Over the past few weeks, there have been a number of high-profile examples of journalists leaving publications to launch their own newsletters. This isn’t a new trend, but as tools like Substack, Medium and Patreon have grown in prominence, the barriers to making a living off working by yourself have come down.

In this special podumentary episode, we talk to journalists at a range of stages, from those that have been flying solo with their own businesses for a number of years, to those that have recently taken the leap. What connects them all is a loyal newsletter audience, although as we’ll see later, that isn’t always enough.

Hear from Platformer’s Casey Newton, Baekdal.com’s Thomas Baekdal, The Business of Content’s Simon Owens, Culture Study’s Anne Helen Petersen and The Media Nut’s Josh Sternberg as they talk about the realities of what it takes to go it alone with reader revenue as a journalist.

We start off by hearing from one of the people who has elevated this conversation in recent weeks: Casey Newton. Casey was previously The Verge’s long-time Silicon Valley editor, where his newsletter The Interface grew to 20,000 subscribers. Now, he’s gone solo with his own paid newsletter Platformer, hosted on Substack.

Unusually, Casey was allowed to take his full subscriber list with him when he left The Verge. But initially, he was preparing to have to rebuild the list from scratch, and it was actually a Twitter milestone that got him thinking about taking the plunge.

Casey Newton: I think that I had come to believe in the value of the thing that I was making. And when I talked to people at the companies that I covered, it seemed like it was valuable to them, too. I asked them, if I were doing this on my own, would you still subscribe? And if so, would you pay for it? And enough people said yes, that I thought it could be worth a shot.

By that point, my Twitter following had cracked 100,000, which was a 10 year project that had finally come to fruition. And I thought it was worth a shot, because ultimately, I only needed about 1,000 of those people to become paying subscribers in order for it to become a pretty good journalism job.

Just a couple of weeks into launching Platformer, Casey has grown the free list to 30,000 subscribers, and has almost 1,000 of those now paying him at least $10 a month. He’s aiming to convert around 10% of his newsletter list eventually, but if you do the maths, he’s currently very well set up indeed; more so than he initially expected.

Casey Newton: I’ve been giving this thing away for three years for free. There’s no telling how valuable people find it until they actually fill out a form and contribute. And so it’s been so tremendously heartening.

The day that I announced that I was leaving The Verge, it should have felt like a really exciting day. But honestly, mostly, it just felt very scary. It sort of had that bad dream feel of like, ‘Oh, wait, did I really do this? Are they really actually cutting off my email address, like, can I go backward?!’

But then by the time that I’d woken up, the next day, so many people had subscribed that I knew I was going to be good into next year. Just using the revenue that readers had already contributed, I was going to be able to make it into 2021 just fine.

If you’re one of those people who are currently considering launching your own paid newsletter, or otherwise leaving a media company to go solo, there are certainly some benefits. But it’s important to note here that Casey is the exception here, rather than the rule. For many other solo journalists, bringing in sustainable revenue is a long game.

Danish media analyst Thomas Baekdal is familiar with some of the pitfalls of going solo, even with big numbers. He started his site Baekdal.com in 2004, and for six years, monetised it through advertising.

Thomas Baekdal: It was fairly successful, I had a million visitors per month. But the problem was, even with a million visitors, I was only making something like £200 per month. It was nothing. I mean, I couldn’t make a living out that. And so I needed to find a way to make it work. And the way to do that was to go paid.

So in 2010, when everyone was telling us that that was the most insane thing I could ever possibly do – I mean, I don’t know if you remember how people were talking about The New York Times when they were also doing it in 2010, and everyone was saying, well, in three months, The New York Times will drop this insane plan they have – so that was the notion back then.

But I started solely because I couldn’t get advertising to work. I had a million visitors and advertising just couldn’t support that.

And well, here we are today. Today I have no advertising, and I make a living off subscriptions.

Now, Thomas’ site is a mixture of free articles, a newsletter, and deep-dive paid reports which you need to be a Baekdal Plus member to access.

Media analyst Simon Owens is another solo journalist who understands some of the challenges with starting out. A few years ago, he launched a Patreon account to try and build a subscriber base.

Simon Owens: So with Patreon, it just wasn’t really well designed for what I was doing, in the sense that, it’s much better designed for podcasts and for YouTubers and stuff like that. And at the time, I didn’t even have a podcast.

