8 mins

Friday Feature: 22 Lessons from Successful Newsletter Creators (Part 2)

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 Part 2 of a two-part series! Missed Part 1? Check it out here →)

Let’s dive in!

Lesson #12 - Octopus vs. Swordfish Ad Strategy

Don’t limit sponsorships to just a newsletter if you have audiences elsewhere.

Amanda Goetz sells sponsorships for her Life’s A Game newsletter. But advertisers get more than just an mention in it.

She takes an “octopus” approach with sponsorships rather than a "swordfish" (single stab) approach.

The Octopus Ad Strategy: create multiple touchpoints for your audiences to discover the sponsor. Include mentions in...

→ Twitter posts
→ LinkedIn posts
→ Instagram feed/Stories/Reels
→ Newsletter edition(s)
→ Community mentions/shouts

Sharing your sponsors with your entire online audience (where relevant) will ensure the advertiser gets the most out of their sponsorship.

Here’s the whole Friday Feature article featuring Life’s A Game →

Lesson #13 - Take a Newsletter-Centric Approach

​Shifting your email marketing strategy to a newsletter content strategy can work wonders.

Tiffany Uman of Peak Performers had been doing email marketing for years.

But then she pivoted to a newsletter content strategy and everything changed.

Her emails became two-way conversations with her readers—instead of a launch or pitch every time it landed in inboxes. Her readers were now receiving valuable content that helped them with their careers.

And the results speak for themselves: she saw 70% subscriber growth in a few months, and engagement rates have also risen.

Here’s the whole Friday Feature article featuring Peak Performers →

Lesson #14 - Scale with Systems

Build a newsletter that generates revenue and runs on autopilot with systems.

Anthony started Bot Eat Brain with the goal of running it “like a machine.”

He wanted to operate a 5-day-a-week newsletter to generate 5x the revenue that he could with a weekly newsletter. But didn’t want to spend all his time writing and running it.

So he built systems to scale.

Anthony hired writers and created templates, schedules, and automations so Bot Eat Brain could operate with Anthony only needing to spend few hours per week managing it.

Here’s the whole Friday Feature article featuring Bot Eat Brain →

Lesson #15 - Social media can drive significant organic growth

​Social media is still a viable organic growth strategy.

Before LeQwane Lynch sold his Alerts Daily newsletter, he was generating over 4M monthly impressions across all social media platforms and his newsletter.

It’s no wonder he was able to grow Alerts Daily 100% organically to over 35k subscribers in 11 months before selling it.

LeQwane understood three key concepts for social growth:

→ Post where your audience is. he knew where his audience hung out (IG & TikTok in his case)
→ Create content they’re already consuming. He understood what type of content would get the most engagement
→ Don’t reinvent the wheel. He repurposed his newsletter content into video.

Here’s the whole Friday Feature article featuring LeQwane Lynch →

Lesson #16 - Pattern interrupts are a powerful tool

Use pattern interrupts to grab—and keep—attention.

​Bill Kerr runs two businesses (Athyna | Open Source CEO) — and uses pattern interrupts to grow them both.

Pattern interrupts help capture attention, avoid content fatigue, and improve brand recall.

That’s why Bill uses them everywhere:

Open Source CEO sign-up page
His newsletter editions
Athyna website
Social posts

Use pattern interrupts to get new subscribers—AND to keep your current subscribers engaged.

Here’s the whole Friday Feature article featuring Open Source CEO →

Lesson #17 - Ad Arbitrage: Get Paid to Grow

Use paid recommendations to do ad arbitrage and get paid to grow.

The guys from Office Party wanted to grow quick, so they started running Facebook Ads.

And at first, they sucked: they were paying ~$9 CPA. Ouch.

But they eventually got their CPA down to under $2.

Which was awesome, because they were at the same time earning an average of $4+ per new subscriber with SparkLoop and paid recommendations.

In a 7-day period, Office Party gained 700+ subs AND earned $3.3k from driving traffic from Facebook Ads. See for yourself.

Talk about ad arbitrage!

Here’s the whole Friday Feature article featuring Office Party →

Lesson #18 - Use these 5 Growth Levers for 5 Stages of Growth

Different stages of growth benefit from different growth levers.

