The 15 biggest problems newsletters face

👋 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-$2M+ / month with newsletters.

New reader highlights: Ryan, Co-founder and Former CRO @ Industry Dive | Zachary, Head of Brand Partnerships @ Short Squeez | Andrea, VP of Advertising Sales @ Merriam-Webster | Jacqueline, Chief of Staff, Revenue @ Morning Brew

Over thirty $1M-$1B+ media brands shared their biggest problems with me this month.

As part of The Newsletter Accelerator, I’ve been doing 1:1 onboarding calls with all of the media companies beehiiv and I invited (40+).

These will inform two invite-only, unrecorded sessions next week that will be co-taught & include fireside chats from brands like 1440, Morning Brew, Industry Dive, and Workweek.

I’m doing no woo woo questions - I want this thing to be extremely tactical for the operators joining.

The goal with my calls was to hear challenges from every newsletter stage/monetization model:

Rather than keep the takeaways for myself and the speakers, I figured I’d share the themes with you.

Below you’ll find a bunch of problems alongside questions I have for our speakers.

And zero answers!

That’s what next week is for.

(We’re bringing on members from the growth/sales teams of our participating brands, so content questions to them next week will be minimal)

As publishers build their newsletter programs, they’re wrestling with how to serve very different audiences - B2B vs. B2C, older vs. younger readers, niche interest groups that rarely overlap.

A few questions I’ve heard from folks:

I’d be excited to hear how Morning Brew is building out its B2B newsletters from the “mothership” (shoutout Brian Morrissey) Morning Brew daily newsletter.

Web-first brands often have large newsletter portfolios with underresourced owners.

Growth, sales, and product are borrowed resources, leaving newsletters stuck in maintenance mode.

Even with the newsletter native brands, several felt stretched on the marketing side - 1-2 team members handling event marketing, paid ads, and analytics.

Imogen (Head of Sales @ Industry Dive), Robin (Head of Growth @ Industry Dive), and Callie (SVP Advertising @ Workweek) have all been with their brands from nearly the beginning.

I’d be curious what advice they have for what it takes to stand up a newsletter program in its early days and how to time key hires.

Your welcome email and the first 30 days of a subscriber’s experience can have a massive impact on the open rate/retention of a cohort.

In the accelerator, I walked through a few welcome email benchmarks - I've seen newsletters have as high as a 70% open rate and 24% CTR on their welcome emails at scale.

We’ve had huge publishers tell me they’re re-thinking their welcome sequences based on the 3rd session on sign-up / welcome flows. Very cool!

If you didn’t join the accelerator, it’s pretty neat - you can click this link to be notified about the next cohort.

Subscriber quality tracking is a mess for most newsletter brands.

Anybody can buy cheap attention.

The best teams are starting to track who stays engaged - who opens at Day 7, Day 30? Who clicks on sponsorships? Who gives the most first-party data?

It’s no coincidence that the newsletters profitably spending the most on growth (The Points Guy, 1440, Morning Brew, and a handful of others) have the best infrastructure around tracking quality.

That’s why I’m opening the August 5th session with a walkthrough on LTV calculation, cohorting data, and all of the other tracking infrastructure that has enabled us to take multiple newsletters to $100k-400k in monthly ad spend.

And I have many, many questions on KPIs for our fireside chat speakers.

Subscription and niche B2B publishers are skeptical of paid ads.

A few are experimenting with Google at low scale (mostly branded terms) and Meta.

The open question: Can you buy high-quality readers - or does paid inevitably dilute audience quality?

I’m really curious to hear how our fireside speakers allocate spend across channels (Meta, buying ads in other newsletters, etc.) and, more importantly, how they qualify readers.

Man oh man, do editorial teams have a lot of power at web-first media companies.

Growth teams are torn between editorial branding and market reality, where raw, unbranded ads often perform best.

A few questions here:

For publishers with significant site traffic, the question is urgent: how do we pull that traffic down to email before it disappears?

Teams are looking for a menu of on-site levers - placements, gating, pop-ups, etc.

We may only briefly touch on this here - Industry Dive gets a lot of direct traffic, so it’s a fair question for them.

Branded social accounts rarely outperform creator-led accounts.

AI’s attack on SEO has made folks more interested in organic social, and there are a lot of open questions around:

Questions, mostly for Workweek and Morning Brew:

Newsletters want to subsidize CPL on day 0. Everyone wants negative CAC.

I talked to a few publishers who (as an illustrative example) have members of Congress, lawyers, CHROs, and retail CEOs all on the same list.

How do you voice that to a sponsor or tee up a program of more dedicated sends for premium CPMs?

For web publishers, newsletters were built to drive traffic back to high-RPM onsite ads.

Industry Dive largely sends to its site (caveat - direct sold, not programmatic ads), Workweek appears to focus on email, and 1440 is doing a bit of both after its Topics launch.

A few publishers want to expand beyond email ads into webinars, whitepapers, and - maybe one day - custom content studios.

Pubs like Industry Dive and WSJ do a ton of this work already.

It’s one of the best ways to go from being a passive recipient of ad dollars to a thought partner who understands the needs of your sponsors’ business.

Many questions:

Big publishers with multiple newsletters face complex bundled buys.

Sales reps aren’t incentivized to sell email inventory and don’t understand how to pitch it.

Without commissions or education, reps default to other products, creating a loop where newsletters can’t prove revenue, so leadership won’t invest.

Advertisers want data fidelity: who clicked, where they are, and whether engagement is meaningful.

That’s the letter.

- Nathan May