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We invited Delia Cai, author of Deez Links, to speak to an audience of Substack writers in New York about how she grew her newsletter to 2,700 signups. Delia started her daily media newsletter as an intern at Atlantic Media.

This transcript has been lightly edited for readability. You can also check out the slides from Delia’s talk..

Takeaways

* Be your newsletter’s wingman. Talk it up to everyone.

* Borrow other people’s audiences to reach new readers.

* Build credibility by getting other people to write about you.

Why Delia started a newsletter

I write a newsletter called Deez Links. It’s basically a daily-ish media newsletter that sends you a link to something worth reading, tied to the larger media industry.

I started Deez Links four years ago, when I was just out of college. I had an internship at Atlantic Media that was cool, and not cool, in that I spent all of my time just reading news about the industry, and I was writing corporate memos. It was cool because I was learning a lot about digital media, but I was also just sitting in a cubicle all day, not interacting with other humans. 

This was 2015, 2016, around when newsletters like Today in Tabs and Ann Friedman's newsletter were getting a lot of hype. I was reading those and I was like, “This is so cool. I want to try to do this. I want to try to write in some kind of outlet that isn't just in corporate memo speak and maybe I can just do this for my friends and it will just be a funny thing that I do during the work day.”

So I started Deez Links. It was on TinyLetter. I made the logo in three seconds in MS Paint. It was an extremely lo-fi situation.

I sent it out to my friends, friends from college, and friends that I worked with and I was just like, “I'm going to do this every day. Let me know if this is interesting.” I had no real aspirations for it other than just getting in the practice of writing about something every day.

Deez Links grew to about 500 subscribers by 2018, which was fine. It was mostly people that I'd met on the internet, or just people that I knew personally. Then I moved it to Substack in 2018, and since then it's gone through this amazing growth trajectory to where I had 700 subscribers and got a shout-out in New York Magazine and Vanity Fair. We're also doing this merch store which is really cool, which has taught me a lot already about ecommerce and supply chains.

Deez Links was mostly people that I'd met on the internet, or just people that I knew personally. Then I moved it to Substack in 2018, and since then it's gone through this amazing growth trajectory to where I had 700 subscribers and got a shout-out in New York Magazine and Vanity Fair.

Looking back over those four years, it seems like there's this very calculated path to growing the newsletter, and I have to be totally honest and admit there was not. I was just bumbling along. This was my passion project. I just tried a bunch of things, so I’ll share with you the three buckets of things that have worked out for me.

Be your newsletter’s wingman

So the first one is super obvious. It's just to be your newsletter's wingman.

I think the really wonderful thing about newsletters is they're so personal. They're tied to you and your name most of the time. Bring it up to your friends, your work friends, while applying for a job. I put my newsletter in my resume. And I was like, “I don't know if this is work appropriate, but this is what I got.”

When you start a newsletter, you may not have a lot of cred to go off of. You don't have a built-in audience unless you're already a writer on other platforms, and I didn't have that. I was just out of college.

Your first 500 subscribers are going to be the people who are just naturally invested in you, your friends and your mom. So you should make your newsletter an extension of yourself and bring it up all the time when you're talking to people in your circles.

I think the trick to this is always consider how to widen that personal circle, whether it's going to meetups, going to hangouts, or interacting with people on Twitter and making Twitter friends, which is my favorite thing. That way you're always adding to the circle and you're being your own best advocate for the newsletter.

Then at the end of the day, after you've bonded and had a normal human social exchange, you can say, “Yo, I have a newsletter. I write about X, Y, and Z. I would love to know what you think about it.” Telling them to Google it, or even texting them the link, is super easy. That way, you’re treating it as a way to stay in touch with people that’s less weird than, “Can I add you on LinkedIn?” It's like “Hey, we bonded. Do you want to support my art a little bit?”, which feels like a more natural ask.

Borrow other people’s audiences

The second tactic  I stumbled upon was borrowing, or being exposed, to other people's audiences. I think this is the most effective one.

