How Jared Newman built Cord Cutter Weekly, a TV streaming newsletter with 32,000 subscribers

A spinoff newsletter that gives tech advice has also grown to 1,200 paying members.

When Jared Newman launched his Cord Cutter Weekly newsletter back in 2016, the streaming TV market was much smaller than it is today, with most TV networks either not having their own streaming app or requiring a cable subscription to access it. But as it turned out, he timed his launch perfectly, as it was only a matter of years before virtually every Hollywood studio pivoted to streaming. Today, his newsletter has over 32,000 subscribers, and a spinoff newsletter that gives tech advice has also grown to 1,200 paying members.

In our interview, we discussed his motivation for launching the newsletter, why his editor let him promote it at the end of his columns, and whether he ever wants to leave his freelance career entirely to just focus on growing his two newsletters.

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Transcript

Hey, Jared, thanks for joining us. 

Thanks for having me, Simon. 

So I have you here to talk about these two amazing newsletters that you launched and run. But before we start talking about that, I just want to hear about how you got into journalism in the first place. You've been a tech journalist going all the way back to 2008 or so?

Yeah. So I guess it depends how far back you want to go. But I guess I say that I caught the journalism bug in college. I went to NYU for journalism school, spent a little bit of time doing local newspapers and then moved out to L.A. in 2008. I don't live there now, but that's when I kind of started freelancing and focusing on technology and that kind of thing. So yeah, I've been doing this for a while and started my first newsletter in 2016.

So you've been, other than maybe those stints at the local newspapers, you've been self-employed pretty much your entire career?

Yep. You know, just racking up freelance clients and kind of building things. I have been writing fairly steadily over the years for a couple sites in particular. I do a lot of writing for TechHive and PCWorld, which are sister sites. I do all my writing about streaming and cord cutting over at TechHive with a weekly column. And I do generally a story a week or two for Fast Company as well. Those tend to be more reported, maybe businessy, maybe some more general consumer tech stuff.

And I know that you've always been in tech, but were you doing any kind of more specific beats? We're going to obviously start talking about Cord Cutter Weekly soon, but were you regularly covering the streaming sector like Netflix and Hulu at the time or anything like that?

Yeah, I mean, it was an area of interest to me since I started freelancing, because it was 2008. I was living in LA. I had very little income coming in. And so that was my impetus for not having cable TV anymore. It was just sort of like a necessity.

And so all that stuff became fascinating to me because it was like, well, how can I watch this and that if I don't have cable? And obviously it's become much different than it was back then, but it was something that was kind of dear to my heart even back in 2008.

And in 2014, TechHive asked me about doing a dedicated weekly column on that topic. So that's when things really started to gather steam.

Yeah. In 2014, to remind people, you know, there was Netflix and Hulu as standalone streaming apps. A lot of the other streaming apps required you to have a cable subscription still in order to use them. They were just like an added convenience, right? They weren't necessarily like standalone apps you could subscribe to.

Yeah, it was very much like if you didn't have cable and you didn't want to pirate things, like you just didn't watch things. And, you know, we didn't start seeing these packages that replicate the cable bundle like Sling TV and YouTube TV and all those. That didn't start until like 2015, 2016. And now we see that as commonplace. But yeah, it was a wild west back then for sure.

And was it you that pitched the column or was it the editor that pitched it to you?

I'm trying to think. I think it was kind of a little of both. I know that they were looking for people to write dedicated columns, and that was something that pretty naturally came to me as I was already interested in it.

Was the column called Cord Cutter Weekly from the beginning?

They picked the name Cord Cutter Confidential. It's kind of funny, like I almost never really talk about that name. I just say my TechHive column. It's not heavily branded or anything like that. But that's the name that we went with and that's technically the name that we still use.

Yeah. And so what was like a typical column, like especially looking back to 2014 or whatever, what was like a typical subject that you would write about?

I mean, a lot of it was sort of covering these new things that were coming about and what they meant, you know, more broadly. So at the time Sling TV was really new, they had a very small number of channels. So some of it was just bread and butter, like, okay, here's all the channels that you get because Sling, for whatever reason, didn't think to put that information on its website. And some of it was kind of like critiquing the DVR and how that worked. 

