Newsletter Circle is the newsletter all about newsletters for indie creators.

👉 Every Sunday, you will read the unique journey of a different newsletter creator and learn more about how to start, grow and monetize your own newsletter.

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🎙CREATOR INTERVIEW

Today, we’re welcoming Jeremy Caplan, who is the Director of Teaching and Learning at the City University of New York’s Newmark Graduate School of Journalism and helps journalists all over the world develop exciting new projects. He is an ex-reporter in Time Magazine and an ex-violinist.

His newsletter Wonder Tools is his creative outlet. Every week he helps his 22,500+ subscribers find and make the most of amazing online resources. He continues to build it with a learn-in-public approach.

In our interview, you will learn;

• what entrepreneurial journalism is and the role of newsletters in the evolving media landscape

• how he started Wonder Tools and grew a mail list with over 22,500 subscribers in 3 years

• monetization strategies and how he manages paid subscription

• the tools and his weekly process

• mistakes, learnings and future plans to boost growth

and more on his experience as a newsletter creator.

As a huge fan of Wonder Tools, I’m so excited to share Jeremy Caplan’s journey. Thanks to his comprehensive answers, our interview is packed with so much valuable insights and regardless of where you are on your newsletter creation journey, you will find a lot to learn.

Let’s start!

🏷 NEWSLETTER IDENTITY CARD

🛠 Tool Stack

• ESP → Substack

• Writing → iA Writer, GDocs, Lex.page,

• Design → Canva, Beautiful.ai and Keynote

• Sponsors → Swapstack (have experimented with Paved and

  Post-Apex)

• Surveys & Feedback → Tally, Typeform, OpinionX and Google Forms

• Website → Substack for newsletter; Tilda for personal site

• Media Consumption→ Readwise Reader for newsletters, online reading; Snipd for podcasts

👋 MEET THE CREATOR

Welcome Jeremy. Let’s start with getting to know you.

Hey there! I'm Jeremy Caplan, and I help journalists all over the world develop exciting new projects!

These days I’m Director of Teaching and Learning at the City University of New York’s Newmark Graduate School of Journalism. I love being part of a collaborative faculty team that’s aiming to help the next generation of journalists be as great as they can be.

One of my roles at the school is leading our new Entrepreneurial Journalism Creators Program, an exciting 100-day online course that over the past two pandemic years has helped more than 100 journalists from 37 different countries start up their own niche ventures. Over the decade prior to that we selected hundreds of journalists from all over the world who spent a semester with us developing new newsletters, podcasts, and niche sites. Many of those projects have since grown into impactful ventures and I continue to advise and mentor our program graduates.

Before I got into teaching, I was a reporter at Time Magazine, where I wrote hundreds of stories about everything from digital innovation to the intricacies of low-wage work. I studied public policy at Princeton University and then went on to earn an MS in Journalism as a Knight-Bagehot Fellow at Columbia University, followed by an MBA at Columbia Business School as a Wiegers Fellow.

These days, I write a newsletter called Wonder Tools, where I share the most useful digital resources — the kinds of sites, apps and services that help make life a tiny bit better.

Fun fact about me: in a past life, I was actually a violinist! These days, I'm happily settled in Manhattan with my wonderful wife and our two amazing daughters. You can find me on Twitter @jeremycaplan, and my website’s at jeremycaplan.com.

🥁 START

What is Wonder Tools all about?

Wonder Tools is a free weekly newsletter that helps you find and make the most of amazing online resources. Every week so many new sites, apps and services launch — the explosive growth in quantity and quality. It can be hard to sort through all of it and determine what’s worth your time and money.

Wonder Tools helps you cut through all the clutter and PR to find what’s genuinely useful. You can use the posts to sharpen your workflow, strengthen your toolkit, and find more time and space in your day for creativity.

What is entrepreneurial journalism?

And as a journalist teaching entrepreneurial and digital journalism, how do you see the role of newsletters in the evolving media landscape?

Entrepreneurial journalism is a field of study and practice focused on sustainably serving the information and community needs of underserved customers. Entrepreneurial journalists are devoted to serving readers, listeners, viewers and other media consumers in creative, constructive ways and filling in gaps in the media ecosystem, particularly for niche communities.