I ended up coming across this tactic in three different ways. One was with classifieds. When I first started out, I was thinking, “I'm a young woman in media. I feel like other young women in media would like this newsletter, what are they reading right now? What am I reading right now?”

I loved Ann Friedman's newsletter. She had this huge subscriber base, mostly women, and her newsletter is tied to current events and news as well. I feel like that's my audience. And she does this thing where she’ll place classified ads on her newsletter. It costs $50 to write a 140-character line about why you should subscribe to Deez Links and put the link in there. So that went out in her newsletter and I got 70 subscribers from doing this, which doesn't sound amazing, but when I first started out, it was like great. I didn't have to meet 70 people to do this. I just put an ad in this newsletter with a very loyal following.

The other tactic that I accidentally came across, in terms of borrowing other people's audiences, was doing weekly Q&As. I first had this idea in 2018 where I was like, “I'm just going to do a Friday Q&A with someone in media, just ask them questions about their job.” Like if you cover Congress, what do you have to wear? What does that mean? Or if you do PR for the avocado industry, do you get free avocados? Just dumb questions that I would ask my friends anyway.

I started doing them with my friends, and then once I ran out of friends to bug, I started branching out to people I really admired on Twitter, people I knew from work. And just realized this golden rule of how the internet and media works: if you interview someone, they're very likely going to share it with their following, and that's how you get exposed to their audience.

If you interview someone, they're very likely going to share it with their following, and that's how you get exposed to their audience.

For example, I did an interview with Alana Hope Levinson, the Deputy Editor of MEL magazine earlier last year. When it came out, she shared it with her followers. And she had a huge Twitter following. Then MEL magazine tweeted out to all of their readers, and I was like, “Oh, this is how it gets done.” With each weekly interview I do, I've noticed I get a handful of followers, especially when it's someone who has a very loyal following and audience of their own.

Finally, honestly, the single biggest boost I got in terms of sign-ups was through a newsletter swap with this lifestyle site called The Good Trade. I wasn't super familiar with them, but their managing editor reached out to me at some point last year. I don't know if she found me through the classifieds, but she was like, “I love your newsletter. We have one, too, it's called The Daily Good. It seems like maybe we would have the same kind of audience. Let's do newsletters.” And I was like, “Yeah, sure.” But I had no idea what that even meant. I was just like, “I'm open to anything.”

What I found out it meant was basically just plugging each other's newsletters. They wrote their own line and I put it in mine. So I wrote, “If you love a good semi-spicy newsletter, subscribe to Deez Links and you get a daily-ish link to something gossip worthy happening in the media industry.” And that was it.

As soon as their newsletter went out, my inbox was just completely spammed and I got 400 sign-ups in one day from this. And I was like, this is really crazy. I didn't even know this community, this audience existed.

Get credibility

The third bucket of tactics is to get institutional cred. I mean that in very loose terms. One of the biggest things that worked out for Deez Links was when this email platform called Revue wanted to do a survey of the top media newsletters in the industry. It was a very unscientific poll. They were just reaching out to people in newsletters and saying “Hey, can you plug this poll? We just want everyone to take this survey.”

So I put it in my newsletter at the time and said, “Hey guys, if you like this newsletter could you vote for Deez Links in this survey?” I only did it because I thought maybe it would be really funny if we got in the running. But it turned out that enough of my subscribers voted for Deez Links that it showed up in the top five between America Press Institute and Digiday Media, really legit places.

When this came out I was like, “Oh my God, this makes us so legit.” And so again, people in industry were talking about it, there was a lot of buzz. A lot of people were like, “What is this one that I don't recognize? I'm going to Google it and subscribe and see what the deal is.” So when that came out I got about 200 subscribers.

Finally, the one that I'm most proud of is when Deez Links was named in Vanity Fair. I'm going to be totally candid and tell you it's because the editor who wrote this piece is a friend from college. When she was researching this piece, she talked to me and was like, “What do you think? What are some people that you think would be good to talk to?” And so I was like, “You should talk to the Substack people. You should totally mention these newsletters.” We just bounced ideas off each other. Then she just did me a hugely gracious favor and quoted me directly and included Deez Links in this piece about the state of newsletters. That was huge, because it felt like this vote of confidence. When this piece went out, I got around 200 or 300 subscribers and bragging rights forever.

