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.

Hi, my favorite group of people in the world, a.k.a Newsletter Circle subscribers 👋

I’m here at your service with the 14th issue, another magnificent interview.

As you may know, I’m fully dedicated to Newsletter Circle and learning more about newsletter business every single day. So, in addition to doing interviews, I love writing and talking about newsletters.

Here is one of my tweets from the last week. Don’t hesitate to show some love if you enjoy reading it. You know what I mean👍

🎙CREATOR INTERVIEW

Today’s interview will give you a lot to learn and digest about growing your newsletter (cough*as always*cough) while putting a smile on your face.

Jeff Maltow is an experienced leader writing a newsletter about leadership. Despite his solid background and huge success as an entrepreneur, he manages to maintain his humble approach.

As a creator, he has a unique writing voice and excellence in expressing himself and he manages to inject humor into his creative work successfully.

In addition to how he started and grew his newsletter successfully, you will also learn details about;

• Why he failed in his attempt to start a paid subscription

• A detailed evaluation of Substack at the time it was launched vs. current

• How he leveraged his newsletter to build a consultancy business

• His growth plans on his way to “mission 100,000 subscribers”

Let’s start!

🏷 NEWSLETTER IDENTITY CARD

🛠 Tool Stack

• ESP → Substack but moving to Convertkit.

• Writing tool → Ulysses 

• Note taking & Idea Capture & Planning → Ulysses 

• Design → Canva 

• Growth → Swapstack and Sparkloop 

• Website & SEO → WordPress 

• Hosting → WPEngine 

• Analytics → Google Analytics

• User Journey → HotJar 

• Podcast Recording → Riverside 

• Social Media → Taplio 

• Surveys → Typeform 

• Payment → Stripe

👋 MEET THE CREATOR

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

Hi, my name is Jeff. I have a wife, a daughter, a dog, two cats, four fishing rods, three bicycles, an electric motorcycle and I am on day 240 of finishing consecutive New York Times crossword puzzles.

I grew up on the east coast of the US, primarily around New York, Washington DC and Boston. Let’s average it out and just say I grew up in Connecticut. That’s easier.

I come from a family of entrepreneurs and started my first business when I was 11. My daughter just beat me and started her first business at 10 1/2.

I am intensely curious about almost everything. I love learning. I read over 70 books per year and my brain has stored so much useless information that I’m really great at cocktail party banter.

I went to school in upstate New York and then jumped in my VW Rabbit and drove to Los Angeles to be in the music business. I worked with some pretty amazing musicians and eventually started a record company that eventually got acquired by Interscope/Universal Music.

The marketing I was doing for my bands eventually morphed into a separate marketing agency called SG Marketing. We developed go-to-market strategies for Fortune 1000 companies like Kellogg’s, Citi, Kraft and others. That company got swallowed up into Alloy Inc, a marketing and media conglomerate, where I became General Manager.

Eventually, I left to start imATHLETE, a sports-centric SaaS platform that got acquired by Gannett Media in late 2019.

After all of my years of making a ton of mistakes while working in big and small organizations, I’ve finally learned how to build a successful company and what it takes to be a successful leader.

Since my last company got acquired, I’ve been hired as a consultant by companies to help them transform and scale their businesses.

I’m a consultant, author, speaker and part-time pain in the a**.

You can learn more about me here.

Jeff’s creator cacoon:

 “Here’s a picture of my desk in a picture of my desk in a picture of my desk.”

🥁 START

What is By Title Only all about?

The name By Title Only refers to my belief that successful leadership has nothing to do with a person’s title. Successful leadership is about one’s behaviors and attitude toward how to treat other people.

I know a fair amount of people who have impressive titles - meaning they have the title of Director, VP or CxO - but their behavior is far from successful leadership. They are leaders by title only.

It may not be the best name for a newsletter since I have to explain it, but I thought it was witty at the time.

Why and how did you decide to start the By Title Only newsletter in the first place?

I’ve been a published journalist for over two decades and have written hundreds of magazine and newspaper articles. In 2020, shortly after the onset of COVID, I noticed a lot of companies were struggling with direction and communication. I began writing some articles/ideas and sending them out to my then-clients to try to help them stay focused and on track.

It turns out that I got some very positive feedback, so I started writing more regularly (2-3x per week).

My audience at the time was primarily within the endurance sports industry. However, after I got my first 3,000 subscribers, I began to expand my focus to leadership in general and not be industry specific.

The fact is that leadership lessons don’t have any industry boundaries. The general habits of great leaders are, for the most part, universal.

