It’s easy to get focused on reaching a specific subscriber count, focusing on hitting 1k, 10k, 50K, or 100K subscribers.
But Nathan May from The Feed Media takes a different approach and built a 7-figure newsletter business with around 1,000 people on his list.
“Did you say you’re running 1 million ARR with a thousand-person list?” Dylan asked, barely believing it.
“Yeah,” Nathan replied, like it was the most obvious thing in the world.
Here’s how he did it – and why so much of what you think you know about newsletter growth is off.
The Invite-Only Newsletter
Nathan’s approach to his newsletter started with the realization that he didn’t need a massive list. He just needed the right people.
He knew that he didn’t need to attract thousands of subscribers, and instead created something that felt exclusive.
“I made it a private newsletter. You had to be invited…to the newsletter.”
He was laser-focused on a specific type of reader. Since his core buyers for the agency were the CEO or the Head of Growth/VP of Marketing, that’s what he focused on.
He realized that in the newsletter space, there are maybe 300 companies he wanted to work with. Since each has about 2 key decision makers: 1 CEO and 1 Growth/Marketing–that’s 600 people total.
“It takes this giant, nebulous world – like, oh my god, how do I do this? Do I run ads? Do I write cold emails? – I was like, ‘No, no, no, no, no. You just need the 600.”
Isn’t that so much simpler?
His Luke-Warm LinkedIn Message
Nathan’s outreach strategy for getting these subscribers is great. He’d message people like Sean Griffey, 1 of the 3 co-founders of Industry Dive, on LinkedIn and say something like:
“Hey, evening Sean. I run a private newsletter for newsletter operators who are doing 7, 8, 9-figures. It’s generally for CEOs and their heads of growth. A couple of people like X and Y and Z read it” [where X, Y, and Z were mutual connections or competitors].
Would you mind if I add you?”
The psychological trigger here is just brilliant.
He’s not asking them to sign up for some random newsletter; he’s asking permission to let them into an exclusive club where their peers and competitors are already hanging out. I love that.
“Now I’ve elevated the status of the newsletter. They see their peers are reading this newsletter.”
Of course, it’s going to be a no-brainer. Everyone in the space wants every “edge” they can get.
The Welcome Strategy That Builds Status
When Nathan sends out his newsletter, he includes a section at the top: “Welcome to [newsletter name]” and lists four or five big names that have joined in the last week.
“It just solidifies the reason I’m reading this newsletter. Like, ‘Oh, Tyler Denk and Nathan Barry are reading this newsletter.'”
This is smart because he reminds readers they’re part of something exclusive. And it works super well for retention. Who is going to leave when they keep seeing these heavy-hitters in the space joining the newsletter?!
Why He Chose a Newsletter vs Cold Email
Why did Nathan choose a newsletter over cold email for his agency business?
“Sean Griffey is not going to get on a sales call with me. Sean doesn’t know me, he’s like who is Nathan, I don’t care about this.”
But with a newsletter:
- The barrier to entry is significantly lower
- You build trust over time
- Every time you hit publish, you have a chance to potentially get on a sales call with somebody
- You write one thing, and it reaches every single person you’d potentially want to work with
“If you’re a B2B business owner, you get on call with somebody, let’s say they don’t close. You’re not going to have a chance to get on another call with that person for maybe another quarter. So maybe there’s like four times per year you could potentially close somebody. Well, a newsletter kind of solves all that.”
Why try building trust on random sales calls when you can build trust week in and week out by proving your value via the newsletter? Then, when a sales call does happen, they’re already bought in.
Quality of Readers Matters A Lot
“When we did the Jesse Puji launch, that did a quarter million dollars on 15,000 people. Small but mighty lists are a real thing.”
He shared another example that’ll blow your mind: there’s a woman on Instagram with 9,000 followers who does over $1 million a year. Her secret? She’s incredibly niche – she works at a hospital system and specializes in billing between hospitals and insurance companies.
“Her thing is like, ‘Yeah, I have lived in how to navigate that and actually get the money that you should have.’ And so that’s worth a tremendous amount to the right type of person.”
“Smaller” lists, but huge results.
There is so much power in being hyper-relevant to a small group rather than slightly relevant to a large group.
The First Question to Ask When You Start
“The first question you should ask is not how I get the subscribers. It’s how am I going to monetize when I do have them?”
You want to think through what the plan is and what your end goal is from that jump. Sure, it can change over time, but having at least some semblance of a goal is a nice place to begin.
I made this mistake early on because I kind of fell into this newsletter. I’m figuring it out now but it would have been much easier to know from the beginning.
The 4 Types of People Who Should Start Newsletters
Nathan identified four types of people most likely to succeed. I think this is an interesting way to categorize people:
1. Creators who already have audiences. If you’re building on X, LinkedIn, YouTube, or any platform, pulling that audience to email should be priority one. “The number one channel for Alexi for the revenue that he makes, it’s not like reels or YouTube or any of that. It’s his email list 100%.”
2. Journalists breaking away from traditional media. There’s a lot of distrust in traditional media houses right now. Nathan works with Oliver Darcy, who left CNN to run his newsletter: “It’s just crazy to see how people love his content, how sticky that is.”
