The best of Jacob Donnelly

👋 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 Brian, Founder @The Rebooting | Chase, Founder @Retailwire | Chris, Director of Sales @Kit | Georgia, Brand Strategist @ Singlegrain | Stephanie, Director of Paid Growth @ Singlegrain

Jacob Donnelly is the man.

I haven’t met him that much (Jacob, I know you’re reading this - let’s hang out), but I’ve been a long-time reader of his publication, A Media Operator (AMO).

He writes what I believe to be some of the best reflection/synthesis content on media businesses.

In many ways, I endeavor to be a tactical, newsletter-specific version of that, and so I love reading Jacob’s writing to help me see the forest through the trees / connect the dots between many media business models.

Once a quarter, I reread everything he's written in the past 90 days.

Usually, I keep the takeaways for myself. But today, I wanted to share a few thoughts from my Q1 re-read.

1. The future 8-figure newsletters look like niches within niches

We don't need another general AI or ‘Milk Road for XYZ’ newsletter.

I worry that people are getting pitched newsletters as the “make money online” of 2025-26 when, in reality, they’re generally just ‘ok’ businesses until paired with something high LTV like an agency, conference, B2B subscription, etc.

And for those back-end business models to work best, they need to serve 1 customer avatar, not 10.

Three days ago, I wrote this LinkedIn post on a buddy with a $1M/year newsletter with 0 salespeople (all AdSense monetized, $60-80 RPMs).

That post got really popular - because it sounds easy. My qualifier was that my friend’s business model is awesome but only works in very certain niches.

And so I want to re-iterate: the most profitable newsletters lean B2B / prosumer and find a niche within a niche.

Look at the players AMO has covered the past 3 months:

• Punchbowl News literally covers ONE building - Congress. That's 535 people. $10M revenue in 2021, $20M+ in 2023, and reportedly valued at north of $100M.

• The Ankler focuses solely on Hollywood insider info for business exes (talent agencies, studios, etc.), pulling in $5-10M revenue with 20-30% margins.

• Blockworks zeroed in on crypto developers and institutional investors like JPMorgan. They’ll grow 50% in 2025 after 150% growth in 2024 (they did $25M in 2022, so are likely a $50M+ business now)

• The Flyover applied 1440's strategy at the state level, with Texas hitting 300K subscribers and Florida 200K. They're making upper 7 figures (~$7-9M).

• Equine Network focuses on all things horses and does $21-25M in EBITDA on a $85M business (25-30% margins)

• Even 1440 is now niching down with its Topics product into high-LTV consumer areas like personal finance

Let’s talk niche within a niche for AI.

The Ankler has a newsletter called Reel AI on how Hollywood is applying AI to the production process - scripting, animation, etc.

Now THAT’S a good AI newsletter.

The pattern is clear: write to high-income people and help them in their jobs (B2B), niche hobbies, or investments (prosumer B2C).

2. B2B subscription models are printing money

You probably know The Washington Post as a household name.

You also probably know they’re not doing so hot (as Jacob details, WaPo lost $100M last year).

Meanwhile, Politico Pro generates $100M+ in revenue with 93% renewal rates on its subscription business.

I didn’t really understand the strategic difference here until re-reading AMO the past few days - Politico has a single product that pulled them ahead.

Politico Pro.

They realized that professionals in Washington would pay substantial subscription fees for specialized coverage that directly impacts their work.

Their customer avatar looks like:

• Lobbyists tracking developing regulations

• Policy analysts researching legislation

• Government affairs professionals

• Corporate executives in regulated industries like healthcare and energy

They gladly shell out $2,000-$10,000+ annually for ‘first and best’ information:

• Bill trackers and legislative compasses

• Alerts on specific policy topics

• Deep reporting across 22 policy areas from 300 professional reporters

• Exclusive events with policymakers

• Etc.

Politico Pro launched in 2010 and by 2018 was driving more than half of Politico's revenue. That’s why Axel Springer paid 5x revenue (an absolutely wild, SaaS-level valuation) when they acquired it in 2021.

This is why WaPo is/was reportedly talking to Punchbowl about an acquisition - the writing is on the wall that B2B subscriptions for information/data is the easiest way to catch up.

Let’s talk one other subscription newsletter.

Jacob got enough information from The Ankler for me to back out most of their LTV / ARPU metrics (estimated - I’m a marketer, not a journalist).

Check this out:

A $500+ LTV (if the 2.1% churn and 21% CVR Ankler told Jacob last year have held) is a wildly good business.

Niche within a niche + subscription = sustainable, high-margin business.

3. The Media Mullet: Content up front, cash flow in the back

Ad-monetized content in the front builds distribution that can be monetized in the back with premium products and services.

Media mullet is way more fun to say, though.

That's when a newsletter business starts to get really interesting.

