What we learned from the Substack writers gathering in New York

Last month, we hosted our first Substack writer gathering in New York City. We were thrilled by the turnout, as well as the broad range of topics that attendees covered, tackling everything from wrestling to Excel.

We also invited a few writers to speak about their experiences on Substack: Delia Cai, Emily Atkin, Terrell Johnson, and Walt Hickey. Afterwards, we invited all four up to take questions from the audience. The session was filled with insights and we wanted to share the lessons with people outside the room, too. So we’ve summarized the highlights here.

This conversation has been lightly edited for readability.

Q: How often should writers publish?

Walt, Numlock News: I write a daily newsletter, so a lot of people come to me and ask if they should do a daily newsletter. And I immediately tell them, “This sucks a lot of the time. You should not do that if you don’t need to.

You should think about, “How often do I need to send a newsletter so that every single time, somebody will be delighted to receive it?” and that’s how you calibrate the answer. The idea is if somebody wants to hear from you every day, once a week, once a month, that’s cool. Just be honest with yourself and with your readers about how much you intend to deliver, so you're never overdoing it and always delivering what they’re interested in.

Terrell, The Half Marathoner: I do a newsletter where there’s not a constant stream of news. It’s about running and so it’s more of a lifestyle newsletter, so I’ve done a little bit of both. Right now I do one free and one paid [per week] and that is a good cadence. I do get that feedback from readers – when I've done less they’ve told me, “I look forward to this. I really savor this.” And I think if I were trying to do it every day, I would run out of things to do.

Emily, Heated: One of the benefits about doing a daily newsletter is that as long as you’re promising that they’re not always going to be the same amount of work, then you’re fine. Some of my newsletters are a lot of work – things that I’ve put a lot of time into – and some take me two hours. And so it’s just about managing your expectations and communicating them clearly with your audience.

That’s another benefit of the newsletter model: you don’t answer to a boss, you answer to your readers. Your readers are your collective boss. They hold you accountable. So if you just say, hey, I've got a lot of stuff going on this week, the newsletter is going to suck this week, they’ll be like, “I hope you’re okay, bye.

Q: If you’ve hit a plateau with your audience growth, how do you break through to the next phase?

Walt: Plateaus happen all the time. The key is to realize that that’s the nature of the business. You shouldn’t look at it as a flat line in growth, it’s just that you have a steady audience. Plateaus not only mean that you are not going up, but they also mean that you are not going down and therefore you are doing something good.

I tend to consolidate when I push people to tell friends and things like that. If it’s always the background of your newsletter – asking folks to subscribe and asking folks to tell friends –  they’re never going to do it. There’s a reason that NPR does “pledge week,” where if you really want to push the gas, you push the gas and then lay off for a month and see how that goes. A lot of the time you’ll find that if readers are enjoying what you're putting out, they'll be willing to share it. You've just got to calibrate expectations in both directions.

“Plateaus happen all the time. The key is just to realize that that’s the nature of the business.”

– Walt Hickey, Numlock News

Emily: If you look at my free list, even the paid list, it goes up right in the beginning when you start, and then it plateaus and then it goes up again. And that means there was a good story, honestly. It’s like that when something that I have written resonates and people are sharing. I think that that’s awesome because it means that you actually get real rewards for doing good work, rather than, if you have a job, you’re employed at a media organization, you don’t get more money for writing a good story. You just get more Twitter followers and that's cool, but it's not tangible. Plateaus are fine because plateaus mean that you have time to work on making your next good thing and it is a great incentive to do better work.

Delia, Deez Links: My newsletter, if you looked at the growth, it’s mostly plateau, but I think the parts where it has jumped it’s lined up with tapping into a slightly different community than usual. I remember one time I plugged something from Outside Magazine, which I didn’t usually do, and so it wound its way to Outside Magazine and that activated that community both on Twitter and through emails.

Or it happens by doing something like the newsletter swap, where I ended up doing this plug with a lifestyle site that I hadn’t really considered before and wasn’t really my core audience at the time, but was like, “Let’s just try this out…” And so I think I’ve always noticed, whenever I’ve unlocked a different social circle, that’s always helped break up the plateaus a little.

Terrell: For paid subscribers, I’ll send out – on a Sunday sometimes – an email to promote the paid newsletter; just a couple paragraphs and a subscribe button. Sometimes for me, I think that can get lost. So I’m like, “Hey.” And it works. I do get a bump in paid subscribers, 90% of the time. 

Q: How do you know when you have enough subscribers to go paid?

Emily: It depends on your goals, right? Are you trying to support yourself with this? Have you ever asked your readers: “Are you liking this so far? What are you liking about it? How much would you pay for this? Or what would you need to…” You could even do a discussion thread about it.

People like that. I just did this discussion thread recently where I gave a bunch of story ideas. I was just like, “I have four story ideas and I don’t know which one to do. Which one do you think I should do?” It was a risk, because I have journalists on the list and they could steal those ideas, but if it were me, I’d feel more connected to the product and I’d feel more likely to support it.

Q: How do you grow your email list to sufficient size before you turn on paid? And as someone who wants to do this full-time, did you have a plan if it fell flat?

