What I Wish I’d Known Before Launching My Newsletter

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Everyone has a few newsletter regrets. Maybe you wish you’d better understood your audience on Day 1. Maybe you wish you’d built around a different monetization strategy — ads weren’t right for your newsletter, but a paid subscription was, or vice versa. Maybe you wish you’d understood more about how to grow a newsletter. Or maybe you wish you’d been a bit more realistic about your publishing schedule. There are just things we don’t know until we go through them.

Last year, we asked more than 20 newsletter operators this question: What’s one thing you wish you’d known before launching your newsletter? We got some fantastic answers, and the resulting story ended up being one of the most popular we’ve ever published on Inbox Collective.

So, we decided to make the post an annual end-of-year tradition! To close out the year, we went back to a different group of friends and colleagues in the newsletter space to ask that same question. What’s one thing these newsletter operators wish they had known at the start? Here’s what they told us.

Aine Stapleton
Head of operations, International Intrigue

The main theme of our most recent team offsite was “Sell, Design, Build.” It was a reflection on how we’ve, in the past, fleshed out a lot of really elaborate ideas. We built up in our heads that we had to have this really fancy product, and we were going to pour all of our time and effort into releasing it, but nobody noticed that we had changed things. We just wasted weeks of our time caring so much about something before letting it out to even a small group of our audience, who would have said, “We never cared about that, anyway. Why are you now doing this?” 

And so now it’s “sell” from both the monetary perspective and buy-in perspective with our readership. We’ve tried to solve a lot of potential reader problems in the past without actually speaking to the reader and asking, “Is this a problem you face?” Something we’ve been working on is, let’s sell it first and design it next. So, for example, we’re trying to think through the niches in our audience, and we think cybersecurity would be one — how could we offer some products for cybersecurity people? I’m not going to build the cybersecurity product until I speak to at least a few users who work in that field and are like, “Hell, yeah, build me that product, and I’ll pay for it.” And so “Sell, Design, Build” is our new motto.

Alex Hazlett
Director, newsletters & audience, Hearst Magazines

Aim for the sweet spot between experimentation and strategy. Don’t reverse engineer all the charm out of your newsletter by mapping out every possible metric for the next X years. Also don’t pour your energy and time into something you haven’t thought through, can’t monetize (if that’s important to you), or will hate in 90 days. Whenever you start a newsletter, there are 3-5 other projects you didn’t launch, and that’s a choice that’s worth trying to make intentionally. Figure out what kind of litmus test you need — be it a time limit, coming up with enough ideas for 3-6 months of issues, or a softer sense of how you know when you’ve given it a good try and are done. Let the idea and the strategy share power. Go for it when you’ve hit “good enough.”

Alexandra March
Deputy director of audience, opinion, The New York Times

I wish I’d learned to have more confidence in experimentation. 

When Times Opinion launched the pop-up newsletter The Next Pandemic, the COVID-19 emergency was about to be declared over in the United States. We used the moment as an opportunity to re-engage readers who had been deeply interested in the storyline and prepare them for the next time we might find ourselves in such a situation. 

Following that pop-up, where we leaned into audience interest around a specific and timebound storyline to meet readers where they were, we decided to take the same approach and experiment with special editions of Opinion’s flagship newsletter, Opinion Today. We sent extra editions during the Trump trial, while interest was high in that news topic, and more recently, we have been doing weekly “takeovers” of that same newsletter by featuring a polling expert in the run-up to the election. 

While consistency in meeting and delivering on the mission of your newsletter is crucial, success might look different than you expect. It’s important to pivot when you see new opportunities and find ways to meet audiences where they are at the time.

Al Iverson
Industry research and community engagement lead, Valimail, and publisher, Spam Resource

For me, email is like a vacation in Las Vegas — you can do it on any budget. You can scale up to spend millions on it or do it on the cheap. I spend less than $1,600 a year on Spam Resource. You can do all of this however you want to scale it. So it can be so easy to do, and there are so many different email providers to help you do it. And to me, it’s driven the idea that I think everybody should do it. The one thing that I’ve done this past year that I haven’t done in years past is driving my email industry friends to all start creating email newsletters. They might be small. They’ve got ways to grow. They’re still figuring things out. But they’re going to miss out on this opportunity if they don’t take the time to actually do it. 

Ann Friedman
Creator, The Ann Friedman Weekly

Things I would time-travel to whisper in my own ear as I created a TinyLetter account in 2013: 

“Everyone” doesn’t have a newsletter already, even though that’s how it feels. (Truly hilarious from the vantage point of 2024.) It’s ok to do things your own way. Consistency matters and will buy you a lot of freedom to deviate when you feel like it. You should not only ignore the most common advice you get — to sell banner ads or sponsorships, to charge more for subscriptions, to put it all behind a paywall — but you should feel great about ignoring it and following your own instincts. It’s a long game, with emphasis on the “game,” and you should keep playing as long as it’s fun. 

