Category: Newsletters Page 2 of 3

Five Key Hires That Took Morning Brew To $40M+

On February 2, 2024

Often times, when we talk about how a newsletter grew or made money, we talk about the tactics they used. But it’s easy to forget there were people behind those tactics. People who, day in and day out, thought about the problems, tried stuff, found solutions.

I’m not talking about founders and CEOs. I’m talking about the people behind the scenes, who actually have their hands in things.

Sometimes they’re well-known. Most of the time, they’re not. But they’re out there, and if you track ‘em down, you can learn a lot from them.

Here’s how I like to do it…

First, I read a few old interviews with the founders of a company, and news stories going back the last few years, jotting down milestones as I find them.

Pro Tip: Founders are typically very slow to talk about this year’s numbers. But they’re almost always happy to talk about last year, so if you just read a few interviews over several years, you can piece together a really interesting picture.

For example, I’m working on a case study for Morning Brew. After just four short articles, I find myself with something like this👇

Ugly, right? This doesn’t have to be pretty

Right away, you can see there were a few fascinating turning points in the company’s audience, revenue, and team size:

2017-2018: They 10X’d the audience, crossing 1M subscribers
2018-2019: Revenue more than quadrupled from $3 to $13 million
2020-2021: They added ~100 people to the team, two per week for a year

Why? How? Most important, who were the people that actually did the work to make this happen, and what have they shared about it? That’s where my mind goes.

I’ve got a process for finding these “keystone employees“, but it’s a bit involved. So to keep this short, I’m going to cut straight to the chase.

If you want me to write it up, click this.

I’ll check the data and if enough people click it, I’ll do a tutorial on exactly the tools and steps I use to reverse engineer some of the most important hires companies make.

At any rate, the rest of this email is a look at a few people you may not know who played pivotal roles in growing Morning Brew to $40m+, along with some of the insights hey’ve shared about how they did it.

We’ll look at four key areas of growth:

Audience
Content
Revenue
Staffing

If you’re hoping to build, “The Morning Brew for XYZ,” think about when you’re going to hire for these roles, where you might find your version of these people, and what you can learn from the ones who did it first.

1. Audience

If you’re deep in the newsletter space, you may actually know of Tyler Denk. Today, he’s the founder of Beehiiv, the very platform this email was written on.

But before that, he was a growth engineer at Morning Brew, and specifically, he was the guy who built the technology behind their world-famous referral program (along with many other things).

He was one of the first two employees* and was there through the acquisition, working on product and growth, and managing 6-figure marketing budgets.

Learn From Him: Back in the day, he wrote two excellent pieces on how the referral program works, and the tech that powered the newsletter. He also did a great written interview on the early days of the brew, and has appeared on several podcasts, to talk about various aspects of the journey…

*Michael Schwartz was their first employee. Both he and Tyler are building at Beehiiv now, which goes to show how these companies can become talent incubators that launch other successful businesses. Smooth Media is another company founded and led by several by Brew alums.

Big Takeaway: Lightning doesn’t strike twice. Rather than strictly copying the Brew’s referral program, you should try to learn from their hiring strategy. Early on, find someone who’s scrappy, independent, can try a lot, and will find/build the thing that becomes your uniquely effective growth lever.

2. Content

Neal Freyman was hired as a writer in June of 2017, which makes him another one of the earliest-ever employees of the company. He quickly became managing editor, and has now been there through the rise of eleven publications, hundreds of employees, and millions of readers.

I don’t think I can name anyone else in the industry with that kind of editorial experience.

Learn From Him: While he writes regularly for various Brew properties, you have to dig a little deeper to find him talking about how he does his job. Still, it’s out there. He’s appeared on several podcasts to discuss…

He’s also done written interviews on Balancing the Grind and Thrive Global, and interestingly, used to publish on Quora before the brew. It’s pretty cool, you can see the style taking shape there.

Big Takeaway: Content benefits from committed guidance. Are you building an environment where someone can and wants to A) rise up through the ranks and B) stick around for a long time?

3. Revenue

The first major jump in revenue came between 2018 and 2019, when the company more than quadrupled from $3m to $13m in a year. From there, they roughly doubled every year until 2022 (my most recent data) when they did $36 million in the first half of the year.

Wild.

A key person behind this was Jason Schulweis, who joined as head of brand partnerships in mid-2019 and helped completely restructure the sales team.

Learn From Him: He moved on in 2022, but left behind a great body of work outlining what that period looked like.

Every year, he did an annual review (Year 1, Year 2, Year 3) that not only included major strategic decisions and their outcomes, but also linked off to lots of other posts he wrote along the way explaining his decision-making, hypotheses, and lessons learned (from hiring, to B2B advertising, to connecting the dots).

He also appeared on several industry podcasts, including…

Big Takeaway: Experience pays. Before the Brew, Schulweis had led teams at Yahoo, Thrillist, Live Nation, and Media Link. He was able to see the structural problems holding the initial team back, and fix them quickly. If growth and content benefitted from having young, scrappy go-getters, revenue seems like the corollary – pay to bring in someone who’s been there.

4. Staffing

Probably the most overlooked part of growing a company, but crucial to building a cohesive team.

Morning Brew made its first HR hire, Kate Noel, in January of 2020, when the company had ~30 employees, and was doing 8-figures in revenue. She’s still there as of this writing, serving as SVP, head of people ops, and has helped the company grow to 300+ employees.

Similarly impressive is their second HR hire, Lily Mittman. She joined as senior director of talent acquisition immediately after the brew was acquired by Business Insider in late 2020, and was the first person in the company to sit in a talent acquisition role.

Over the course of her first year, she helped take the team from ~75 to ~175 people. Two hires a week. Every week. For. A. Year.

Learn From Them: I can’t imagine the stories these two could tell (although I suppose the first rule of HR is you don’t talk about what goes on in HR). Perhaps for that reason, they haven’t published a ton of inside baseball. But they have appeared in some places…

Someone really needs to sit down with these two though and talk about what it’s like to handle the people side of a media company going through sustained hyper-growth.

Big Takeaway: Brew co-founder Alex Lieberman once wrote that, “I’ve realized that it’s very difficult to ever hire too early for HR,” which on its own is an interesting insight for people who are scaling.

Wrapping Up

Scaling a newsletter is about more than tactics. It’s about the people behind the tactics, how they looked at the problem of growth, and what they learned from what they went through.

The founders, yes. But increasingly as it grows, the people lower down who are closer to the work.

Find those people, talk to them or learn from their work, and you end up with a much higher-fidelity understanding of what you’re going to encounter, and how to deal with it.

What’s Your Advantage?

By Ethan

On February 2, 2024

In Newsletters, Rambler, Writing

I was on the phone with another local newsletter founder the other day. He’s doing 7-figures across a handful of publications, and he asked me what I thought the gap was that my Austin newsletter was filling.

It’s a great question. And to be honest, I hadn’t thought about it much. I guess the way I’m trying to go about this newsletter is I’m building the thing I think one or two of my friends would like to have.