So I had this weird setup where – it was so many things wrong – where I was publishing super long form, super well researched articles to Medium, articles that would take an entire week and involve interviewing three or four people, high quality articles, but super time consuming. Publishing it to Medium, then trying to drive people from Medium to sign up for my TinyLetter newsletter. Then from the newsletter, that’s where I was pushing people to the Patreon, which is a separate platform.

So they would land on there and subscribe, and then I would have to either, for my paid content, which that was another snafu in the sense of, I couldn’t get a sense of what people actually wanted to pay for. So I was just sending them little mini essays and curation and stuff like that, stuff that really just wasn’t adding that much value.

And I think by the end of it, at the end of 10 months, I had something like 35 paying subscribers, which is really pathetic, even though I had done all this work. So at the end of that I was like, this is just not working, I need to shut this down.

Simon admits he was naïve about what it took to launch a paid subscription programme. He’s now trying again, with lots of learnings from his previous attempt. He launched a podcast called The Business of Content back in 2018, and a paid Substack newsletter in February of this year.

Simon Owens: So flash forward to February 2020, this year, it was just the right combination of, after thinking about it for a long time, but thinking that it was going to be a lot longer before I would launch a paid newsletter, there was just something where I was just like, you know what, I should just launch it. And just try to grow it slowly and not focus on this marathon, where I’m just working on it full time, but just try to work on it part time while I’m doing the other stuff and hopefully, gradually transition to working on it full time.

Simon isn’t the only journalist to have seen 2020 as a year of opportunity. Anne Helen Petersen was a Senior Culture Writer for Buzzfeed until August of this year, when she quit her job to devote more time to her weekly newsletter Culture Study, as a paid option.

Anne Helen Petersen: I had been doing the newsletter, I started it as a TinyLetter in 2016, right after the election, and then moved over to Substack when Substack came on my radar, which was pretty shortly thereafter. The CMS on substack is just so superior. So I was like, ‘Oh, this is great. This is easy. I’ll do this.’

[Substack] started recruiting me pretty much from the beginning. They were like, ‘Why don’t you do this paid?’ And I didn’t want to have a secondary hustle on top of my main job. I really liked that the newsletter was something that felt natural and felt unmonetized, it wasn’t a monetized side hustle as we talk about in the burnout stuff. And it just felt kind of like a release valve.

Rather than try and monetize it as a side hustle, Anne left her full time job to go all-in with Substack. But not all good newsletter writers are in a position to monetise.

Josh Sternberg launched a daily newsletter called The Media Nut after getting caught up in AdWeek’s pandemic layoffs. In just a few months, it’s grown to over 3,000 subscribers, but that’s just not enough for Josh to be able to look at monetising it.

Josh Sternberg: I’ve got two kids, and a wife, and a mortgage, and health insurance, and food bills, and internet bills. Having a newsletter wouldn’t sustain that, the economics aren’t there.

It’s great if you could do it, but you would need 10s of thousands of subscribers. I’ve got 3,400 so I don’t think that I’d be able to turn this into a business that would allow me to have the life that I’ve been living for quite some time.

In an ideal world, Josh said he would find a newsroom position which would allow him to keep The Media Nut going as a side project that he enjoys.

So if you’re going to go this alone, what kind of numbers do you have to have to make it a success? Casey Newton launched Platformer by migrating 20,000 subscribers from his previous newsletter The Interface, and for Anne, it was a similar number which prompted her to make the move.

Anne Helen Petersen: I had about 19,000 subscribers when I made the shift. The Substack rule of thumb is that you can usually depend on about 10% of your subscribers of your total email list to go to the paid format.

And then also – people talk about this pretty openly – Substack, because they had been recruiting me, they gave me essentially a grant, that was like, ‘We’re going to give you a bunch of money, and you can take 15% of your revenue for this year.’ It’s essentially an incentive to come over to the platform if you’re nervous about making enough money in the first year.

So they gave me a grant, which I think of as just my salary, and then what I am making, I’m getting 15% of that for the first year. And then a year in, I can say, ‘Okay, I want to go to the format where I just get 90% of my subscriptions.’

So for those without a newsletter database at that scale, or a grant from Substack, what can they expect to convert? Thomas Baekdal had high expectations back in 2010 with his 1 million site visitors, but found the reality a little more difficult.