3. B2B business owners. “Every founder in B2B should have a newsletter. I think you are being financially irresponsible if you do not have a newsletter.”
4. Newsletter-curious people with a plan. These are people who set a timeline (3-6 months) and focus on monetization from day one rather than just growth.
I’d also add authors who are looking to build an audience for their upcoming book. This can be a great way to get feedback while writing and build trust with readers along the way.
The Media Mullet Strategy
Nathan loves this concept (which CJ from Mostly Metrics shared on the podcast recently).
Every successful newsletter business follows this pattern: “Media in the front, product in the back.”
The Hustle: Ad-supported newsletter in front, paid Trends community in the back (15-20k paying users, $5-7M ARR business with maybe 3-4 people staffed on it).
BlockWorks: Newsletter and podcast in front, events, agency business, and enterprise data platform in back.
The Van Trump Report: Subscription content on agriculture – $20 million a year with two employees.
“You want something high LTV in the back. Even if you’re a creator who has 5,000 followers, think about what skills do you have that you could teach somebody. Can you get one person, two people to pay you $250 a month to start for your time?”
The beautiful thing about selling your time first is that you’re getting paid to do your own customer research.
The B2B Opportunity Everyone’s Missing
When I asked him about the biggest B2B opportunity in newsletters, Nathan didn’t hesitate: “Tools.”
I had to hear more 🙂
He pointed to Figma’s recent IPO: “There are salespeople who made $1 million, $10 million. Some of the top salespeople made $15 million in that IPO. Why isn’t there a newsletter that’s like, ‘We teach you everything Figma?'”
His framework for B2B newsletters follows Industry Dive’s playbook (they went from 0 to $110M in revenue in 7-8 years, sold for $525M):
- Is this industry highly regulated? If so, that’s good because people care about news as things change constantly.
- Do people spend a lot of money? Advertisers will pay more to reach buyers.
- Do people meet at trade shows and conferences? Easy to find advertisers and executive readers.
“You do not need to be first. The Rundown is Morning Brew but for AI. It’s an execution game.”
The One Thing You Should Never Delegate
Nathan was adamant about this: never delegate the writing of your newsletter to a content team.
“The leverage in the newsletter is that it comes from you, the founder, and it’s your words. And somebody replies, they reply to you, not a member of your content team.”
He mentioned Eric Siu from Single Grain as making this mistake: “I think the mistake that Eric is making is he’s delegating it to his content team. I think that’s the worst thing that you can do.”
I’d agree with him, especially for personal brand type/founder focused newsletters. The whole point is that it’s replacing a personal email or call, why outsource that when the deal could be worth tens of thousands of dollars?
Everyone wants to run to AI to replace everything, but the ones who win are going to be the ones who do the “hard” thing and write their actual thoughts down vs asking AI to think for them.
Why Nathan Thinks Paid Newsletter Aren’t Great
Most creators dream of charging for their newsletter, but Nathan’s experience suggests it’s harder than people think:
“I think paid newsletters are really hard. Really, really hard.”
He identified only two times where paid newsletters work well:
- You have a giant hyperfan audience (like if Rowan from The Rundown started a paid newsletter)
- You are the one breaking news, or your analysis is really thoughtful (like Oliver Darcy breaking major stories)
For smaller-scale success with paid newsletters ($100-200K/year), he thinks you need to fit into 1 of 4 categories:
- Life transformation (lose weight, etc.)
- Investing (Market Beat does $40M/year, about $5M from subscriptions)
- Jobs (helping people get better at their work)
- Niche hobbies (like the guy making $150K/year teaching Lego investing)
It’s hard to do this otherwise because getting people to pay consistently (and continue paying) is a tough model.
I feel like there are quite a few outliers, though – and I clarified that if you’re looking to do this as a solo person, then who really cares if you hit multi 7-figures? Most of us will never need that kind of money.
Niches Are Even More Important
Nathan shared a story that perfectly illustrates why going niche beats going broad:
“I was scrolling Instagram 3 months ago and I saw this ad for a paid ads agency that worked with dog e-commerce brands. I clicked through because I like to look at people’s funnels, but in my head I was like, ‘Dude, this is terrible. This has got to be the tiniest business.’ And then I go to LinkedIn, and it was like 25 employees, up and to the right.”
If you think you are niched down enough, you’re probably wrong.
Why does this work? “If you’re a designer, do you want somebody who just does all general DTC Facebook ads, or do you want the guy who wakes up every single day and all he thinks about is how do I get people to buy wet dog food for $30 a month? You want that guy.”
And he’s right.
The old way was to build a massive audience, then figure out how to monetize.
The new way is to figure out exactly who you need to reach and what they’ll pay for, then build the smallest possible audience that can sustain your business.
“Small but mighty lists are a real thing.”
When everyone is chasing scale, Nathan proved that niche audiences beat scale 99% of the time. He didn’t need 100,000 subscribers. He needed the right 1,000 who will pay him multiple thousands of dollars each month to help them grow their business.
And that changes everything.