Emily: I had no plan. A personality defect of mine is that I’ve never had another plan. I remember when I went into journalism, my parents were like, “Well, what’s your back-up plan for not getting a journalism job?” And I was like, “What do you mean?” But I do think that that’s also part of how you succeed. You’re just like, “I'm doing this. I’m putting everything in here, there's no backup plan.

I think I had 18,000 [signups] when I launched. Part of that was I benefited from being on Twitter for 10 years and being a journalist for eight years. I think when I launched, I had a Twitter following of 20,000 people. So that was good. And before that, I had a job. I think just the message, “I quit my job to do it,” made people like, “Oh!.” That did a big bump. I honestly couldn’t tell you exactly why I got so many subscribers, but I benefited from just being out there and just being bold.

I also tried very hard to not do it like anybody else was doing it. I specifically didn’t read other people’s newsletters because I didn’t want to try to imitate anybody else’s thing. I just wanted to do the thing that I wanted to do. I remembered when I first started, people were like, “Your newsletter is weird," compared to other newsletters, but I do think that’s also why it works.

“I specifically didn’t read other people’s newsletters because I didn’t want to try to imitate anybody else’s thing.”

– Emily Atkin, Heated

The other thing is I go out of my way to be very personable with my subscribers, constantly telling them to reach out and drink water and eat bananas and do pushups and “take care of yourself because you can’t fight the climate crisis if you’re depressed in bed all day”-type stuff. And that’s not something everyone’s willing to do. But I also just tweet the crap out of it all the time. In an annoying way.

Q: What’s the best way to incorporate interviews? Should you publish them behind a paywall, since the interviewee won’t be able to share it as widely?

Walt: Interviews are great. Everybody should do them. You just get them on the phone. People are always better on the phone versus a calibrated email.

What I do is to tell them, “Here’s how many folks subscribe to this and will receive it in their inbox on Sunday. Here’s how many folks subscribe to the free newsletter, and I'm going to, one, plug the interview that we did in the free newsletter and [two], I’m also going to plug your work, the article, your book, whatever it may be, in the free newsletter.” So even though folks aren’t necessarily reading the interview, it's still going out.

Terrell: You could do a discussion thread with someone you interview and then an interview behind your paywall. I’ve done that with two book authors last year. I didn’t put anything behind a paywall, but I did a couple of ‘ask me anythings’ (AMAs) with the authors for my audience. I should have turned that into a two-part thing.

Delia: I would counter Walt’s point – for Deez Links, at least, doing interviews take the most time. I actually do them over email. For me, it’s still this growth strategy of not a lot of people knowing about Deez Links, but a lot of people knowing Heather Havrilesky and being a huge fan of hers. And so when she tweets out an interview, I know that that access to her audience is valuable. I'm still in this very early growth stage for Deez Links where I'm like, that's more valuable than throwing a paywall on this and hoping that it works out the other way. 

Walt: Sometimes I’ll tell them I’m going to drop the paywall on Monday. “If you want to tweet it out on Monday, I’ll put it back up on Tuesday.” But if you want to give them an opportunity to put it out there –

Emily: Yeah, I do that.

Walt: What I’ll often do is say, “Hey, we talked about your book, if you want to tweet it out or anything like that, I’m going to drop the paywall on Tuesday.” The idea is you want to give people an audience.

Emily: You can also tease the interview in your free one and give a third of it away and then be like, “[In the] extended version for paid subscribers, they talked about this and that. You can only read it if you pay.

Q: To what extent have you changed your writing based on audience feedback? Was there anything where the audience really helped you shape it?

Walt: I started paying a copy editor. I realized that I am a typo machine that occasionally makes words, and I need somebody to take a glance at this before it goes out every morning.

You take their critiques and then you roll with it. You don’t want to necessarily adjust your vision for the loudest members, but sometimes people make some really valid points about how you spell ‘receive.’

Terrell: I’ve done some Survey Monkey surveys. I ask multiple choice questions like, “What’s your age? What’s your gender?” And then I ask questions where they can fill it out. I used to work at The Weather Channel, and years ago, a friend of mine who was a meteorologist there used to say that we give these people all this complicated information, but all people really want is the basics. That’s what most people want. And that struck me, I keep remembering that as I see the survey responses.

Just in my topic area [running], there is this very narrow spectrum of people who are very much experts, and there's many more people who really just want the basics, and that just keeps coming back to me. I find myself delving into the more narrow technical subject area sometimes and I need to remind myself, stick with the basics. So that has helped me.

Emily: Listen to positive reinforcement more than negative feedback. I've done surveys. I created a spreadsheet of over 100 reader responses, just asking why they like it. I read every single email. Some people are like, “You’re too snarky” and then I'm like, “Go read the New York Times,” which is something I actually say. That’s fine. There are so many other newsletters for you. But the people who like it, they like it.

Walt: The creator of the comic Nancy is this writer, Olivia James. She took it over and took some heat in the beginning, but she said once in an interview that criticism is like food, in the sense that if someone you respect made it and someone that you trust makes it, you should listen to it. Consume it, don’t necessarily define your life by it. But if it’s just a rando blowing by on the internet, don’t lick subway poles. You need to be very conscientious about where feedback comes from, how you internalize it. Make sure that you're getting it from people that you like and respect and then listen to it.

