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Jeremy Caplan Discusses Being Too Focused on Writing, Creative Productivity Tools, and Growing his Wonder Tools Newsletter

I was aiming to give myself a space to share some of the stuff I love using — the sites and apps I find useful, because I found that many of my colleagues didn’t know about resources that I thought might be super-useful for them.

- Jeremy Caplan, Wonder Tools

Jeremy Caplan moved from journalism into teaching, and was looking forward to having a space that was open and free and flexible for him to choose what he wanted to write about.

He also wanted to learn more firsthand about the process of launching, developing and growing a small niche newsletter since he oversees a program all about helping journalism creators develop new ventures - the Entrepreneurial Journalism Creators Program at CUNY’s Newmark Graduate School of Journalism.

So, he started Wonder Tools, hoping to figure out three things:

  1. What to focus on
  2. How to style and design a Substack post
  3. What length and tone to take, and how much to include in each post

Here’s what he shared with on his biggest learnings throughout the process:


How do you grow your newsletter?

In terms of how I’ve grown the newsletter from 0 to >5.2k readers this year, the 2 biggest tactics:

  1. Partnering with other newsletters - by writing guest posts, or swapping mentions with other newsletters. This has led directly to new sign-ups each time I write for another newsletter or another newsletter mentions my newsletter, so I consider it to be the most useful tactic.
  2. Aiming to write consistently useful posts that are somewhat evergreen so people share them, return to them, spread them and subscribe and tell others to subscribe.

What are the hardest concepts for creators to understand about building newsletters?

People are often super-focused, understandably, on writing. 

More specifically on researching, writing, editing and publishing. But that’s only one piece of the three-part puzzle. 

The 2nd piece is community and growth. 

The third piece is revenue and sustainability. 

So spending 80-90% of your time on the content means foregoing the opportunity to find new avenues for growth and sustainability. 

At the beginning, creating great content and improving upon it is crucial, because that’s the foundation on which everything else rests. But as you start to get into a content rhythm and validate that what you’re producing is of value and resonates, it’s important to start allocating time, effort and focus to those other two crucial legs of the stool if you want to build something that’s more than just a hobby for the pleasure of your own writing.

What does the process for creating your newsletter entail?

For my newsletter, I typically focus each weekly post on a particular category of digital site or tool. 

For example, recently I’ve written posts on newsletter creation tools, resources for creating graphics and drawings, presentation tools, brainstorming and whiteboarding tools, etc. These are at https://wondertools.substack.com/archive.

The process for creating my newsletter entails the following phases:

Step 1

Adding to my curiosity and exploration list. This is a list of I’m trying out, using in new ways, or learning about. 

For example, right now I’m exploring for future newsletter posts, among other things: Time tracking apps and services to get a better handle on how my time ends up being allocated (vs how I WANT it to be, or how I assume it is). I’m exploring new Zoom apps, new privacy, and security tools, and sites and apps for sending pictures and cards and gifts to friends and family.

Step 2

Spending time using various sites and apps to learn what they’re useful for, find their limitations and costs, seeing how other people use them, and seeing how they work in my own workflow.

Step 3

Outlining a few key thoughts on whichever category I’m focused on.

Step 4

Expanding on the outline by adding key points, thoughts, and examples

Step 5

Adding graphics, images and buttons (Subscribe, Comment, Share) and sponsored message if I have one for that post.

Step 6

After a pause of a couple of days, taking a fresh look at the post and editing it again, refining it, shortening it and clarifying the text.

Step 7

Final proofreading and scheduling it to be sent — mine are posted Thursday mornings at 7am ET

Hopefully that gives you a little window into the production process! Sometimes I spend a few hours on a post, sometimes many hours, if I include all the time spent trying various tools.

Can you expand on your process for partnering with other newsletters?

I’ve made a point of reaching out to newsletter writers I like and whose work is in a related arena, and I’ve had writers reach out to me. 

I’ve also met writers through Swapstack’s Slack. And because I want to be true to myself and remain authentic to readers, I’ll only do that with newsletters were a collaboration makes sense. 

It’s turned out to be a great tactic, and I’ve seen it work for other newsletter writers as well. (It works for podcasters to be mentioned on other podcasts as well, by the way, or to guest host an episode, etc).

What do you do when a piece falls "flat" or doesn't fully resonate with your readers?

When a piece falls flat, I try to think about why it may not have resonated. 

Here’s an example: I wrote a post about tools for Twitter that had a lower open rate than the pieces before and after it, for example, and it may have been that my readers just aren’t that curious about Twitter apps and services, or that the headline didn’t make it seem interesting or useful. 

In general, I’ve found that the open rate has hovered around 40% pretty consistently. 

Open rates were closer to 50% in the early days, but drifted toward 40% as more people signed up. Some of the later sign-ups over the year probably had lower interest levels than those close enough to me to find it early on.

If the internet didn't exist, what would you be doing?

I would be doing two things: Teaching and Playing Violin. Neither requires the Internet, and both are passions of mine. 

I would still be teaching at CUNY’s Newmark Graduate School of Journalism in New York, where I teach now, and I probably would be playing more chamber music and reading instead of Substacking.

What are the most under-loved creative productivity tools on the market right now? And in your opinion, which are the most over-hyped?

Under-appreciated creative productivity tools that I like include: Eagle, Craft, Coda, Projector, Copy.ai (I could go on & on….) and over-hyped ones include Microsoft Teams & Mailchimp(sorry Microsoft and Mailchimp fans).

Are there any major gaps you see in the productivity tool landscape right now? Or areas that haven't seen much innovation as of late?

One thing I’m eager for is more tools for personal knowledge management (PKM). 

Specifically, within that domain, tools for managing the overwhelming ocean of content and connecting threads from across content creators. 

This addresses the following challenge for any ambitious content consumer: on any particular niche topic in any given week there are a sizable number of podcasts, newsletters, YouTube channels, sites, books, magazine and newspaper articles, Netflix shows, Medium publications, Whatsapp groups, Discord and Slack instances, and dozens of other content worlds…. tools for helping filter, curate, annotate, draw connections between, highlighting surprising or new takes or updates. 

There have been some useful tools and experiments like Nuzzel, Mailbrew, Joggo are interesting, but there is so much more to be done in this arena imho.

What are the niche newsletters and communities that you're most impressed by?

A few to start with: 

I’m a fan of Anne-Laure Le Cunff and her Ness Labs community is neat.

I like Janel’s Brain Pint.

I like the Swapstack community and the Substack communities I’m part of. I have way too many newsletters that I love as reflected by the way-too-many Substacks I subscribe to.