But the longer I spend in business, the less crucial I think an actual gap in the market is. Most of the wealthiest people I know are plumbers, and closet installers, and house painters and the like. They’re not tapping into new markets, but just serving a big existing one with lots of healthy competition.

But I do think a lot about advantages, and what, if anything, allows you to differentiate yourself and stay in business, even if others are serving the same customers you do. And I’ve always liked the framework put forward by Tim Ferriss that says there are essentially three possible advantages you can have:

Informational
Behavioral
Resources

I don’t have millions to make the newsletter work, so I can’t out-spend or out-wait competitors.

As for behavior, I’m a default-introvert who’s quite happy (too happy, really) to lounge around at home rather than going out. Oh sure, I can be social. But there’s no compulsion I have that would make me better at writing a local newsletter than someone else.

The thing I plan to lean on is an informational advantage, and this is may be interesting to you because it’s (I think) the one thing you can choose to develop.

I’ve heard it said that a well-curated Twitter feed can be more valuable than an MBA, and I agree.

So the first few weeks of this process have been largely focused on building the kind of information flow that will allow me to curate something fascinating for readers.

The process is simple, really. Just time-intensive, and you can’t rush it.

I have an RSS feed, Twitter, and a Google doc.

The RSS feed is subscribed to a few great news sources around town, and on Twitter, I keep a list of individual people who say and do interesting things here too.

Each morning, I spend a couple hours reviewing both closely. Anything that seems like a good fit for the newsletter gets dropped in the Google doc for use later.

That’s where most of the content comes from, but the secret is that as I’m reading, I take the time to continue updating both the RSS Feed and the Twitter list.

So if I read a story about an interesting local founder, I may add them to my Twitter list to stay up to date on ideas they share in the future. If they have a personal blog, I may add that to the RSS feed too. Depending on the situation, I may also reach out, introduce myself.

With each new addition to the info stream, I get a better and better sense of what’s going on around town, and what little-known things readers might like to hear about.

It’s really very simple, but it takes time and you can’t force it, and that’s why most people never do it.

With time, you can get to a point where you’re seeing things long before most other people, or you have access to information others can’t get. Then, your audience is locked in because everyone wants access to information that’s hard to find.

This pipeline of information is one of the most important assets you can have as a writer, and it’s one you can build virtually for free.

Launch Playbook for Local Newsletters

By Ethan

On January 26, 2024

In Case Study, Newsletters, Rambler

When Gunnar S. Holm revealed that he was paying $0.50-$0.60 per subscriber (less than half the typical cost) to grow a local newsletter in Oslo, people said exactly what you’d expect…

“Well, yeah… You’re building in Norway! Try doing that in the US and then come talk to me.”

So to prove the point, he spent a month running the exact same playbook on an audience in San Francisco (thousands of miles from where he even lived), and it worked there too.

The other day, he took me through the whole thing, and I think everyone can learn from what he did. So real quick, I’m gonna run you through…

His Content Strategy: The Reverse Lead Magnet
Launch: How He Went from 0 to 1k (and 1k to 10k+)
Monetization: What Worked and What Didn’t

He shared his exact copy, best performing ads, plus a bunch of data and we’ll get into all of it.

Even if you’re not building a local newsletter, a lot of this is applicable, and may just help boost your conversion, cut your growth costs, or add a revenue stream where you weren’t expecting one.

Let’s dive in…

1. Content Strategy: The Reverse Lead Magnet

Having grown up in Norway, the concept he picked for the local newsletter was simple and specific: “Five of the best events taking place in Oslo, delivered every Thursday.”

“I thought of it like a lead magnet,” he told me. Start with one clear problem you solve, then you can expand content from there if you want.

Personally, this helped me a ton. I was getting hung up on the landing page for my own local newsletter because the content was an eclectic mix of local business events, artists, news from around town, and more. I couldn’t figure out how to describe it!

But this “think of it like a lead magnet” approach broke all those mental barriers for me. I ran with a slight variation on his hook (“5 cool events for business owners in Austin”) and sent the first issue the very next day.

Interestingly, this is a concept Matt McGarry and Ryan Carr actually explored this week on the Newsletter Operator podcast too (around 7:57).

They talk about how a newsletter is like a lead magnet people get every week. A reverse lead magnet, if you will.

Because a typical lead magnet offers readers something they want in the moment. It’s a quick hit of adrenaline, and then a crap-shoot on whether they ever open another email from you again.

The best newsletters position themselves to not just send recurring content, but solve a recurring problem, which makes it more likely readers come back.

In the case of Gunnar, that problem was, “What should we do this weekend in Oslo?” And in less than nine months, the simple promise of five cool events each week grew the list to to over 10,300 subscribers with an average open rate of 61.6% and clicks around 9.4%.

By the way, if you’re hoping to build a local audience, starting with event curation seems like the way to go. In fact, Ryan Sneddon built a six-figure newsletter in Annapolis, and recommended something similar (live music listings) in his interview on the Newsletter Operator podcast.

I think it’s smart for three reasons:

It’s useful to readers
It’s a pretty light lift to write
People will keep opening week after week

But how do you actually get readers? Well, let’s take a look…

2. Launch Strategy: Reddit First, Then Paid Ads

Reddit: Gunnar got his first 1,000 subscribers from posting event roundups in the local Subreddits every week. He did this for both his Oslo and San Francisco experiments, and the approach/reception were similar in each.

Here’s an example from SF (screenshot below). You can see, he’s not shy about promoting the newsletter there.

I was surprised by that, and asked if anyone gave him shit for doing self-promo. The short answer: No.

“In big subreddits, like r/Entrepreneur, people are very aware of self promotion,” he said. “But in smaller local channels, they’re not as strict.”

He’d post every Wednesday, and occasionally, someone would gripe. But the moderators were happy to have some valuable posts in the group, and most feedback was positive.

Not all of his posts garnered 100+ likes. But even the less popular ones delivered a healthy number of subscribers, because Reddit is more of a meritocracy than other social channels. Posts don’t need a lot of likes in order to be seen by many, many people in a channel.

Facebook Ads: Around 1,000 subscribers he started using Facebook ads to grow the list faster. If you’re new to Facebook ads, there are a couple different types newsletters tend to use:

Traffic Ads: When you click these, it sends you to a specific landing page
Leads Ads: These can have an email capture right on the ad where people can sign up to your newsletter

He tested both and found that the CPA was roughly the same. But he prefers to send people to a landing page for a few reasons…

First, it makes it possible to integrate Sparkloop, or another newsletter recommendation service where you get paid for referring subscribers to other newsletters (more on this below).

Second, he feels it’s less likely the email addresses are coming from spam bots.

And finally, he says, people are just more likely to remember your email and engage with it if they’ve experienced your landing page, seen your branding, and maybe even read one or two past issues before signing up.

His best ad: “This is by far the best performer,” he told me, sharing the ad creative below from his SF campaign. He tested a lot of these short ads with text in the foreground, and a simple shot of the city in the background.

“The copy is based on months of testing for the Oslo newsletter,” he said. “The copy – Struggling to find things to do in {city}? – works very well in my experience.”