Look at these examples:

• AIN Media Group (aviation) went from 100% advertising revenue to an events division that already represents 25% of revenue and data subscriptions representing 10% in the past 2 years

• Blockworks has built out events, an advisory business, and a ‘Bloomberg for Crypto’ enterprise data/research platform

• The Van Trump Report generates $20 million primarily through premium content subscriptions in the agriculture space.

• Bootstrapped Giants, Jesse Pujji's newsletter with just 20,000 subscribers, drives over half a million dollars through a cohort course for B2B founders

• Axios is converting 1-2% of their readers to $1,000 subscription products (insider access and invitation-only events), adding $10-20 ARPU - a massive improvement over typical ad-supported newsletters

When you move beyond $5-15 ad-supported ARPUs to products with $500-1,000+ price points, even modest conversion rates create dramatically better businesses

4. Communities will be king

These niche newsletters pair perfectly with communities.

Sam Parr recently said that people laughed at him for thinking newsletters could be a big business 10 years ago.

Now, he thinks communities are the undervalued asset everybody will be kicking themselves about.

Some cool community businesses have emerged:

• Hampton serves 7-9 figure founders looking for the emotional side of community - net worth, purpose, dating… the human side of entrepreneurship

• Daniel Fazio runs a community for agency owners (does $300K/month) that’s the tactics version of Hampton - specialized calls for landing pages, cold email, ads, etc.

• Exit Five (featured in AMO here) focuses on B2B marketers with highly tactical content, playbooks, and frameworks

• Bootstrapped Giants runs an accelerator with Jesse Pujji, who's done 9 figures of revenue in B2B businesses + now teaches folks his playbook

• Workweek built a profitable media business with 30% margins to 7 figures, then raised $12.5M to go into B2B communities and cross the 8-figure milestone

I’m a big proponent of community.

Last year was my year of focus - I moved to Columbus and did nothing but work.

I made a lot of internet friends, who I love… but nothing has hit the spot more than being back in NYC the last 3 months and seeing people in person.

There’s a guy I met 8 weeks ago, Josh, who started an agency when he was 19 - he’s 20 now, doing $50k+ a month. How wild is that?

I co-work with a lot of these types of folks, and it gives me an incredible amount of energy.

In-person rocks!

I'd love to do a newsletter for bootstrapped B2B founders based in NYC.

That’s a great newsletter idea because it’s a niche within a niche. And I’m the customer.

Which would make me at least an ok writer for that audience.

Could I hang out with cool people for $2-3 a lead? That sounds amazing. Ha.

That’s the type of place more of these new newsletter ideas should come from. Not this make-money-online stuff.

5. Partner with creators, own a category

Adam Ryan (CEO, Workweek) wrote extensively on how AI might kill newsletter businesses the other week.

If you agree that content will become more commoditized / the inbox more competitive, then it follows that distribution will be king.

And that distribution will go to folks who are known/liked/trusted (everything else will be progressively eaten by AI summaries, says Adam).

If prosumer/B2B is the right audience, high-LTV the right monetization, and creators the right messengers, then it follows that B2B creators have some of the biggest opportunities in newsletter/media businesses.

This is the thesis of Adam’s company - Workweek has creators across franchise owners, hospitality, HR, DTC, etc.

Workweek has a good business model.

But Jacob has written about some of its missed potential: economies of scale.

The ad inventory/communities are difficult to cross-sell because each creator is so unique/different than the others.

That means more salespeople, content writers, and community managers.

Here’s a cool idea - imagine you did Workweek but niched down into a single category.

Let’s say you owned the D2C space with a team of specialized creators:

• Chase Diamond talking about email marketing

• Alex Cooper on how creative strategists can leverage AI

• Nik Sharma (already part of Workweek) on DTC advertising

• Ron & Ash on taking Obvi into retail stores

• A logistics/ops expert (does a personal brand around this exist?)

Suddenly, you've got it all. You're covering the entire e-commerce organization.

You can sell to the same brands.

Go to the same conferences and pick up founder/exec subscribers.

The flywheel works together so much more when you stay in one vertical.

You don’t even need to own the entire newsletter stack (content, growth, sales) for it to work - Alex Lieberman and I went on a run this past weekend and one of my takeaways was how much the ‘own a category’ playbook works for ad sales.

Example: there’s ONE GUY who sells the ad inventory for all the major cybersecurity newsletters and a few YouTubers. Smart!

Smooth media is arguably the most successful version of this in newsletter land and it’s largely because they work with only Prosumer/B2B-leaning knowledge creators and sell ALL of their inventory (YouTube, in-person events, newsletter, etc.).

Examples:

• Miss Excel (Excel lessons for corporate folks)

• Calum Johnson (entrepreneur podcast)

• Jaclyn Dallas (consumer tech)

Niched down partners with horizontal monetization.

Anyway, if you take away one thing - Jacob is great, AMO is great, go become a reader here.

That's the letter.

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