ghost.org is the platform that we use. I love Ghost, and I love Substack. Honestly, people will ask me all the time, other newsletter writers will come and say, “Hey, I’m thinking about switching off Substack or coming to Ghost,” or, “I’m curious why you left Substack or how you like it.” There’s only one reason I left Substack, and it’s because they take a 10% fee on your revenue, and we got to a point where we’re making $200,000 a year and $20,000 a year was a salary for somebody, like a part-time person, obviously not a full salary, but I could get part-time help with $20,000 a year and I was not ready to just pay a newsletter service for that.

I think Substack is an incredible tool and I love the guys over there. I think they’re awesome, I think they’re really smart. I think they’re going to end up allowing ads and other things like that that other newsletters do. I think they’re bound to cave on that. It sounds like they’re already moving in that direction. Ghost is awesome because it’s independent. They have really, really good customer service. The website and all that stuff is a lot more dynamic, you can build what you want. If you have any technical sophistication, which I do not, but a lot of people do, you can make whatever you want to make over there.

I have Ghost and then I also use this company called Outpost that is like the in-between for me and Ghost. They manage my website and help with all the welcome flow stuff and set up all sorts of different features whenever I say, “Hey, I want to try this or that.” They’ve been really helpful. Awesome team over there, too. Yes, for me, it was just like we wanted a little bit more freedom and I wanted to save that money. Now I think we have, whatever, 100,000 members, and on Ghost, we pay, still, a fraction of that $20,000 I was paying Substack when I had 30,000 or 40,000 members, so it’s a lot cheaper and it gives us some more flexibility.

The other problem Substack’s having right now is they have some brand stuff where there’s a lot of chatter in the media world that there’s this specific brand of person that’s on Substack, which wasn’t an issue when I left, but I think if I were there right now, would be something that concerned me a little bit. I’m glad to be on a lesser-known, in-the-background type platform where there’s no kind of association with it.

Jacob: Now, Tangle started as a solo operation, but you’ve started bringing on a team. As someone who was at the solo stage and the only one for AMO and thinking about bringing on people, can you talk through what made you decide to start hiring and where you made your initial investments on people?

Isaac: Yes, so the thing that made me start hiring was twofold. One, simple terms, the work just became too much to do on my own. All I could do was write the newsletter and send it out. I was coming from a newsroom background, so I knew that we needed a social media operation, we needed an ad ops operation, we needed editors. We needed all this stuff that I didn’t have and I really just missed the team. I would say that was the big, second reason, was I love being in the trenches with a group of people and I love being in a team atmosphere, and I just didn’t love working alone.

When we hit a certain revenue, I think it was probably $100,000 or something like that, a year, in revenue, I started looking for some part-time help. The first person that I hired is the woman who, to this day, is like my right hand. Her name’s Magdalena Bokova and she runs our social media, and now she runs our ad operations. I just got somebody who had a different skill set than me. She had graphic design skills, social media background. She had done lots of local reporting as a journalist, rather than national reporting. She was interested in getting involved on the sales side, doing business operations stuff, a lot of the things I didn’t want to do.

Yes, she was– the best first decision I made was bringing her on, and she’s been with me ever since. After she was in, it was like a decision about what we needed as a unit, like, where were our blind spots? I had some part-time editors from the beginning. Actually, my dad used to just copy-edit the newsletter for me before I sent it out, so it was kind of this mom-and-pop shop. Then one of my old college buddies I was in a writing group with was editing the newsletter in his free time for like an hour or two every day while he was at his job as a programmer, and he was such a good editor.

I’ve had tons of different editors throughout my career, and he was so good that I just eventually offered him a full-time position to come on and help support me. Now he works under the Managing Editor title. Then we launched the podcast and the YouTube channel. I needed someone who could edit podcasts and YouTube, so I hired that person. Then the last hire we made is a guy who– he’s an editor, he’s a researcher, he’s a booking person. In some capacity, he almost functions as an assistant of mine where just everything that is overflow from me, I ask him to help pick up the slack.

