What I Wish I’d Known Before Launching My Newsletter

Two years ago, we asked a few friends and colleagues in the email world a question: What’s something you wish you’d known when you first started working on newsletters? We got lots of great responses, so we asked some more friends last year, and got even more wonderful suggestions.

Why stop now? To close out 2025 here on Inbox Collective, we reached out to 20 more newsletter operators this year to ask them the same question. They gave great advice about what to launch, how to balance all of your newsletter tasks, when to grow your team, and more.

Here’s what they told us.

Alisha Ramos
Writer and editor, Downtime

I wish I had known that it’s not all about growing your subscriber list. It’s more about how engaged your readers are, how engaged you are with your readers, and that it has to be a dialogue. That’s the beauty of newsletters. I wish I had focused a little bit less on growing the list size and more on respecting the reader, investing in our existing readership, getting engagement up, and getting that word-of-mouth going again. That’s the key. It’s not about how big your list is.

Ashley Woods Branch
VP of growth & publisher success, BlueLena, and former co-founder, Detour Detroit

When Kate Abbey-Lambertz and I launched Detour Detroit, we were moving so fast just to get to a point where we could even pay ourselves. We did a lot of great experiments. Some of them worked, some of them didn’t, but we learned so much. I wish we had the time or the bandwidth to document and circulate more of those learnings in the moment. I was afraid to share what didn’t work because we were fighting for survival; I was afraid to share our successes because I felt like an imposter. If I could do it all over again, I would hope I could operate with less fear and more openness.

Caitlin Dewey 
Founder, Links I Would GChat You If We Were Friends

When I started this newsletter in 2014, it was a jokey side experiment that I was doing in my free time at work. I had no concept of how locked in I would become to that beat and that topic. It’s honestly comical to me now that I started this thing when I was 25 and still thought it was appropriate to do tequila shots on a Wednesday night, and now I’m still doing it as a homeowner and a mother and a person with real concerns, and also not insignificant hatred of social media, the topic that I presumably cover.

I think, like many reporters, I was used to the notion that you can change beats at the drop of a hat, and there’s a lot of mobility. But a newsletter, though it may look and act like a beat in some ways, is actually a product. And once readers have come to you for a certain interest area, it’s difficult, if not impossible, to move away from it. I’m not saying I would want to move away from what I’m covering, per se, but I certainly didn’t know when I started the newsletter that I would be defining the terms of my career for the next decade plus. 

Especially for folks who are starting out and have that latitude and flexibility to be intentional about what they want to spend — for maybe a significant chunk of their career — covering, be intentional about it.

Carlos Greaves
Creator, Shades of Greaves

One thing that was super helpful for me on Substack was engaging with some of the channels, like Substack Writers at Work: communities of other writers who are also trying to grow and figure out the platform. Finding a community there, finding people who can help you demystify the process — I wish I had done that from the get-go, because I spent a lot of time not understanding how Notes worked, not understanding Substack. It just felt like I was writing in a vacuum for a little while.

It wasn’t until I started engaging with other writers and making an effort to immerse myself in that community that I ended up meeting lots of people and building more of an audience. 

Claire Zulkey
Editor, Raising Evanston

This year, I accepted an opportunity to craft, launch and edit a parenting newsletter from my local independent newspaper, the Evanston RoundTable.

My original newsletter, Evil Witches, began as an experiment/project that stuck around. Over the years, I have played with topic, format, voice and schedule — always communicating with other people but working on my own. My main goals were to learn, express myself, have fun, explore what mattered to me and my audience, network, to do good work, make some money, and keep it up. 

With Raising Evanston, I’d be not only doing the editorial legwork of crafting a weekly newsletter, but I would also be joining a staff. I received a new Google account identity, Slack channel, and learned how to operate their content management system. I worked with freelancers. I learned what has to happen when to get the newsletter out on the same day to its over 13,000 subscribers.

I don’t think it would have been possible to establish a rhythm for sending Raising Evanston without some necessary growing pains and mistakes. I felt pretty overwhelmed at the onboarding process and figuring out a rhythm for a completely new project. I think it would have been helpful, ahead of time, to read the advice in Dan’s story for Inbox Collective, “How Often Should I Actually Send My Newsletter?”:

My general rule: Assume that for every email you send, you’re going to need at least two to four hours to write and produce the newsletter. That might be an undercount, too: I often spend at least 5-10 hours working on the content that goes into each of my newsletters.

