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- đź”´ He spent $20M growing newsletters
đź”´ He spent $20M growing newsletters
ft. Matt McGarry, a newsletter growth expert, creator of Newsletter Operator, and GrowLetter agency owner
Francis Zierer
January 17, 2025 • Estimated Reading Time: 13 minutes
Your guide to the newsletter world — new stories every Friday. Brought to you by beehiiv.
Today’s guest is Matt McGarry, an expert at helping newsletter-focused businesses grow their audiences. He runs an agency called GrowLetter, a course called Write, Grow, Sell, and a newsletter called Newsletter Operator.
Matt is one of the best purveyors of tactical newslettering advice out there, so I kept this issue tighter and more tactical than most. At the bottom, I’ll link to a few of the most useful posts from Matt’s newsletter.
In this issue:
✍️ Creating first vs. making a plan to monetize before creating
📧 Newsletter-only vs. newsletter-focused businesses
đź’Ż A short guide on going from 0 to 1,000 subscribers
— Francis Zierer, Editor
P.S. Watch our full interview with Matt on YouTube or listen to it on any podcast platform.
The Newsletter Guy
On the creative-to-entrepreneur spectrum, Matt McGarry is firmly an entrepreneur. Few people have spent more money using advertising platforms to build newsletter email lists over the last few years. He and his teams have spent “between 10 and 20 million” dollars to generate “over 10 million” subscribers for their clients.
The client list on GrowLetter’s website (Matt’s agency) features many of the last decade’s most successful newsletter-centric businesses. First on that list is The Hustle, the company where Matt settled into newsletter growth work, which was acquired by software company HubSpot for a reported $27 million four years ago, when it had 1.5 million subscribers.
Matt’s journey — dropping out of college after one semester before teaching himself marketing, building a portfolio through Upwork gigs, parlaying that into a series of full-time jobs, leaning into consulting, and building an agency around his consulting work — is a variant of the classic bootstrapped entrepreneur story. Teach yourself the skills; contextualize them by spending a couple years in the workplace; take those honed skills to market at a premium.
I asked Matt if he identifies as a creator: “I do and I don’t. I’ve never created for the sake of creating.” His newsletter — a valuable, free resource for entrepreneurially-minded newsletterists — is less a standalone editorial product than marketing content for his various services. “I’m creating as a business owner, an entrepreneur,” he says.
“Before I create something, I always have a way to monetize it first, which is, I think, the opposite of what a lot of creators do. And that's why I would describe myself as a founder.
I always start with the end in mind, and most creators don't do that. That's totally OK, too. You can you can win both ways.”
When Matt said this, it immediately sharpened my understanding of the creator economy’s creative-to-entrepreneur spectrum. Last year, I interviewed musician and seasoned YouTuber Andrew Huang on the occasion of his book release, Make Your Own Rules, which clearly sees its audience as creative types struggling to make a living doing the work they love or even to begin thinking of it as a business endeavor. The book seeks to show creatives a palatable, achievable, and sustainable path to creative-entrepreneurialism.
Consider the act of essaying. In school, I was taught that to essay, as a verb, is to approach a topic in search of a conclusion, of answers; you certainly can essay with a predetermined conclusion in mind, but the higher purpose of writing an essay is to advance and deepen your understanding of the topic in question. An essay written towards a predetermined conclusion is a marketing document in an essay-suit.
As long as the creator-economy entrepreneur’s prime goal is revenue, there is nothing they’re obliged to learn from the creative. This isn’t to say there isn’t anything for them to learn. But in this industry, quality content isn’t the only business model; there are many ways to capture attention.
As long as the creator-economy creative’s prime goal is revenue, however, there is much they’re obliged to learn from the entrepreneur. As bushcraft when lost in the woods, so entrepreneurcraft in the creator economy.
Let’s learn from Matt.
A newsletter operator has three jobs
The name of Matt’s program comes from an observation he credits to Morning Brew co-founder Austin Rief: a newsletter operator has three jobs: “Write, grow, sell.” That term, “newsletter operator,” is specific and worth defining, as Matt did:
"[Newsletter operator is] a catchall term for people who write, grow, operate, and monetize newsletters.”
Any creator — whether a newsletterist on the open internet or a mono-platform creator in the walled garden — shares these same essential responsibilities, which we can generalize as create, grow, sell. You create content, find ways to grow the audience, and find ways to monetize between the two.
Newsletter-only vs. newsletter-focused businesses
“Newsletters are a strategy, not a business model,” Matt tells me; he sees a newsletter as just one egg in a business’ basket, not the basket itself. I bring this up to underline his newsletter-only vs. newsletter-focused framing.
Successful newsletter-only businesses are rarer, says Matt, than successful newsletter-first businesses. They are those where the only product is the newsletter itself, monetized through one or both of advertisements and subscriptions. Isaac Saul’s Tangle is a great example of what success looks like here. But even those businesses that start newsletter-only often branch out; Morning Brew, for example, has become a newsletter-focused business by adding a number of other thriving content verticals, merchandise, and events.