I do want to acknowledge that there was a huge advantage in terms of starting my newsletter when I had a day job in media, and still do, and it automatically exposes me to this whole network of people with these followings and power, like the way the Vanity Fair writer had when she was writing this piece.

I also want to acknowledge that there is nothing that media people love talking about more than their own industry. So that also was a huge help. But nevertheless, I do think that no matter what industry your day job is in, no matter what your newsletter is about, it's a really good exercise to just think about, “Who is my intended audience? What do I think that they're listening to or reading now? And how can I find these middlemen or platforms that can serve as a megaphone for reaching this audience?”

Growing your subscriber base is like making friends

It's like when you move to a new city and you don't know anyone. You can go and try and meet people one-on-one, but it would take a long time. The better route is to call up your super-popular, super well-connected friend in the city and be like, “Hey, can you introduce me to all of your friends?” And they do, and that's just so much faster. You get exposed to these various communities a lot quicker, and you come with this vote of confidence from your popular friend.

It's cheesy to think about growing your subscriber base in terms of making friends, but I do think that it speaks to this very personal nature of newsletters. You're sliding to their inbox every morning, or every week, and your subscribers can just hit respond and tell you what they think. That's something really precious and beautiful. It does take longer to build up in ways that, say, maybe blogs were different. But I do think it's worth investing in those relationships, because once you become friends with these people, they’re there for you forever. They'll introduce you to their friends, and then your community just keeps on growing.

For more advice on growing your newsletter, check out how Sarah Noeckel's Femstreet went from zero to 5,000 subscribers.

Photo by Bess Adler

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com

We invited Emily Atkin, author of Heated, to talk to an audience of Substack writers in New York about how she successfully launched paid subscriptions. Emily left her job at The New Republic to start Heated, which offers original reporting and analysis on the climate crisis. Her newsletter is now her full-time job, bringing in six figures of revenue.

This transcript has been lightly edited for readability.

Takeaways

* Focus on building your free signup list first.

* Announce a paid launch date.

* Offer a discount for early birds.

* Every day during your launch week, give people a different reason to subscribe.

* A day before your first paid post, make a final pitch.

I write a newsletter called Heated. It’s been in existence for five months now, and it’s going well. It’s my full-time endeavor.

Being able to make a living off my writing has always been my dream since I was in college and I took my first journalism class. Eight years and a lot of failures later, Substack provided me with a platform to be able to succeed. It’s honestly allowed me to achieve my dream. I make more money now than I had at any salaried journalism job.

I make more money now than I had at any salaried journalism job.

I’m going to talk about how to grow your free newsletter into a paid newsletter. At this point, you’ll already have had a newsletter for a while. You’ll have enough subscribers that you think you can convert some to paying. You’re ready to go.

I’m going to share the tactics I used. You can adapt these however you like. I only launched my paid newsletter a little over two months ago, and I’m already in the six-figures range. I’m not a genius; I just followed a formula.

Make your newsletter free for as long as you can

Step one is to make a free newsletter, and make it original. Make it consistent. I think consistency is really important; that’s something I’ve heard from a lot of my subscribers. I have a little over 20,000 signups on my free list and a little over 2,000 on my paid list, including subscriptions I’ve given away.

Give your newsletter away for free for as long as you possibly can. Especially if it’s getting a lot of traction off the bat, and people are like, “I would like to pay you for this. Can I pay you for it?” Don’t let them. Hold on for as long as you possibly can, because almost all the paid subscriptions you’ll get will be conversions from your free list.

People don’t just sign up and pay. They want free content first, so they can decide if they want to pay. From my analysis, the average amount of time that people take to convert from free to the paid list is about a month, although I don't have much data yet.

Give your newsletter away for free for as long as you possibly can. People don’t just sign up and pay. They want free content first.