Q: What’s one thing that’s surprised you during this experience?

Walt: It’s always incredibly gratifying to see your audience interacting with you. A lot of journalism can be impersonal, and you struggle sometimes to place who exactly is reading what, and so it’s just nice to have the same people on the same journey with you.

Terrell: I was surprised that people were willing to pay me at all, to be honest with you. I was like, “I did it for free for three years.” And I’m like, “People really do this? And they do.

I’m being a little bit flippant about that, but really, the unique thing that you have to offer is your voice and the way you see the world. Somebody wrote this to me the other day because I just wrote this newsletter about my son. I have a six year-old son, and we’d just gotten a dog, and I wrote about that. And you think, who’s going to care? But one guy told me he became a paid subscriber because of that issue. If people connect to you and if they like the way you see the world and it resonates with them, then I think it's meaningful to them.

“I just wrote this newsletter about my son. We’d just gotten a dog, and I wrote about that. And you think, who’s going to care? But one guy told me he became a paid subscriber because of that issue.”

– Terrell Johnson, The Half Marathoner

Emily: The thing I'm most surprised about is how much more impactful I feel this is than working for a large outlet. I was so scared when I left The New Republic that I would have to fight so hard to make my work have an impact because I lacked this institutional support. But I don't know. I've never seen the type of impact that I've had in a 10-year reporting career than what I've had with such a smaller news audience, and that's because these are passionate people. These are people who are there because of you, and they're invested in you, and they take what you do and they yell about it. And then that reaches other people in a way that people who read The New Republic, they're just like, “Yeah, I read The New Republic. I don’t care.”  I was so scared, and I can't believe how wrong I was.

“I was so scared, and I can't believe how wrong I was.” – Emily Atkin, Heated

Delia: For me, the most surprising thing about having a newsletter and doing Substack is all the doors it has opened for me. When I started out, I was working this corporate internship. The job I had after that was working in branded content, so we didn't have another outlet to write the things that I wanted to write. So this self-fashioned opportunity let me experiment and try to develop a voice and figure out what I cared about writing about.

When I was applying for my current job, a lot of these jobs I was looking at, there was a lot of writing and editing. And I think if I didn't have the newsletter, it would have been a really hard case to make: “Yeah, so I know how to write corporate decks, but I can also make quizzes.” So it was this wonderful portfolio and showcase for skills that I couldn't really display at the job that I had currently been at. I remember it got to the point where when I was interviewing at BuzzFeed, they were like, “Ordinarily, we would have you do a writing test, but I just subscribed to your newsletter and so that can be your test.

“This self-fashioned opportunity let me experiment and try to develop a voice and figure out what I cared about writing about.”

– Delia Cai, Deez Links

Q: Have you had any success with paid user acquisition?

Walt: I've done some of that. I do a lot of this experimentally and I'm in it for a longer view and so I'm down to try out different things. I tried A/B testing on Facebook ads. The best thing that I got out of that was I started getting much better at pitching my newsletter to people because it helped me clarify what messaging was most effective. “Numlock is informative. Numlock is funny. Numlock is a good way to wake up.” Each of those is a separate idea that I could try to turn into one pitch, and it really helped me figure out as a person – who is not natively a business human – how to best articulate what I do well at.

As far as the best way to get more people, the most cost-effective thing I've seen is referrals and encouraging people to do some word-of-mouth. I built some incentives for that that I've been trying out. You get merch stickers, stuff like that. Beyond that, it's still super experimental.

Q: How do you measure success, beyond number of subscribers and emails?

Terrell: One of the things I think about is churn for paid subscribers. I've been doing this for about a year and a half now. So I didn’t know how confident to be about this until a year later, because all these people bought annual subscriptions. How many people are going to stop? How many people are going to unsubscribe? Thankfully, relatively few unsubscribed and that, to me, is a sign that you've got something that people value. 

Delia: This is my own made-up metric, but I keep track of when someone who's big in the media industry subscribes, I keep it on a note and I look at it sometimes when I'm sad.

Emily: You should have a doc that's called “praise” and then, every time a big person praises your stuff, put it in there so that when you're launching it you can be like: “That's what I did.” That's why my launch announcement was like, “Bill McKibben said this!” It was literally a doc I created.

Walt: You want to make sure that folks are continuing to subscribe. That's the best referendum a lot of the time on how you do. To echo Terrell's point, I was very, very uneasy as I was coming up on the one year renewal because when you launch, a lot of the folks that you get to sign on are going to do one year instantaneously, and so that July tends to be a big month for me. I will say that Substack put together a great operation when it comes to making sure people renew, keeping that stick rate high.

Some of you folks are in the middle of that year. Don't worry about the other side of it, it's going to be good. And yeah, keep the praise folder, that's always good. It doesn't need to be something that you put out there. Just keep track and notch every damn one that you can.

For more advice, check out our summaries of Walt, Emily, Delia, and Terrell’s presentations.

Photos by Bess Adler