I’ve Sent Over 1,500 Newsletters — Here’s What I Wish I Knew When I Started
No, “being consistent” is not the key.
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So you want to start a newsletter?
Or you’re wondering when this newsletter thing will finally pay off instead of feeling like a huge burden every single week?
I’ve got you covered, my friend.
When I sent my first newsletters back in 2017, I felt anxious every time I was about to hit the “send” button.
I hated it.
Sending emails to people I didn’t know felt scary and weird, and it took me years to finally fall in love with newsletters.
After more than 1,500 emails, I can proudly say that writing newsletters is now one of my favorite tasks as a business owner.
In case you’re wondering why or how newsletters can be fun, it’s because writing emails to my audience is now the most impactful but also flexible task.
I’m running a typical creator business with a stupidly simple business model:
I publish content — mostly on Substack and Medium, sometimes on YouTube.
I invite readers to sign up for my newsletter and bribe them through freebies.
New subscribers receive an automated welcome series, followed by promotional emails. Ideally, I already make money at this stage, but usually, I don’t.
Next, the subscriber receives my weekly newsletter, which is a mix of actionable insights, links to my content, and personal stories.
A few times per year, I run product launches, which are cash injections that generate a large amount of money in a short time.
And then I rinse and repeat: I create content, grow my email list, nurture subscribers,..
Easy-peasy.
Just kidding — building a simple business isn’t easy. In fact, keeping things simple is usually harder than building a complex system.
If I could go back in time and teach myself how to run a newsletter that actually makes money, this is what I’d say:
Your newsletter will suck if you don’t love it
If you’re a writer, creator, coach, consultant, or solopreneur, your newsletter is a reflection of you.
No one will be excited about reading your newsletter if you’re not excited about writing it.
A newsletter is all about writing emails people actually enjoy, and that’s not possible if you dread the process of creating it.
One of my first newsletters was called “Personal Growth Letter.”
Each week, I’d compile a short email containing:
1–2 articles I had written
a book recommendation
and cheesy self-improvement quotes
I hated writing that newsletter but created it for almost an entire year because everyone kept saying, “You have to be consistent to see results.”
I was consistent, but the newsletter sucked because I wasn’t even a tiny bit excited or passionate while creating it.
Most new creators think of their content and audience in abstract numbers.
They chase vanity metrics like followers or email open rates without thinking about what those numbers actually mean.
The truth is that your creator business will only thrive through human connections.
In 2024, “delivering value” is not a viable strategy for growth anymore.
ChatGPT can deliver value much faster than you. Why compete with it?
Focus on your human side instead. Embrace the fact that your content is meant to create a conversation with other humans.
If you hate running your newsletter, your readers will sense that something’s off.
When I ran a newsletter I hated, every email felt like a dread.
As a result, the content was flat, boring, and unoriginal. It didn’t connect or convert.
If you want to create something worth reading, you have to find joy in the process, even if it means pivoting a dozen times.
You might have to switch up the format, topic, or style of your newsletter until you find out what you genuinely like doing.
When you enjoy writing your newsletter, your content becomes more engaging, relatable, and, ultimately, more successful.
Writing my newsletter is now my favorite task because I genuinely enjoy the process.
I don’t promise to send my emails on a specific day of the week.
I don’t even say how many emails my subscribers will receive.
Sometimes, I send two newsletters a week, and sometimes, none — depending on my creative flow, workload, and life.
Instead of forcing myself to write a newsletter I don’t feel like writing, I wait to be inspired.
Yes, being consistent with your newsletter matters, but sending great emails is more important.
There are only 3 ways to grow your newsletter
This is how starting a newsletter goes for most creators: Everybody tells you to launch your email list to be independent, so you do.
You create a newsletter, add a nice freebie, and write your first few emails to a handful of subscribers.
After a few weeks, you realize your list barely grows, and you’re frustrated because you know you can’t make any money with your email list if nobody subscribes.
So you go on a mission to grow your email list and discover dozens of strategies that sound promising.
The problem with most of those strategies is that they don’t work because there are only three viable ways to gain more subscribers and grow your email list:
1. Views on content
Your content is the gateway to your newsletter. The more eyeballs you can get on your content, the more potential subscribers you reach.
It’s as easy as that: If nobody sees your content, nobody will sign up for your newsletter.
If you have a list growth problem, you probably also have an organic reach problem.
2. Collaborations and referrals
Let’s say your content gets a decent number of views, but you want your list to grow faster. One of the most accessible leverages you can use are partnerships with other creators.
Leveraging the audiences of others is one of the most powerful and overlooked growth strategies for creators.
Collaborations and referrals are about building relationships with creators, influencers, or brands that align with your niche.
When you collaborate, you’re tapping into a pool of potential subscribers who already trust the person or brand you’re working with.
This can happen through guest appearances in other newsletters, joint content like webinars or courses, or simply asking your current subscribers to refer your newsletter to others.