3. Monetizing: What Did and Didn’t Work

When it came time to monetize, there were a couple of surprises…

First Surprise – Sparkloop Didn’t Work: Gunnar runs a newsletter growth agency called GrowJoy, and one of his specialties is the Sparkloop + Paid Ads combo.

Essentially, you pay for ads to grow your newsletter, then add Sparkloop and get paid to recommend other newsletters to your readers, offsetting some or all of the money you spent acquiring them.

He wrote about it in more depth here.

This chart is for a different newsletter, but the growth combo (ads + Sparkloop) is the same he tested for his local newsletters.

Typically when he sets up SparkLoop, he sees something like this from new subscribers…

~50% of new readers opt into other newsletters
~50% of those meet the criteria needed for Gunnar to get paid
Publishers pay ~$1.50-$2.50 per accepted subscriber

So the math looks roughly like this…

.5 x .5 x $2 = $0.50

For every new subscriber he gets to his newsletter, he can theoretically count on $0.50 from a Sparkloop partner. And since the local newsletter was growing for ~$0.50 per reader, his ads would have essentially paid for themselves…

But, alas… No!

For some reason, his local readers opted into other newsletters much less often than expected.

I asked him why he thought that was, and his theory is that there’s a mismatch between the themes of a local newsletter and some of the broader tech newsletters that pay for referrals.

People signing up for a local event roundup aren’t in the mind-space to subscribe to a crypto newsletter.

If true, it’d mean people are paying close attention to the recommendations. So if you’re going to test this, try hard to find newsletters with serious overlap.

The Second Surprise – People Were Willing to Pay: Toward the end of his experiment with Oslo, he’d grown the list to ~10k readers, and started experimenting with paid subscriptions, signing up 240+ people at $5/mo.

Here’s how it worked:

Subscribers joined the list for free
After 2 months, they got an email saying that to continue getting the newsletter, they needed to become a paid subscriber.
Anyone who didn’t pay was segmented to a marketing list that got the newsletter once a month, along with “FOMO” emails every so often, showing events they could have found if they were paying subscribers.

Overall, the response to his request to pay was pretty positive. Some thought $5 was over-priced (some people always will). But generally, people seemed more than willing to support a local creator.

4. Wrapping Up

Ultimately, he shut both newsletters down because his main focus is his agency, and a lot of these side projects are just experiments he uses to refine or prove out what he’s doing with clients.

But I learned a ton from him, and am using parts of his playbook directly to help grow my local newsletter in Austin. More on those experiments in a future email.

In the meantime, if you want to learn more, Gunnar publishes a bunch of stuff about this on Twitter. You can follow him there or check out his company.

How Creator Economy NYC is Pioneering Local Industry News

By Ethan

On January 19, 2024

In Case Study, Newsletters, Rambler

Recently, I said that I think there’s a huge opportunity in local newsletters. Not just local news – but niche, industry newsletters designed to serve specific cities.

This week, I have a perfect example.

Brett Dashevsky runs Creator Economy NYC, (shout-out to Chenell Basilio for turning me onto his work).

I got a chance to chat with him and while it’s early days for the brand, I’m convinced that in 1-2 years this can be a multi-million dollar business. Here’s why…

Background: Brett’s got some really interesting experience with newsletters already.

Back in 2020, he and his brother launched Healthcare Huddle, which they grew and sold to WorkWeek in summer of ‘21. As part of the acquisition, Brett joined WorkWeek’s core team, eventually overseeing Creator Success and helping their stable of writers launch and grow other newsletters.

It was useful experience, but being immersed in the creator ecosystem, he always knew he wanted to get back into building his own brand…

He Started with Just Events: After moving to New York, Dashevsky wanted to build connections. So in January of last year, he started hosting regular creator meetups at a local bar.

They snowballed from 15 attendees to dozens, then hundreds as word spread.

For almost a year, there was no formal newsletter. This was essentially a side project, and it was focused on in-person conection. Then, after parting ways with WorkWeek toward the end of the year, he decided the time was right to go all in, adding a newsletter component and making a real push to turn CENYC into something bigger.

Event Platform:
People sometimes ask what tools are good for hosting events right now. Brett started on Partiful, but switched to Luma last year because he felt it had better features for professional community-building.

“You can build out an events calendar for people to subscribe to,” he said. “It automatically captures RSVPs emails and provides them to you, and events automatically add to an attendees calendar.”

Luma’s also a bit more email-centric, whereas Partiful is built around SMS.

Don’t Reinvent The Wheel: One big advantage Brett had when launching CENYC was experience. He’d built Healthcare Huddle, and spent years helping WorkWeek creators launch their newsletters. So he already knew a lot of the important things about how the newsletter should be built.

He leaned hard on the branding, and I gotta say, CENYC has probably got the best branding of any newsletter I’ve seen recently. Seriously, check this out.

The look is designed to mimic the NYC subway, and every section of the email is a subtle nod to NYC culture. They even hide easter eggs in each issue. It’s great.

There’s also stuff in there every newsletter operator should think about. For example…

1 . Use the same intro line across each issue. It reminds people quickly why they’re there and what they can expect to get.

2 . Remember that people will forward your email to friends – drop a subscribe button up top for anyone who likes what they see.

At Trends, we used to put this at the bottom. I haven’t seen any data on whether one or the other is better, but up top makes sense to me if you have the space.

3 . Use the Rule of Three in your lists or articles. A lot of writers get themselves in trouble trying to create huge lists or round-ups each week. Three is plenty, it’s useful to readers, and visually satisfying.

Growth & Monetization: So far, events have been the main driver of growth for the list, followed by social media posting, and Beehiiv’s recommendation network. It’s early though, and I suspect this year we’ll see those shift as the newsletter becomes more of a focus.

As for sponsors, some big names have taken notice. CENYC has worked with brands like Teachable, Mekanism, Notion, and more.

At this point, many of the sponsors are helping with event logistics, paying a few thousand dollars for food or meeting space. But that’ll change too as the community gains steam and the price of tapping into it goes up.

Why I Think This Will Work: The short version is that CENYC is in a big city, targeting a professional audience. Sheer numbers are on their side.

There are ~20 million people in NY Metro area
Many people want to be creators (like… most of GenZ)
Lots of brands want to partner with creators, and CENYC is uniquely positioned to make that connection

Plus a lot of the content is valid to readers outside NYC. Similar to The New Yorker I expect a decent chunk of their audience will eventually be outside the city. But even if it’s not, the math is still on their side.

If they only ever reach 1% of readers in the metro area they’re still looking at a list of ~200k well-targeted subscribers, and that’s more than enough to build a 7-figure business on.

I think The Newsette is an interesting example to learn from here. In 2021, they did $40 million in revenue with a list of ~500k subscribers, which is incredible.

Almost half of that was ads, and the rest was agency services they sold their advertisers on the back end (e.g., “Look how well your ad worked in our newsletter. We know content. We can help with yours!”).

Creator Economy NYC will have a lot of options when it comes to monetizing – ads, affiliate deals, event tickets, paid creator communities, etc. But the trick will be finding the highest-leverage one.

A creator marketing agency might be an interesting option. After all, they’ve got an ever-growing list of up-and-coming creators. And founders like Mae Karwowski have built these kinds of agencies to incredible exits.