Foster your community. Make people want to pay for your stuff. Market your newsletter in a way that will almost make you uncomfortable, because it sounds like you're just talking and promoting yourself all the time.

Announce you’re going paid

So you've done all that, and you're ready to launch your paid subscription. Don't just put a paywall up. Give your readers at least a week's notice.

I write my newsletter four days a week, Monday through Thursday. So, two weeks before I put up a paywall, I said, “Okay, guys. Now's the time. It's been three months. Next week, I'm going to give you the ability to pay.”

I wrote that on the bottom of a Thursday newsletter, the last one of the week. I told my readers that I've written this newsletter for free because I wanted to demonstrate its value first. I said that next week, I’ll start accepting payments, and I'll announce the rates then, but it’ll still be free all of next week.

Once you turn on payments on Substack, the format changes. You unlock the ability to write preambles to your newsletter. That's where I did my marketing. I went personal on it. I was like, “Guys, I'm scared. I quit my job to do this. Please don't let me fail.”

That's another thing about newsletters. You can get personal. I did some positive marketing for this, too. I was like, “If this works, imagine how many more people we can reach; if I can hire a research assistant; if I had a copy editor...”

Kick off a paid launch week

The next week is your paid launch week, where you remind people every day that you’re going paid, but you still keep all your content free.

Make sure your content is really good all week. Put in extra work. Every day, in your preamble, try to give a different reason why people should subscribe.

Set your price high – higher than you’d think. During your paid launch week, offer a discount. I did 25% off the first two days and then 20% off the second two days so I could say, “All right, you missed 25% off, but you still have 20% off”. Then the price goes up from there.

For day one, I focused on a personal appeal and giving a discount. I made it feel like: “Today’s a special day, cue the air horn sounds!” Especially after you've been giving stuff away for three months, you've built up a community, so it should feel like, “Yay, now it's your turn.”

I made a personal appeal there that was, “I gave this to you for free, but it's not sustainable for me. I want to be able to do this every day. I want this to grow. I have so many aspirations for this. We, together, can make this a thing. Let's make it a thing.” People are like, “Yeah, let's make it a thing!”

I also do this thing where for every 100 people who sign up, I'll give 10 subscriptions away to people who need it. It helps. It's good because it helps grow your paid list, but it also gives your stuff to people who can't afford it. People are like, “Oh, okay, if I can afford it, I’d also like your writing to go to somebody else.”

For day two, I used the excitement from day one for momentum. You can send different emails to your free and paid list. So I sent an email to those who’d paid on day one that was like, “Guys, you signed up. Yes. Thank you so much. You're amazing.”

Then I sent an email to my free list that said, “If you're getting this message, that means you didn't sign up. How dare you? After all I've done for you.” But then I said, “This is the last day you can get 25% off, so you're going to want to do it today.”

Build upon your momentum from day one. Include quotes from people on Twitter who are signing up for your newsletter, even if it's just one of your friends.

For the next two days, experiment with different tactics. You know your community, so you’ll know best what would appeal to them.

For day three, I tried this messaging about how the fossil fuel industry poured billions of dollars into disinformation. My newsletter is about climate change, but it's specifically about powerful people and climate change. So for day three, I used that angle. I was like, “Let's combat this with information. Let's produce journalism that makes the truth louder than their lies. That can only happen with your support.”

On day four, I didn't do any marketing. I just did an ‘Ask Me Anything’ [AMA]. I used the discussion threads feature on Substack, which is a way to interact with your subscribers. On that day, people had a lot of questions about the paid launch, so I was able to go in there and answer their questions.

I did five newsletters this week instead of my usual four, because I just wanted more opportunities to promote my launch. I decided to make my last day something big, to demonstrate the value of this work that your money would buy.

On the last day, I launched a project I had been working on for a long time. I published a large anthology of fossil fuel advertisements. There was an embargoed study in there, some interviews, all this stuff. Instead of having my marketing preamble at the beginning, this time I did it at the end. I said, “This is an ongoing project. There's so much we're going to do, but it can only happen with your support.”

Make your final pitch

By the end of this week, you've asked people to pay you every single day. It’s now the weekend. Take a break.

