The Best Piece of Advice I Ever Got About Newsletters

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There is a lot of newsletter advice floating out there — heck, we’ve published plenty of it ourselves here on this website. If you’re lucky, you stumble up on a good piece of advice and it shapes your work for months or years to come.

An interesting thing about good advice is that it can come from just about anywhere and apply to things both grandly theoretical to prosaically practical. Ask a dozen newsletter writers for advice, and they’ll give you a dozen different answers. Sometimes, the general advice will sound the same, but the context will give it an entirely different wrinkle. Sometimes, the advice will even contract other pieces of advice you’ll hear — and that’s OK!

We know because we asked.

We reached out to some friends and colleagues in the email space — some who run their own independent newsletters and others who work on one at their jobs — to ask them this question: What’s the best piece of advice someone else gave you about newsletters?

Here’s what they told us. Your next favorite piece of advice, we hope, might be in here.

AJ Daulerio
Founder, the Small Bow

• Consistency — publish on a regular weekly schedule so readers know to expect your newsletter.

• Don’t get alerts for or pay any attention to unsubscribes.

• Don’t try to game the system with spicy headlines. 

• Answer every email from readers.

António Tadeia
Creator, the António Tadeia newsletter

The best piece of advice I got about newsletters was to build a newsletter and leave the website business, as the insane search for scale is killing journalism in a small market like Portugal [where I’m based]. The best work I did was getting no response from readers, as my website depended much on social media algorithms. We were being held down by engagement rates, which were lowering by the day to the point where we had to give it all up. I refused to compromise to the ways of converting serious journalistic operations into social media hoaxes, clickbaiting, and all of that sort. So one day, a friend of mine who used to write about media and tech pointed me to the newsletter business as an alternative. My newsletter just completed its third anniversary, and even if growth is slow, it’s steady. The regret I have is not to have started it sooner, as now I can concentrate on the content and not so much on the ways to dribble through social media algorithms.

Amy Cavanaugh
Co-founder, American Weekender

Shortly after launching our newsletter in July 2023, my co-founder Kenney Marlatt and I heard from Dennis Lee, who writes Food is Stupid and The Party Cut. He told us that when he started, he did not receive much support and that writing a newsletter could be a lonely process, so he wanted us to feel seen.

We had been experiencing firsthand how starting a newsletter can feel like sending emails into the void. We rarely heard from readers, and growth was slow — we worried we’d never move beyond a few hundred subscribers. But finding out that this lonely period was part of the process for many operators made us realize that if we published consistently and made good on our promises to subscribers, we could push past this. We now have and it was that email from Dennis that made us see what we had to do — keep going.

Claire Zulkey
Creator, Evil Witches

I’ve gotten lots of great advice over the years, especially working at Inbox Collective, but I wouldn’t be here as a so-called expert if it wasn’t for The Ankler’s Richard Rushfield encouraging me to just go ahead and monetize my newsletter. My newsletter did not start out as a newsletter. It began as a Facebook community, but over time the style, tone, and range of conversation led to friends encouraging me to do “something” with it, to perhaps launch a newsletter or a wider online community or brand. My experience, schedule, and temperament made me reticent to start something larger, but writing emails, essays, funny and reported pieces? I can do that! Richard, a longtime colleague, was an early observer of the potential in paid newsletters and encouraged me to take the experimental missives I’d been sending via Wix over to Substack. He knew that after my years blogging and from my general writing, I had a few things going for me: a voice, a point of view, an ability to write relatively articulately, and to play the long game content-wise. I’m grateful he encouraged me to just go for it! 

Dan Oshinsky
Consultant, Inbox Collective

I quote this line from Ann Handley on a weekly basis: With newsletters, it’s not just about the news — it’s about the letter. It’s so easy to focus on what you’re trying to promote or sell and to forget that the best newsletters are usually the ones that you connect with on a personal level. Be yourself and let readers into your world. They’ll stick with your newsletter a lot longer if you do.

Devorah Heitner
Founder, Mentoring Kids in a Connected World

One piece of advice is “reuse/recycle.” It is newer for your readers than it is for you! I did this in a recent issue. I have new followers every year who want to know, “When is my kid ready for a phone?” or other perennial questions. I can repurpose, polish, and update old answers, but I don’t always need to reinvent the wheel! 

Emily Ryan
Co-founder, Westfield Creative

The best advice I’ve ever heard about sending a newsletter is to not overthink it. If you simply share content you enjoy, then your subscribers will enjoy it, too. I always ask myself, “Would I honestly read this article I’m sharing?” If not, then I don’t share that content. Most of the time, people skim emails. What matters is that you’re sending emails to your audience often and that you’re not overthinking every little detail. (After all, it’s just an email, and we get hundreds in our inbox each day.)