While I do track the time I spend writing on my own newsletter, Evil Witches, the way I define working time can be very flexible. It can be writing, copy editing, catching up on my inbox, responding to comments, researching, reading other newsletters, so I’ve never really gauged how long it can take to write an issue on average. 

It was a little bit frantic in the beginning as I got the ropes of Raising Evanston, and I hate feeling frantic! Maybe if I had read Dan’s advice ahead of time, I might have blocked the hours necessary leading up to each newsletter issue, and the process might have been a little less stressful. 

Elizabeth Holmes
Creator, So Many Thoughts

People ask me all the time about starting a newsletter. My former colleagues at the Wall Street Journal ask me, “How can I do what you do?” I think people underestimate the hustle, the amount of work it takes, and how solo it can feel. I have brought in people to work with me because I enjoy working with other editors and writers, but it’s just a hustle to write a newsletter. It’s a lot of work. But I think often about what Dan [Oshinsky] told me: “Make your newsletter work for you. You don’t work for your newsletter.” I constantly have to remind myself that because I’m always thinking, “Oh, I could send this out. I could do this.”

It’s a hustle, it really is, to write a newsletter. Just know that going into it. I think sometimes people think it’s like, “Start writing, and the money rolls in.” It’s been wonderful for me, but it is this constant beast that you have to feed.

Fernando Caralt 
Founder, Espresso Matutino 

Good content is always the foundation for everything. But with a newsletter that monetizes through advertising, it’s not a content business — it’s a sales business. It’s getting enough sales to monetize properly. 

I’ve talked to every salesperson and every newsletter I could think of; I’ll pay them for an hour of their time to learn everything that everyone’s doing. Turns out it’s just grinding. It’s just sending emails, talking to people, and getting better at sales.

Sam Parr of The Hustle once said that it’s tough to succeed when ads are at the center of your business model. It just never ends. You hear that and don’t process it, but once you live in it and it’s 20 to 22 ad slots per month to fill out, you just have to fill them out. I think that grind is not something you see from the outside. It turns out it just takes work to get sponsors. Monetizing is the hard part; that’s why people go to subscriptions or find other things.

For me, advertising was the model I was going for, and it is working now. But most newsletters are not going to go from zero to half a million in sales in six months. For most people, it’s just going to take a long time figuring out monetization. 

Heather Ciras
Deputy managing editor for audience, The Boston Globe

The best newsletters don’t perform for readers — they sit down with them. My favorite ones are a table, not a stage. When I first started in newsletters, I was focused on cadence, open rates, and clever subject lines. I still care about those top-line metrics, but the qualitative ones matter so much — the replies, the suggestions, the moments when readers feel recognized. Even the folks who write in with copy edits! They care so much. 

And if you’re truly trying to meet your audience where they are, you can’t think inbox-only. None of us reads just newsletters; we’re creatures of the entire internet. So the work needs to live across formats and reach people in different ways, wherever they choose to engage. Just don’t overdo it. 

Jenni Gritters
Creator, The Sustainable Solopreneur

When I started my newsletter, I wish I could have reminded myself that I was allowed to evolve, again and again and again. I spent a lot of time trying to make the newsletter’s description, verticals, and branding perfect. But it turned out the look of the newsletter mattered a whole lot less than just showing up, imperfectly, week after week, to serve my audience. 

These days, my newsletter drives thousands of dollars in coaching sales. And even now, it’s not about perfectly understanding what I’m doing or who I’m talking to! Instead, it’s a place to evolve in public. And the newsletter’s success is about consistency, trust, and transparency. To me, a truly effective newsletter feels like a hand-written letter — like building relationships with the real humans on the other side of the subscribe button!

Jessica Palombo
Editor, Jacksonville Today

Our newsletter comes out at 6 a.m., six days a week. With production falling on a tiny team — just a newsletter writer and me — I wish I had figured out a sustainable work schedule for both of us sooner. We lost one writer to burnout. Since then, I’ve set some harder boundaries around work time and have learned to say, “We can do that tomorrow” more often. 

Kate Samuelson
Editor and director, Cheapskate London

Consistency is so important. It’s a huge undertaking, deciding to launch a newsletter. You have to really want to do it, because to really connect with your audience, you have to be consistent with when you’re sending it. So, that might need to be every week or every day, or whatever your cadence is. Once you start, you’re saying, “Okay, I’m in now. This is what I’m doing.” So you have to be really passionate about what you’re writing about, because it is a big undertaking.