(It’s still fun.) 

Ann Handley
Chief content officer, MarketingProfs, and author, AnnHandley.com

The fuel for your newsletter is not technology, list growth strategies, subject-line optimization… or any of that stuff. It’s writing that’s entertaining and valuable.

None of the rest matters if you don’t get the writing right.

The reason people will read it, love it, refer it… hinges on just one thing: What you say, along with how you say it.* Only that builds a relationship with a reader.

*Isn’t that two things? Well, is a package of two Reese’s Peanut Butter Cups two candy bars? Or is it one really superior one?

Annafi Wahed
Founder and CEO, The Flip Side

Know who your audience is and who it isn’t. It’s okay to say to someone, “I don’t think this is what you’re looking for,” and refer them elsewhere. For example, our primary target audience is news junkies. For someone just tuning into the news and current events, The Flip Side can be overwhelming, and that’s okay! They’ll find us again when they’re ready. If you try to please everyone, you’ll end up pleasing no one.

One more thing: Humility, transparency, and clarity of mission go a long way in building trust. If you make a mistake, apologize and issue a correction ASAP. If you make a controversial editorial decision, explain your thought process and let readers know you welcome their thoughts. (Bonus points for sharing their thoughts – the good, the bad, and the ugly — in the next edition!) If you are pivoting or trying something new, explicitly explain how the new direction is tied to your mission. Even if it’s obvious to you, it may not be obvious to the casual reader. Your readers will not agree with every decision you make, but they’ll stick around if they understand why you made them and trust that you’re operating in good faith!

Arielle Retting
Growth editor, NPR

I used to think a lot about the intended audience we wanted to reach, but I wish I had spent just as much time thinking through the newsletter’s jobs to be done. The more you understand why audiences might value a certain newsletter, the better you can tailor that newsletter to them and what it does for your organization.

Also, don’t be afraid of rethinking your job to be done when it’s time for a refresh. Your audience will grow and evolve over time, and naturally, readers’ preferences change. You need to be ready to change with them.

For example, maybe they started out wanting to be the first to know quick updates in a breaking news situation, and now they need more analysis to understand something that’s become more complicated.

Paying attention to audience feedback and making tweaks based on their behavior will go a long way and keep them more engaged and stick with you.

António Tadeia
Writer, Tadeia

I wish I could have started sooner. I see work as a constant learning process; I have to do it. I keep on challenging myself, doing different stuff, doing things differently. For instance, one of the perks my paying subscribers have [is] a Telegram channel. But only I can post there; they cannot. They get my pieces read aloud because people keep on saying, “I don’t have the time to read. How am I going to pay for something if I don’t have the time to read?” So I tell them, “Okay, you can listen to the text if I read my texts and you have the Telegram channel to hear them.”

I keep on evolving, adding new ways of doing things and learning from my failures. The only thing I regret is the four or five years I spent on [writing] a website, which was doomed to fail because we don’t have any scale. 

Brett Perlmutter
CEO and founder, Bulletpitch

Data is key. When I did my early events, I was so focused on getting people there that I was worried that if I collected too much data, no one would come. And if you look at the survey form for the most recent event, we asked questions like “What bank do you work with? What law firm do you work with? How much money did you raise?” So many questions, and people want to answer them because people want to come to the event. Those kinds of things, I can now turn around and say to my sponsor, “Hey, there are 500 people at this event that use this bank and not yours. I bet you could probably go convert them.: That’s really powerful, but I was so focused on “How does my brand look?” that I was nervous to do some things that could potentially become a hindrance to people signing up, even in the sign-up flow for the actual letter itself. I never wanted to ask any questions. Now we do, and people answer them.

Dominik Grolimund
Founder, Refind

Focusing on paid acquisition was a pivotal moment for me. It forced me to really think through and understand unit economics. In the process, I’ve built a tool to predict the lifetime value of any cohort or even an individual subscriber — the essential piece when evaluating ad campaigns.

Edith Zimmerman
Creator, Drawing Links

I wish I’d known how to seriously divert my eyes from metrics! (Views, open rates, subscriber numbers, etc.) That stuff made/makes me insane. For what I’m doing (an art newsletter), it’s not super important, although coming to accept that it’s not has been a long path. And I’m still not totally convinced. I wish there was an “Art Mode Substack” or something so I could hide all of those numbers from myself, although I’m not positive I would actually turn it on. 

