A reflection on 100 published editions.

Remember 2020? What words come to mind?

COVID. Global pandemic. Shutdown.

One of those, right?

I relate. And it was a tough year. But as tough as it was, 2020 was an inflection point in my online journey:

  1. I got more active on Twitter.
  2. I started listening to more podcasts.
  3. I began working remotely full-time.
  4. And I heard about this thing called Substack.

I worked in marketing and understood the importance of building an email list. A newsletter seemed like a good way to do it.

So I signed up for a Substack account in September 2020.

One Problem: I had no idea what to write about.

And I had nothing to sell. But after months of plan-crastination, I finally hit publish.

My first Substack newsletter included a few thoughts on leadership and cool things I was consuming online. Things like: tools, articles, courses, Twitter threads, communities, etc.

I had no “original” content, so I published a lot of curated links paired with my opinion. I enjoyed the process of creating a newsletter and sharing it.

But for all intents & purposes — my newsletter was an aimless pursuit.

TL;DR — This reflection article covers:

  • The one simple goal I made to myself that got me to 100 editions
  • Why I switched newsletter platforms
  • How and why I niched down — twice.
  • How I stumbled into newsletter ad monetization
  • The mistakes I made & lessons learned

So I made ONE simple newsletter goal

I promised myself I would publish 100 editions before I quit.

I quit everything: blogs, jobs, routines, journaling, gluten. So I knew I had to commit. If I committed to publishing regularly, I’d figure out this “aimless” issue. Eventually.

Why 100 editions?

I knew it would be impossible to publish 100 editions of a newsletter and not benefit from it.

→ It could create opportunities (relationships, collaborations, jobs)
→ I would own that distribution (ie. email list)
→ I could earn an income (eventually?)

So I published every week. But after ~30 editions, it became clearer that Substack was not the right fit for me.

When & Why I Left Substack for ConvertKit

There’s a long version and a short version. Here’s the longer version:

» Why I Broke Up With Substack and Moved to ConvertKit

Here’s the short version

Substack makes money from writers charging newsletter subscriptions — not from ads & sponsorships. Their platform & analytics are not optimized for other forms of revenue or traditional email marketing functionality (just look at your click counts and you’ll know what I mean).

And I didn’t want to publish a paid newsletter.

I needed  more features that ConvertKit offered and Substack didn’t. After 9 months on Substack, I made the switch to ConvertKit — and saw my open rates shoot up from 43% to 58% on the first send!

How I found my newsletter audience (2x times)

Honesty time: I had no idea “who” I was writing for when I published my first edition, but quickly realized I was creating & curating content for creators.

Everything I published revolved around the creator economy. It was a result of the “side hustle” & “creator” content I was consuming — along with the audience I was engaging with on Twitter.

So for a year, my newsletter audience was “anyone creating content online.

That’s way too broad. And I knew it. But  I was scared to niche down. I worried I’d:

  • cut out a large portion of my audience size
  • run out of content ideas fast
  • pigeon-hole myself to ONE topic

Plus, I’d begun earning some ad & sponsorship revenue so I was hesitant to make any big changes.

This “shove” made me niche down…again

I had a Hot Seat with Jay Clouse in The Lab community explaining my niche challenges — and promptly got a gentle “shove” to niche down to focus on newsletters.

Forever grateful for Justin Moore's comment 🙏

I thought about it for a few hours — then went all in. It was the push I needed. Besides…

A niche isn’t like a birthday — you CAN change it.

The Unexpected Benefits of Niching Down

Since changing my newsletter’s focus to *ahem* newsletters in March of 2022, I’ve experienced many unexpected benefits :

» How To Unlock Ideas: The Niche Key

Since then, I’ve…

My advice: if you’re talking to “everyone”, you’re talking to no one. A niche audience will help you, not hinder you. Find yours. I wish I’d found mine sooner.

Stumbling into a newsletter media business

I didn’t start a newsletter with the intention of earning advertising revenue.

There was always the goal of eventually monetizing the newsletter — I just assumed it would be from product or course sales. Not advertising. I’ve never sold ads or sponsorships. I don’t even like sales — or so I thought (maybe I was just selling the wrong thing).