Newsletters play a valuable role in the evolving media landscape because they allow writers to reach readers directly without an algorithmic intermediary.

They allow those of us who are writers to write in an authentic voice and to customize the frequency, style, length, and design of our work. Newsletters also allow writers to earn money for their labor through a variety of revenue streams. These include direct monetization — like paid subscriptions, sponsorships, and syndication, as well as indirect methods, such as coaching, speaking, consulting, advising, and providing other professional services.

Why and how did you decide to start the Wonder Tools newsletter in the first place?

With pent-up energy early in the pandemic, I felt compelled to create something new to share with people. Amid the loneliness of that period, I wanted to share the digital resources I was exploring so others could potentially benefit and to nudge myself to document my own exploration and learnings. As a teacher who has counseled hundreds of past students on their niche entrepreneurial projects, it was time for me to adopt a beginner mindset again and to learn by doing to strengthen my own teaching.

How did you gain your first 1000 subscribers?

It took 88 days. I wrote two guest posts for a newsletter that had a big audience. Each time I wrote a post, about 250 readers signed up for Wonder Tools.

I kept thinking the subscription number would stop rising when it hit 100 or 500 — when I had found the group of people who care enough about sites, apps and tools to sign up — but that didn’t happen.

🚀 GROWTH

22,500+ subscribers in 3 years is a huge success. Which growth channels do you mainly use?

Cross-promotions have been the most fruitful avenue of growth for Wonder Tools. I like referring my readers to good newsletters they may not yet know about. And having Wonder Tools mentioned in other newsletters is a great way for people to discover it. I don’t advertise or buy lists or use tactics that would feel too self-promotional.

I do show up every single week with the best work I can do for readers. I boil down weeks or months of experimentation and exploration into a five-minute weekly read. People appreciate concise consumable newsletters that have actionable info. They share that type of resource with friends, colleagues and their own readers. So the consistent effort I put into the newsletter has been a key part of its growth.

What are the most effective growth strategy & channels?

Being mentioned by other newsletters and media outlets has been hugely helpful in growing the newsletter’s readership. Beyond that, when I give talks, I mention the newsletter as a way for people to dive deeper into the topics I’m talking about.

How did your growth strategy evolve in parallel to your subscriber list growth?

In the early days, writing guest posts for other newsletters was helpful.

Over time, cross-promotions have been most helpful. I’ve paid for one sponsored message, which was low-cost and remarkably effective in driving new sign-ups. That’s the only paid marketing I’ve done.

Regarding growth efforts, what would you do differently if you had a chance to start over?

I might have experimented with interviewing/including some well-known people early on, given that their sharing might have helped further boost early growth.

What are your plans to continue growing?

I’ll continue with cross-promotions with relevant partners; I’ll continue experimenting with other formats, including audio and video, which allow me to show what I’m writing about in new ways and which may help reach people in new channels; I may explore new partnerships to reach people who don’t read Wonder Tools.

💸 MONETIZATION

How do you make money with your newsletter? Can you share the breakdown of your revenue streams?

• Sponsored Messages

  I include sponsored messages to introduce readers to interesting new services and to let service providers reach new people who might be interested in what they do.

• Paid Subscriptions

  I recently opened up a paid subscription option to provide bonus value to loyal readers. They get full archive access, live office hours, handouts, tipsheets, site lists and resources, as well as free access to try out new tools.

• Syndication

  I have a paid syndication deal to republish my pieces on Fast Company. I’m in discussions for additional syndication.

• Coaching

  I have a small number of private clients who I help to work more creatively, productively enjoyably and effectively.

• Speaking and Training

  I speak to various kinds of groups — some of those engagements are related to the newsletter.

How did your monetization strategy evolve in parallel with the growth of your subscriber list? Could you take us through your monetization journey?

I’m fortunate to have a full-time job (Director of Teaching & Learning at the CUNY Newmark Grad School of Journalism), so this is a side project for me.