And then there’s the money stuff, which also made me insane. (If I’m not getting the amount of $$ I had hoped to, am I a failure? A bad writer/artist, etc.?) I had paid subs turned on for a couple of years, but then I turned them off and refunded everyone. My newsletter then went on hiatus for two years. I started it back up again a couple of months ago, but so far, just for free, so it can be 1) fun for me again and 2) a vehicle for selling my art through Etsy. (I ran an “ad” in a recent installment and plan to do it again soon.) So it’s both the exact same newsletter and totally new (for me, conceptually) because instead of the newsletter being the product, my art is the “product.”

I’ve lost like 2,000 subscribers since I brought it back, though. Not that I’m keeping track…

Ellen Donnelly
Writer, speaker, and business coach, The Ask and Monday Mornings

I wish I’d known more about the customer buying journey stages since The Ask markets my coaching practice. Initially, I followed advice suited to content creators and news outlets where the content is the product — unlike my newsletter, which is more of an engine for coaching business growth. This distinction was an important, if delayed, lesson. Now, with my new newsletter, Monday Mornings, content is the product. I’m excited to create two distinct platforms and embed those learnings as I enter my fifth year writing newsletters.

Emma Varvaloucas
Executive director, The Progress Network

One thing I wish I had known before launching the “What Could Go Right?” newsletter at The Progress Network is that the most successful newsletters — and the ones I personally look forward to opening and reading — are all about community. The editorial content has to be of quality, of course, but if I could do things over, I would have focused more on how to create and nurture a space that readers feel belongs to them, at least in part. That sense of ownership is key to reader engagement and loyalty as well as the product’s growth and sustainability, and perhaps most importantly, it provides the connection that makes all of the work that goes into creating a newsletter feel worthwhile.  

Hannah Boufford
Newsletter editor, Block Club Chicago

One thing I wish I had known when launching newsletters was how important it is to identify key metrics, set goals around those metrics and have robust methods of reporting and tracking those metrics ahead of launching. It’s so much more complicated to go back to find historical data, especially since newsletter metrics — subscriber counts, engagement rates, etc. — are always in flux.

Isaac Saul
Founder, Tangle

I wish I had known the volume of work required to write a daily newsletter. I think I would have either not done a daily, or I would have structured everything about the Tangle in a way where it was a lot easier for me to hire a team or a partner that I could pass work off to. It’s so centered on me now, and we’re so trapped in the daily format that I don’t get any kind of break — not even to not work, but just to work on longer-term projects or just spend two weeks on one article — because we have the drumbeat of newsletters to keep up with. So I don’t think I planned for that as well as I could have because, you know, I didn’t expect us to be as successful as we’ve been.

Jonathan Stark
President, Jonathan Stark Consulting

The one thing I wish I’d known before launching my newsletter is that sending daily is easier than weekly. I know this is 100% counterintuitive, but it’s actually a common experience with people who switch to daily.

When I did weekly, it was torture. I would be going to bed late Sunday night and suddenly remember, “Crap! I forgot to write an email for tomorrow!” Then I would drag my butt to the computer and stare at a blinking cursor for a couple of hours with total writer’s block, only to ultimately grind out something crappy just to say I didn’t miss a week.

Eventually, a friend convinced me to switch to daily. Almost immediately, I started seeing ideas everywhere. Writing became a joy, like a meditation, something I look forward to. I’d rather quit doing it than switch back to weekly. 

Kaitlin Jessing-Butz
Newsletters director, New York Magazine

When I first started working on newsletters, I spent a lot of time digging around in various analytics dashboards, trying to find clues about what our readers might want in the email space. And while that data has definitely informed our decisions, the biggest editorial successes we’ve had — the newsletters that readers write in to praise, peer publications have copied, and fellow editors have DMed me to compliment — are often the ones that started with a hunch about what our audience would enjoy that couldn’t necessarily be found in the numbers

Kristen Wile
Founder, Unpretentious Palate

One thing I wish I’d known when launching a newsletter is that good content is good content. In my head, I thought a newsletter was just a vehicle to get people to read our stories. Now that we’ve been publishing for six years, I realize that something doesn’t have to be posted as an article to be quality journalism. Not all of our readers are going to click to the site — and that’s okay. Our newsletter content has just as much value as content posted in a traditional news way — as do our social media posts. Good storytelling is good storytelling — the platform doesn’t qualify its value. The best thing you can do is ensure people have quality journalism on whatever platform they use to consume media.

Patrick Trousdale
Founder and CEO, The Daily Upside

I wish I’d leveraged zero-party data much sooner. [Editor’s note: Zero-party data is any data a reader chooses to share with a newsletter — like their first name, location, or job title.] In the early days of The Daily Upside, all subscribers were (more or less) created equally. We were squarely focused on building as large a list as we could. The thought was that more subscribers meant more clicks on our ads and a more successful business.

