8 mins

Friday Feature: 22 Lessons from Successful Newsletter Creators (Part 1)

Top newsletter strategies on growth, monetization, and content creation—from successful newsletter operators.

Dylan Redekop

We began publishing the Friday Feature back in Summer 2023.

The goal was to extract the biggest lessons from our interviews with successful newsletter operators—and turn them into actionable takeaways for YOU to implement in your newsletter.

In this edition, we're sharing the biggest lessons learned.

(PS - This is a 2-part series. Stay tuned for Part 2 next week!)

Let’s dive in!

Lesson #1 - Create a paid growth flywheel by reinvesting revenue

Michael Houck from Houck’s Newsletter shared a valuable insight when we interviewed him last year:

“Newsletter publishers need to run their newsletters more like a startup.” — Michael Houck

What does that mean? He’s running his newsletter with close to 0% profit margins.

Houck’s Newsletter is approaching $1M in revenue, including $250k in ARR — and at the time of our chat, Michael wasn’t taking out a dime. Every penny—after minor expenses are covered—goes back into growth:

  • FB ads
  • Twitter/X ads
  • Megaphone (his other startup), and…
  • SparkLoop Partner Program

Doing so has allowed him to scale his newsletter that much faster.

Here’s the whole Friday Feature article featuring Houck’s Newsletter →

Lesson #2 - Create irresistible “Chocolate-covered Almond” content

Katelyn Bourgoin of Why We Buy observed there are two main types of newsletter content:

→ Chocolate content: sweet and enjoyable but lacking nutrients and substance.

→ Almond content: dense & rich with information but missing the “wow” factor — making it boring to consume.

But when you combine the two, you get...

Chocolate-Covered Almond content: educational, helpful content and delivered in a fun, delightful way. Not only do you feel smarter after reading it, you actually are.

And that's what Why We Buy does so well—the proof is in its success:

Why We Buy, once a side project, has become a media business cruising along at over 64k subscribers and…

…over $300k in revenue 🤯

And she has her chocolate-covered almond content strategy is largely responsible.

Read the whole Friday Feature article featuring Why We Buy →

Lesson #3 - Owning a niche perspective pays off

The Pour Over (TPO) newsletter delivers the daily news with a twist.

And that "twist" has been its key to growing to over 550,000 subscribers.

Jason Woodruff started The Pour Over because so much Christian-based news leans heavily conservative. He was tired of getting news with a political slant.

Jason wanted a politically-neutral, Christian-based newsletter.

So he started one.

“We’re politically neutral. The only bias is towards foundational biblical principles. We just want to be a good, trustworthy news source.” — Jason Woodruff, The Pour Over

That perspective helped TPO carve out a niche in the daily news cycle and reach over half a million inboxes.

Here’s the whole Friday Feature article featuring The Pour Over →

Lesson #4 - Unlock incredible ROI with “free” giveaways

The SEOFOMO newsletter serves SEOs, digital marketers, and consultants.

Founder Aleyda Solis started running milestone giveaways with SparkLoop as her newsletter approached 5k, 10k, 20k subscribers.

But she needed a prize her subscribers would *really* want to win

So she pitched different SEO SaaS tools & businesses on the idea of being part of her prize bundle.

In exchange, they’d get exposure in SEOFOMO every week until the subscriber milestone was reached and the giveaway ended.

In doing so, SEOFOMO’s giveaway grand prizes included thousands of dollars in SEO products and services — all of which cost Aleyda $0.

Here’s the whole Friday Feature article featuring SEOFOMO →

Lesson #5 - Reddit is an untapped channel for organic growth

Eric Lam grew his newsletter Exploding Ideas organically with Reddit.

Exploding Ideas grew to 1,000 subscribers in the first two weeks (now 6k+) —and it was all thanks to the unique way he’s using Reddit to grow for free.

Check it out here →

Eric isn’t sure the Reddit strategy will get him to 100k subscribers, but he’s confident it will get him to 10k.

Here’s the whole Friday Feature article featuring Exploding Ideas →

Lesson #6 - Freemium newsletters are winning

Since the dawn of Substack, the question plaguing newfound, bright-eyed newsletter publishers has been: “Free or paid?”

But some of the most successful newsletters are somewhere in the middle—taking more of a Freemium approach:

  • A free tier, including regularly scheduled, free content
  • A paid tier offering more and/or different content, including deep(er) dives, additional strategies, and other perks & bonuses.

Exhibit A: the "more" approach with Exploding Ideas

Exploding Ideas goes out free as a Sunday version. It features a new business opportunity based on growing Google Trends data.