Most of Matt’s clients are, as he says, newsletter-focused businesses.
“I think the idea of having an audience and never selling them a product or service is pretty crazy. And I think that's equally as crazy as having an audience and only monetizing a small percentage of them through your product or service and not monetizing them through sponsorships.
I think modern media companies have to have both, have to have a product or service you sell [your audience], could be anything that's a fit for them and a fit for you. And you have to have sponsorships or advertising to monetize your entire audience, not just a small fraction.”
“Don’t start a paid newsletter or content subscription for consumers”
Given he’s “The Newsletter Guy,” I was surprised by Matt’s bearishness on both advertising and subscription-based newsletter business models. I situate his bearishness, again, in the context of his entrepreneur-first outlook; GrowLetter rarely works with clients that don’t have at least 20,000-30,000 engaged newsletter subscribers and aren’t generating at least $30,000 per month in revenue. I’d say his bearishness is on any given newsletter-only business being able to hit numbers like this through a mix of ads and paid subscriptions alone.
“How do you grow an audience, especially a newsletter audience? You have to grow that audience through publishing content, and if all your best content is behind the paywall, you never really have the audience.
[Paid subscription newsletters] have this chicken-and-egg problem that never gets solved. And then if you don't have an audience, you have to grow using paid acquisition, and most people, especially writers, don't know how to do paid acquisition profitably.”
Bullish predictions
I don’t want to give the impression that Matt has a negative outlook on newsletters in general; it’s more that his pragmatist, entrepreneurialist outlook has little patience for businesses that don’t pass the standards he holds his clients to.
I’ll leave you with the areas he sees as major newslettering opportunities:
I'm very bullish on B2B creators, local newsletters, local media, finance, investing, and not just B2B creators, but B2B media companies.
And just anybody who has a unique perspective and can help people through their content — there's room for you to succeed.”
Connect with Matt on Twitter or LinkedIn.
Read and subscribe to Newsletter Operator.
Matt is hosting a conference in February, the Newsletter Marketing Summit.
🎙️ This was an excellent conversation and longer than our usual podcasts. If you’re looking for more depth on some of the tactical newsletter business topics, you should give it a listen. Matt does a masterclass.
📱 How Matt turns his newsletter issues into well-engaged social media posts
đź‘€ How to achieve a low, sustainable subscriber ads CPA (cost per acquisition)
📧 A breakdown of GrowLetter’s newsletter audit process
Listen on your preferred podcast platform or watch on YouTube.
How to go from 0 to 1000 newsletter subscribers
This is one of the questions readers send me most. 1,000 readers feels real, represents some critical mass, the potential for word-of-mouth growth, and content-market fit. I asked Matt how he’d advise getting there.
1. Figure out your newsletter’s offer or value proposition
“If your newsletter isn’t valuable, people aren’t going to sign up." It’s difficult to grow something that isn’t good! Quality is a tactic.
2. What is your launch plan?
Message your network (don't add them to the newsletter subscriber list unawares): "Send an email and text to everybody you know. Here's why you should subscribe, here's the link to join."
Send 100-500 messages to your network. “Maybe you get 50 to 100 subscribers from that, maybe less.”
“Do an announcement on social, even just your friends and family, do an announcement on all the social posts you have. Add it to all your digital real estate. Do you have a website? Add it there. Do you have a link in bio? Any digital real estate you have where people can sign up, add it there. Even physical real estate, if you have business cards or a physical business, add it there.”
With a concept set and an audience in place by whose reaction you can judge and refine your concept, send out the first issue. Then you put out your shingle — chop it up for social media (Matt talks more about this on the podcast).
3. Publish your first newsletter and be loud about it on social media
“We repurpose that content onto social media because the best way to grow a newsletter is through content-led growth.
Send your first newsletter
Repurpose that content across social media, choosing one primary platform to focus on
“Try to have thoughtful, but not super aggressive, calls-to-action on all the content that we post on social, with a well-optimized social bio that drives people to the newsletter landing page. You can get to 1000 subscribers just with that.”
Bonus: Paid growth and pre-newsletter CTAs
To get more momentum, Matt recommends experimenting with paid advertising, encouraging spending as low as “$5 to $10 a day on paid ads.” It’s enough to get the ball rolling — “I wouldn’t spend much more than that.”
Another tactic is the "pre-newsletter CTA.” It’s simple: the day before publishing the newsletter, post a preview on your socials and remind people to sign up.
Listen to the latest episode of Tasteland, the weekly podcast about media, tech, and business hosted by Spotlight editor Francis Zierer and Dirt Media CEO Daisy Alioto.
This week, we’re joined by writer Greta Rainbow to chat about food influencers replacing food critics, the legacy of Apple’s Photo Booth app, the death and/or future of alt-lit, and why Daisy dislikes “scenes.”
And I’ve selected a few tactically useful issues of Matt’s newsletter for you:
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