I see it as a learning and sharing journey more than a money-making one. Having said that, I started exploring monetization when people reached out to me about sharing a sponsored message in the newsletter early in the journey once I had hundreds of subscribers. More recently, I added a paid subscription offering so I could provide some additional things to readers who want to dive deeper into some of what I write about.

Can you elaborate a bit on how you manage paid subscriptions?

I had about 20,000 subscribers when I added a paid subscription option. In retrospect, I would encourage people to offer a paid subscription early on because having both free and paid options doesn’t necessarily impede growth. It signals that what you’re doing has value.

Substack allows for a pretty simple suite of offers — monthly, annual and founder. I chose to discount the annual offer — $72/annual — from the monthly price — $8/monthly to incentivize loyalty and commitment and to land at around the price of a nice coffee once a month as part of an exchange of value and a way for people to support the newsletter.

The founder package is a way for people who have a little bit more to share to allocate whatever amount they see as suitable.

Do you have any plans to increase your revenue?

If the number of paid subscriptions continues to grow steadily over time, that will yield increased revenue. And sponsored messages may grow in value over time as well.

I also enjoy coaching, consulting and other opportunities to engage with people in real-time and in living color, so I’m open to finding new ways to do more of that. I also am interested in creating some new supplemental asynchronous materials that people can watch/listen to flexibly, which might have a revenue side, though that remains to be seen.

📩 E-MAIL SERVICE PROVIDER

Why did you choose Substack? Pros and cons?

I liked the simplicity and the focus on writing and reading.

Many other newsletter platforms at the time were focused on marketers— like Mailchimp, Constant Contact, SendinBlue— are focused on serving marketers. Their user-interface and feature set is not aimed at journalistic newsletters or serving writers. Substack was also free, so it felt easy to experiment with. Finally, I knew and liked Hamish McKenzie, a Substack co-founder who had visited my class to speak with students in the past, and I trusted that he would continue strengthening the platform over time, which has definitely turned out to be true.

In terms of limitations, Substack doesn’t yet have plug-ins or automation, so you can’t automate a welcome series of emails, for example, or easily plug in a referral program. But the recommendation system it has is great, so lots of my subscribers are referred to Wonder Tools from one of 90+ Substack newsletters that recommend it. That helps drive grow readership in a meaningful way. And I can, in turn, help others gain subscribers when I recommend their newsletters, so it’s helpful in building a supportive ecosystem.

🧩 SYSTEM & PRODUCTIVITY

What is your typical weekly process from creating to distributing a new issue?

I wrote about my workflow and toolkit for writing the newsletter after writing my first 100 posts, and my process continues to evolve.

Basically, I have a few phases of development for newsletter posts.

• Experimentation and exploration: I’m continually trying out new sites and apps, whether for note-taking, making visuals, multimedia-editing, managing my calendar or anything else that’s part of my day-to-day creative workflow. When I find and try something that turns out to be useful, I’ll plan a post around it.

• Drafting: I’ll draft a post in rough form by outlining what’s most useful about this site or app. I’ll list out use-cases— things I’ve found it useful for — as well as the most helpful features, with examples. Then I’ll note the limitations it has and alternatives. I want a reader to be able to quickly get a sense of what this site or tool is, why it’s useful, what to use it for, what its limitations are and its alternatives. That way I’ve saved the reader the time they would have had to spend in figuring all of that out for themselves, so they can focus their creative energy on their primary work and offload the experimentation and exploration to me.

• Polishing: Once I have a draft, I’ll let it sit for a while so I can get a fresh view and cut out a big chunk of the excess material that’s flabby or less relevant. I’ll add in screenshots or a screen recording video to provide a visual sense of the site or service. I’ll add relevant links, examples and resources to make the post as useful as possible.

  At any given time, I have a handful of posts in development. Some are in the experimentation phase, some are in draft form, and some are in the process of being polished. I’ll move up a post when it’s ready, or hold back I post when I’m still experimenting or learning about a tool, or when there’s something new I want to compare it with.

  When I’ve managed my workflow well, I’m working a few weeks ahead, meaning I have between 2 and 4 completed posts ready to publish. Sometimes, though, I end up racing to finish a post the night before I publish it.

How do you explore and create time to try new tools continuously?