At any rate, this is one I’ll be keeping an eye on. If you want to follow along too, check ‘em out here:

Black Swan Newsletter Growth

By Ethan

On August 12, 2023

In Newsletters

Something interesting happened this week at Hampton that’s updated the way I think about organic newsletter growth in the early days of a publication.

First, some background:

Currently, our strategy for growing the newsletter is 100% organic. Both of our co-founders have large social media followings, so there’s a lot of juice to squeeze there before needing to go paid. We’re also still learning a lot about our audience and what they want – figuring out the content.

So organic is the way.

The official plan basically riffs on Justin Welsh’s system. We…

Lean primarily on Twitter, LinkedIn, Reddit, and Hacker News
Post 1-3 times per day, occasionally linking back to our blog
Do pre- and post-newsletter calls for signups (like this and this)
And generally try to share cool stuff people actually like

The “plan” has been to gradually build the reach of those audiences, so that each time we link to our site, we drive more and more traffic, and grow the list faster.

Then, this happened…

This off-the-cuff Tweet from Sam sent thousands of clicks to our site, many of whom signed up for the newsletter. All-told, we hit ~70% of our growth goal for August off this tweet alone.

I know what you’re thinking.

If you know Sam, you’re probably thinking, “Of course he can pull this weight. He’s famous.” And to some extent you’d be right. A decent percent of our monthly traffic still comes from him Tweeting about Hampton or retweeting our posts.

But the conversion on this was much higher than normal.

Hence, my updated idea…

Before this, I would have said that the most important part of early organic growth was consistency. You plan your content schedule, and you stick to it, tweaking and getting better as you go.

Now, I think differently.

The most impactful part of early organic growth are these black swan events. And the consistency is only important to the extent that it forces you to take shots on goal, increasing the odds you land one of these.

It is probably inaccurate to say that these black swans drive more growth than consistent posting. Over a long enough time span, I bet consistency wins.

But early on, they definitely account for your biggest growth swings. And more importantly, they offer some kind of signal about what your audience actually craves.

So what about all the other Tweets?

Do you keep sending them? When one post out-performs weeks worth of content, it’s easy to question the purpose of it all.

But I learned something there too. Because a day or two after this crazy viral hit, Hampton’s account sent a tweet that got just a handful of likes (low even for us).

But multiple readers re-shared it with messages like this, and it reminded me of something important:

The purpose of your content is not to “perform” or “drive traffic.” Not really.

Its purpose is to move people.

It’s easy to forget, or get caught up in the numbers. But the reality is that the real measure of worthwhile storytelling is the ability to get one idea out to someone where and when they need it.

It Takes Less Than You Think

By Ethan

On July 23, 2023

In Business, Newsletters

I bought a course this morning.

I wasn’t looking for a course. At least, I didn’t think I was. But I bought one anyways (for $80 no less) after seeing an offer appear in my inbox. And it’s got me thinking about what it really takes to monetize an email list.

I think we have a tendency to over-complicate the sales process.

That’s mostly because, when we talk about building a course or other paid media, we’re talking about building a media business – something designed to pay all your bills, and to keep you and others fed for years to come.

And that indeed does take a lot.

But when it comes to the moment of the sale, I think all you need is…

A product that solves a specific pain point at a reasonable price
A clear, simple email offering it for sale
A decent reputation

At least, when I reflect on what got me to spend $80 out of the blue, those are all that come to mind.

Let me break them down here real quick.

Solve a Specific Pain Point at a Reasonable Price

I wasn’t looking for a course. But for months, a little voice in the back of my head has been saying, “You really should learn more about AI.”

I’ve taken some steps to work on this – like reading more AI newsletters, or testing a handful of tools. But really, I feel like the space has grown so fast, I don’t know where to start anymore.

Then, poof.

This morning, in my inbox, a magic email offering to give me an overview of a few popular tools. And an offer for 60% off.

A Clear, Simple Email

I offer, for your review, a look at the exact sales email below:

There’s no fancy graphics. No long sales page. I’m not even entirely sure who sent me this email (I just know the brand name of the newsletter – more on this soon).

Funny enough, I’m not even really interested in the initial offer of saving two hours a day. I like how specific that is – it got me to read the email. But I like my schedule just fine now. I’m not interested in changing it.

I also didn’t really read it that much.

I saw, “ChatGPT,” and “MidJourney,” (two big, recognizable names, and tools I’ve been wanting to understand better), and that was enough for me to click.

Clicking the link takes you straight to a Stripe page.

There is a sales page, but I didn’t see it, proving that in at least some cases, it’s not necessary.

At $199, this would be in the “no man’s land” of pricing – too high to be a front-end product, but too low to be a back-end.

But with the coupon code, the price comes down to ~$80 (comfortably inside impulse-buy territory) and that was enough.

But why would I be willing to spend even that much? That’s where I think the final piece of the puzzle comes in…

Decent Reputation

You don’t have to be famous.

People just need to know your name, and that you either:

Create great work, or…
Hang with people who are known for creating great work

I mentioned that I’m not really sure who sent me this email. It’s signed from someone named Jordan but I don’t know who that is.

All I know is that this newsletter is from YPNAR, and that brand is associated with Greg Eisenberg.

This is embarrassing, because Greg is well-known in startup/solopreneuer circles, but to be honest, I don’t know much about him or his work. But I know he associates with people like Sam Parr, Sahil Bloom, and others, and I respect their work.

And in this case, at this price, for this pain point, that was enough.

Wrapping Up

I think there’s a lot of people like my on YPNAR’s list, and on yours. Going through this was a good reminder that selling doesn’t have to be so complex.

How The Hustle And Others Maximize Email Signups

By Ethan

On July 9, 2023

In Case Study, How-To, Newsletters

You’ll have to excuse me if this issue comes across informal – I’m writing it at the very end of a vacation.

I’ve been off work the last two weeks, mostly tramping through the woods of New England with my dog. But the last two days have been a big party with the family. So I’m sneaking this in under the wire.

When I go back to work tomorrow, it’ll be primarily to focus on growing Hampton’s blog and newsletter. Both are new (just two months old), and up to this point we’ve been scrappy – our strategy hasn’t gone much further than:

Publish cool stuff on the blog
Promote it on social to draw readers to the site
Use a (cleverly-worded) pop-up to grab emails
Rinse and repeat

It’s a lot of work to publish great articles, and before we press the gas on traffic, I want to be pretty sure that the site is set up to turn as many visitors as possible into email subscribers.

So the question I sat down to answer this week was…

Which calls to action should you definitely have in place on your newsletter’s website before going hard on promotion/growth?

To find out, I texted my buddy Matt McGarry. If you don’t know Matt yet, he runs a newsletter growth agency called Growletter, and is one of the best in the biz.

We worked together at The Hustle, and he’s since gone on to help grow a bunch of the most successful newsletter companies out there.

I’ll get to his thoughts in a sec, but while I was waiting for him to respond, I decided to visit some of his client’s sites just to see how they’re doing things.

Matt’s pretty focused on Twitter, Meta, and TikTok ads. So I don’t think he touches much when it comes to site design.