Ines Bellina
Creator, The Cranky Guide

While it’s OK and even expected to have a specific niche, your readers will keep following you because you bring your own unique voice and perspective to whatever you write. Don’t be afraid to expand your scope! To branch out! To experiment! My newsletter used to be hyper-focused on making it as a freelance writer. But since I’ve widened my topics to include all aspects of what I call a creative, unbound, nomadic life — travel, my status as an unmarried and childfree woman, cultural commentary on my hometown — I’ve seen my subscriptions rise, not fall. 

A second piece of advice: Take a break and don’t fret about it. Most readers won’t notice or care all that much. They’re already receiving a massive glut of newsletters and prefer you send out something meaningful than filler.

Isaac Saul
Founder, Tangle

The best piece of advice I got is to focus way less on all the different gimmicks, tactics, and strategies to grow your audience that you can find on tons of different websites — they’re all helpful and, I think, useful at the edges. I read the Inbox Collective newsletter, and now and then, I’ll find this unbelievable gem about a strategy somebody’s using that I never thought of. But the main thing has to be the content: You are offering something that is unique and valuable and is not being executed in the same way somewhere else. You can have the best strategy and tricks and gimmicks in the world, but if your content is mediocre, you’re never gonna go anywhere. So give growth the 5 to 10% of your attention that it needs, but spend the vast, vast majority of your time thinking about how to make the content really good. That is advice I got early on, and I think it’s a big reason why Tangle is where it is today.

Josh Spector
Content strategist and writer, For The Interested

I had Dylan Bridger on my podcast to talk about how to write emails that drive sales, and he mentioned the importance of sending a lot of emails over the course of a marketing campaign. That may seem obvious, but his reasoning behind it was something I hadn’t heard before — each email should target a different reason for readers to take action, and the fewer emails you send, the more pressure you put on those emails to perform.

This concept can also be applied to newsletters — any action you want readers to take should be presented to them multiple times, in multiple ways, with multiple different approaches.

JR Raphael
Founder and editorial director, The Intelligence

The most important advice I’ve received has been around the mechanics of creating a newsletter and making the most of its unusual form.

Plain and simple, email isn’t like any other publishing medium. People aren’t necessarily sitting down to read a sprawling essay. They want to be able to skim, see what’s interesting or important to them, and digest info easily — even on a small screen.

Way back when, some sage suggested I think carefully about finding a format that makes sense for that purpose. That led to me creating a framework that still stands today, featuring lots of short sections with consistent purposes and clear visual separation.

Readers know what to expect and where to find it, and the emails are easy to scan and take in — whether someone’s making their way from top to bottom or skipping around and enjoying only the specific nuggets they’re interested in sampling.

Leslie Price
Co-founder, Gloria

Stay focused on what your brand brings to the table. It can be very easy to get distracted and feel like you have to cover the same stuff that everyone else seems to be talking about, but people come to us for a specific type of content — reported features, essays, Q&As, and more on topics that are relevant to women ages 35+. Know your lane, own your niche, etc.

Cadence is also important. You want to build a habit, so readers need you to deliver every single week. Given that, don’t commit until you are ready to do so. 

You will get feedback that feels very personal because this is a personal medium. If your audience truly cares about your work, you’ll see it reflected back to you. Savor the kind words, and try to let the negative emails roll off your back. (This is easier said than done!)

Margaux Maxwell
Director of platform and product, Oregon Public Broadcasting

The best piece of advice I’ve ever gotten about newsletters is that you don’t need to have something perfect to launch, and you can be real with readers about that. Start with a minimum viable product, embrace each issue as an opportunity for iterative co-creation, and be honest with your audience about your experimentation. Readers do appreciate the authenticity and the local focus. That opportunity to weigh in can be part of how you build community over time and reminds them that a human being is behind the words they see on the screen.

Megan Bungeroth
Creator, Sleight of Brand

Think about what you want to get out of this newsletter. Is it to sell a product or service? Grow a community? Flex your writing muscles? Build your network? Then, think about what you want the audience to get out of it. Hopefully, those things align. For me, I wanted to create a resource for fellow branded content professionals that would prove insightful. I also wanted a way to grow and strengthen my own network, which is why I decided to do an interview format. It’s allowed me to meet and talk to amazing, smart, talented people in my field, and I get to learn alongside the reader. Whatever you want to achieve from your newsletter, let that guide your format, your title, your voice and your approach.

Focus on growing the RIGHT audience, not the biggest. I have purposefully not asked (most of) my friends and family to subscribe to this newsletter because they don’t all work in branded content. And while I know they would support me, I need to find an audience that signs up because the content is valuable, not because they’re blood relatives. (Except for my mom, obviously. She’s a subscriber.)

Natalie Moore
Digital strategy and audience engagement manager, Texas Highways

The best newsletter advice I ever received was to always A/B test. While subject lines are obvious and easiest to test in most cases, it’s worth considering other areas like images, content, length, calls to action, personalization, send times, etc. Just make sure to test only one variable at a time to get clean results. You may be surprised by what your audience shows you through their engagement.

Another important factor is that it’s okay to be wrong in your hypothesis or even fail with a product. This provides valuable data, giving you tangible evidence on how to move forward and succeed next time.