Thomas Baekdal: I had to learn this the hard way like everyone else. So the scary thing is that I had a million visitors. I launched Baekdal Plus, and I had this idea that I could convert something like 5%. That was my plan. So 5% of a million, that’s a lot of subscribers, and I would get rich, basically, within a couple of months. That was my idea in my head.

After three months, I had 29 subscribers. That was it. And so I went from thinking, ‘Oh, this is the best thing ever,’ to ‘Oh, my freaking God!’

An important point came out from this. Even for journalists with a large audience, monetisation isn’t instant. Thomas took three years to reach the point he was cashflow positive with Baekdal.com, and he says the only reason he was able to keep it going to that stage was because he had saved up a lot of money.

Thomas Baekdal: So I basically spent five years before I started saving up, so I had more than a year of salary in my bank account when I started. And I burned through that almost completely. I almost went bankrupt within the first three years. I was also saved because I was hired to do some media consulting for some companies. But if I didn’t have that, Baekdal Plus wouldn’t be a thing today.

So that is the crazy scary thing about the start of that is that it was much, much harder than anything I ever imagined. When people ask me about this, and those journalists thinking they want to start something on Substack on or whatever platform and they say, ‘Oh, we have this idea,’ I say, ‘Great. How much money do you have?’

That’s my first question. Because they need to have a year’s worth of salary in the bank account to start. If they don’t have that, they need another form of income the first year, or even the first couple of years.

For media companies, this is not a problem because they have investors, or they have owners who are investing money initially. So Axios can afford to spend the first three or four years just building up an audience until they get profitable.

But if you are a single individual, you still need to pay rent, you still need to buy food, you still need to do all those kinds of things, and you don’t have investors. And so you need that money up front in order to do something.

There are other parallels between individual journalists and media companies beyond the need to set expectations around profitability. One theme that came up quite frequently was the other work these entrepreneurs all did on the side, either to make up a shortfall or to strategically diversify – like a media company.

Anne has a number of different strands of income, despite having strong newsletter subscriber numbers to Culture Study.

Anne Helen Petersen: The interesting thing is when you go full time on Substack, you’re a freelancer. So I was offered small freelance opportunities. I wrote for the New York Times, and I just finished a piece for Elle, I have these secondary things that are also going on.

I knew that because of my book [Can’t Even: How Millennials Became the Burnout Generation], because that was my third book, I just sold another book, I have these other income streams that are all, I think of them all together. So while I’m researching this new book, which is about working from home, I can take some of that research and feed it into the newsletter. They all are kind of coming into the same space.

Simon Owens also does freelance and consulting work, but since launching his paid newsletter, he has actively tried to cut this down in order to focus on converting subscribers. He says that finding a balance with this and working to a point where you’re able to switch to focusing on paid subscribers full time is a huge challenge.

Simon Owens: It’s really painful, because it’s really hard to say no to short term revenue, I just did it a couple times within just the last two weeks. And I am just not making a tonne of money right now! I’m lucky to have a patient spouse with a steady job and some savings and stuff like that.

But going into this, you do have to have a plan, because if your plan is like, I’m just going to do this on nights and weekends, I mean, there are going to be days where you’re just so exhausted, at the end of day, you just want to watch some Netflix or something. Same thing with weekends, like there’s going to be a day where you have an all day barbecue you’re going to or something like that.

And in order to have the kind of consistency that you need, not just with the free newsletter – because you really have to put a lot of time in both to the free and the paid, because the free newsletter is how you generate new free signups to your newsletter which become part of the funnel of people that you’re going to start trying to convert into the paid cylinder. So you have to have really high quality free content.

But then you have to give people enough of a reason to actually want to pay to subscribe, because they’re not going to be subscribing out of the goodness of their heart, or at least most of them won’t. They actually want something of high quality. If you’re going to go into this, you’ve got to be realistic and be like, ‘Okay, how am I going to carve out significant time during the work day each week to do this?’ So that’s just something, that’s the harsh reality that you face.

Simon’s initial goal is to get to 600 subscribers, a number he says will enable him to bring in enough revenue to dedicate 100% of his time to it.

So why are newsletters now the vehicle of choice for journalists going solo? For Anne, going direct to her readers with a newsletter means that she doesn’t have to frame her pieces in the context of what will perform well on social media. Building her own audience has meant her content can be framed in a more nuanced way.