But his speciality is growing newsletters from 100k to 1m+ subscribers, so I figured that anyone on his list has their act together enough to build a 6- to 7-figure audience.

That’s good enough for me.

I spent an hour digging into The Hustle, 1440, and Chartr, and can boil the learnings down to 4 areas:

The Five Basic Email Captures Common To Newsletter Sites
A Universal Framework For Newsletter C2A’s
The Importance Of Customized Interactions
Inspiration And Unique Design Elements

I’ll go through each quickly, then share Matt’s insights too.

1. The Five Basic Email Captures Common To Newsletter Sites

Spend any time comparing major newsletter sites side-by-side, and one of the first things you notice is that a lot of them look… like… really similar.

After a few years in the space, I chalk this similarity up to two things:

It’s a small world: There still aren’t that many people who specialize in designing, publishing, or growing newsletters. The ones who do all talk. So you see the fingerprints of the same few people across sites
This design works

Great. That’s gonna save us time. Each of these companies is testing, tweaking, and trying to optimize conversions. So whatever they have in common should be a safe baseline for our purpose.

I opened an incognito tab so I could browse all three sites like a new reader, and found that while the details vary, they seem to have these five email-captures in common:

Above The Fold
Footer
Nav Bar
In-Content
Exit Intent

We’ll zip through an example of each real quick…

1. Above The Fold

“Above the fold,” is an old newspaper term used to describe any content on the top-half of the front page of a newspaper (a.k.a. the part people actually see before picking the newspaper up).

We use it in websites too, to talk about anything you see without scrolling when you hit a landing page.

As you can see in the image above, while The Hustle has their daily and featured stories listed lower down on the homepage, the space above the fold is mostly focused on capturing email addresses.

That same is true for other newsletters too. For example, Chartr and 1440…

It’s interesting to see that Chartr and 1440 don’t curate stories to their homepage or have a nav bar.

Makes sense. Both can be distracting, and these pages are designed to capture as many email addresses as possible.

The Hustle’s homepage used to be the same way. I’d be interested to know what led to the change, and how it’s performing.

*An archived version of The Hustle’s homepage*

Regardless, the point is clear — when people land on your site, the first thing you want to do is show off the newsletter and give them a way to sign up (more on exactly how in the Universal C2A Framework in section No. 2).

2. Footer

This one’s simple — at the bottom of each site, there’s another email capture.

3. Nav Bar

I almost missed this when I did my first inspection of the sites, but each has a link to join their newsletter somewhere in the nav bar.

As I mentioned above, Chartr and 1440 don’t show their navigation on the homepage. But if you dig to pages deeper on the site, the C2A is there.

If you’re a little OCD (like me), and wondering why this is third on the list when it’s positioned the highest up on the website, here’s why: If two of three case studies can afford to leave these C2A’s off their homepage, I’m assuming they’re less effective than the things I mentioned earlier.

4. In-Content

When you click to read an individual story, each newsletter has a clear email capture visible somewhere on the page.

For example, The Hustle uses these forms embedded directly in the text (one always about 20% into a story, the other at the very end). If a story is short, they skip the first one, and simply use the second at the end:

Chartr is similar. Their stories are all quite short, and begin & end with embedded forms like this:

But 1440 is different — they use a sticky subscribe form that’s locked to the bottom of the screen.

I like this idea, especially for longer stories, since it makes it easy to subscribe at any time as you read an article. You never know which sentence is going to connect with someone and make them think, “Wow, where has this been all my life?”

But when that happens, you want the subscribe form to be close by.

5. Exit Intent

Finally, the pop-up. Not just any pop-up though. An exit-intent pop-up (meaning that it triggers when someone moves their cursor out of the website tab, as though they’re attempting to navigate somewhere else).

That’s it.

Each of the newsletters has other things individual to them (we’ll get into some in sections 3 and 4).

But when it comes to major similarities, and 5 good email captures to start with, those are the five.

2. A Universal Framework For Newsletter C2A’s

Okay, so we know which email capture forms we’re going to start with. But how do we design them to be most effective?

Well, obviously, that’d take some testing (each site/audience is different). But if you scroll back up through the examples above, you’ll see that most newsletter signup forms contain these four things:

Promise: What will you get if you sign up?
Cost: How much does it cost to sign up?
Audience: How big is our audience (aka social proof)?
Time: How long will it take you to read (aka how much effort will you need to invest in order to get the thing we promised)

Promise. Cost. Audience. Time. PCAT for short (or cat pee, if you’re seven).

Now obviously, you would want to adapt these depending on the type of newsletter you’re running. If you write 5,000 word deep dives, you probably won’t jump on the “5-minute” bandwagon.

The trick is to realize what each of these is actually doing so you can adapt for yourself:

Promise: Gets the reader thinking about what’s in it for them
Cost: Lower the barrier to entry by showing how little is needed
Audience: Build trust by showing other people like/trust you
Time: Show how your newsletter saves people time (even if it takes more than five minutes to read)

3. The Importance Of Customized Interactions

Here, I want to pause briefly to look closer at a couple of email captures we’ve already discussed — namely, The Hustle’s…

In-Content Forms
Exit Intent Pop-up

The Hustle is a particularly interesting case study because it’s owned by HubSpot, so they’ve got a ton of resources to work with when it comes to page design.

Not only do they have way more manpower and money to test/optimize/design, but HubSpot is the marketing platform used by thousands of other companies – so they have internal data from users on what’s working best to grab attention and capture leads.

And one thing they’re doing that the other two aren’t doing quite as much, is customizing the copy on email capture forms to match the interaction the reader is having at the moment they see the forms.

It’s subtle, but I noticed that this felt different as a reader, and I think (if done well) it’s got to have an impact on your conversion rates.

1. In-Content Forms

As I mentioned, The Hustle serves two different in-content forms. One embedded about 20% into the piece looks like this:

Somehow it feels a little more engaging than a generic email capture. Because they’re acknowledging what I’m doing (reading/enjoying the piece)

2. Exit Intent Pop-Up

The same goes for the exit pop-up. Look at the copy, and how they’re almost having a live conversation with me as I try to exit the site.

It seems like a little thing.

I think the reason this stood out to me is because I know that my default personality would be to NOT do this. I’m not typically the person who digs into the settings to customize things perfectly to my needs.

It’s tempting to just throw up a basic pop-up, and focus more on driving traffic.

But I bet little customizations like this make a difference, and after experiencing these as a reader, I’m going to look for opportunities to do this kind of thing on our site (and probably… ugh… my personal site too.)

It will be very interesting to see what generative AI offers in this regard soon.

4. Inspiration And Unique Design Elements

The last thing I’ll point out before we close with Matt’s advice is something I can only call “style points”.

Each of these newsletters does cool little things to encourage readers to sign up.

For example, a lot of newsletter companies have this mobile phone aesthetic on their homepage, but The Hustle takes it a step further – this is actually a custom slide-show that gets updated every day with headlines, and photos from the last few newsletters.

Think about what that does for conversion when you land on this page and see images, stories, or headlines you recognize from social media chatter the last few days.