The last thing that happens is to make your final big pitch. For me, this was the Monday after my paid launch week.

This will be the last time your newsletter is free. After my final pitch, I put up a paywall, and now 75% of my content is paywalled. I told my readers that after three months, this will be the last time you're going to get it.

Write a post explaining everything that you've accomplished while your newsletter was free. If you’re thinking about going paid, you should always keep a list of every good thing that has happened, like getting a nice email, a good tweet, seeing your work cited in another publication – just any way you can say you've been influencing the conversation or making people feel good. You want to be able to say, “This newsletter is original in this way. Nothing else like this exists.” 

Write a post explaining everything that you've accomplished while your newsletter was free. You want to be able to say, “This newsletter is original in this way. Nothing else like this exists.”

That's what I put into my final pitch. I showed what I’d accomplished in the past three months. I had sections about how this reporting is making a difference, how it’s shifting the national conversation, where it's been cited. Every amount of praise that has ever happened, I put into one place. “Vox called it great. Earther called it wonderful. Environmental Health News called it a unique blend of insight and smartass.”

Back when my newsletter was still free, I’d done a survey where I asked people to tell me why they liked the newsletter. I compiled that into a spreadsheet and used it for marketing. I was able to say things like, “Six people said that they felt less alone when they read this newsletter. It's helping you guys feel better, and that's what makes me feel better. So let's keep this going.”

Your first and your last pitch are the days where you’ll get the most subscribers. The first day you launch, you get a lot. The second day, especially if you do a two-day discount, you get a lot. Third and fourth day, you're like, “Uh-oh, it's over.” And then on the final day, you’ll get a lot.

The final step is to put up your paywall. After you do that, your daily audience will become much smaller. At that point, I probably had 18,000 free signups. All of a sudden, with my paid subscribers, it's 1,000. For the majority of the week, I'm now writing for a much smaller audience, which is actually way easier, because they like me enough to have paid me.

After launch week is over, you might panic because you think it's all over and no one will ever pay you again. But just keep that process going. Every time you have a free newsletter, try to say something to encourage people to go paid.

How do you know if you’re ready?

You might be asking yourself, “Am I ready to launch?” So I came up with a list of considerations that might help you decide:

* How many free subscribers do you have? Conversion rates tend to be around 4 to 10 percent, according to other Substackers I’ve talked to. If your free list isn’t very big, consider waiting.

* How much money do you want to charge? Have you asked your subscribers what they’re willing to pay, or looked at similar newsletters to yours? 

* What impact have you made that you can point to? People like knowing they’re supporting something meaningful. Have you asked your readers for feedback?

* What makes you original and worth paying for? Before you launch paid, you should feel really comfortable saying why your thing is different than anybody else's thing and why it should exist. You’re going to have to make your case and do a lot of shameless self-promotion around it. It’s going to be awkward. Get over it.

If you have a highly specialized niche audience, you might be ready. That means people who like you, really like you. Some of the best advice I got was that you don't have to please everybody, but you have to please some people a lot. Not everybody has to like you, but a small amount of people have to really like you.

Your impact doesn't have to be big. Use language to make a small impact seem bigger. We were cited in this local paper with a circulation of 20,000. That might not feel big to you, but people like to feel like they're part of something. That's why the newsletter model works. Your readers want to feel like they're part of this community that's growing and making a difference.

The most important question, though, is: Do you feel ready?

The most important question, though, is: Do you feel ready? This process is really different for everybody. Since starting my newsletter, I've talked to many other Substack writers who are going through this, and their newsletters and communities are so different from mine. Their subject matter is different. Not everyone is a reporter. Some of us do creative writing. Some of us compile links. We all have different communities.

In the end, I feel like you'll just know. Even if you're scared, you'll have a gut feeling that you think it might be time, and you might be willing to make it work. Just trust that feeling, because that's what I did, and I'm still winging it.

For more advice on launching a paid publication, check out our guide to going paid.

