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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Here is how he describes First Class Founders:

“First Class Founders is the destination to learn the best growth tactics for founders & creators each week. Join 1,900+ entrepreneurs for free.”

🎙CREATOR INTERVIEW

Today, we’re welcoming Katie Hawkins-Gaar, who is the creator of “My Sweet Dumb Brain” newsletter that reaches 12,200+ subscribers every week.

She started “My Sweet Dumb Brain” in September 2018, a year and a half after her husband died at age 32 while running a half marathon. Since then she puts herself out there and shares her emotions bravely in her newsletter.

It is admirable how she manages to transform her pain and creates something valuable that helps others out of it. Her readers embrace life’s up and downs, face their vulnerabilities and struggles and learn to be kind to themselves with Katie. Writing heals Katie and what she writes heals her readers.

My Sweet Dumb Brain shows the strength of accepting how vulnerable we all are in our unique ways and it is a great companion on this finite journey called life.

Let’s learn how it all started and how it goes from Katie.

🏷 NEWSLETTER IDENTITY CARD

🛠 Tool Stack

• ESP → Substack

• Writing → Google Docs

• Note-taking → iPhone Notes and a regular old notepad!

• Planning → Google Docs to keep a running list of future newsletter topics

• Design → Canva (Sometimes)

• Promotional & Social presence → Instagram

👋 MEET THE CREATOR

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

Hello! I’m a freelance writer and journalism consultant living in Atlanta. In addition to writing My Sweet Dumb Brain, I advise on membership, program growth, and workplace culture for places like the News Revenue Hub and The Carter Center. I’m also the founder Digital Women Leaders, a mentoring initiative that connects women and nonbinary journalists with other journalists via one-on-one mentoring calls. Professionally, I wear a lot of different hats, but I love the variety and flexibility that freelance life affords.

Outside of my work life, I’m a mom to a two-year-old with my partner, who is a musician. We love having family adventures together—hikes, trips to the zoo, exploring new places around the city—and are slowly but surely making friends with other young families in our neighborhood. I’m also a voracious reader and love tackling home decorating and organization projects whenever I have the time.

🥁 START

What is My Sweet Dumb Brain all about?

My Sweet Dumb Brain is a weekly newsletter about navigating life’s ups and downs, all while being kind to yourself. Each Tuesday, I share a short, first-person essay about a different topic in life: usually, something I’m struggling with or feel vulnerable about. I try to sprinkle in a few life lessons and a bit of hope whenever I can. The act of writing these essays has been so helpful for me in processing my own challenging feelings or situations, and I’ve heard from plenty of readers that my words are helpful for them, too!

Why and how did you decide to start My Sweet Dumb Brain in the first place?

I began My Sweet Dumb Brain in September 2018, a year and a half after my husband died at age 32 while running a half marathon. In the time since his death, I’d amassed a ton of emotions and thoughts about grief, depression, hope, guilt, sadness, and joy. I shared some of those thoughts on social media but wanted a place where I could write more deeply and intentionally. And so the newsletter was born. It became a place to process everything I was experiencing and to share the hard-won things I’d learned with others.

You put yourself and your thoughts/emotions out there and share with thousands of people bravely every week.

How do you do that? Can you mention the healing side of writing?

This is a great question! I do my best to forget the size of my audience whenever I write. I usually try to write solely for myself—to put words to the things I’m wrestling with. If I do think about my readership, I usually pick one person I’d like to reach. It might be a particular friend I’m thinking of, or a random reader who might be going through an especially hard time. By keeping my target audience small while writing, I’m able to write much more personally and vulnerably.

Besides going to therapy and taking long walks, writing has been the most important thing I’ve done to help myself heal not only from the grief of losing my husband but also after traumatic moments like when I experienced postpartum psychosis. There’s something about taking all of the messy, swirling emotions in my head and putting them neatly into words that makes me feel calmer. In doing so, I often manage to find a lesson or reason to feel hopeful that I hadn’t seen before.

Now, whenever I have a particularly hard day or am struggling with an especially difficult situation, I tell myself that I can write about it later. It always makes me feel a little better.

How did you gain your first 100 subscribers?