*Notice how the subject lines are starred too – a subtle hint that you will love this newsletter if you sign up*

The Hustle also just does a good job of using motion in general to bring the homepage alive.

This content section looks like something out of The Daily Prophet.

1440 uses motion too. They have this cool little ticker on the homepage that shows how many people have opened the newsletter so far that day.

When it comes to audience social proof, this is one of the cooler implementations I’ve seen so far (though I have no idea if it’s real, or just a nicely designed ticker that counts random numbers over two million).

*Their URL is also “*join1440.com” — a subtle call to action, which is cool

Finally, Chartr has gone ahead and updated the title tag on their homepage so that their organic Google result has a “Subscribe” call to action in it.

Helps readers know they found the right result, and primes them to sign up.

5. Matt’s Advice

Okay, so we’ve seen a bunch of common email capture forms the big dogs are using. We’ve dissected how they structure their calls to action, and the role that customization and “style points” can play.

Then Matt came back and gave me two pieces of guidance I found really helpful:

First: He shared this list of 52 ways to grow your email list
Then: He said to pick at least 4 (ideally more) to add to your site

The list is from Dan Oshinsky, who led newsletters at both Buzzfeed and The New Yorker. He knows his stuff.

And of course, Matt knows his stuff about email capture too.

“One dedicated landing page. And three other ecap options isn’t a ton,” he told me.

“Count how many units popular media companies have,” he said, pointing to even bigger brands, like Motley Fool, or NYT.

It’s a good idea. And I’ll do it one day. But this email is already longer than I meant for it to be, so this’ll have to do for now.

Breaking Down Peter Zeihan’s Business Model

By Ethan

On July 3, 2023

In Case Study, Newsletters, Writing

Today, we’re lookin’ at Peter Zeihan to see what he can teach us about being a high-priced creator/consultant.

If you don’t know Zeihan, he’s a geopolitical analyst who’s gotten famous over the last few years for his opinions on China, the US, and the future of globalization (namely, that there isn’t going to be one).

But my fascination with him has less to do with his public opinions, and more to do with how he spends his time.

He seems like the paragon of a paid thinker…

Author of several books and a near-daily newsletter
Lives in the mountains of Colorado, close (but not too close) to Denver
Long hikes every day to think and record Youtube thoughts
Travels often to give paid speeches and seminars to big companies
Likely doing 7-figures in annual revenue without much of a team
Doing well enough to donate 100% of book proceeds to charity
Funny

Basically, when I grow up, I wanna be like Peter.

So this week, I spent a few hours digging into his business to uncover any key learnings. We’re going to look at three:

Business Model
Ideas > Optimization
Chosen Relevance

1. Peter Zeihan’s Business Model

Before we dive in, remember that all media companies essentially make money in one of three ways: Free products (which are monetized via ads and affiliate deals), front-end products, and back-end products.

Free Products

The core of Peter’s media footprint includes two key properties: his newsletter, and his Youtube channel. Both are free, but that doesn’t mean they don’t earn money:

His Youtube channel is monetized, and averages ~1.5m+ views per week. At an estimated $5 CPM, that’d be ~$7.5k per week from Youtube alone
Both the newsletter and Youtube include plenty of calls to action selling his other products (below)

One smart thing: In videos, lectures, podcast interviews, and writing, he continually emphasizes the fact that both his newsletter and Youtube videos are, and will-always-remain, free. That’s a good way to help growth.

If you read my piece on how $1m+ newsletters maximize email signups, you know that emphasizing the “free” aspect is an easy and important tactic many miss.

Front-End Products

Traditionally, front-end products are paid products that run roughly $50-$100 (cheap enough to be impulse buys).

Technically, the only thing Zeihan offers in that regard are his books.

However, he also does something I haven’t seen a solo-creator do before: He sells high-ticket webinar recordings. He’s got more than half a dozen webinars priced $650-$750/ea., and covering topics from inflation to the Ukraine War’s impact on energy, food, and materials industries.

I’m going to lump these in as front-end products for two reasons:

His remaining products are likely much, much more expensive, so relatively speaking, these are still his “low barrier to entry” offerings
The corporate clients these are designed to appeal to are less price sensitive than typical consumers (more on this soon). So again, in relative terms, these are “low priced”.

Back-End

Finally, on top of these, Peter also does:

Speaking: He’s represented by several speaker bureaus, and in this interview with Joe Rogan said that he did 179 seminars last year. Hard to know if those are all in-person or a mix or live + online, but either way, it’s a lot.
Executive Briefs: I’m not quite sure what these are, but I’d imagine they’re high-ticket, highly specialized research projects undertaken for execs at a specific company. Maybe something like this PDF he wrote back in his days in private intelligence.
Consulting: Always a mystery.

2. Ideas > Optimization

I don’t know much for certain about how much money Peter makes each year. But I do know…

From this podcast that he’s looking forward to retiring soon.
From this newsletter (posted Friday) that he’s doing well enough to donate 100% book proceeds to charity.

So he’s doing well. And yet, anyone who’s spent time focused on growing an audience would look at the website and see at once that it’s kind of stitched together – not really optimized for conversion.

There are plenty of email capture forms. But they don’t really flow, the pages are just a little chaotic, and there are clear gaps in the funnel.

For example, there’s no nav button for the webinars. The only way to find them is by clicking through random newsletter, or Youtube video archives. Maybe they’re not a priority. Or maybe it was just overlooked.

Chaos (but pushing the newsletter hard, which is good)

And yet, my conservative estimates place his annual revenue in the seven-figure zone when you factor in speaking and consulting fees.

So what’s the point?

The point is that even if you don’t optimize every last detail of your site, you can generate more than enough money by getting the big things right:

Own your audience with an email list
Be an expert in your space
Share interesting ideas in public
Understand how to monetize

Speaking of monetization, that brings us to the next interesting lesson I feel Peter’s work has to offer us all as professionally curious people…

3. Chosen Relevance

I’ve mentioned a few times now that a lot of his time is spent speaking to, consulting with, and writing for executives. Specifically, executives in the agricultural, industrial, and energy sectors.

a.k.a. People with deep pockets.

These are big industries where a lot is at stake. And there’s an important lesson there: Zeihan has purposefully found a way to make his passion (geopolitics) relevant to big companies who can pay him lots of money to hear how his research can make/save them even more money.

Let that sink in for a second.

He purposefully figured out the link between what he was interested in, and what big companies are willing to pay to learn, then used that as the foundation for a (likely) multi-million dollar publishing and consulting empire.

I don’t know about you, but this has me thinking questions like…

What big industries would care a lot about topics I like researching?
What are the specific angles they would care about?
How much is on the line for them? What’s it worth?
What would they need or want from me? (in terms of webinar topics, executive briefs, etc.)

To take things one step further, he’s even found ways to have a positive impact on some of these major industries by showing them where there’s incentive for them to go greener, or more local.

How Justin Welsh Makes $1m+ with Zero Employees

By Ethan

On June 26, 2023

In Case Study, Newsletters

Now I’ve known about Justin Welsh for a long time, but it wasn’t until I saw this clip on Youtube the other week that I realized just how big his media empire is (starts at 4:04)…

There’s nothing I like more than when I find someone who’s making way more money than I expected, and doing it on their own terms.