I soon realized that there aren’t many leadership newsletters that do what I do, which is:

• Make you completely rethink your daily habits

• Provide insights in a funny way that keep you smiling and laughing

• Tell stories to keep you engaged

• Appeal to leaders at all-sized companies, from the solopreneurial start-up to the corporate behemoth.

Can you take us through the process of creating the first version of your newsletter?

The newsletter was originally called “I Am Jeff”. I had a series of YouTube videos and random articles that were specifically catered to companies in the endurance sports industry. That had been floating out there for a year or two. It started off with videos to promote my company. But it soon morphed into videos and articles that help people drive growth.

Once COVID hit, I got inspired to talk about the companies I saw doing great things and those not doing well at all. It was a somewhat natural extension of my “I Am Jeff” voice, so I kept calling these ramblings “I Am Jeff”.

From this, the BTO newsletter was born.

I had always felt uncomfortable with the name “I Am Jeff” for the newsletter. It felt too self-centered and positioned me as the know-it-all, which I’m not. As I mentioned above, I’m just curious to learn. Sure, I sometimes write stories from my life, but in the end, it’s about the reader, not me-the-writer. So in 2021, I changed the name to By Title Only.

How did you gain your first 1000 subscribers?

My following started with the aforementioned “I Am Jeff” videos and articles. Those were primarily directed toward my company’s client base. That base allowed me to get above 1,000 subscribers very quickly. From there, I continued to expand.

🚀 GROWTH

Which growth channels do you mainly use?

This is a really timely question because I am altering my growth strategy right now. I originally hosted the articles on Hubspot. However, Hubspot is like the Tesla of CRM/marketing. At the time, I didn’t need to pay for all the bells and whistles of a Tesla-like CRM - a good solid VW Jetta was all I needed.

So I moved to Substack for the newsletter. Back in 2020, Substack didn’t have the tools they do now, so I did a bunch of joint promotions with other newsletters. That worked well, though word of mouth was definitely my best channel.

Since my newsletter is free, and Substack is very much about a closed environment (they don’t integrate with other software), I am currently moving my newsletter and growth channels off of Substack.

I built a website with Wordpress and my newsletter is there.

I just started using Swapstack and Sparkloop for promotion on other newsletters. And I’ve enlisted ConvertKit for marketing automation.

On top of that, I’m building out a variety of new offerings (quizzes, courses, etc.) to bring people into the By Title Only ecosystem.

I’m also very active on LinkedIn.

What are the most effective growth strategy & channels?

So far, promotions with other newsletters have been, by far, the most effective growth strategy. 

Sometimes I do paid placements, and sometimes it’s just working out a trade.

I’m just diving deep into the Sparkloop offering and I’m very optimistic that it will drive further growth.

I also spend a fair bit of time posting on social (currently LinkedIn and soon to be YouTube). That steadily drives new subscriptions.

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

Word of mouth amongst my existing client base was absolutely the most important in the beginning.

As the subscription list began to grow, joint promotions with other newsletters and my social engagement then became the most important channels for growth.

Now that I’m above 6,000 subscribers, I know my voice and I know my core audience, the paid promotion strategy has already proven to be highly successful because I can target the exact reader I want.

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

I love being an early adopter, so I was very early on with Substack. Unfortunately, I believe that stunted my early growth. At the time I moved to them (in 2020) they had very few marketing tools - they didn’t even have the referral network that they have now. Over the past 6 months, it seems that they’ve really focused on creating more robust growth tools. However, the sophistication isn’t yet there for mid-size and larger newsletters to compete with offerings from, say, Convertkit and Sparkloop.

If I were starting my newsletter again in 2020, I wouldn’t have gone with Substack before they really built out their tools. That said, if I were starting a newsletter today, Substack is actually a really good place to start.

What are your plans to continue growing?

I’m investing my efforts in a few different things:

1. Advertising on other newsletters (via Sparkloop)

2. Launching a new podcast that will be on YouTube as well as all the podcast networks

3. Creation of lead generation tools, like quizzes and white papers

4. Creation of courses and MasterClasses

💸 MONETIZATION

How do you make money with your newsletter?

In 2021, I launched a paid version of the newsletter. Though I got about 100 paid subscribers pretty quickly, I realized it was a bad move. I didn’t have the time to really create a compelling offering for those subscribers, so after 7 months, I canceled the paid version and refunded the subscribers.