The beauty of this method is that it’s not just about numbers — it’s about quality. The subscribers you gain through referrals or collaborations are often more engaged and loyal because they’ve been introduced to you by someone they already trust.
My own list has grown significantly thanks to free recommendations through Kit’s referral system.
3. Paid growth
Last but not least: Pay to play.
The reality about some of today’s largest newsletters is that they are growing by paying for each subscriber.
A prime example is Sahil Bloom, who has quickly grown an email list with hundreds of thousands of subscribers by leveraging paid growth.
If you can put money behind your work, you’ll be able to grow your list much faster. I’m currently doing this through Sparkloop’s referral system by paying $2 per qualified subscriber.
The key here is knowing your audience and targeting them effectively so every dollar you spend brings in subscribers who genuinely care about your work.
Stop obsessing over vanity metrics — do this instead
Running a profitable newsletter is hard because you can do it in a million different ways while making a gazillion different mistakes.
Most newsletter creators obsess over metrics like subscriber count and open rates, but the truth is that numbers alone don’t matter.
If you have 10,000 subscribers, but none of them actually care about your emails, you won’t get very far.
Similarly, a high open rate is great, but it’s not necessarily a guarantee for a successful newsletter.
You can get people to open an email by writing a clickbait subject line, but if they don’t care about the content, they probably won’t ever become paying customers.
The most absurd thing I ever saw was a creator friend who almost threw a party if nobody unsubscribed from his weekly newsletter. He was so attached to the fact that nobody unsubscribed that he created dozens of social posts about it.
It was nonsense.
A profitable newsletter isn’t just about pleasing your readers. It’s about experimenting and discovering how to reach your financial goals as a creator.
Total subscriber count and open rates are shiny objects. The more you obsess over them, the less time you have to deal with what truly matters: creating great content and building relationships with your readers.
Open rates will never tell you how much impact an email has. The response of an individual subscriber will indeed tell you.
Talk to a friend, not an audience
Most newsletter sucks because they sound robotic.
If you want to write emails your readers will genuinely love, you’ll need to *connect.*
Guess what the best way to build a connection is?
Treating your subscriber like a human!
Write your newsletters as if you’re writing to a friend.
Imagine sharing something valuable, insightful, or funny with someone you care about — someone who genuinely wants to hear from you. That’s the tone and style you should aim for.
Nathan Barry, the founder of Kit, for instance, uses a simple method to consistently write newsletters that are valuable for his subscribers: He has a big catalog of questions his audience shares with him.
When he sits down to write a newsletter, he picks a question and writes a reply to hit. He starts by writing, “Dear Sinem..,” then replaces the name with the liquid code to personalize for each subscriber.
He sets himself up to write the answer for one reader, which removes pressure and ensures he’s writing the most helpful reply possible.
Writing with this mindset makes your content more relatable, personal, and authentic. It strips away the formality and allows your true voice to shine through.
Readers can sense when you’re being honest with them, and that’s what keeps them coming back for more. They’re not just opening an email — they’re catching up with someone they trust.
Don’t try to impress or speak to the masses.
Focus on having a conversation.
Share your thoughts, insights, and stories as if you’re having coffee with a friend. That’s how you turn subscribers into loyal readers and, eventually, into a community that appreciates your opinion, perspective, and content.
What’s the role of Substack in all of this?
Since you’re reading this piece on Substack, you might be wondering about what role Substack plays in my newsletter/content strategy, so here goes:
For most writers and creators, Substack can be a one-stop shop to:
Publish content
Build their audience
Make money
And run a newsletter
I did, however, have a fully fleshed digital writing business before joining Substack in 2024, which means it was an addition to my existing channels and not a replacement for our newsletter on Kit.
So here’s how we use Substack right now:
Substack is our main content hub. While I still publish on Medium, a large part of our content is created with the Substack-first mentality because of the large ROI we see here.
Substack is a growth channel, which means we use it to attract new readers who are not aware of our work yet. Hundreds of new subscribers discover our work through Substack every week.
These subscribers also receive our emails through Kit - here’s how.
On Substack, we publish Notes every day, recordings of our live events and interviews, and two posts per week - one free, one paid. We also host a monthly Growth Workshop for our paid subscribers.
This system allows us to perfectly leverage Kit, Substack, and our other channels together while leveraging the content we create in multiple places.
Let me know through the comments if you have any questions on our repurposing strategy - I’m happy to share more!
Our next Substack Growth Workshop is happening on March 10 and you have the opportunity to get in-depth feedback on your paid offer.
Upgrade to our paid tier right now to join us live or get access to the full replay.
It took me a long time to understand that referring to Substack as a "newsletter" is a misnomer. I had a blog site and the advice I got was to write a "newsletter" in addition to the blog. They are one and the same to me. Referring to Substack content as a "newsletter" limits its potential and is confusing to people like me who were just starting out.
appreciate this post so much, thank you!