Anne Helen Petersen: I like the idea that I have a base of readers every single time my newsletter goes out – I’m at 25,000 subscribers now – who already approached me in good faith. I do not have to convince them from scratch every single time I write something, that what I’m writing is interesting or important. They come to the article with that understanding.

However, when it comes to offering newsletters as part of a paid product, there is not necessarily more value in hitting people’s inboxes more often.

Anne Helen Petersen: One of the things that some of my readers have said to me is. We like the forums, that’s a totally different thing. But we don’t want more than two newsletters from you a week. We don’t want a new article in my inbox every week, I want this small amount of information.’

So to be able to have the newsletter itself, still have a personality and a uniqueness, I want to keep it just being me.

‘Less is more’ is a principle that Simon Owens has also found is important when designing his own paid offering.

Simon Owens: One of the lessons I learned very early on is that a lot of people go into this, they assume that the difference with the paid and the free version is you just offer more of the free version, that you send out one free newsletter a week, and then you send out one paid newsletter a week, and they’re completely identical, and people will just want to pay you to get that extra newsletter.

And you learn early on that that’s just not enough for much of a value proposition because a lot of your subscribers are like, ‘Eh, I’m already like reading a lot of content. Do I really need that extra newsletter a week? Like, is that really serving me?’

One of the first questions someone needs to ask when they’re looking at a paid offering is how much to charge. This is a difficult question as it will largely depend on the market, and to a certain extent, how much people are willing to pay.

Anne’s Culture newsletter is available for $5 a month, whereas Thomas, Simon and Casey all offer their own B2B content at $10 a month. Simon warns against undervaluing work in a niche market.

Simon Owens: If you have any kind of niche type of market that you’re writing about, it’s really hard to go under $10 a month. Because you just think about how hard it is to convert people into paid subscribers, and even 1,000 subscribers, which would get you to about $100k in revenue, or even 600, which would get you to $60k, which would be around the average salary of a journalist, that’s going to be really, really hard to get up to that number. And it would be even exponentially harder to get to twice that number.

So you have to price it decently. You can’t think about, what is the New York Times or some other kind of high volume general interest publisher charging.

A lot of people go into this like, ‘Ah, I’m not really producing that much value,’ or ‘I’m not producing consistently enough, I’m just going to charge as low as I can, which for Substack is $5 a month, and then I’ll try to just make up for that in volume.’

And you can’t really think about it like that, because let’s say you want to get to 1,000 subscribers at $10 a month. If you lower it to $5 a month, yeah, you might be able to get some extra subscribers because you’re at a lower price point, but you probably won’t be able to get twice as many subscribers, if that makes sense.

Subscription fatigue is a question that has been raised a great deal recently, as more publishers and creators turn to their audiences for revenue. But for now, this isn’t an issue that concerns any of the people I spoke to for this.

Anne emphasised that it comes down to confidence in convincing people of the value of what she is creating.

Anne Helen Petersen: It’s interesting, I think that I’ve just made the proposition to people that if they’re reading something on the internet that they value, then they should consider paying for it, if they can afford it. Thus far, people have really responded to that. Maybe in the future, if that somehow isn’t working, but thus far, it is done very well.

I think it’s going to change when people have to be faced with the prospect of many different newsletters that they want to pay for and express their gratitude for. But right now, it has worked well.

I give free subscriptions to anyone who is unemployed or underemployed or a contingent worker in some capacity, that’s fine, I don’t care. They don’t have to explain, they can just ask for a free subscription, and I’ll give it to them.

Simon is also not worried about subscription fatigue. He says journalists need to focus on converting their most obsessed users into paid subscribers.

Simon Owens: I think subscriber fatigue is a little bit overrated and a little bit overplayed in terms of a worry for it. The reality is, the vast majority of your subscribers are going to be the free subscribers, and you’re just going to be converting your most obsessed users into it. And if you do the math, let’s say there are a billion people in the English speaking world and on average, each one only subscribes to one publication, there are so many different ways you could splice a billion subscriptions in terms of how many creators that could support.

Ben Thompson has another way of putting it where it’s like, people tend to underestimate how many people are on the internet. There are so many people out there that it is possible for a lot of different newsletters to find their thousand true fans.

Don’t get me wrong, it’s so hard, there’s going to be so many people who try it and fail. But it is possible.

However, Thomas Baekdal cautioned about the hype around the stories of writers like Casey Newton, highlighting that this is not a ‘get rich quick’ scheme for the majority of people.