In 2023 I began doing some advertising. This is my sole direct channel for revenue generation. I’ve only been doing it for a few months, so there’s not a ton of money to be made. If I make $1000/month now, I’d consider that a good month. I expect that to increase as I get more educated about it.

The newsletter is really an indirect promotion of my consulting business. From that perspective, it generates well into the 6-figures of indirect revenue.

Can you elaborate on your attempt to run paid subscription?

It was around 2021, shortly after Substack started getting some traction and everybody was talking about paid subscriptions. I didn’t really understand the dynamics of subscriptions for a newsletter like mine. I assumed that I’d get about 7-10% of people subscribing just because they wanted more. After all, who wouldn’t want more of what I write, right?! (please read that with a lot of sarcasm). I did the quick math… at the time I had about 5,000 subscribers. If I could get 500 of them to subscribe, that’s an additional $25k per year.

So I took the “If I let them subscribe, they will pay” approach.

Bad idea. Don’t do what I do, kids.

It wasn’t until after the subscription plan launched that I realized the work I’d have to put into it. I started by doing an extra subscriber-only article every week. But I found myself wanting to make sure it was good quality, but not TOO good that I’d be annoyed it was only read by a small group of people.

In the end, the two things that did me in were

1. Not having the time to provide more benefits for subscribers.

2. Not wanting to limit my writing to a small subset.

The fact is, even if I did get $25k from subscriptions (which I didn’t), the work that would have to go into creating that experience is not worth the value I’d get out of it.

I don’t see myself going back to a paid version anytime soon.

How did you find your first sponsor?

I posted on Swapstack in late 2022. Lo and behold, in early 2023 I got proactively contacted by my first sponsor and it was Hubspot!! Not only is it nice that a big company wanted to sponsor my little ramblings, but to have it Hubspot…. well, anybody that knows me knows how obsessed I am with Hubspot (See “Trust” article by Jeff Maltow).

If you asked me in 2022 what “success in sponsorship” would be for me, I’d probably have said “having Hubspot sponsor my newsletter”. So to have them be the first sponsor still has me all giddy.

How do you leverage your newsletter to find customers for your consultancy service?

I tend to write articles about challenges my ideal customer may face.

I also put a call-out at the bottom of every newsletter for the services I offer. And when you sign-up, you get a welcome message that also describes how I can help your business grow.

Do you have any plans to increase your revenue?

Yes. I’m very focused on creating courses and MasterClasses that will drive revenue.

📩 E-MAIL SERVICE PROVIDER

Why did you choose Substack? Pros and cons?

The Substack offering that exists now is much more robust than the Substack offering in 2020 when I started using them. And they haven’t even begun to realize their full potential. With that said…

Substack Pros when I first started

• Great, crisp and clear user interface

• Incredibly easy to create and format a newsletter

• Incredibly easy to build a mailing list

• Very easy to add on a paid offering

Substack Cons when I first started

• No marketing tools

• No SEO capabilities

• No ability to integrate with other products

Substack Pros now

• The same great user interface to create and format a newsletter

• A wonderful referral system for/from newsletters within the Substack ecosystem

• Starting to get into the SEO game

Substack Cons now

• Doesn’t integrate with other products

• Limited marketing tools (e.g. no ability for drip campaigns, no ability to integrate advertising, etc.)

🧩 SYSTEM & PRODUCTIVITY

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

I write every day and have about 30 different article ideas in various forms of development.

Tuesday, I usually come up with a concept I want to talk about.

On Wednesdays and Thursdays, I begin drafting the article.

By Friday, I’m fine-tuning the message and finishing it.

I put it online over the weekend and have it queued up to launch on Monday mornings.

At 7:01am PT every Monday morning, it gets sent out to my readers.

All in all, it probably takes about 4-6 hours per week.

How do you generate new topics to write about continuously?

Ha. I have no shortage of topics. There are leadership and growth lessons in everything; you just have to start looking. After doing this for so long, my mind is constantly looking for unique ways to talk about successful leadership and growth.

For instance, I’ve been using Focusmate every day to help keep myself productive. Last week I used a Focusmate session to write my article. As I sat there with a blank sheet in front of me, I tried to figure out what leadership lesson I could talk about. So I started with Focusmate, because that’s what I was doing. The result was this article about the Hawthorne Effect.

Another day I got into the age-old debate with a friend about the Beatles vs. the Rolling Stones. The next day I sat down and figured out leadership lessons from the Beatles and Rolling Stones. That turned into this article.

