Why I switched from ConvertKit to Substack

Also: how to get your first 1k subscribers (Stew's Letter #93)

Howdy, everybody – happy Tuesday.

To all the new subscribers this week, welcome.

It’s a beautiful day in Brooklyn, but I’m locked inside… my allergies have returned with a sort of rapture-like presence.

I’m not sure what people like me did before the invention of Claritin, but I suspect they died young. I’m writing this with bleary eyes and an unenviable antihistamine high (most disappointing drug ever).

This week’s email is short and sweet, so let’s get to it!


Why I switched from ConvertKit to Substack:

Last week, a few of you noticed that this email looked different than usual.

I was flooded with questions about why I left ConvertKit and am publishing on Substack now.

In case it’s helpful for other people considering a switch, here’s my answer:

  • I needed to focus on just writing. I was wasting way too much time tinkering with my old setup, which ran on ConvertKit and WordPress. The simplicity of Substack reduces my natural temptation to tinker instead of doing the thing I need to do.

  • My ConvertKit setup was terrible for growth — the newsletter was not very shareable, whereas Substack makes it dead-simple to share individual emails.

  • Finding my backlog of newsletters was clunky. Substack makes my backlog visible and searchable. It also automatically spotlights my most popular posts.

So far, I have no regrets.

My open rates did tank last week (dropped from 50% to 30%), but I suspect that’s because I didn’t warm up this new domain before blasting out my first email.

I plan to keep using ConvertKit at Foster because we need a more robust set of email features, but Stew’s Letter will be happily housed here until further notice.


How to get your first 1,000 subscribers

Rich people talk a lot about how hard it is to get your first $100,000. Charlie Munger said it best: “the first $100,000 is a bitch, but you gotta do it.”

After you land your first chunk of cash, though, accumulating more of it becomes easier. Not necessarily easy, just easier.

The same thing is true of building up an audience online…

Growing this email list to 1,000 was an enormous struggle. But now that I’ve done it, it’s become a bit easier to grow. I have some built-in distribution for all of my work, which guarantees that my best work is more likely to get picked up and spread organically.

But it was a long road getting here, and I’m now realizing that my path here was pretty common…

This morning, I published a thread breaking down the most common tactics that some other writers I’ve talked to used to get their newsletters off the ground. I hope this saves you some time on your own journey:


Join Foster in June:

We’ll announce some of this publicly soon, but wow…

We’ve been busting ass behind the scenes at Foster working on a product that we think will help just about anybody on the planet write more interesting things.

We’ll be rolling it out exclusively to our existing members long before we do any sort of public release.

If you’re planning to invest more in your writing this year, you should consider joining us this June.

We just opened up applications and you can apply here.


Other Stew’s Letter Things:

  • Rice Mountain update: I’ve got one big update this week. Salim (Sound’s founder) has generously offered to swap out the current waters we have in storage with some in their new product line. This will 1) give us access to some fresh-looking new product and 2) will push out the expiration date of the waters, giving us more time to land a better trade. With that, this trade is drastically de-risked.

  • Fire TikTok: This is a profoundly stupid joke. Bravo.

  • Finding Your Signature Move: I wrote about the incredible story Bill Grundfest – the guy who discovered and advised some of America’s most famous comedians early in their career. In a fun twist of events, Bill hooked up me and my fiance with tickets to the Comedy Cellar, which ended up being more fun than I could have imagined.