So I dug in deeper, listening to hours and hours of podcast interviews, reading other deep dives, and buying his course to see what I could learn from the way he’s grown.

TL;DR
Superpowers
Background
Business Model
Growth
Tech Stack

1. TL;DR

In 2023, Justin Welsh will do ~$1.7m from his solo creator business…

About 76% of that comes from sales of his courses ($150/ea.)
The rest is a mix of consulting, ads, and affiliate/subscription sales
All of this is powered by his LinkedIn, Twitter, and newsletter

2. Superpowers

After reviewing a lot of his work, I’ve come to the conclusion that he’s got two main superpowers:

Systems Thinking: The thing that stood out most to me is that Justin has an incredibly dialed-in system for writing and distributing content (more on this in a bit). He’s a total mercenary here, with systems designed to let him produce consistently, even when he doesn’t feel inspired. This is huge.

He also comes across as a bit dispassionate, observing what works and cutting what doesn’t, without getting caught up in the mystique of being a “creator.”

Playing A Long Game: This is the part that’s hardest to internalize, but he’s willing to spend a year or more building up an audience somewhere before ever selling to them. For anyone starting this journey, this is torture to hear. But it’s also a common thread you see with a lot of successful creators.

3. Background

The first thing you need to know is that Justin isn’t a writer. Or at least, he wasn’t…

He was a sales guy. But after more than a decade in ~~high-stress~~ high-growth startups led to drinking, an overwhelming panic attack, and a visit from EMT’s, he started planning his escape.

The background in sales is important for two reasons.

First, it should give you hope if you don’t consider yourself a writer either. This trade is learnable, for the most part. It’s not as precious as some would lead you to believe. Justin’s an example of just how much is possible, even without a “writer” background.

Second, you’ll see how it informs his approach to the business (I believe this is one of his unique advantages).

At any rate, about seven months before he left his job as a sales exec, he started publishing to LinkedIn with the idea of eventually landing consulting gigs to replace his job.

It worked. And as his audience grew, people started asking him more and more about how he was doing that. Today, most of his work actually focuses on helping people grow their own audiences.

4. Business Model

Remember, the main business model for these kinds of media companies is simple: They’re monetized via free, front-end, and back-end products. (More on each here)

It would be tempting to focus exclusively on the part of his business that does most of the revenue – the courses.

But if you do that, you’d miss the bigger picture. So instead, let’s go through the bullseye model in-full.

Free Products

While Justin has built an audience across LinkedIn, Twitter, and a newsletter, he currently only monetizes ads on the newsletter:

Look at how simple this sales page is.

He runs up to two ad spots, both at $3k/issue. And each ad is text-only, up to two sentences.

What that means is that the ad business is set up in such a way that it doesn’t take much of his time. Advertisers likely buy, submit their ad text to him async, and he schedules/runs without much else.

According to the interview he did with Noah Kagan, of the $1.7m he’ll do in revenue this year, ~$30k will come from affiliate deals, and ~$120k will come from the ad system above.

If you’re doing the mental math, $6k/wk times 52 weeks is a lot more than $120k. I chalk the difference up to one of a few things:

That estimate could be old, based on lower pricing (the price was $2k until very recently)
He may have <100% fill rates. Many newsletters do, so plan accordingly
Ads may not be a priority for him (with 75%+ of revenue coming via courses)

Of these, I lean most toward No. 3.

Front-End Products

As a quick reminder, front-end products are primarily defined by their price. They can be one-time payment (like courses) or subscriptions, but typically hover in the $50-$100 range. Low enough to be impulse buys.

This is where the bulk of his business sits, and it’s comprised of two major revenue streams:

Courses: He sells 2 courses on Gumroad for $150/ea.
Subscriptions: He runs a paid newsletter ($9/mo) where he shares the social media templates he’s using to drive traffic.

These are both comfortably in “front-end” territory. And between the two, he’ll do ~$1.4m this year (the vast majority of which is represented by course sales).

The paid subscription is an up-sell for members of his course, and I want to take a second to point out how smart this is.

One of the most important and often overlooked aspects of paid subscriptions is that they give you recurring revenue.

To understand just how great this is, let’s pretend you’re selling a course, and like Justin, you’re able to sell $1m worth of seats this year.

That’s impressive. But do you know what you need to do next year?

That’s right – sell $1m worth of seats all over again. More if you want the biz to grow.

Now, pretend you make $1m selling a subscription product, and 50% of those people renew for a second year. You start year two with $500k in the bank, and even if your ability to sell stays capped at $1m in sales per year, your overall revenue continues to grow.

More money for the same work. That’s the magic of paid subscriptions.

His model is a little different. I believe the paid subscription is billed monthly, which changes some of the math.

But the big idea here is that it’s smart as a course creator to experiment with value-added subscriptions and recurring revenue.

The other thing he did well… when designing the paid subscription was to focus on different rather than more.

Newsletter writers often struggle with this when deciding when/how to take their newsletter paid.

The option many default to is to offer more. (E.g., Free subscribers get one email a week, but paid members get two or more.)

That’s a mistake.

Generally speaking, unless you’re sharing verrry valuable information that’s directly tied to your reader’s income, they just aren’t that motivated to get more of your emails. For the most part, they barely have time to read the ones you already send.

So a more strategy will always limit your income to only your most dedicated readers.

But if you sell a subscription that offers something different from the free newsletter (ideally something valuable, that helps them make money, save money, or save time) it becomes harder to resist.

Social media templates to grow your solo-preneur business is a great example.

Back-End Products

Similar to front-end products, back-end products can be one-off or subscription-based products that are primarily characterized by their price (typically $500 and up).

In media, when you talk about back-end products, most people think about high-ticket subscriptions. But I tend to lump consulting and coaching into the back end as well, because…

It’s a higher-ticket, higher-touch service
It can be sold using free or front-end products

According to his interview with Noah, Justin does ~$150k in coaching each year.

He doesn’t talk a lot about what kind of coaching that is. It’s not clearly available on his site. Nonetheless, it’s a good example of how building a large audience brings valuable opportunities. Even the side income is a great salary on its own.

5. Growth

I’m actually not going to spend too much time writing about how Justin grows for two reasons…

First, many others have already done a great job deconstructing his process. Here are a few of my favorites:

Chenell Basilio’s deep dive is a must-read
Justin’s interview with Noah Kagan is similarly fantastic
This episode of Bootstrapped Stories is probably the best single interview I found – and includes detailed thoughts on his approach to social media, content creation, networking and more.

But more importantly, the topic of how he grows is the main thing Justin himself writes about.

It’s the topic of both his current courses, and he’s also broken it down in detail for free many, many times. (Like here)

I took his Content Operating System course. It’s great. Specifically for anyone who knows what their niche is, but isn’t sure what they should do day-to-day to grow their audience on Twitter or LinkedIn.

If I were to break down my personal takeaways, they would be:

Promotion > Production: After writing an article, he finds about a half-dozen different ways to package and share insights from the piece (e.g., contrarian take, listicle, etc.) then uses a tool like Hypefury to pre-write and pre-schedule that content on his social channels over 6-12 weeks. I like this ratio of promoting much more than you publish.

