Recap: Newsletter Marketing Summit

👋 Hi friends -

Welcome to The Newsletter Growth Memo. Twice a month, I share short reflections with my newsletter clients + other operators.

Zero formality, ads, or affiliate links - just a guy sharing learnings from working with media operators doing $25k-$1M+ / month with newsletters.

New reader highlights: Welcome to Varun, Head of Growth @EssentiallySports | Harit, Co-founder @EssentiallySports | Mike, Chief Brand Officer @ Optimism | Suryansh, Co-founder & Growth Lead @EssentiallySports

In case you missed it...

I just got back from The Newsletter Marketing Summit last week.

The content was top-tier and I came away with pages of notes on what's working right now in newsletter land.

But more than anything - I’m feeling energized and fortunate to be surrounded by awesome people.

As usual, I wanted to give you my top takeaways from the event.

These editions always run a little long - but they’re worth it. Enjoy!

1. Build out 1 discovery and 1 relationship platform

I love Jay Clouse’s frameworks and think he was an excellent choice to kick off the conference.

His TLDR is that anyone building an audience should be posting across two tiers of platforms:

• Discovery platforms (Instagram, TikTok, YouTube) that give you distribution in exchange for content that keeps people scrolling

• Relationship platforms (Email, Podcasts) that give you direct access to your audience without an algorithm in the way

Too many creators focus on the vanity metric of followers and never convert that attention to something they own.

And they end up undermonetized for the effort they put in.

2. 4 flywheels behind million-dollar newsletters

Nathan Barry had a very complementary session to Jay’s on asking yourself how each part of your business can be turned into a flywheel.

E.g., a cycle where your inputs create outputs that directly add either more or better inputs.

Quick example - here’s my content flywheel:

1. Each week I reflect on the work we’ve done / the questions I get in calls with media/newsletter operators

2. I use those questions to create newsletter content

3. Someone from my team + I turn that newsletter content into LinkedIn posts

4. That content turns into new conversations with operators and I repeat step #1

Nathan Barry sees four flywheels across the largest creators on Kit:

1. Content (more content with less effort)

2. Distribution (get your work in front of more people)

3. Reinvestment (turn profit into business growth)

4. Equity (turn attention into wealth)

He’s written about these at length here.

3. Negative CAC Is The New Black

My friends Andy + Joanna of The Assist are spending $50k+ a month on ads.

And recouping ALL of it upfront.

How? They show new subscribers CPC deal offers with B2B sponsors immediately after sign-up:

Sign up -> 5-question typeform -> partner offers from Monday, Notion, and other B2B companies.

I was lucky to be a part of building up The Assist’s first 100k readers and it’s been awesome watching them dial in this funnel.

Andy + I sidebarred a bit with Ryan Johnston (6AM City) about what it might look like for B2C newsletters where CPCs are lower.

The prosumer version might look like partnerships with:

• Real estate agents

• Investment accounts

• Other high-ticket consumer services/products (Ninja blenders, local services, etc.)

More on my two favorite, wildly profitable sign-up flows here.

4. Re-visit how your tech stack can give you leverage

Steph Smith built the Trends product for The Hustle (0 → $6M in under a year).

She shared 25+ tools for identifying trends, social listening, and creating content.

Three that stood out to me:

1. PodEngine sends alerts when specific topics appear in podcasts (great for newsletter research)

2. Flourish creates premium infographics/charts for your newsletter (think Visual Capitalist or Chartr, which differentiate via content)

3. Gummysearch helps you listen into your audience’s favorite subreddits (great for newsletter content and ad ideation)

5. Newsletters should be studying D2C for their paid ads playbook

My buddies Alex Cooper and Ali Quereshi gave a masterclass panel + standalone session on what newsletters can learn from other niches.

Two key insights:

First, newsletters should be stealing from DTC brands.

It’s the most competitive niche with battle-tested copywriting and a playground for net-new ad formats.

Follow RYZE and other top DTC accounts for inspiration.

Second, AI - when primed with the right data and prompting - will give you incredible leverage for ad creative.

Just a few use cases we’re leveraging here at The Feed:

• Analyzing client open rate / CTR data to tease out great headlines for ads

• Building out personas in a newsletter based on survey data and email replies

• Writing draft UGC scripts + replacing (some) actors

• AI summaries of Reddit that help us source ad ideas + hooks

I wrote about my 6 favorite AI tools for this here.