My very first column was sort of like, well, here's why your TV bill is so expensive. And a lot of times people think it's because of your cable company. And what it really is oftentimes is the TV networks that bundle everything together and ask for more money and more and more money. And so if you're Spectrum or Comcast, you kind of have to raise prices to cover that cost. So everybody shares some of the blame. And so sometimes I try to break that down for people as well. So they have just a better understanding of what's behind their bill increases.

And this was kind of like a general consumer type column, like your everyday consumer who might be  dabbling into cutting their cable cord and having to navigate this kind of weird constellation of disparate apps and stuff like that.

Yeah, I mean, I always wanted it to be, you know, not strictly like an industry thing. I want to have value for people that were trying to get rid of cable, which there was a ton of interest in that. And there's still a lot of interest in that. People our age maybe are used to streaming and there's a lot of folks who are not. And they're kind of like thrown into this because cable is so expensive, they don't really have a choice. And so I'm always bringing on new people across different demographics that are coming to this in different ways. I'm still trying to explain things and make sense of things. And it's always changing. So there's always something new to kind of break down.

And so when and why did you decide to launch your own separate newsletter on the subject of cord cutting?

It was on Twitter. Somebody was like, do you have a newsletter? I can't say that I really had thought about that much. I was maybe kind of aware of some people that were doing stuff, and this was 2016, so it was pre Subsstack and pre newsletter boom and all that. But the inspiration was like, Oh, maybe people would want to just get this directly. And I had at that point been a freelancer for six years, and so I didn't really have that relationship with readers. You're this hired gun, you write stories for a publication, and they get all the feedback and everything. I liked the idea of maybe kind of opening up this direct connection and decided to see how it went,

I asked my editor at TechHive, like, hey, can I link to this newsletter in my column? And he said, yeah. And that was kind of what I needed to know that I could maybe have a good go at it. And it took off pretty quickly. I mean, that was really an exciting time for people trying to get rid of cable and stuff. And so I know that by the end of the year – I launched it in the middle of 2016 – and by the end of the year, I had burned through MailChimp's limit of free subscribers. So I ended up moving over to a different system that cost a whole lot less. And yeah, it just kind of grew naturally from that.

You said you could plug it in your column. It's like a little line at the end of the column saying, you know, sign up for Jared's newsletter, Cord Cutter Weekly, and you get yada, yada, yada, basically. 

Yep. Yep. That's pretty much it.

And so because that column was on a high profile website that got a lot of traffic, that was driving the majority of signups for the newsletter?

Yeah. I probably could do more, but I really have, for better or worse, been dependent on that. The newsletter now has about 32,000 subscribers. And I would venture to say that nearly all of them have come from just reading my stuff online and clicking through to sign up.

Interesting. And how does the newsletter differ from the column?

So I kind of set this up intentionally from the beginning that the column that I write is almost the centerpiece. I excerpt a few graphs from it. And I very prominently at the top say, like, this week on TechHive...

My idea was that when I went to my editor about this he might be more likely to agree to the idea if it seemed like [TechHive] was getting something in return, so I made it very much like I'm promoting my work on TechHive. So there is that intro that encourages people to click through the column and then I have a few weekly news items that are a couple paragraphs each, just the news and a tiny bit of analysis and then a round up of a few quick links.

And when I started the newsletter, I spotlighted one notable deal of the week. A lot of times that was, you know, a streaming device, like if Roku was taking $20 off a streaming box or something like that. That's kind of what it started as. That's increasingly become a meatier part of the newsletter because now it's sort of like the streaming services themselves are offering running discounts and things like that that people don't know about. So I've kind of turned that into its own section where I'm like running through different deals. And I have a page on my website that I update every Friday. It's kind of like the full list of everything that I know about at the time. So, you know, there's like a dozen or more different streaming deals going at any one time. And so I'm always sending people there to be like, hey, if you ever just need to see the latest ways to save on Peacock or Paramount Plus or what have you, YouTube TV, you just go to this website and I have the full list of everything.

And is it acting like a TV Guide in some ways of informing people that these XYZ streaming shows are debuting on this service? Or is it just purely about how you get access to these different services and stuff like that?

Yeah, I've kind of stayed away from that. It is interesting because there are a lot of streaming and cord cutting websites where their bread and butter is explaining how to watch this show, how to watch this channel, whatever. And it's kind of a grind and it's a slog. I don't find a lot of joy in doing that. I figure there's plenty of other people that do that. And, you know, I just tell people how to get the services that they want and figure that they can kind of keep track themselves of what shows are coming up and deal with all that themselves.

