Reset Button: What 21 Top Newsletter Creators Would Do If They Started from Zero
If you struggle with building your newsletter, this article is for you!
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Over the past two years, I’ve had the chance to interview more than 80 newsletter operators—each with their unique journey. These conversations have been full of valuable insights on how to start, grow, and monetize a newsletter business.
Every creator's path is different, and so are the lessons they’ve learned along the way.
One of the most powerful ways to reveal true learnings is going back to the days when we hit the road and reflect on what we might have done differently.
That’s why I asked them:
“If you had the chance to start over, what would you do differently?”
And now, here we are with the answers from 21 newsletter operators, including 15 Substack bestsellers.
Here’s a glimpse of what you’ll find in this issue:
The growth strategies many creators would tweak if starting again
Why some would change how (or when) they approached monetization
How content choices play a bigger role than expected
Why quite a few wouldn’t change a thing
and more…
Let’s dive in. Enjoy!
Shoutout and many thanks to , , , Chris Cerra, , , Matt Brown, Brennan Dunn, Dmitri, Adriana Tica, , , , , , , , , , , for sharing their insights with me.
GROWTH
“I’d have leaned into Notes and Chat earlier.”
Between being pregnant, feeling sick every single day, and having a kid in the house, it’s a miracle I managed to publish multiple newsletters a month and show up on Medium every single day (thanks to batch creating, of course!)
As for the community aspect?
I could’ve definitely leaned into Notes and Chat way earlier instead of just writing about it.
But hey, live and learn, right? If anything, it just proves that even in total chaos, showing up consistently pays off.
“I’d have done cross-promos more aggressively.”
I’d start doing cross-promos as soon as possible and I’d promote it more aggressively from day one.
It took me far too long to understand how much work growing a newsletter really is.
“I’d have been more consistent on LinkedIn.”
I do know now that revenue grows faster when I spend a little time on LinkedIn every day, so I would try to be more consistent with that.
“I’d have started growing with paid ads sooner.”
Wait longer to launch the paid newsletter, and start running IG and FB ads sooner.
When the pendulum swings back and the focus becomes converting more users to be paid, it’ll probably be part of a wider shift: re-evaluating the welcome sequence and introducing or adjusting drip campaigns triggered by any clicks on the premium links that don’t convert, etc.
One strategy I’m sure I’ll explore in the future (but not in this next phase, is targeting existing (free) subscribers to upgrade using paid social ads.
“I’d have been more careful with partnerships.”
Be careful who I partnered with.
We do this thing where we see people who have a bigger audience and get flattered if they want to collaborate with us, but we really need to make sure our values and integrity are aligned.
I see promotion as everything you do in public, so if you support writers just because they have a big following, it can burn you later.
CONTENT
“I’d have focused more on serving my readers.”
Analog.Cafe was built to promote and showcase creative photography. This website still serves that purpose, but it is mostly discovered by people looking for camera reviews and guides.
If I were to start over, I’d focus more on serving the readers (while still publishing creative, unprofitable content) and do a better job with product photography.
“We’d have ensured our lead magnet was related to our products.”
We’d probably ensure that our lead magnet was directly related to the products we were trying to sell.
For many years there was a mismatch. But we’re now confident that our updated report (coming April 2025) will entice professional fundraisers to subscribe to The Nest Egg and that our free and paid content is accurately targeting the right audience.
MONETIZATION
“I’d have set a clearer monetization strategy.”
I have really enjoyed my journey because I learned by doing and grew thanks to my own experiences and mistakes.
I wasn’t in a rush to grow, but in retrospect, I wish I had been more strategic from the beginning and more deliberate about monetization.
“I’d have integrated my newsletter into my business better.”
I probably would have set it up differently looking back so it better integrates with at least one part of my business.
Now, we spend a lot of time trying to position it so it doesn’t take away from anything else, and I’m not sure we do a great job of it all the time. I would really look into where this stood on my value stack and wonder if it was worth it.
Frankly, I’m not sure it would be in the end. Maybe I shouldn’t say that in an interview promoting successful newsletters, but this is easily the hardest thing I’ve ever had to sell, and I have sold a book about a pickle drawn by me (and I can’t draw).
That said, if I knew how hard it was to make a business work, any business work, I’m not sure I would have done any of it. I’m not one of those people who magically makes money in their sleep. I grind for it, and it’s exhausting, even though it gives me a ton of freedom.
Personally, I would have been a lot more calculated about how exactly Create & Sell would play into RightMessage.
Right now, I sort of just expect that longterm readers of C&S will eventually become customers of RightMessage.
“I’d have charged a higher price for paid subscription.”
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