Lennart Schneider
Founder, Subscribe Now

My newsletter is a companion piece to my podcast. The podcast is the leading medium; I do an interview, and then I write down some of the learnings from the podcast. The main change in my concept was that at the beginning. I had a news part that I cut out after one year because it was too much work. When I deleted it, nobody seemed to care. That’s a good sign that it wasn’t necessary and people didn’t need it. In fact, I’m so proud I did it.

One thing I learned along the way is about selling advertising. The advertising really took off when I started bundling the newsletter advertising with podcast advertising and a LinkedIn post. I always have one sponsor per podcast episode, and they also get an ad in the newsletter, so I can combine different reaches from different mediums because the podcast itself only has 500 to 1,000 listeners per episode, but combined with newsletter and LinkedIn visibility, it’s something between 5,000 and 10,000 ad impressions per episode. That’s something I don’t think many people are doing, but it really helped me in selling advertising.

Manny Reyes
Founder and CEO, Boletin Growth

When it comes to growth — and specifically paid growth — I implore any newsletter operator to understand two things on the topic. The first is why. Why do you want to run paid ads? Is it for top-line growth with a hard number you’re simply looking to reach, or do you have your payback period and subscriber LTV all calculated out to justify the amount you’ll pay to acquire that subscriber? 

The second is related to the first and also to the one metric everyone chats about when entering paid growth for your newsletter: The cost you pay per email address. Different people will use different acronyms for this metric — some call it CAC (customer acquisition cost) or CPA (cost per acquisition) or CPS (cost per subscriber) — but the amount you pay per subscriber can be very closely related to the metrics you calculate for LTV and payback period. Sometimes it’s simple to chase the lowest CPA possible, but when it comes to getting the right subscriber, especially for B2B newsletters, my six years of running paid growth for newsletters have clearly shown that paying more for a subscriber can be a good thing. So in short, don’t always chase a $1 CPA if it’s not bringing you the right subscribers who engage with your content and/or contribute to your monetization models. 

Meggie Baker
Digital products manager for news, The Berkshire Eagle

When my team took over newsletters, I don’t think I ever had unrealistic expectations about the speed at which our newsletter audience or engagement would grow — though I know there were some big numbers and optimistic time frames floating around the organization. 

Even so, I spent so long in the beginning trying to understand why our readers weren’t behaving the way I thought they should, or why they were interacting in ways that surprised me, and in ways that didn’t seem to be replicated by other organizations. In the end, all of my endless questioning didn’t matter. You’ve got to meet your readers where they are. If you’re paying attention, you know what subject line will get them to open your newsletter. You know what article will drive clicks. And you’ve got to be ready to pivot. When our reader engagement changes, we just figure out what our readers are interested in now instead of trying to hold on to how we were doing things yesterday.

We talk with our editors, share our stats, and they go after what we know our readers want to see. We collaborate with other teams to have newsletter sign-ups be a part of contests, surveys, and events. We launch new newsletters, refine them, keep them, kill them.

Be flexible. Listen to your audience. We’re heading into our fourth year since taking on newsletters, and we’re finally closing in on those big numbers.

Melissa Rutherfoord and Jonathan DeRuiter
Creators, Around Evanston

Melissa: I think we knew that we were going to need to grind it out, but not necessarily to the degree that we would have to. Have the expectation that starting a business means you’re going to have to put a lot into it and maybe not get that much out of it monetarily at the beginning. But I do think we’ve gotten so much more than just money out of this newsletter, like the connections with the community we wouldn’t have had if we hadn’t done this.

Jonathan: Regarding a lot of the technical details, I would say: Don’t sweat it. Just go for it. Don’t overthink things. But also, you need to be committed. You need to decide how many times you’re going to send per week or month, however you’re going to structure it, and tell yourself, “All right, I’m going to give this two years,” or something like that. Don’t be like, “Oh, it hasn’t taken off in three months, I’m going to end it.” These things can take a while to pick up. 

Mike Sacks
Creator, Mike Sub-Sacks

I do this every time: I jump in knowing it’s going to be a lot of work, but I do it because I know if I overthink it, I won’t do it. 