Yeah, so I'm trying to get a key understanding of your coverage. So I was reading your most recent newsletter, and if I remember correctly, it was talking about the bundle between Apple, Comcast, and Netflix or something like that. So that's a little bit broader. What's the kind of right story that's like a Cord-Cutter Weekly type story?

I feel like nowadays that's sort of my meat and potatoes, right? So Comcast is coming out next week with this package. It's $15 a month for Netflix with ads, Peacock with ads, and Apple TV Plus, which doesn't have ads. Sounds like a pretty good deal, but I always like to find other ways to make it even cheaper than that. And so people don't necessarily realize Peacock pretty much always runs promos. You can save money on Peacock without bundling something else. Apple TV always does these like extended two, three month trials that you can sign up for as long as you don't have an active subscription. So it's kind of like, all right, well, if you just do these things, you can save another $5 a month without being locked into Comcast Internet for life. So I like to find those little ways to save.

That's something I'm increasingly interested in as the streaming services raise prices and kind of become what cable used to be. I try to find little workarounds and things like that. So yeah, it is not explicitly about cutting cable and satellite TV anymore. It's more under the broader umbrella of like, how do you actually save the most money, whether you have cable or not.

So it's all just tips and tricks of how you access content and get the best deal so that you're paying the least amount or whatever.

So that's a focus. There's also kind of the element of like, all right, well, how do you use your devices if you have a Roku, or should you even buy a Roku? Should you buy Fire TV or Google TV instead? So I'm interested in that element of just kind of the hardware that you set up and how to make the most of those devices. There's a whole little like sub-genre of the war over where content appears when you turn on your TV. There's different firms that are kind of jockeying for position on home screens and different agreements that go into where something is allowed to appear or if it's allowed to appear on the home screen at all. Because people want that kind of universal TV guide – they don't have to go into Netflix and go into Amazon and go into Hulu to see what what's available, they want basically one menu. And that's not that easy to offer because every company has different stipulations about where their content is allowed to appear. So I like to get into that kind of stuff as well, so I guess that the umbrella is just anything that helps people make sense of streaming TV and how to save the most money and how to find the stuff that you want to watch efficiently and how not to get one pulled over on you by the streaming providers.

So you mentioned that you've grown that newsletter to 32,000 people. In what ways do you interact with your audience and what's your general sense of who that audience is?

Every week I encourage people to email me, so I get a lot of email. My sense is that it's my age and up. I don't really aggressively collect information data on readers,  but yeah I do get the sense that there's a lot of people that are coming into this feeling like they're being kicked off of cable, and they’re not necessarily like the early adopter, high tech people, although there’s definitely a contingent of those as well.

Are there any ways that you monetize Cord Cutter Weekly directly?

I just started something. It's basically the first time I've actually tried to monetize Cord Cutter Weekly directly. I have a Buy Me a Coffee link at the bottom, which, you know, it's nice. It pays for the coffee, maybe a few video games or something like that every month. But it's not substantial. Earlier this month, I put together a complete guide to cord cutting. So for people who still do have cable or satellite TV, it's a series of six articles, each of them fairly in-depth, on my website. There's no ads or anything like that. Everything's just kind of in one place. And I said, just pay me what you can. I set the minimum price to $1. I put the default price at $10. I said, if you can't pay anything, just email me and I'll send you a copy. So I launched that a few weeks ago, three or four weeks ago. I have up to about $4,000 in net revenue right now. And it seems like it'll just kind of trickle in from here over time. So that's got me thinking about the pay-what-you-can model in general and just kind of doing more one-off guides like this, especially for something like Cord Cutter Weekly.

It's fundamentally about saving money. It feels weird to aggressively paywall content, you know? But if I can do something where people who have the means can pay me and anybody can still access the knowledge if they can't, that feels pretty good to me. And it's something I definitely want to explore more in the future.

And so you eventually launched a newsletter called Advisorator. What was the premise of that?