He’s a younger guy who came from a public policy and PR background and just has a lot of really transferable skills. That is essentially our team. We all work as a unit together and cover those different channels, and we have some part-time people and some interns who help out a little bit on the fringes. It’s basically just, for me, it was finding people who were good at things that I couldn’t do and then this last hire was bring in somebody who could do the things I could do and take some stuff off my plate personally because it just got to be too much basically.

Jacob: You’ve mentioned that people feel an attachment to you, right? That you put your piece in each newsletter, and when the twice-a-year email comes out asking for money, you talk about there’s a connection to you, you put your photo in there. How do you think about the evolution of Tangle where at some point, you might want to step back? How do you evolve the brand where it’s not the Isaac show, but it’s the Tangle show?

Isaac: A big conversation we’re having right now. [chuckles] It’s really hard. I have a few different ideas about how we might do it. I think, fundamentally, what I’m doing right now is not sustainable. I think if I made any mistake, which who knows, maybe it wasn’t a mistake, but in retrospect, if I could change anything, it’s that I wouldn’t be a daily. It’s so hard to produce this volume of content on a weekly basis. It basically means my only day off is Saturday and the drumbeat just never stops, and I’m working 12-hour days, so I know that I can’t keep doing this for the long term.

We have a few different ideas. I think one is introducing the staff as contributors or even hiring people expressly for the purpose of writing and have this character group that takes different newsletters on individual days throughout the week. The other is just making what is, right now, my take, “our take,” and becoming more like an editorial team, Tangle, the team. The risk of that is we lose a little bit of that personal connection, and that’s what I’m really scared of. I’ve thought about different things I could do. Like, for instance, I mentioned that Friday editions are behind a paywall. What if every Friday edition, that was me? That was like Myspace, Tangle CEO, founder, whatever, I get to write about whatever I want. Then I have one newsletter a week and the rest of the week is this “our take” section that’s just like the whole team is working on it together.

I think there are different ways to play with that but, yes, it’s a really big challenge. Early on, I sent my first newsletter to 13 people, so this was not a problem I was thinking about back then. I was just trying to make a little bit of supplemental income and build something I thought people would read. Now I’m in the spot where I’m like, “Oh shit, I need to find a way to detach myself from the brand but keep people really interested in me.” Maybe it’s just I’m the podcast host and I write this one edition a week and we have the rest of the week being the newsletter.

I’m really not sure and I think it’s going to become even more interesting if or when we start to franchise Tangle out a little bit, which I think is something, long-term, we could do. I’d love to jump verticals, Tangle Sports, like one big sports debate a day, something like that. I’d love to go international. I’d love to go down to the state level, bring this format that we have, which I think is part of our special sauce, to France, or bring it to Pennsylvania and just find the Isaac of France or the Isaac of Pennsylvania and give a writer or reporter like that some seed money to start a newsletter and then share the profits with them.

I think that’s a model that could work. That’s pretty long-term. Yes, it’s going to be really tough. If you have any suggestions, I’m totally open for some advice because it’s something we’re trying to figure out right now. [chuckles]

Jacob: I appreciate that. It’s something I’m thinking about, too, and we can always talk about that. You started talking a little bit about the future. Where do you see Tangle over the next three to five years?

Isaac: I am of the opinion that I do not want to become the next New York Times or CNN or whatever. I’m not trying to build a newsroom. I want to build a really well-paid team doing lucrative work that’s really important and feels mission-oriented. I would love to have sort of the Cook Political Report, like this family mom-and-pop type business, $25 million a year in revenue, whatever they’re doing, and they employ eight people. That’s a great ratio to me. That’s like you have this small team that knows each other and loves each other and is committed to the work they’re doing, and a really loyal audience that’s willing to pay for your service because it’s so valuable, and everybody makes a bunch of money.

I’d love that. That’s my North Star, and I think in order to do that, we have to stay focused and move slow. As much as I want to do the Tangle franchise or Tangle Sports, or whatever, a lot of that is still a distraction. We have to get the newsletter to a million subs instead of 90,000 or 100,000. We have to get our revenue to $5 million instead of $1 million. We want to build this YouTube channel, we want to build the podcast. That stuff is starting to happen now and it’s starting to build, but I know it’s a slow grind. Yes, for me, a small, really tight-knit, well-paid team is what I’m shooting for versus take a bunch of seed money and pay for an audience and build out a hundred-person newsroom or whatever. I have no interest in doing that.