I love trying new sites and apps because I’m always curious about how something can be done in a new and more creative, efficient or enjoyable way. I love discovering new services the way other people like discovering new foods or songs or shows. (I like those too). I wrote about some of the ways I find new stuff. Over the past year, I’ve received more outreach from people creating new things, which helps create a pipeline for seeing and trying what’s new.

I’m particularly interested in new note-taking and personal knowledge management tools these days, because we all have SO MANY notes and so much info to juggle, so I’m exploring lots of tools in that category these days, from Capacities, Anytype and Bloks to Mem, Tana, Obsidian, Reflect, Logseq, etc.

🎢 NEWSLETTER EXPERIENCE

How did writing Wonder Tools contribute to your life professionally & personally?

Wonder Tools is a creative outlet for me. I used to write for Time Magazine, and after that other publications, and got into the rhythm of writing regularly. Now I have more freedom than ever before to choose what I write about.

I love meeting new people through the newsletter and it’s opened up new professional opportunities for writing, coaching, speaking, and training.

I’ve learned a lot about the process of developing, growing and monetizing a newsletter, which is helpful for the teaching I do.

What is the most challenging part of writing a newsletter and how do you handle it?

Creating something I feel good about consistently, week after week, for 150+ weeks is challenging. This is a side project for me, so my day-to-day work is my priority — my newsletter has to fit in my evenings/weekends/early mornings/late nights and that can be challenging when I have to make trade-offs.

Can you tell us one big mistake you made during your newsletter journey?

A few mistakes: I started my newsletter long after I should have.

I haven’t devoted enough effort to finding collaborators to reduce the burden of continual content creation.

I turned on paid subscriptions later than I should have.

I have too often underestimated how much time something would take to create at the level of quality I’m aiming for.

🎯 FUTURE

What is next on your newsletter journey? What is your ultimate goal/dream about Wonder Tools?

I’m looking forward to experimenting with new formats.

I’d like to learn more about creative new ways to develop, create and share audio, and to learn more, I’ll experiment more. With video, I’d like to create workflows that allow me to show and share things I’m learning through efficient videos. That way I’ll learn-by-doing while also sharing and building on the text foundation of the newsletter.

I’d like to continue refining my workflow so I can spend more time on the exploration side and creative side and less time on the technical aspects of the newsletter.

I’d love for Wonder Tools to continue being a creative outlet where I can learn-in-public, explore new tools and share the best of what I’m finding for the benefit of readers and be useful in my own small way. And I’d love to find new ways to collaborate with others through Wonder Tools.

📌 RECOMMENDATIONS

What would it be if you had the right to give one piece of advice to aspiring newsletter creators?

Write less. Use the Smart Brevity approach to focus on the core thing you have to say. Cut out at least 10% of every post before you send it. Cutting 20% is better.

Narrow your subject. Focus on a distinct subset of things that you care about so you can delve deep in a distinct way.

What are your favorite newsletters that you can’t wait for the next issue?

• For the Interested by Josh Spector

• Next Draft by Dave Pell

• The Rebooting by Brian Morrissey

• One Useful Thing by Ethan Mollick

• Brain Pint by Janel Loi

• Creativerly by Philipp Temmel

• Product Hunt Daily by Product Hunt team

• Ness Labs by Anne-Laure Le Cunff

• Recomendo by Cool Tools team

• Ben’s Bites by Benjamin Tossell

👋 FINAL WORDS

I’m hosting periodic live online “potluck” gatherings with newsletter writers where we share tips and trade questions — drop me a line if you’re interested in participating.

Thank you so much, Jeremy. We’ll be excited to continue discovering the most amazing resources with you and look forward to seeing the new formats that you’ll experiment.

🔗 Where to find Jeremy Caplan and his work

• Wonder Tools Newsletter

• Website

• Twitter

• LinkedIn

• New EJ Program

🔎 3 Popular Issues from Wonder Tools

• Wonder Tools 🔖 The best new reading app

• Wonder Tools 🤖 7 ways to Use ChatGPT

• Wonder Tools 🏆 Best of 2022

That’s all for today. Thanks for reading.

See you next week.

Ciler