But it’s a lot of work. And this is just releasing two fresh pieces twice a month. It’s consistent. And I am not good with consistency. If I have to do something every day, I don’t want to do it. I have to feel that I want to do it. 

I would recommend that before you put out a paid option, take a month and write for yourself and see if it’s something you want to do. I used to edit columnists for the Washington Post who were locked into that world, two columns a week — that’s your life. It takes up, no matter what type of writing you do, a lot of your time. 

Suss it out first and see if this is something you want to delve into, because I would recommend that if you do it, stick with it, not to say, “Oh, I only have this amount of paying subscribers, fuck it.” I think it’s something you should stick with for a year, but know that it’s going to take a lot of time, and it’s a different type of writing than you might do otherwise.

Nada Alnajafi
Founder, Contract Nerds

I wish I’d known you don’t need to be everywhere at once.

When I first started the Contract Nerds newsletter, I knew I wanted to offer it for free, and I knew that I wanted it to provide educational value to subscribers. What I wish I would have known is that I wasn’t just creating a newsletter, I was building a media platform. Platforms work within an ecosystem that relies on multiple systems. But I wanted to preserve a single experience, a single brand, and that tension between expansion and focus held me back.

I worried that if I didn’t expand across multiple channels, I’d miss out on reaching people where they were. But here’s what I didn’t understand: every channel you add dilutes your ability to do one thing really well.

The newsletters that I admired most weren’t trying to be everywhere. They were just showing up consistently in one place — the inbox — and doing that exceptionally well. They understood that depth beats breadth, especially when you’re starting out.

If I could go back, I’d tell myself to resist the pressure to build an empire on Day 1. Focus on making the newsletter itself so valuable that readers forward it to colleagues. Master that single touchpoint before adding complexity.

A platform isn’t built by being everywhere at once. It’s built by being indispensable in one place first.

Renae Reints
Newsletter editor, TED Conferences 

I wish I had earlier realized the power of the subscriber’s user journey. As a writer at heart, I want to believe that just putting good content into the inbox will ensure fantastic engagement rates forevermore. That’s not entirely false — content quality is absolutely essential — but you also have to put on your product management hat to build something that truly succeeds. How are you welcoming subscribers to your list? What time of day is your email arriving? Are other teams at your org sending emails at the same time? How are you gathering feedback from your subscribers in a sustainable way? How are you learning about who they are and what you’re interested in (because let’s be honest, ad sales matter too)? 

All of these questions involve writing fantastic copy, sure, but they also require org-wide strategy and automated lifecycle flows that reach subscribers at specific points in their relationship with your newsletter. If you have a powerful framework behind your newsletter, your emails (with your beautiful copy) will be much more successful in the long run. 

Rob Gurwitt
Publisher and writer, Daybreak Upper Valley

I can’t believe it took me the better part of two years to understand the power of idle chatter. Readers hinted at it in passing in their emails: “I was talking to my wife over breakfast this morning…”, or “Showed my colleagues that story you linked to…”, or “A friend mentioned that photo you ran the other day and I had to check it out…”

Eventually, it dawned on me: Giving people stuff to talk about isn’t just a nice diversion for a newsletter. It’s a value proposition on both sides of the “send” button. For readers, it’s a common touchpoint, a shared experience that, like a ball game or a favorite streaming show, deepens their sense of community and connection with one another. For me, it’s been why my local newsletter’s grown by thousands of readers entirely by word of mouth. It’s helped build reader loyalty. It’s been an inspiration to keep the writing fresh and the items I highlight chatter-worthy. And since I’m running this newsletter solo, it’s been the hovering editor in the back of my mind. “Yeah, we had a good laugh over that at work,” ran one email not long ago, after I made a forehead-slapping mistake. But hey, at least they were laughing.

Priti Patnaik
Founding editor, Geneva Health Files

I would’ve focused more time on identifying people to help me early on, at least on the editorial side. Geneva is expensive. It’s not so easy to hire people, and the subject [global health] is technical, so it’s not very easy to find journalists who also understand technical matters.

Having a team is like the chicken-and-egg problem. It’s difficult to have a team right at the beginning, but that would’ve helped because those were very, very difficult years. You’re trying to build an audience, you’re trying to build credibility, you’re publishing non-stop, you’re creating a following, and you’re showing up no matter what. In the first year, I broke my hand. I was at a playground with my then-toddler. I took a week off, and then I started typing with my left hand.