Thomas Baekdal: The funny thing about this is, on Substack, we see all these celebrities, and they make a tonne of money, and they’re super successful, and it’s crazy. For the rest of us, it’s nothing like that. For the rest of us, we make enough money to live our lives. But we don’t go out and buy fancy cars, and we don’t live in fancy houses. I mean, you don’t become a writer because you want to get rich. That’s basically how it has always been.

You don’t need that many subscribers to actually make this work. The problem is just that going from say, having enough subscribers to make the same amount of money you used to do as a journalist, to making so much money that you become rich, that is a huge gap between those two.

I mean, it’s relatively easy to get, say 300 – 500 subscribers. It’s insanely hard to get, say 3,000 – 5,000 subscribers. There’s a huge gap there.

As well as not getting caught up in the hype, it is important to realise that, like many trends in media, this is not new, as Josh Sternberg explains.

Josh Sternberg: I look at it perhaps a little bit differently in that, to me in newsletters, especially now like this rage of journalists moving over to these platforms is very similar to what blogging did in the middle 2000s. And you’re seeing voices come in the form of newsletters where the idea is less about, if I’m blogging on my site, I am trying to get people to come to me.

Whereas with the newsletter, I am trying to get to people. You get my work because you signed up and it’s coming into your inbox. You don’t have to do anything. Whereas with blogging, you had to actually go out and search for it.

But I think that tool of being able to democratise media, where you’ve got an internet connection and a keyboard and you’ve got some thoughts whether tight or loose, that’s all you need.

Simon Owens and Thomas Baekdal both credited the New York Times’ paywall move in 2010 as being a key kickstarter in the movement towards conditioning people to pay for content. But what has really accelerated this trend is the availability of tools like Patreon and Substack, who do a lot of the heavy lifting in terms of systems; making content easy to deliver, nice to read in terms of formatting, and straightforward to pay for.

But this in turn has created a different set of challenges, and journalists are at risk of underestimating the difficulties still inherent in striking out on their own, as Thomas explains.

Thomas Baekdal: You need more than just exposure. You need to have a very, very specific form of value, and you need to be known for that value before you can do this, or it’s going to take a long time to build up. And that’s the problem.

I mean, there’s a lot of journalists right now, who are thinking, ‘Oh, my God, we can just do a Substack, and I don’t have to do this boring job at this boring newspaper.’ But it’s not that easy.

I don’t want to discourage people, because running your own business is wonderful. And stressful. And you also have to do all the accounting, something people often forget. But it’s hard. And especially if you’re a journalist, and just doing it on your own, not only do you have to do all this work, you have to sell yourself, you have to do all the marketing, you have to do all the accounting, everything, you also have to do all the mental health things, because you have to carry every single burden on your own shoulders. And that is a lot harder than thinking, I’m just going to make a company.

Starting your own business is one of the most rewarding things anyone can ever do. But it’s also the most stressful thing. And I’ve seen a lot of people just crash and burn out.

Josh agrees, and draws a parallel between the Substack hype, garage bands and rockstars.

Josh Sternberg: I think having a dose of reality, or at the very least some pragmatism of understanding that the odds are always against you, and you need to be able to have multiple contingency plans.

And if you are going to say, ‘You know what, screw it, I’m going to leave my cushy job, and I’m going to go out on my own,’ I mean, it’s an exhilarating feeling. And it’s a fun risk. But it’s a risk nonetheless. And the odds that you become that prototypical example are small, right?

My career started out as a musician. I was in a band, we made an album, we toured up and down the East Coast. We had delusions of grandeur of becoming professional touring musicians. We didn’t, because it’s really hard to get to that level.

And I think the same is true with newsletters. I mean, it’s true in journalism, right? There are only so many New York Times White House beat reporters.

As this trend picks up pace, and the tools available make going solo a more attractive proposition, where will this end up in the future, and is this something publishers should be worried about?

Simon theorises that independent creators will end up coming together again in pseudo media companies.

Simon Owens: Both of these sides are going to become more porous, you’re going to have full time reporters leaving their jobs and launching their own newsletters and reaching their thousand true fans. So you’re going to start seeing some competition with the mainstream media on this.

But then you’re going to see it move in the other direction where some of these creators are going to be so successful, and they’re not going to be satisfied with just 1,000 true fans. So they’re going to start hiring people for support or other writers and stuff like that, and starting to look like a more traditional publication, or media company. And they’re going to find that tools like Substack aren’t robust enough.