But when I saw ads popping up in newsletters I was reading, it dawned on me:

If they can sell ads, why can’t I?

After 8 months of weekly publishing, I landed my first paid ad with fewer than 700 subscribers (thanks to Swapstack.co). Didn’t even realize it at the time — but I had just started a media business.

» How I Booked a Paid Ad For My Newsletter (with less than 700 subscribers)

I began to sell out my newsletter ad inventory. So, I increased my inventory by adding more ad spots per edition. And I increased ad rates. By May 2022, I began earning $1k in monthly ad revenue — only 8 months after selling my first ad.

» How I Book $1k per Month in Newsletter Ads

This past summer, ConvertKit launched their Sponsor Network (CKSN). I applied — despite being well under the prerequesite of 10k subscribers. I was graciously accepted. Now my newsletter ads are sold & managed by the CKSN team, taking a LOAD off my plate. I couldn’t be more grateful.

Mistakes Made & Lessons Learned

Monetization Mistakes

In hindsight, I made 2 big mistakes managing ads.

  1. Mistake #1 — I didn’t send ad reports to my advertisers. My advertisers never asked for reports so I never sent them. But then I had a chat with Andrew Kamphey (of BetterSheets.co) who strongly recommended sending ad reports — requested or not. Why? It helps you track ad performance, and gives you a natural follow-up with your advertiser where you can try to sell more ad spots.
  2. Mistake #2 — I raised my rates based on demand, not on success. It seemed like the right thing to do to increase my ad rates if the ad inventory was selling out. The problem: ad performance wasn’t *great*. So most advertisers didn’t rebook. Which means I had to find new advertisers every week. That’s a lot of work. Keeping my rates low to the point of rebookings being automatic (like Josh Spector does) would’ve been easier to manage.

Growth Mistakes

I’ve created & launched two lead magnets over the last 2 years — and had success both times:

  • 1st lead magnet brought in over 150 new subscribers before I turned it into a paid product.
  • 2nd one has brought in over 700 to date.

» How I Built A Free Email Course — and Gained 210+ Subscribers

The mistake? Only making two.

Growth is hard enough. When you find something that works, double down on it. But I prioritized newsletter/article creation over exposure & attraction for the newsletter (ie. lead magnets).

In 2023, I’m going to increase focus on growth strategies like more mini courses and lead magnets to help grow the newsletter.

Email List Mistakes

  1. I didn’t delete cold subscribers. Cold subscribers are defined by ConvertKit as a subscriber who hasn’t opened or clicked an email in over 90 days. I finally trimmed my cold subscribers 13 months after switching to ConvertKit. I deleted 290 subscribers (over 10%!). Cold subscribers affect open & click rates, and could negatively impact your deliverability & sender reputation. Get over your email list vanity metrics and delete ’em. Good riddance.
  2. I wasn’t segmenting subscribers. As I began planning out product & service offerings for 2023, it struck me: I had no idea where my readers were at in their newsletter journeys. For example, it wouldn’t make sense to offer consulting services to a subscriber who’d just published their first newsletter. Nor would it make sense to offer a “Newsletter Launch System” to those already publishing for months. Lastly, I couldn’t personalize anything — and personalization is proven to improve sales.

Final Thoughts & Growing A Media Business

I’m convinced the only reason I’ve built a small media business is because I put ZERO pressure on myself to build a business. That paradox won’t work for everyone. But it worked for me.

And I believe this is just the beginning.

2 years ago, I hadn’t published a single edition. Now, 100 editions later:

  • My newsletter earns over $1.4k/month in revenue
  • I’ve templatized the newsletter creation & curation process
  • I’ve niched down (twice) with a focus on helping others grow & monetize their newsletters
  • Working on plans to expand the business by hiring help curating & crafting the weekly newsletter…
  • …while I continue to focus on content creation, marketing, and building newsletter-related products (courses) and services (coaching, consulting & DFY).

I hope I can continue to help you build the newsletter of your dreams in 2023 and beyond.

More From Me.

→ Check out my FREE 5-day email course to help you get 1,000 newsletter subscribers 🚀
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