Regular Growth C2A’s: Every week, he promotes his newsletter once the day before the email goes out (“sign up to get XYZ tomorrow”) and once the day after. I’ve already begun testing this at Hampton and it’s extremely effective, sometimes driving more clicks and signups than even our most popular and helpful Twitter threads. That’s a big deal because the threads take way longer to write.

This is a business: An aspect of Justin’s work that I think often goes over-looked is that he’s not here to “have fun.” Sure, he’s having fun. But his business functions like a machine – the newsletter is short and to-the-point, it’s written on a schedule, promoted in the same ways each week, and those posts publish consistently, at the same times. In a world where many people romanticize being a “creator”, I find this refreshing.

There is, of course, a lot more to get from his course. But these were the things that had the biggest impact on me.

6. Tech Stack

I was a little surprised by the tech stack Justin’s using – I hadn’t heard of most of the tools on it.

Kajabi does most of the heavy lifting, powering his site, courses, and email list. The rest is mostly tools for pre-scheduling the afore-mentioned social media content and analytics.

One thing I’d love to know is more about how he uses his analytics suite. If you go back through enough of his work, it’s pretty clear that he tests things pretty systematically. I’m guessing that’s a holdover from his days leading sales teams.

It’d be interesting to learn more about how he tests, and what he tracks.

One cool thing to note is that he’s also become an affiliate for several of the companies whose tools he relies on to run his business.

It’s not a huge income (Roughly ~$25-$30k according to Chenell Basillio’s breakdown of his business).

But that’s enough to go on a few killer vacations a year. All for passively recommending tools he already uses.

It makes me think about how all of us have some similar opportunity. No matter what you do, chances are there’s something the people around you know you for. Something they ask you about.

You don’t have to be a business owner to benefit from this.

Even if you’re an employee, and you write about the work you do at your job. It wouldn’t take much to put up a simple tools page with some affiliate links.

Actually seems like a great first-step for people trying to build a personal following around a topic they already know well. Having the affiliate links up would allow you to monetize without having to build an entire course, and can free you to focus on publishing.

The income would likely be small at first, but its growth would be a good indicator of the trust you’re building with your audience, and more important, a signal that people are willing to buy things from your recommendation. Once you have that, you can build and launch products much more confidently.

My Community Newsletter Playbook

By Ethan

On June 18, 2023

In Newsletters, Writing

Someone recently asked me for the playbook we use to write our community newsletter over at Hampton. He was hoping for a one-pager he could give his team, so they could write something similar for their industry.

That was a big compliment.

It was also a little daunting because the last thing I wrote about content strategy was, like… Fifty pages. After cutting.

So I’m going to try and write something shorter and more actionable here. We’ll focus only on the real stuff I do each week to produce our email, and we’ll cover:

Developing A Template
The Importance Of Your Drop File
Writing The Bones Each Week
Editing + Style
The Final Step

None of this is Hampton-specific. It should all transfer.

1. Developing A Template

When I talk about a newsletter template, I’m talking about the overall structure for the email – the major sections, and what goes in each.

Having a template for your newsletter is important because…

It makes the email easier to write each week
It helps you think about the purpose of each segment you include
Over time, it sets expectations with readers, and helps them skim and find what they’re looking for faster

The easiest way to start is to copy the format of a newsletter you already like, and iterate from there as you see what works and what doesn’t with your audience.

Each week, when I sit down to write, the very first thing I do is duplicate the last week’s email. I remove the old content, and the rest of my job is just filling in the structure with new content.

This saves a ton of time and energy. In fact, steps 1-3 are all about saving time and energy so you can spend it on step 4 (styling), where it’s most valuable.

So have a template.

The important thing to know is that your template evolves over time, and will take a while to solidify.

I’d estimate it took us about 2-3 months of weekly emails to settle on a pretty good structure at Hampton. And even then, it’s still evolving (currently in the middle of a visual refresh, though structurally, it’ll remain mostly the same).

Ours currently looks something like this:

Brief Intro
Recap Of Popular Slack Posts
New Members From This Week
Upcoming Events
A Post From The Blog

Every one of these is designed to do something specific (like get people excited about the Slack group, drive event RSVPs, or get eyes on the member interviews we publish on our blog).

And each of those, really boils down to the same single thing – helping members connect with one another.

That’s the essence of a community email. It’s about creating points of connection between your readers.

There are a hundred little tactics (for example, we intentionally include a lot of names in each issue – names, names, names!), but if you just write with the intention of creating connections between your readers, you’ll find your way.

2. The Importance Of Your Drop File

Okay, so you’ve got a template. Now how do you fill it in each week?

Answer: Your drop file.

The drop file is a simple Google or Word doc that you keep handy all week long. As you stumble across things that could be cool for your newsletter, you drop them in the drop file, and forget about them until it’s time to write.

I keep mine right in my bookmarks bar.

The structure of the drop file is simple. It’s a running list. Just bullet-items for each idea you come across, and maybe a few quick thoughts or follow-up links to help you write later.

You can find ideas anywhere. But over time, you’ll narrow the list of sources down to a few that deliver great options every week.

At Hampton, most of our content starts with our Slack channels. We’ve got hundreds of members in there, and our weekly active users have hovered between 85-89% from day one. So every week, there are a bunch of great conversations going on.

When I come across one I want to remember, it gets added to the drop file.

Then, whenever I sit down to write newsletters or do content planning, I open the file to jump-start the process.

3. Writing The Bones Each Week

With your template and an active drop file, the process of writing the newsletter is actually pretty simple.

It’s usually a process of…

Looking at your template – what needs to be filled in?
Looking at your drop file – what fits where in the template?
Match one to the other.
Rinse and repeat to fill in the major sections of the newsletter

On the first pass, I don’t write much. I’m just slotting story ideas in to make sure I like how they all fit.

Sometimes, a story or link might be a good match for more than one section of the newsletter, and it’s not immediately clear where it should go. But a little plugging and playing usually helps sort things out as I see the broader email take shape.

As things start to click, I’ll add more detail to each section, writing segments the way readers will eventually see them.

4. Editing + Style

Ultimately, your voice is the most important part of your style, and that’s different for everyone.

But here are a few editorial best-practices we used at The Hustle, which I’ve carried to Hampton, and which (I feel) make the newsletter easier and more pleasant to read…

Use simple language
Short paragraphs (no more than 2-3 lines in a Google doc)
An image at least every 200-300 words to break up text
Use bullets and bolding to make it skim-able

Axios really pioneered this style in recent years. You can learn more from them in their book, Smart Brevity.

5. The Final Step

Finally, testing. You want to a send test-version of the email to yourself.

When you get out of the editing window, and review in your inbox, you’ll pretty much always catch at least one thing you missed.

At minimum, you should read the newsletter on your phone, and click each link to be sure it’s headed to the right destination.

It can also be a good idea to read it in dark mode if it’s very design-centric. A surprising number of readers leave dark mode on all the time, and it can throw off certain design elements or make certain text hard to read.