Through word of mouth! A couple weeks before I published my first issue, I told people about my newsletter on social media and encouraged them to sign up ahead of the September 5, 2018 launch. I got my first 100 subscribers that way. I started My Sweet Dumb Brain on tinyletter but within a few months, moved it over to Substack.

🚀 GROWTH

Which growth channels do you mainly use? Which one/ones is/are the most effective?

The most effective growth channel, by far, is Substack’s in-network recommendation program. Recommendations from other Substack publications have brought me more than 3,000 new readers, and that number continues to climb steadily.

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

I have to admit that I don’t have much of a growth strategy! My strategy has been to show up each week and deliver solid content. I’ve done that for almost five years and it’s paid off. Besides times when I’ve announced a break in advance, I’ve never missed a Tuesday newsletter. I keep showing up, and so do my readers.

Since day one, my most solid growth strategy has centered around consistency and word of mouth.

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

Last year, we launched an Instagram account for My Sweet Dumb Brain. If we’d done that from the beginning, I think we’d have an even bigger audience and have experience using that platform in a variety of ways.

What are your plans to continue growing?

My plans are what they always have been: To keep showing up, week after week, and continue to be my authentic self. One of the things I often write about is feeling overwhelmed by technology and feeling the pressure to do too many things, which is why I hesitate to jump onto all of the latest features that Substack offers or send multiple emails a week. I keep things simple because that’s what works for me and my sweet dumb brain. I like to think it works for my readership, too.

💸 MONETIZATION

How do you make money with your newsletter? What is your monthly revenue?

I make money from paid subscriptions. We currently have just under 700 paying subscribers (out of 12,000 total readers), which is amazing! Those 700 readers bring in an average of $1,990 a month, after Substack and Stripe fees, plus the 5% we donate to a different nonprofit each month.

When and how did you earn your first dollar with your newsletter?

I announced paid subscriptions with an essay about the importance of getting paid for your work. That netted me 23 paying subscribers. The following weekend, I sent a follow-up email and 20% discount reminding readers about paid subscriptions and received 41 additional paying subscribers. It was a very successful launch!

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

I offered paid subscriptions almost a year after launching my newsletter, and after a number of friends and readers nudged me to do so.

My initial pricing was $50/year or $5/month, but I’ve since changed that to $45/year or $5/month ($5 a month is the lowest amount that Substack will allow).

I’m cognizant of the fact that I do deserve to get paid for my writing, but also that my readers have a lot of things vying for their attention—and their money! I try to keep an eye on things like my paid subscriber retention rate (currently at 74%) to make sure I’m pricing my newsletter fairly and offering content worth paying for.

What do you offer to paid subscribers?

Each Tuesday, I send out an essay to all readers. Paying subscribers receive a special expanded version of that newsletter, which includes updates about my life, reader responses, related resources, and a mental exercise for the week ahead. I also recently started mailing My Sweet Dumb Brain logo stickers to readers—to their physical mailboxes! That’s a fun treat.

Do you have any plans to increase your revenue?

I’ve been experimenting with running newsletter subscription “campaigns” a couple times a year. Instead of bombarding readers with requests to subscribe throughout the year, I’m offering specific discounts and sending more frequent pitches once in spring, once in summer, and once in the fall. It’s like a less intense version of the NPR and PBS membership pledge drives, and it’s working well for me so far.

📩 E-MAIL SERVICE PROVIDER

Why did you choose Substack? Pros and cons?

Substack makes it easy to set up paid subscriptions, so that was a real plus for me. It’s also very intuitive to use. I like how the posts appear and appreciate the extra features, like auto-generated images for social media, which we use on our Instagram page. I’m also incredibly impressed with Substack’s recommendations feature: it’s brought thousands of new readers to My Sweet Dumb Brain.

As far as cons, the Substack fees (10%) are pretty hefty. I don’t take advantage of all the new features they’ve built (like Notes, which was released this week). If I’m being honest, I find the volume of new features and speed at which they release them a little overwhelming and hard to keep up with. My sweet dumb brain needs less to do, not more!

🧩 SYSTEM & PRODUCTIVITY

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

I keep a running list of essay ideas, but I also try to keep my mind open to inspiration as it hits. I typically start jotting down rough ideas on Friday, set aside a few hours to turn those rough ideas into an outline on Sunday and turn that outline into an essay on Monday.