So a good example is, there was Defector, they didn’t go on Substack. They have a hodgepodge of a tech stack that uses things like Pico, this other company called Alico, stuff like that, that built a custom CMS for you. There’s one good example called the Discourse Blog, which is a bunch of defections from Gawker Media, from a publication called Splinter, they started on Substack. They were really successful. And now they’re moving off Substack onto the same platform that Defector is using.

So I think you’re going to see some of that where some of the most successful creators are actually going to start creating these media companies that are looking more like traditional media companies.

Thomas says that for independent creators, there are cashflow issues which more often than not will prevent them from properly building out their own media companies. It’s something he himself has wanted to do for a while.

Thomas Baekdal: If I had the funds I would hire two, three more people. So I would hire someone to basically be in charge of the newsletter. So I could do a newsletter at least every week, but probably every day. And I will hire someone else to also write reports, because that would give us that double level of reports that I need in order to actually make this work. But that’s definitely something that I know, if I did that, I could make my business much more profitable and much, much bigger.

So the problem I have today is, I have reached the limit of how much I can get as just one person. And if I want to take that above that, I need to hire more people. But I mean, when you are just one person, and you run your own business, hiring just one person, that means doubling your revenue. And you need to basically double your revenue before you hire them, because you need the money to hire them.

And so I’m stuck. I mean, I don’t know how to do it.

However for Casey Newton, creating a mini media company isn’t on the cards. He’s more interested in nurturing collaborative efforts between journalists, and seeing where that leads, potentially sharing some costs along the way.

Casey Newton: Something that I have been thinking about a lot is YouTube, where influencers collaborate all the time. It’s one of the main ways that they grow their audiences. We haven’t really seen journalist collaborations like that. But they seem really obvious and interesting to me.

My publication links to the work of dozens of great journalists, and there are a handful of characters who are appearing multiple times per week, right? And so even though their journalism is appearing elsewhere, on Platformer, in a weird way, they’re these kind of pseudo correspondents for it. So I can imagine a more intentional version of that relationship where I’m bringing in a star reporter on the TikTok beat or on the Amazon beat to maybe do a little bit of journalism, maybe just do a Q&A, but kind of build out that ecosystem a little more.

And from there, I think we can figure out some other interesting things. We could figure out bundles, we could figure out special collaborations, we could work on a podcast together.

I don’t think it rolls up all the way back to becoming a publication. One of my jokes is, I don’t want to work in a newsroom anymore, but I’m really interested in a Scooby gang, like five or six people who get in a mystery van and drive all over solving platform mysteries. That sounds really cool to me. And all of those people might be supported in their own ways. Maybe we would share some costs; maybe we would share an editor or maybe we would share a designer.

But it just seems like there’s a lot of really rich potential there that enables the individual journalists to pursue their own aims on their own schedule, while retaining some of the things that we liked about working in newsrooms.

On the flip side, how will publishers respond to this trend? Josh Sternberg has some theories that this will also follow the blogging route.

Josh Sternberg: It’ll be interesting to see how entrenched media companies embrace platforms like newsletters, the way that they’ve embraced, perhaps begrudgingly over the years, blogs.

I’ll use the New York Times because they’re just a fun example, but they were like, ‘This is the paper of record.’ And they tilted their nose up at digital in the early part of the century. But then as blogging became more prevalent and easier, and they were able to put the technology into their CMS, The New York Times started to do their own blogging. Every time there was an Apple event, they live blogged it. So they co-opted the idea of blogging inside of a mainstream publication.

They’re doing the same thing with newsletters now, they’ve got a great parenting newsletter, for example. So I think that as more media companies embrace different modes of being able to get their writers to connect with their audiences, that’s where things move. And it’ll just be interesting to see which publications opt to not do that.

Now some of you may have spotted a trend with all the recent newsflashes of writers going solo. Most of them have been men. Is this reflective of media and journalism generally, or is there more going on behind the scenes? Anne shared some of her thoughts.

Anne Helen Petersen: Even if you just look at the top 10 on Substack there’s just a bunch of white dudes. So one of the ways that someone like Casey Newton is able to succeed, or Bill Bishop, they are writing essentially trade newsletters. And so those subscriptions can be expensed.