Samuel Hunter
Newsletter strategist, MediaNews Group

My previous boss used to always emphasize the importance of collecting email addresses at every opportunity. Whether it’s hosting an event, setting up a booth, running a contest, or even printing new business cards — there should always be a way to sign up for your newsletter. One easy, actionable way to promote your newsletter is to include a link in your email signature.

We’ve had some great success growing our newsletters by thinking outside the box in this way. 

Sean McNulty
Creator, the Wakeup

Be very diligent about being consistent. Even if you’re not yet getting paid or paid enough to make it your full-time gig — treat it as such. Your audience should know when they’ll hear from you, and if you become erratic with that, getting a reader back can be harder than establishing the signup in the first place. Ideally, people look forward to getting what you’re writing! So don’t drop the ball.

Otherwise, know who your newsletter is for before you begin, and know what need are you solving for that reader or the entertainment you’re providing (that someone out there isn’t doing already). A newsletter isn’t about you if you’re looking to make it your livelihood — it’s about your reader.

Simon Linde
Copywriter, Et Rigtigt Nyhedsbrev (A Proper Newsletter)

When I was co-editor at Denmark’s biggest communications newsletter, I received an email from a former colleague who had moved to Canada. She wrote:

“Guys, where is my benefit? Why should I read this week’s blog post? Take a look at the email you just sent out, and ask: ‘So what?’ five times. When you have done that, then you have a clear benefit.”

My first reaction was: How dare you?! 

But then I read the email. And she was right. There was no benefit for the reader. So I did the exercise: I asked ‘So what?’ five times about the email copy to our 25,000 subscribers. And damn… if only I had known that advice sooner.

Sri Juneja
Founder, Readable Moments

Here’s some advice I have received that I found particularly helpful for my neuroses 

• For me, being baffled by what resonates: Sometimes, the things you didn’t think would take off somehow do. The essays you pour your heart and soul into barely get any interest. You can’t plan for virality, so just do the damn thing of writing the piece.
• For me, being cranky about growth: Consistency is king. Just keep showing up with your work, and slowly, your writing will improve and your audience will build.
• For my imposter syndrome: A writer is someone who writes. Don’t let other people’s qualifications intimidate you.

Tanmoy Goswami
Founder, Sanity

So here’s the advice I love the most:

I once told my friend Alan Soon from Splice that I have this bright idea but I am stuck and don’t know what to do. Alan, who’s also an amazing coach, patiently heard me whine for 10 minutes and said, “Hmm. It looks like you already know what you want to do, but you want someone else to give you permission to do it.” Mic drop moment — when you are a solo operator, you don’t need anyone’s permission to do stuff. It’s difficult advice for people who have been jobbers all their life and depend on instructions to know what to do, but it’s transformative if you take the leap.

Terrell Johnson
Founder and author, The Half Marathoner

“They want to feel at home, but they also want to be surprised.” 

That’s what Bruce Springsteen said once in an interview when he was asked what fans are looking for from their favorite musical artists, and it’s always stayed with me. I take a lot of inspiration from artists in other mediums, especially musicians, because they shake up what they do — they try different styles, different sounds. Not only for their audience but also so they’ll stay interested — which is really key. I’ve been writing my newsletter for almost a decade, and I’ve learned you always need to look for new terrain to explore. It helps you stay fresh, curious, and interested, and your readers will feel the energy when you do (and especially if you don’t!).

Wale Lawal
Founder and editor-in-chief, The Republic

Newsletters are not just a platform; they’re a product. We made the mistake of just thinking about it as a subset of a platform. I’m glad that we learned over time, but I think if we had thought about it as a distinct product, we would have been able to rack up more attention early on. It’s not second-tier; it’s not behind the scenes. It’s an actual product, and it can actually give you its own audience, its own monetization stream, all of those things. It’s not a small space at all. 

The second thing is about innovation. There’s a group that we work with called the Nigeria Media Innovation Program. It’s set up by one of our funders, the Media Development Investment Fund, and they have this program that they run in South Africa and Nigeria. When we joined, their lead, Bilal Randeree, told me that innovation isn’t just this grand thing. It doesn’t just mean paying a big amount to get AI to write your newsletters. Innovation is literally taking things a step up. I think that that really changed the way that we approach newsletters. Initially, I thought that if we scaled this newsletter, we would need to invest in huge technology and do all of these fancy things. What I’ve learned over time is that it’s not really about those fancy technologies. It’s more about upgrading the work that you’re doing in as simple a way as possible. What that has meant for us, for example, is thinking about things like the design of the newsletters. It’s exploring different platforms. It’s re-introducing daily quizzes. We have done it in the past, and we had retired it because I felt like we probably needed more tech investment into that. But we found that those daily quizzes have helped us build and retain audiences, because readers look forward to the answers in the next edition. Little things like that can actually make a big difference. A newsletter doesn’t have to require so much investment. You can actually start small but just have a very unique and interesting way of doing things. And that’s innovation as well.

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