I try to follow the same routine every Monday morning: From 8:30-11:00a, I write and finalize my essay draft. After that, I send it to my editor, Becca, for her thoughts. During that time, I go for a walk, return home for lunch, and then work on all the paid subscriber extras. Monday afternoons are a mix of making newsletter edits and scheduling the post, plus juggling my other freelance jobs. Then, every Tuesday morning at 8:00a ET, the newsletter automatically gets sent to readers’ inboxes.

What is your weekly newsletter content distribution/ promotion system?

We share each issue on Instagram. I also try to share new posts to Twitter, but Twitter has really become a mess lately. That’s about it! Becca and I don’t put a ton of effort into promoting each post, for better or worse.

🎢 NEWSLETTER EXPERIENCE

How did writing My Sweet Dumb Brain contribute to your life professionally & personally?

I am so glad I decided to create My Sweet Dumb Brain. It’s changed my life for the better. It’s made me a stronger writer and thinker and has given me much-needed confidence in my creative abilities. I’ve always wanted to be a writer, but I quickly landed on the managerial track in my career—editing and helping others to be better writers and journalists. It wasn’t until my husband died that I was reminded that now is the time to chase my writing dreams.

The fact that I get to share my thoughts, week after week, to thousands of willing readers—and get paid for it?! It’s honestly surreal. It’s a dream come true.

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

I think the most challenging part is constantly coming up with inspiration for fresh ideas and topics to write about. Lately, I’ve handled it by owning up to my audience when I don’t know what to write. That’s been incredibly freeing.

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

For over a year, I published two newsletters a week: The Tuesday essay that went out to all readers plus a subscriber-only issue that went out on Fridays. Producing two newsletters a week took a ton of work and stressed me out, but I had convinced myself it was the only way to offer value to my paying readers.

Then, in October 2021, I created a survey for newsletter readers. One of the biggest learnings was that many of my free readers weren’t becoming paid subscribers specifically because they didn’t want another email to read each week! Moreso, my paying subscribers could take or leave the Friday issues, which were essentially a round-up of reader responses to the Tuesday essay. What everyone liked—and what everyone wanted to support—was the Tuesday essay that went out to all readers!

That’s how I landed on the model I have today: I add paid subscriber extras to the end of Tuesday essays and only send out one newsletter a week. It’s much more manageable, and it’s boosted the number of paying subscribers. Sometimes doing less really is more!

🎯 FUTURE

What is next on your newsletter journey? What are your short-term and long-term goals?

I’m not entirely sure. I’d love to keep writing My Sweet Dumb Brain for as long as I can—and I’d love for the newsletter to become more successful revenue-wise. In the short term, though, I’m managing as best as I can, week to week. I’m juggling a lot outside of writing my newsletter (working several demanding freelance jobs, plus raising an also demanding but very cute toddler), and I don’t have as much capacity as I’d like for thinking big-picture about the newsletter.

One thing I do every summer is taking six weeks off from writing essays. That’s usually a time when I can breathe and think about the newsletter in a different, more expansive way. I’m looking forward to that upcoming break!

📌 RECOMMENDATIONS

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

Write for yourself.

Write the newsletter that you want to read.

Create the offering that you’ve been looking for. I guarantee there are other people who are looking for that very same thing.

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

I just love the way that Anne Helen Petersen thinks.

I want to move into Kelton Wright’s impossibly charming log cabin.

I always feel happier after I read R. Eric Thomas’ words.

👋 FINAL WORDS

Thank you for inviting me to do this interview! It’s an honor.

Thank you so much, Katie. You are a true inspiration and thanks for helping so many people to be better at processing feelings. We all need it.

🔗 Where to find Katie Hawkins-Gaar and her work

• My Sweet Dumb Brain Newsletter

• Website

• Instagram

• Twitter

• LinkedIn

🔦 Circle Spotlight - From You

Matt Ragland shared a solid list of newsletter operators and experts that you should follow. I’m honored to be included alongside some of the best names in the newsletter space. Thank you Matt!

👇 Check it out.

That’s all for today. Thanks for reading and don’t be shy to leave your comment by clicking the below button.

See you next week.

Ciler