6. Everyone wants to be 1440 (here’s how)

Tim Huelskamp got extremely transparent about 1440's stats:

• $21M+ annual revenue

• 21 employees

• 300,000 new subscribers monthly

They’ve built a list of 4.4M fanatics. How?

Do simple things that don’t scale: Tim + the team read hundreds of reader emails daily.

This feedback loop ensures content-market fit and has led to new products like Topics, which is quickly helping them expand to high-CPM niches like personal finance.

I’m a huge proponent that every problem in a business can be solved and every opportunity discovered by talking to your customers.

I run an agency - we provide a high-touch service, and so that feedback loop is naturally built into the product.

With a newsletter, it’s much easier to let this slip. Don’t!

Do the hard things other newsletters won’t do: 1440 tracks cohorted LTV:CAC ratios with surgical precision.

Their average: 7x LTV:CAC

Tim pulled up a table of cohorted revenue from their readers - early cohorts still generate $45,000 every single month on an initial $125,000 acquisition cost.

The data they track has helped them scale with revenue-based debt financing (much more favorable than equity) and make the right decisions for paid growth.

7. YouTube is an untapped acquisition channel

Ryan Hashemi from Jubilee gave a masterclass on using YouTube to go viral and convert viewers into customers.

One story that stood out: a single YouTube video that generated 200k+ views and a $3M purchase order for an air filter company.

Air filters!! 

I think YouTube could work beautifully for newsletters.

But only those with high-LTV products + services on the back-end.

Think The Rundown, Workweek, The Assist, etc. with products that have $100+ LTVs.

They could use tactics-focused content to convert B2B readers on communities.

The playbook already exists, btw: Nick Saraev is doing $100k+ a month with YouTube videos about automation that funnel to a paid community. Wild!

8. Chemistry is everything

Alex Lieberman shared Morning Brew's journey from college startup to exit in 35 photos, each with its own story.

Two insights on chemistry stuck with me:

On co-founders: Alex described his co-founder dynamic like a racehorse + jockey. He has tons of energy and ideas, but would run right off the track without Austin there to keep him focused.

Alex needs Austin's laser focus; Austin needs Alex's energy.

I’ve had 3 people I’ve met in my life where there was an instant, co-founder-level energy.

We’ve never quite been in the right place at the right time to be co-founders, but I’d love to work with them one day + I try to spend as much time with them as I can.

On podcasts: Chemistry trumps individual talent every time.

Morning Brew has launched multiple top media podcasts using this principle.

Alex + Austin found that two B+ hosts with A+ chemistry will always outperform two A+ hosts with B+ chemistry.

Similar takeaway for me - those 3 people I mentioned above… our calls feel like podcasts we just forgot to hit the record button on.

That’s how you know you’ve found someone you should work with!

A practical guide from Shaan Puri on IDing a great co-founder.

9. Local newsletters can be a great business model

Ryan Heafy's presentation on 6AM City had everyone rethinking local - in a good way.

While most readers on this list won't pivot to local, the model is compelling (a handful of 6AM cities are doing $1M+ with 2 staff members).

They’ve succeeded by:

• Targeting tier 2 cities

• Launching regionally (where sponsors overlap between cities)

• Breaking in with list acquisitions + keeping the team lean as long as possible

The most actionable insight for independent operators: niche verticals win.

Specific community focuses like:

• Local sports

• Parenting

• Entrepreneur scenes

Will a local newsletter make you rich as a side hobby? Probably not.

But it might be the most fun business you could start.

If I were back in Columbus, Ohio (where I spent much of last year), I'd be tempted.

It's an incredible way to meet people and build a solid "lifestyle business" revenue stream.

10. Our industry is full of amazing people

My biggest takeaways at these events, always, is that I love the people here.

I got to spend time with so many people who read this little newsletter of mine - Isaac, Ken, Ali, Tim, Joanna, Erika, Andy, Brad, Chenell, Louisa, Jesse, Ryan, Andrew, Nic, Guy, Colin, Jelmer, Wouter, and easily 20+ others.

Thanks for hanging out and I can’t wait to see you again 🙂 

A few photos from my and Andrew Warner’s camera rolls…

That's the letter.

Nathan May

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