Photo by Bess Adler

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com

We invited Walt Hickey, author of Numlock News, to share with an audience of Substack writers in New York how he thinks about spinning off multiple newsletters for fun and profit. Walt started off with Numlock News – where he writes about the numbers behind the news – then added paid subscriptions, an Oscar Awards supplement, and a book club.

This transcript has been lightly edited for readability.

Takeaways

* Multiple newsletters are a lightweight way to experiment with new ideas.

* Use your main newsletter to create spin-offs, so you never have to deal with the “zero subscriber” problem again.

* Get creative with your paid subscriptions. You don’t just have to send one free and one paid post. Depending on your topic, you might consider publishing paid content during a peak season, quarterly in-depth reports, or more.

I run a newsletter called Numlock. It’s a daily morning newsletter about the numbers inside the news.

I started it after working at FiveThirtyEight for about five years, where I’d started a newsletter called Significant Digits. As a guy with a math-y background, I realized that my biggest liability as a person in journalism was that I needed to get better at writing, and doing something every day was a really effective way of practicing.

I really enjoyed writing that newsletter, and then it hit a point where the scuttlebutt was that FiveThirtyEight was going to be sold. I looked at where Sig Dig was and realized there was more value in there than we were currently unlocking. The open rate was great. People enjoyed receiving it. In building the case for why FiveThirtyEight should keep me, I actually built the case for why I should leave and start my own newsletter. I did that, and it's been great.

How he started multiple newsletters

My main newsletter is Numlock, it’s my bread and butter. It’s what I've been doing for more than two years now. I have a product that I think is good, and that my audience thinks is good. As a result, I have a good “in” with people who enjoy reading my work. If I were to describe Numlock in Uber-for-pizza terms, what I think of is, “It's Good Morning America for nerdier folks.”

This being Substack, at a certain point, it came time to monetize, so I launched a Sunday edition. For $5 a month, I talk to either a writer who wrote a really cool story that I put in the main newsletter, or I talk to an author who's got a good book out. This is a really fun way to add value.

If you think about traditional media ecosystems like late night shows, there’s a reason they have written jokes in the beginning and then an interview at the end. It’s because interviews are easy to book, and people tend to like them a lot. It’s a nice way to have something that’s less work than the newsletter itself, but gives people more insight into the stories that we find.

But I’ve also started a couple of other spin-off newsletters, one of which is the Numlock Awards Supplement.

I’m a culture writer, and I love predicting the Oscars using math. It's a good time. I started about two years ago and wanted to keep doing it. I think we learn a lot about ourselves, and how we can predict things, through this institution that is very obscure. It's a fun little puzzle.

So I started a pop-up award season newsletter. It runs from November-ish, or whenever I feel like starting it, until Oscar night and the week after. It's a nice opportunity to talk about a thing I'm really passionate about, but not have to throw it at my traditional people who just want to watch Good Morning America and never talk to me again.

That spawned another idea. I love engaging with audiences, and discussion threads are such a cool feature that Substack has built. I wanted a way to tap into that without compelling people who just enjoyed the passive nature of newsletters to participate.

So I thought, again, having interviewed a lot of authors and seeing the response that that gets, my audience is one that enjoys reading things, learning new things, cool ideas, cool books and stuff like that. I figured one way to expand that was through a book club.

The Numlock Book Club is kind of a democracy, and it's also kind of an experiment. The idea was we're going to vote on books to read, and then we're going to vote on these books. Whatever book you pick, we're going to read, then it's basically just going to be a managed reading thing.

We've gone through three so far. We're in the middle of our fourth, and it's really fun. You get a chance to cover things that you wouldn't normally cover. You get to engage with readers that you might not normally be able or willing to, based on how you normally interact with your newsletter.

Spin-offs make it easy to try new things

Here’s the real reason that you should make spin-off newsletters. Who’s having fun in media anymore? I think about this question constantly, because I'm having fun in media, but many other people are not. So I made this list of all the people I could think of that are currently having fun in media:

* Top TV talent

* Private equity capitalists extracting enormous quantities of wealth for a style of business operation not entirely unlike the episode where Tony Soprano busted up that camping store

* Walt Disney

* People who make a living directly from their audience

* People that get residuals from NBC television shows that aired in the '90s and early 2000s

* Jake Paul

I can't be any of these except for one, but it’s really fun. To give you an example of other people who’ve tried this, I’d like to highlight the example of the McElroy brothers, which is a family of brothers who have podcasts.