This stemmed from Cord Cutter Weekly being pretty focused on the consumer and how they can get more out of their devices and how to make sense of all this stuff that is out there. And for me, that's been, so to speak, one room in the house. I like writing about streaming stuff, but I also have interest in a lot of other tech topics. And I'm using phones and playing with iPhones and Android and, you know, pretty enthusiastic about technology and came from the place of like, hey, I would like to tell people about the stuff that I know, similar to how I'm helping people with cord cutting and streaming. So what if I just launched this kind of broader tech advice newsletter and used Cord Cutter Weekly as kind of the main way that people would discover it? 

So I launched Advisorator in 2018. It was initially a strictly paid-only newsletter, and I've kind of been dabbling in a free version over the years, the past few years especially. But yeah, the main avenue is still people who read Cord Cutter Weekly grow to trust my tech advice in general, feel like they're comfortable with my voice and the way I explain things, and may want to pay me to write for them about a broader range of tech topics.

Yeah, that's interesting because you don't get many instances where you launch a paid product that's in some ways a lot different from the free product, and in some ways targeting maybe a slightly different audience. But it seems like there was a lot of overlap between people who wanted to know about cord cutting news and great deals for cord cutting and also wanted to have more broad tech advice.

Yeah, it was almost a small thing, but like I remember getting an email from somebody in that 2017 timeframe. It was like, I don't know a lot about technology, but I'm trying to learn. And they didn't say specifically what kind of technology. And I was like, huh, maybe I could, you know, broaden the scope a bit, and it had been on my mind. How would I monetize? How would I make a paid product? And maybe having it be somewhat distinct and not something that's just specifically about saving money, but just about being a savvier technology user in general. And so what's a hypothetical topic for an Advisorator newsletter? I'll tell you something that's always popular. I wouldn't say this is like the only thing I focus on, but you know, how to use a password manager, how to choose a password manager, different things that you didn't know that you could do with the password manager. Obviously I'm not just writing about password managers, but staying safe online and secure is something that's always on everybody's mind. I have opinions about, you know, which software you should use and how to use it. So that's kind of a good example.

For the format of the newsletter, there's a feature column at the top. And below that, there's some news items and some quick tips. And then I kind of do the same thing where there's like deals at the end that are for hardware and things like that, you know, savings on iPads and Macs and that kind of stuff.

How much do you charge for Advisorator? 

It's $5 a month or $50 a year. That's what it's always been. You know, I can't say it'll always be that, but I kind of like the idea of it not being a super expensive thing that a lot of people can take advantage of.

And I think you told me you have about 1,200 paying subscribers. 

That's right. Yeah. 

And so how do you drive those subscriptions? Is it just like a call to action in Cord Cutter Weekly? Like what's the main kind of conversion strategy there?

Yeah. For much of the past five, six years, that's what it's been like every week in Cord Cutter Weekly. I'd be like, here's what I wrote about at Advisorator. You sign up, I'll send you the issue. Last year I started pushing a free version of Advisorator more aggressively. It has a lot of what's in the paid newsletter. It doesn't have that top feature column most weeks. It doesn't have all the stuff that I'm putting on the website. I have a big collection of standalone evergreen guides and archives and all that stuff. And I have a Slack channel for paid subscribers. So there's definitely some benefits for paid subscribers. But I've been trying to move Cord Cutter Weekly people over to that free version as well so they have a starting point. So now it's kind of... It's a tricky thing, but it feels like that's opened up Cord Cutter Weekly a bit for me to do things like the guide that I mentioned. Because then I don't worry about, oh, I'm not promoting Advisorator this week. I have this other thing. And I'm not loading the email with a million calls to action. I can just focus on one. 

It's going okay. You know, Advisorator, the free version, does not convert necessarily to paid as well as Cord Cutter Weekly did. So I'm finding ways to balance that. I usually do one or two big sale periods every year for a couple of weeks, usually one in January, one around mid-year. And I'm still promoting those in Cord Cutter Weekly. And the last one that I did in January was actually my most successful to date. I think I added like 150 people.

So you mentioned the Slack channel. Is that like super active, or like what kind of dynamic does that add to it?

It's pretty calm. You know, I'd say there's like a handful of people that chime in regularly. There's actually a few other technology journalists that are in there because they subscribe to the newsletter and they like it and they do chime in. So it's not super active, but the people that are in it really appreciate it. So I keep it going and I enjoy having it. It's a nice place to kind of talk with other people that are into this stuff. To be honest, I haven't totally figured out how to make that a bigger thing because it seems like not everybody is super into that idea. The people that are in the Slack channel don't necessarily like the idea of a forum instead. So I haven't totally figured out a way to make that a bigger piece of the subscription. But it is there. And maybe it's something I'll kind of pick out over time.