A follow-up Tuesday edition is sent to all subscribers, but most of the newsletter is locked behind a paywall and is only accessible with a paid subscription.

The free Sunday edition acts as a lead magnet for his paid, high-value content—which now boasts over 500 paying subscribers at a rate of either $20/mo or $99/yr.

Exhibit B: the "different" approach with Houck’s Newsletter

Similarly, Houck's Newsletter uses the same formula of “one free + one paid” newsletter each week.

Michael teases readers by using a similar gated section for his paid edition — but instead of driving subscribers with a “more” approach (like Exploding Ideas), Michael uses the “different” approach.

Houck’s Newsletter showcases Michael’s knowledge, experience, and authority in the startup & founder space, so offering access to a founder community, workshops, and IRL events is different — and more valuable in this case — than adding “more” content in your inbox.

Lesson #7 - Unearth your overnight success

Jon grew his Amazon business to $10M over 5 years, giving him a huge advantage from Day 1 of publishing his newsletter.

Think about it…

→ he'd grown & sold a successful Amazon business before ever hitting send on the first edition.

His newsletter, Amazon Insiders was an overnight success 5 years in the making.

Unearthing your 'overnight success' isn't about instant fame or luck—it's about leveraging unique experiences, skills, and relationships built over time.

For Jon, this meant drawing on learnings over 5 years and tapping into his network of fellow Amazon sellers and clients.

Here’s the whole Friday Feature article featuring Amazon Insiders →

Lesson #8 - Earned Media can be a boon for *FREE* newsletter growth

When Matt Brown got laid off, he needed his new newsletter Extra Points to grow quickly:

“I started Extra Points because I needed a job,” Matt told us.

He was desperate to grow and couldn’t afford to pay for the growth he needed.

Earned media can be a useful growth strategy for newsletters lacking budget for paid growth.

But what is it? It’s external press or publicity you don’t pay for.

Things like…

→ social media shares
→ written articles
→ mentions on TV, radio or podcasts
→ or any other unpaid public mentions.

The trick? You need to publish content that will earn you publicity.

Here’s the whole Friday Feature article featuring Extra Points →

Lesson #9 - Create efficiencies by bundling ads

Filling ad inventory still takes precious time:

→ prospecting for advertisers
→ cold emailing
→ negotiating rates
→ dealing with ad creative…

…it’s all time-consuming.

So when a complementary newsletter ~3x the size of The Merge asked to bundle newsletter ads, founder Mike Benitez was all in.

They pitched their combined newsletters & audiences to brands and quickly stuck up a deal.

In doing so, Mike halved the ad operations work and got a larger sponsor in his newsletter than he might have otherwise been able to.

Here’s the whole Friday Feature article featuring The Merge →

Lesson #10 - Be flexible and adaptive with monetization

Sam Klemens runs The Rollup.

Sam's goal from the beginning planned to monetize with ads & sponsorships.

He assumed the magic number for selling ad spots was 10k subscribers.

When hit 10k and started pitching ads—all he heard were crickets.

After struggling to bag $100 for ad spots, Sam saw what Anthony Castrio was doing with Bot Eat Brain:

→ pitch ridiculously low ad rates to attract advertisers and “sell out” ad spots—then gradually increase ad rates as each edition sells out.

And it worked.

Here’s the whole Friday Feature article featuring The Rollup →

Lesson #11 - Sponsorship-audience alignment is critical for long-term success

Brad Barrett runs the ChooseFI newsletter & podcast.

ChooseFI is a successful business built on a foundation of 7 years of trust. So, when it comes to driving revenue with ChooseFI, Brad is extremely cautious.

As the ChooseFI audience has grown, so have the inbound requests from brands hoping to advertise with ChooseFI.

Does Brad promote every endorsement or affiliate opportunity that comes his way?

Not a chance.

He is extremely selective in endorsing products and services he personally uses and believes in, like specific finance tools, platforms, and credit cards.

This ensures brand sponsorships are seen as genuine recommendations rather than advertisements.

Here’s the whole Friday Feature article featuring ChooseFI →

That's a wrap—for Part 1! But stay tuned…

If you enjoyed this, stay tuned for next Friday when we share Part 2 of the 22 Lessons from 22 Friday Features. Subscribe here →

Here are 3 things to do next:

  • Check out the Send & Grow podcast where we have these conversations every week ...
  • Check out our blog →
  • Give us your take: what newsletter is doing something different and innovative we should feature next? Maybe it's yours... EMAIL US and let us know!

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