They started with a podcast called My Brother, My Brother, and Me. Then they tried to do one episode about Dungeons and Dragons, and it went well. So they spun that off and made a podcast called The Adventure Zone, which ended up becoming a lot more popular than the original podcast. Eventually, they started adding some other weird spin-off podcasts. Some of these then turned into other opportunities to cross-promote.

The idea is, if you like The Bachelor, you can listen to Rose Buddies. If you like medical history, you can check out Sawbones, which promotes everything else they have. Everything they do internally plugs into one another.

So if I’m a person who likes the first thing, I can eventually wind my way to other things that I like. Maybe you don't want to listen to Sawbones, but you might be really down for The Adventure Zone. And this also turns into other opportunities like a book, or a graphic novel, or the fact that they had a podcast called The McElroy Brothers Will Be in Trolls 2 and eventually it happened – they're in Trolls 2.

Spin-offs are great. They address a lot of things that are annoying about starting a newsletter from scratch, namely that you know the people who like you the most already. They're the ones who currently subscribe to your newsletter. So you can reach the people who are most likely to subscribe to your other newsletter.

Spin-offs are great. They address a lot of things that are annoying about starting a newsletter from scratch, namely that you know the people who like you the most already.

The Golden Rule I've found is that every new subscriber is slightly easier to get than the previous subscriber, because networks scale. It's very difficult to go from zero to one. Going 10 to 11 is easier. Going 99 to 100 is easier than that, and so on. So you never really need to relive the “zero-subscriber newsletter” that really takes guts to send.

As long as you come into it like that, you can say, “I don't know if this is going to last forever. This is just a fun little thing I'm going to do on the side.” But your spin-offs have an opportunity to bolster the way that you interact with your audience. You might get that hit. You might make a sidebar newsletter that ends up being bigger than your initial one. Nobody really knows what's good anymore, but experimenting a lot is a good way to try that.

Also, collaborations are great. I do my Oscar Awards one with the person I’m dating, who knows much more about the Oscars than I do.

Get creative with paid subscriptions

The internet spent a lot of time figuring out how to really optimize ads. We know a lot of ways to make money off advertising to people. We also now know that, yes, subscriptions are great. Last night I wondered: what is the average frequency with which a paid newsletter sends out paid posts?

I pulled the top 25 Substack newsletters and found that 14 of the 25 were sending about even amounts: one paid post for one free post. Some were more like me, where you do five free, one paid. And then some were the opposite direction, where you get five paid and then one free per week.

So we know what tends to do well when it comes to subscriptions, but I want to point out a few other business models that I think people should try. There are different ways to use subscriptions that are not simply, “Half my posts are behind a paywall and the other half is free.”

For instance, you can use what’s almost like demand-based pricing. If there's an election going on, in October lots of people are going to be interested in that stuff. And so maybe you have something that’s like, “We're an elections newsletter. In October, only paid subscribers get the really timely material.”

On the other hand, you could have a paid-only edition that arrives quarterly or yearly. You just have to figure out what you need to promise and then deliver on that. It doesn't need to be once a week. It doesn't need to be twice a week. It doesn't need to be once a month. As long as you figure out your social contract with your readers, you can do whatever you want. It can come in the form of, “I cover an industry and once a year, you're going to get a big report from me and that's what the money's for.”

You can promise to do 20 paid-only editions per year and only send them when there's actually news on your beat. I'm not going to monetize my Oscars newsletter, but maybe I have one that’s awards all year-round, and then I only send the paid editions when the news is hot, which is going to be in January and February. There are all sorts of ways that you can use ancillary newsletters to both experiment with content and experiment with delivery formats.

For more advice on growing your newsletter, check out “How to build community around your publication.”

Photo by Bess Adler

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