And do you get the sense that the demographics for paid subscribers for Advisorator are similar to Cord Cutter Weekly? 

Yeah, it's probably similar, especially by virtue of the fact that people are coming over from Cord Cutter Weekly. There may be some folks that are younger. There's definitely some folks that are not in the U.S. Cord Cutter Weekly is pretty focused on the U.S. streaming market because it would be impossible for me to kind of say what streaming is like in Spain. I couldn't really tell you that. But you know we have subscribers in the UK and Australia and other places. It's not a huge contingent, but people that still get value out of hearing about useful apps or how to how to deal with password managers. All that applies no matter where you are.

So you have 32, 000 free subscribers on Cord Cutter weekly, and an additional 8,000 free subscribers on the Advisorator. These are pretty lucrative niches. Have you ever considered sponsorships or advertising or anything like that?

It's something I think about every once in a while.  I think I saw your recent post where you're talking about sponsorships as well. I think we're probably of similar mind where we don’t want to spend our time thinking about how to hunt down sponsors. It's not fun. It's not something that I want to spend a lot of time on. The other nuance is that I still freelance, right? And my freelance agreements say, like, you can't take money from a company that you're writing about. So if I was going to say, like, run an ad for Roku in Cord Cutter Weekly, that becomes a conflict if I want to write about Roku anywhere else. So then it becomes a challenge of like, all right, well, how do I find something that's relevant enough to the newsletter, but not so relevant that I would write about them? It's just a whole set of challenges that to be honest I don't really love the idea of dealing with, so you know it's not something I would rule out but it's not like the top thing that I want to try to figure out

So speaking of your freelancing, how has this success with these two things kind of affected your freelance career? Are you still doing just as much as you always were? Or has it allowed you to dial back and be more choosy in terms of what you do? Because back of the envelope math, you're generating like $60,000 a year through paid subscriptions for Advisorator. So that has to have some pretty decent effect on your income right now.

Yeah, it does. And it's the kind of thing where it's taken meaningful pressure off of the freelance side. You know, I probably spend across the two newsletters, maybe the equivalent of like a couple days a week on them, you know, and the rest of the time I'm doing my freelance stuff. And it's, you know, it used to be when I started out, it was basically like all freelance all the time. And Advisorator was something I worked on on the weekends when I had time. It actually started off as an every two-week newsletter, and I switched it to every week maybe a year or two into it.

So it's the kind of thing where you're kind of trying to grow these two things at the same time. Like I want to increase the amount of money that I make from tech journalism, and I also want to increase the amount of time that I'm spending on my newsletter relative to freelancing. So I'm kind of trying to balance and juggle those two things. But it's definitely the kind of thing where, you know, it used to be that I might feel like I had to write this other freelance story a week. And now I'm kind of like, all right, I don't have to do that. It's going to be fine. And it's also just kind of nice to know that there's this thing that is my own, it can't be taken away from me. And, you know, if something blows up with one of these freelance gigs, maybe that's the excuse I need to finally put even more time into the newsletters and all that.

Do you think that's something in the future? Like, could you see you deciding one day that it makes more sense to just focus 100% of your time on growing this because you get 100% of the upside of the success?

It's like in my mind. I rely on the stuff that I'm writing online to bring in readers. So that's not really going to go away. Maybe there'd be a setup where I'm like very much more explicitly focused on, all right, everything I write for another website has to be promotion for the newsletters, which is not always the case with every single thing I do as a freelancer, but yeah, if I could get to half of my time on the newsletters, I'd be in a pretty good place.

And what about future ambitions? Do you want to move into more niches do you want to expand into new mediums like podcasts or anything like that?  

For one thing, I think just the media business being where it is now. I'm happy if it just exists and continues to grow at a modest pace. I've started doing a little bit of having freelancers contribute things, especially when I'm going to take a week off or something like that. I would love to just showcase more of other people's writing, especially when they have an expertise that I don't necessarily have. 

I have ideas for another newsletter that's a little bit different from these two, but it's still kind of floating around in the back of my head. It’s too early to really say anything about that.