Every Tuesday, I post something on LinkedIn called #TuesdaysWithTayTay, in which I take a Taylor Swift lyric and give a leadership lesson from it. (Follow me on LI to get those lessons)

As I said, if I need to find a leadership lesson, all I have to do is look for it.

How do you promote and distribute your content?

I post a lot on LinkedIn both as me and, now, as By Title Only.

I am trying to do more on Twitter and Instagram. But will definitely be doing more on YouTube soon.

I co-promote with other newsletters.

I’m open to other ideas as well! If you have some, let me know.

🎢 NEWSLETTER EXPERIENCE

How did writing By Title Only contribute to your life professionally & personally?

I love writing and I love writing my newsletter. Regardless of how many people read it, coming up with the articles is fun for me. I’m lucky in that it’s helped me build a very good consulting business. Plus, a lot more people know me and it’s fun meeting people who read my newsletter regularly.

More than a few people have said it feels like I’m writing to them personally and that my ideas have really impacted them. That makes me so gosh darn happy.

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

I get frustrated on those weeks when I’ve written a piece and think it could be better but I just don’t have the time to improve it. I’m committed to getting this sent every single Monday at 7:01am. This means no matter where the piece is at, I’ve gotta start posting it on Sunday.

Now, crazy as it seems, some of the articles I thought were really bad turned out to be some of my biggest crowd-pleasers. Who knew.

What is the biggest AHA moment along this journey?

It took a couple of years but I’ve finally found my writing voice. Once I realized that, it became a huge A-HA moment and has led to how I position myself on my website, how I put together my social posts and how I’m writing the books that I’m writing.

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

There are two that stick out in my mind.

The first was going to Substack so early in their growth trajectory. I shouldn’t have done that.

The second is tangentially related - it was launching a paid subscription model. I spent 7 months of time and mental energy trying to make that work.

🎯 FUTURE

What is next on your newsletter journey? What is your ultimate goal/dream about By Title Only?

I want to get to 100,000 subscribers and I’m working on some ideas to get there.

Courses, social, videos and more.

I am always looking for people who have similar newsletters - talking about leadership/growth topics and injecting humor or light-heartedness. I have ideas on how to do some promotions there. So if you know similar newsletters, please tell me about them!!

📌 RECOMMENDATIONS

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

Write. Write every day for 15 minutes. Even on those days, you don’t want to write, still write. It is completely like a muscle; the more you use it, the better it becomes. And if you take time off, it atrophies.

AI systems like Type.AI can definitely help get you going.

So write and then when you start coming up with ideas you like and think you can continually write about, start posting. Substack makes it super simple for new newsletter creators to get going.

Once you have 2 articles, tell all your friends and family to subscribe. Once you have 5 articles, tell your social media following to subscribe. Once you have 10 articles, reach out to other newsletters on Substack and see if they’ll put you as one of their recommended (you put them as your recommended as well).

You will grow followers from that Substack recommendations channel.

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

The two newsletters I read every day are For The Interested and 1440.

For The Interested is a must for anybody creating on digital. Josh Spector is the master of digital creation and the newsletter takes less than 15 seconds to read every day. It’s gold.

1440 is the best, mostly-unbiased, daily news newsletter around. It provides short bites on what is happening around the world and does it with personality.

Also, from a leadership perspective, my two friends put out amazing pieces every week:

DCX is about the Digital Customer Experience. Mark Levy is a CX leader with amazing insights.

Monday Memos are thoughts that Eric Futoran sends to his staff every week. Eric is one of the best entrepreneurs around (his last company, Scopely, just sold for $5B) and is the master of creating high-growth businesses.

👋 FINAL WORDS

Thank you very much for including my newsletter in your newsletter about newsletters! I’m honored and humbled.

If anybody is interested in subscribing to By Title Only, you won’t be disappointed.

Thank you so much, Jeff. I’ll be following you closely for another interview when you reach 100,000 subscribers!

🔗 Where to find Jeff Matlow and his work

• Website

• Twitter

• LinkedIn - Jeff Matlow

• LinkedIn - By Title Only

• Instagram

• Youtube

🔎 3 Popular Issues from By Title Only

• Inspirational: 'Cause F**k You. That's Why.

• Better Business: The Greatest Con

• Better Leader: Iceberg of Ignorance

🔦 Circle Spotlight - From You

Before you go, I have a few last words.

I think it is the greatest feeling when you find value in this newsletter and share it organically. So; in this section, I will include comments coming from you because this newsletter is FOR YOU and this is our “circle”!

Thank you James and Corey. You both made my day!

That’s all for today. Thanks for reading.

See you next week.

Ciler