Some of the more successful newsletters and things like that, so just in society, a lot of our thinkers for a long time have been white men, it makes sense that they also dominate this top 10 list. So that’s interesting to me than that this is what is dominating.

But I do commend Substack that they are taking measures to not only diversify who is writing in terms of race, but also location and subject and all that sort of thing through their Substack Fellowship Programme. So they, I think, are aware of the whiteness and maleness of their top list and are trying to work with it.

I do think that there is just a general confidence thing [with women] in terms of like, ‘I don’t want to ask people for this,’ right, ‘Oh, that’s brazen of me to ask people to pay me for my labour.’ And a lot of that has to do with, the intersection of, just the idea that there’s so much unpaid labour that goes on on the internet, you’re like, ‘Oh, I’m just doing this for fun, like this is just a thing that I do.’ And then also with women in general undervaluing work that doesn’t unnecessarily fall under the rigid description of work.

Whether you’re thinking of going solo yourself or have just been watching recent trends with interest, I hope this insight into the realities of running a paid newsletter or media outlet by yourself have been useful. There are many things to take into consideration, from the time it takes to put valuable content together, to the financials behind the scenes.

Finally, here is some advice from the interviewees that they would give to anyone thinking of launching their own paid offering:

Thomas Baekdal: The most important thing, when people ask me about this, specifically, if it’s a journalist asking me, I would say, think 10 years into the future. That’s the first step. So if we are planning to start something, what is the 10 year plan? And how will you get people to subscribe to that for 10 years? I mean, they’re not going to do it for 10 years. Nobody’s subscribes for 10 years. But what is the business model, the value, the idea that people have in their minds that is so strong that they can actually work for 10 years? That’s my starting point of this. The problem that we have in the world today is we have so many different things. And if we just flood people with more content, nobody’s going to subscribe. So we have to come up with something saying, okay, I want to do this specific thing that helps people in a very, very specific way. And it has to be formalised inside your brain as a 10 year plan.

Anne Helen Petersen has some advice around building a community before taking the leap.

Anne Helen Petersen: I think it’s easier if you have a community already. I wish that it was as easy as being like, ‘Oh, I’m a writer,’ or ‘I’m a journalist, why don’t I start this!’ I had had that unpaid Substack for three years and had grown it from nothing to 19,000 subscribers.

I’d also been working on building my followers on Twitter. That’s not a conscious thing, I’m not like, how do I get more Twitter followers?! But it’s more, I was tweeting with a frequency that encouraged people to follow me, I guess. And so that’s part of it is just engaging with Twitter and engaging with the people that follow you helps build more of a community, even if it’s a diffuse community.

And I also have a Facebook group that I’ve run since 2010, that has 44,000 members. That group is also a community of people who, even before the newsletter, knew my writing, knew my approach to writing, approached what I wrote in good faith. And so by no means is there, not everyone in that group is a follower of my newsletter or a paid subscriber, but I already have those community spaces that helped do it.

Last but not least, Simon Owens recommends taking some time to work out what your unique offering is.

Simon Owens: One thing that you always hear from Substack’s owners, the people who run it, is, don’t launch a paid newsletter right away. You really need to be running a free newsletter for a while to get people used to your voice, to try to fill out, ‘Okay, what am I actually even offering with this newsletter?’

I launched my TinyLetter in 2014. If you look at those early TinyLetters, they look nothing like what my newsletter is now. I developed the voice and a format and stuff that people tended to respond to. I perfected my calls to action, I learned little things along the way that I incorporated into future newsletters.

There’s just so much you can learn from just running a free newsletter. You can start building up your free list so that when you launch a paid newsletter, there’s a list there that you can start converting right away. So that’s the first piece of advice.

Second piece of advice has to do with the time factor. You’re thinking about launching a paid newsletter. Okay, how are you going to make this real, you’re going to be making a promise to your subscribers, because in your calls to action, you’re going to be like, ‘I’m going to give you XY and Z if you pay,’ so are you really set up to deliver that? Are you going to have the time? Or are they going to subscribe and then start getting pissed off right away that you’re not giving them that paid newsletter that you promised every week?

So really thinking through that. Thinking about what is your value proposition to them? If you’re trying to get them to pay for something, is it something that somebody would actually give up $10 a month for, especially when they’re comparing that $10 a month to a Netflix subscription or a subscription to The New York Times? These are all comparisons that they’re going to be making in their head.


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