There are these things that you cannot be prepared for, and I feel that I certainly did not know that I was getting into a 24/7 role. Media entrepreneurship and journalism entrepreneurship are extremely difficult. You have to be on top of the product, and you have to always pay attention to the business side of things; otherwise, it won’t work.

Sam Shedden
Creator, The Melbourne Snap

The first thing you’ve got to realize is the level of consistency that is required. Consistency is all-important. Don’t sign up for something that you don’t think you can do.

If you say to people, “I’m going to do it once a week,” stick to it. If you don’t think you can do it once a week, that’s fine, but say what you think it’s going to be.

The other thing is the peaks and troughs, and dealing with them. A newsletter curve can go like this [makes curvy gesture], so how do you deal with it when it’s flat or plateaued? That can be quite demoralizing. 

I don’t know if I’ve cracked that. I think I’m better at it. To get through that means knowing your purpose. Why are you doing it? I genuinely want to see if I can provide a better way to get local news and to get people interested in their area. You could say, “Well, it’s also self-serving, because it’s helping you.” I would say, “Yeah, but I put in more than I get back.”

Seamus Hughes
Reporter, Court Watch 

Unless you’re an established name, it’s an absolute grind to build a newsletter. Social media algorithms downvote links, and the way people consume their content is constantly evolving. There will unlikely be one big moment or story that helps you break into the zeitgeist. Instead, to be successful in this field, you need constant and consistent production of content over a long period that has a voice and provides a viewpoint or information that is not readily available elsewhere.

There is no editor somewhere that will wave you off a bad lede or colleague to bounce story ideas off of. You have to trust your gut on the pieces and write in your own distinct voice. If you do that, the readers will eventually find you because they’ve been searching for a place online that speaks to them and their unique interests. And while there will not be overnight success, over the long term, the benefits of owning your own platform far outweigh the alternatives.

Stuart Schuffman
Editor-in-chief, Broke-Ass Stuart

I’ve been doing a Broke-Ass Stuart newsletter of some sort since 2010 or earlier, so a lot of the tools that we have now didn’t exist when I started. But with that aside, I wish I’d taken newsletters more seriously as a platform far earlier.

At first, they were just a way to keep my readers updated, like “come to my book reading” or “buy some merch.” But as traffic from search and social media has dried up so profoundly over the past five or so years, it’s become strikingly apparent how important it is to own your audience and create value for them specifically in newsletter form. I wish I’d figured that out sooner than I did. 

Tim Barnes
Creator, Letters From African America and Alternate Timeline

I wish that I had given myself more time to figure out how all [of Substack’s] different features work. It is very daunting when you first dive in. It was a series of little promises that I made my subscribers about what this is about and why I’m trying this. Like every artist, no matter what thing you start with, you start to have this unease about the method with which you started off on it. And so there are all these different versions of stops and starts.

I now have a very solid idea of why people subscribe. You start off with why you think people will, and then you find out why people do. It’s the same thing with stand-up. You start off having this invention of yourself as a comedic presence, but the audience tells you who you are and what tools you get to play around with.

Now I just have a stronger sense of what my writing capabilities are and why people like what I do. So, I’m just trying to lean further into that. So I would say, I wish I had given myself more time to experiment before I even had the paid subscription version of my newsletter.

Tyler Morin
Founder, The Water Coolest

It sure would have been helpful if someone had given me a heads-up to get to know The Water Coolest’s audience better from day 1. And I mean really get to know them. It’s so easy to get caught up in the vanity metrics and growth at all costs (especially with an ad-supported model).

But I’m convinced that not taking the time to collect more data upfront (at sign-up) and throughout the readers’ journey (via surveys) is one of the biggest mistakes I made early on. Collecting demographic data is the obvious stuff, but I really wish I had obsessed over readers’ interests, reading habits, other content they love, etc. That’s where the gold is.

In the early days, it would have helped us dial in the content and voice to build a must-read newsletter. I’m a believer in writing each newsletter with one specific persona in mind (I even name them).

And, of course, when we reached the point when we were looking to scale, we could have doubled down on our ideal customer profile versus casting a wide net and hoping for the best.

Plus, that data would have been super beneficial when we began working with advertisers and eventually when I went to sell. Knowing my audience better would have made our story so much easier to tell.