And while there is some merit to that strategy — scale is valuable — our calculus of audience growth has changed significantly. These days, we’re focused on bringing the readers who fit a very specific persona into our ecosystem, and we’re tracking our lists to make the majority of our readers match that ideal audience.

While we used to do annual surveys of the audience, now the process of gathering zero and first-party data is “always on.” Every interaction our audience has with our editorial, whether that be on our newsletter or our website — we want to tie all of that together to create a crystal clear picture of our readers.

And that’s basically what’s required in the modern marketing landscape. You need that level of data in order to compete with the platforms (Meta, Google) of the world. When you collect all of that data, you can make smarter editorial decisions and create really powerful marketing products for your supporting sponsors if you are ad-driven.

Pit Gottschalk
Writer, Fever Pit’ch

I was on vacation in Miami Beach, and before that, at the end of 2018, I was an employee of a traditional media company. I decided I’d start a newsletter for football. Without thinking about anything else, I just started to create [it]. I promoted this newsletter on my social media accounts, and overnight, I got more than 800 subscribers.

Then it got serious, and I had to do it on my holidays and every day on vacation. I started to optimize. I asked my subscribers some questions about their wishes, what I could improve on, and what topics they wanted to read more about.

I started an ongoing process to optimize, optimize, optimize. So, just start without thinking, and then start listening and improving. 

Dr. Pooja Lakshmin MD
Psychiatrist and author, Real Self-Care

I wish I’d known that a good newsletter is one that grows with you. Growing a newsletter takes time — it’s a marathon, not a sprint, and if you are doing it correctly, you should be able to look back over time and recognize different versions of yourself in it. I started a version of my newsletter in 2019, and it was just a couple hundred folks, mostly friends and colleagues, who were just following to see what I was up to. I didn’t really have a message or a voice yet. Now, five years later, I’ve published my first book and have a newsletter of 15,000 people of the same name and message — Real Self-Care. If I’m doing it right, in another five years, my newsletter will have a larger audience, but perhaps more importantly, it will be a different thing altogether. I like this approach because it’s less about the numbers or “success” and more about having the newsletter be a thing that evolves over time like we all do in our own lives. And usually, you see that evolution most clearly from the rearview mirror. 

Ryan Broderick
Writer, Garbage Day 

I wish I had been more aggressive in the beginning about figuring out the business side of Garbage Day. I didn’t have a ton of confidence in the project or belief that it could be a media company of any size. I thought it would just be a fun thing, and I treated it like that for too long. I spent the next few years having to cram and get up to speed when the business side was coming into focus. When you turn on paid subscribers, you have customers. Even if you have three, those people are paying you money. 

I think it is a very journalistic impulse to write that stuff off, partly because of the culture of journalism — you shouldn’t know what’s going on the other side of the office. This attitude, “Good journalism will become good business,” isn’t useful when you’re on your own. Nobody is going to do it for you. 

I wish I had gotten over that squeamishness and started to figure out what moves the needle here. What do I do that makes people pay more? What is the line between what I’m willing to do and what I need to do? Once you start digging in there, it’s really fun. 

The metaphor I use a lot is no one in their right mind would hire a chef for a restaurant who didn’t know how much ingredients cost. Now that I’m running my own restaurant, if I commission a writer, how long should it be, what is my budget, do I do long-term reporting projects, and what do people pay for? 

There’s a bunch of models. Casey Newton traffics in scoops, and he hired someone to help him do even more scoops. I realized early that one of the things that fit me better was information and increased amounts of aggregation and curation. So I started a paid issue that’s aggregation, and monthly that’s paid analysis. I know another who gets people to pay because he has access to a CEO. You should learn why those things work or why those things don’t work for you, figure out all that stuff, and know before you put on paid subscriptions. The thing that most readers are seeing is that “just turn it on and see what happens.”

Wesley Verhoeve
Publisher, Process

The generosity that you put in is something that you can expect to come back to you. 

I see some newsletters here and there that are new to the concept of creating community. I see people taking shortcuts. I can tell some newsletters are written with the help of ChatGPT. I don’t think there’s anything wrong with using new technology, especially not, for example, to check for spelling or any of that kind of stuff, especially if you’re not fluent in the language. But you can see that there are whole chunks that are just ChatGPT blubber, really. I think that is probably short-sighted. I get it if you don’t have the ability, but then maybe a newsletter is not the thing that you should do, you know?

I think they don’t think that they’re doing a bad thing. I’m not even saying it’s a bad thing. I just don’t think it’s good for the reader. Mostly, I don’t think it’s good for the newsletter.

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