Who knows what happens along the way, if there’s a path for me to step back and work less and maybe there’s a partner or a sale, who knows? I keep my options open. I’m open-minded to a lot of that stuff, but right now, I feel like we’re doing really important work. We have a sustainable business model. I have an incredible team of people that I really love to work with around me, and I’d love to pay all of them super well and make a bunch of money and do something that feels like important, positive work in the media space. That’s what I’m focused on.

Jacob: I want to end with the same two questions that I ask every operator that comes on the show. First, what is a mistake that you have made in your career and what did you learn from it?

Isaac: I’ve made a lot of mistakes, definitely have made a lot of mistakes. At the risk of being redundant, I would say, in the context of this conversation, the biggest mistake I made when I started Tangle was I didn’t have enough trust in myself to think about where I wanted to be in five years. I was really short-sighted about the goal and my intention. It was I had this product idea for this newsletter format that I thought would work, I had a mission statement that I wanted to get people out of their news bubble and bring people together a little bit, and I had the skills to pull all that off, but I didn’t think about building a difference between Isaac and Tangle.

I didn’t think about any of the ramifications of doing a daily newsletter five days a week for the next 10 years. I didn’t think about a lot of the stuff that, in retrospect, were very obvious sort of, “Where are you going with this? What’s your ultimate end goal?” Because I had so little faith that it would succeed almost. I was so day-by-day, “I’m just going to try this, see how it works.” I think if I could go back to that version of myself knowing that I had a chance at making this what it is today, I would’ve been more thoughtful about separating myself a little bit or what I had the capacity to do from a work-volume perspective.

For operators who are, I guess, in that kind of seed phase trying to plant something or build something, I would say be really conscientious of that and think about really, “If this goes well, where am I going to take it and what do I want that to look like?” Because I had all sorts of plans for if this didn’t work and the fallback and plan B and all that stuff, but I didn’t have a great plan for if it succeeded and what it would mean if it turned into the thing I was trying to make it turn into. Funny enough, that was the one thing I wasn’t prepared for in a lot of ways, and I think that’s a mistake I reflect on a little bit.

Jacob: Second, perhaps building on that, what is some advice that you would give operators looking to grow their media businesses?

Isaac: I would say the classic entrepreneurial advice that I use that I think is really handy, is build the thing that you want. I was so tired of reading The Washington Post, reading The Wall Street Journal, watching CNN, watching Fox News, listening to Ben Shapiro’s podcast, listening to The Young Turks podcast all about the same issue, and then, at the end of the day, being like, “Okay, I’ve spent eight hours listening to all these different things and now I think I understand what the right and left are saying about this issue. I wish I could find this in one place.”

That was my feeling, “I wish this existed all in one place, compact, straight to the point, easy to consume,” and so I built that thing that I wanted and it turns out there’s a ton of other people who also want that, who also want that information in one place. I think, think about something that you want and understand the fact that if you want this product, there’s probably a bunch of different yous out there. Then from a really crude business idea, be really realistic about what you’re offering, and how valuable it is, and how much it should cost people. We just bumped our prices up and it has not slowed down our subscription conversions. It has not changed the way people think about us or how accessible we are to the people who want to pay for us. We went from $50 a year to $59 a year. I basically increased our revenue by 20% a year for the new subscribers coming in and it seems to have not changed anything in terms of our conversion rate. I’ve been doing this for four or five years and I was like, “Oh, we were underpriced.” That’s what that’s telling me, is I undervalued what we were offering. There are other places who I go to subscribe to support them and I’m like, “No way, I’m not paying $250 a year for this, it’s not nearly that valuable.”

Be realistic, ask people. That’s what we did, we asked people how they’d react to a price increase. When I launched paid subscriptions, I asked the audience how much they’d be willing to pay and I undercut what they said they would pay, which was dumb in retrospect. It’s a really good practice to just be really crudely honest with yourself about how valuable what you’re offering is. In either direction you go, if it turns out you’re less valuable than you think or more valuable, by pricing yourself right, you’re going to make more money in the end, which I think is the goal for people who are trying to start a good business.