Yong-Soo Chung is a serial entrepreneur who’s built his Personal Holdco to $20million. He’s also the creator behind the First Class Founders media brand (newsletter + podcast).

And he's building it all with the help of models and frameworks.

One of his favorites is The 5 Growth Levers:

  • Growth Lever #1: 0 to 1K+ subscribers = Organic content
  • Growth Lever #2: 1K+ to 5K+ = Partnership & Collaboration
  • Growth Lever #3: 5K+ to 10K+ = Virality
  • Growth Lever #4: 10K+ to 15K+ = Direct sales
  • Growth Lever #5: 15K+ = Paid ads

The great part is these growth levers compound as you continue adding more in. Which can scale your growth that much quicker.

Here’s the whole Friday Feature article featuring First Class Founders →

Lesson #19 - LinkedIn Growth Hacks to 35k+ subscribers

Leverage the power of LinkedIn’s algorithm to scale organic growth.

Tom Alder’s story of growing Strategy Breakdowns is a case for perseverance with audience building.

Tom's story begins with a simple challenge: post on LinkedIn for 30 days in a row.

He started it in January 2021.

But he didn't stop after 30 days.

Fast-forward 2 years later: he'd gained 25k LinkedIn followers—and 5k of those had signed up for his Strategy Breakdowns newsletter he had yet to launch!

In the following 9 nine months, Tom…

→ Launched Strategy Breakdowns to 5k subs
→ Grew his LinkedIn following to 75k+ followers
→ Grew Strategy Breakdowns to 35k+ subscribers—with ~70% of subs coming from LinkedIn

Tom truly mastered the LinkedIn algorithm to increase impressions. But also figured out how to best convert those eyeballs into subscribers.

And he explained how he does it here.

Here’s the whole Friday Feature article featuring Strategy Breakdowns →

Lesson #20 - Consent-based marketing is good for business

An engaged email list that chooses to hear from you is valuable—no matter the size.

Tarzan understands the value of an audience that truly wants to hear from her.

Her readers are engaged because they *choose* to be.


Tarzan operates from a consent-based marketing approach.

And her “small”, engaged audience (<20k subscribers) has helped Tarzan’s business drive over $1million in revenue.

3 ways Tarzan uses consent-based practices:

  1. Optional Opt-in for lead magnets
  2. Option to stop receiving promotion emails
  3. Freedom to receive emails whenever readers want to

Here’s the whole Friday Feature article featuring Tarzan Kay →

Lesson #21 - Creating “better” content is a growth cheat code

Good content gets opens. "Better” content gets shared.

Chenell Basilio sent her first edition of Growth In Reverse to 4 people.

A year later, she sent it to over 30k eager subscribers.

That’s an impressive growth curve—but even more impressive is it was 100% organic.

Chenell’s organic growth can be attributed to several factors—but the most important one is that the quality of content has led growth.

She goes the extra mile (or ten) to publish a research-based newsletter at a level nobody else is. She puts in over 20 hours of research per edition.

That’s her differentiator. And it's why people love—and share—her newsletter.

Differentiate your newsletter by doing content “better” or “different”.

Here’s the whole Friday Feature article featuring Growth In Reverse →

Lesson #22 - Infuse a unique tone in a saturated niche to differentiate

Where Growth In Reverse differentiates with in-depth research, Noor Chopra and her Touristy newsletter stands out with tone.

Touristy is a business, tech, and consumer culture newsletter—but with a snarky “side of millennial sarcasm.”

Most business & tech news publications are super dry.

Informative, sure. Exciting? Not so much.

Noor wanted her business and tech newsletter to be the opposite—one that educates and entertains.

So she started experimenting with GIFs, memes, and an injection of personality and sarcasm.

And it’s worked well—to the tune of over 110k subscribers.

Here’s the whole Friday Feature article featuring Touristy →

That's a wrap—for this mini-series!

Don't forget to check out the first 11 Lessons from last week's edition if you missed them.

And we'll be back next Friday with a brand new Friday Feature deep dive on a newsletter expert who's grown multiple newsletters to 50k+ subscribers—and sold one of them in under than a year.

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? Email us and let us know!

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