The Newsletter Conference: 5 Takeaways

👋 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 J.T., VP Sales @beehiiv | Adam, Co-founder & CEO @ Workweek | Kate, Editor in Chief + GM @ Every | Nathan, CEO & Publisher @Foundr

Last week marked year 2 of The Newsletter Conference.

The longest-running event in our industry! Ha.

Jesse and Ryan hosted an amazing event, as usual.

The energy was different from last year. Less "how do I grow my list" and more "how do I build a business."

1P data, media mullets, analytics - the nerdy stuff that gets you to $10M+.

Here are a few of my takeaways.

1) Product-market-fit and sponsor-content-fit are measurable. Measure them.

Adam Ryan of Workweek tracks three numbers religiously and was kind enough to share them with us.

1. Total Opens / Unique Opens This measures subscriber engagement depth. When people re-open your emails, your ratio goes up. Bigger is better.

• Most newsletters: 0.6-0.7

• Good newsletters: 0.7+

• Great newsletters: 1.0+

Back in the days of The Hustle, the team knew they had a viral piece of content on their hand any time a newsletter ratio was 1+.

2. Advertising/Sponsor CTR

• B2B: 0.75%+ target

• Consumer: 1.5%+ target

Quick note: I know successful newsletters slightly below these benchmarks.

Workweek likely sees above-average sponsor performance because many of their newsletters have creators attached with sticky audience relationships.

There’s a lesson in there!

3. Cohort Retention: Adam is one of the only folks I’ve talked to properly cohorting his data. He shared what a healthy unsub rate curve looks like for the WW portfolio:

• Month 1: 15%

• Month 2: 8%

• Month 3: 5%

• Month 4: 4% + levels off

I like this, but would tweak it to focus on cohorted open rates.

Why? The #1 newsletter killer is apathy.

Folks who stay subscribed but never open or stop caring about your content enough to even realize it’s in their inbox.

I covered cohorting open rates + using them to back out LTV extensively last week.

2) 1st Party Data is your Moat

Sean Griffey built Industry Dive into a $100M+ business entirely with direct ad sales.

Their moat? Custom content (webinars, whitepapers, etc.) that turned them from a marketing channel into a marketing thought partner.

That was powered by collecting data on their readers to understand who the decision-makers were, what they wanted, and how sponsor content could fit in tactfully.

Sean's data evolution:

1. Basic email + industry/title collection (here’s their sign-up page)

2. Email enrichment (Company email → build out full profile)

3. Behavioral tracking (the content/topics you like)

4. Inferred intent modeling (taking #3 and inferring strong-fit sponsor content)

You must collect 1P data. And you must collect it early.

We see 70%+ opt-in rates for 1P data during signup vs. 2-3% if you ask later.

The real estate in your sign-up flow is your most valuable real estate, period.

Use it wisely.

3) We’re getting real ‘save time / make money’ use cases from AI

Every is one of the first media companies I’ve heard openly share an AI strategy that was tactical.

More of that, please!

They built Spiral to break long-form content into multiple pieces, giving the editorial team leverage.

Quick aside: Alex Lieberman's Distro is also interesting - AI that interviews you and generates content (replacing $2-4k/month ghostwriters). It’s early, but it’s getting better.

Every is also using AI to create personalized CTAs and seeing a +25% lift in CVR on their product bundles.

I love personalization in sales. I don’t know enough about Every’s strategy to go deeper here, but Justin Welsh has a really compelling use case with Kit / Rightmessage.

Justin used onboarding survey responses to personalize sales pages and launch emails based on each subscriber’s revenue level and pain points.

The result? A $1M launch became $1.6M - a 60% lift from a few minor headline/email copy changes.

Case study on that here.

I also wrote about the 6 AI tools I love for newsletter growth here.

4) Build out your media mullet

Ads in the front, high LTV products/services in the back.

Lots of great mullets among the speakers this year.

Paid subscriptions: The Ankler

• $5-10M business, historically driven by subscription revenue

• 20%+ free → paid CVR

• 30k+ paid subscribers, 145k+ total

• Wants an even mix between ads, events, and subscriptions this year

Paid subscription + events: Jacob Donnelly's A Media Operator

• Just 9,000 subscribers

• Sponsorships + subscriptions: $450k+ in revenue

• Events: $170k in 2023, so certainly no less than that now

• 6-7% free → paid CVR

• Webinars: sold for $10k each

• Deep dives: sold for $7k each

SaaS + services: Every

• $3M+ in lifetime revenue

• AI consulting business (trainings, custom tools, implementation)

• 5% reader conversion to paid products

High-ticket digital products: Jaspreet Singh

• YouTube → Newsletter → Briefs Pro ($300-500 AOV) → Hedge fund research ($1k+ AOV)

• Started a newsletter to monetize excess YouTube sponsor demand

• Now the newsletter is more profitable than YouTube

5) Is AI Going to End Your Newsletter?

That was the topic of Adam’s opening talk.

And the subject of some very spicy Twitter back-and-forth with a popular newsletter marketer last month.

(FWIW - I am Switzerland, no sides taken!)

Do I agree with Adam that AI-enabled inboxes are going to eat your distribution?

I’m not so sure, but frankly… it doesn’t matter.

The ‘so what’ is the same: You need to build high-LTV products, services, communities, etc, behind your newsletter to have an interesting business these days.

Adam sees it as the only defense for our industry. I see it as the biggest offensive opportunity.

Whether you’re more personally motivated by the carrot or the stick is up to you.

A bit of an aside: I have always wondered if Workweek is a good business in the context of its cap table (they’ve raised a lot of money).

A lot of operators on this newsletter have the same question - that’s no dig at Workweek, it’s just that most of us run bootstrapped businesses, and we don’t know what we don’t know.

So I asked.

Not sure I can/should share the exact metrics Adam gave me, but their community conversion rates, DAU:MAU, and ARPU are much stronger than I realized.

They're basically building multiple mini-Doximities ($10B social network for medical professionals, $250+ ARPU).

It’s one of the bigger swings in our industry right now and I’m excited to see how it plays out.

That’s the letter.

- Nathan May

P.S. I gave away 20 media kits that have done $50M+ in ad sales on Thursday. That post blew up - we’re just under 1,000 comments asking for them, grab ‘em here.

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