The Write to Roam

How To Write Stuff No One Else Can

On February 9, 2024

Last week, I wrote a piece about five of the key hires who took Morning Brew to $40 million in revenue.

I mentioned that I had a process for finding such people, and was surprised by how many of you were interested in hearing more about that.

So this week, I’m going to show you that process, but I want to ground it in something a little more important – namely, why look for these people in the first place?

Well, here’s why…

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In any business, including the creative ones, there are really only three types of advantages you can have over your competitors:

Resources: You have money to burn, and they don’t
Behavioral: You naturally do something that they don’t
Information: You know something they don’t

When a writer buys $200,000 worth of their own book in order to guarantee it lands on the bestseller list (yes, this happens), that’s a resource advantage. They have enough money to manipulate the system, giving them an edge, even against people who may be better writers.

If someone writes compulsively, and just can’t help themselves, that’s a behavioral advantage. They have an edge over the person who has to force themselves to sit down and write.

Personally, I prefer an information advantage because I think it’s the only one you can choose to cultivate, and is most resilient to AI.

And when it comes to information, the biggest moat that you can have is access to people. Not famous people. But rather, the people behind the scenes who have just as much insight and far less attention.

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Stephen Hanselman, Heather Jackson, Donna Passannante, Tara Gilbride, Ilena George, Lindsay Mecca, Kate Perkins Youngman, Laura Hurlbut.

Do you recognize any of those names?

Probably not, but they’re some of the first people that Tim Ferriss thanked in the acknowledgements section of The Four Hour Workweek, and they belong to his agent, editor, marketing director, and publicity director, respectively, along with the four interns who helped him get the project over the finish line.

Isn’t that interesting? The stories they could tell…

That book spent more than four consecutive years on the New York Times best-seller list, and fans like me default to giving Tim all the credit for that. But he himself considers these people absolutely crucial to the success of the project and we don’t even know their names.

And this is the big point – there’s an asymmetry between the people who have interesting experience and insight on any particular topic, and the people who get the attention.

It holds true in every arena. Every company. Every creative project. Attention flows like water towards a few people at the front. But for every CEO, or lead actor, or author, there are lots of people slightly behind the scenes who have just as much fascinating insight. Maybe more.

More?

Yes, maybe. Check this out…

A quick Google of Stephen’s name reveals that he didn’t just work with Tim on each of his five books. He also worked with other incredibly popular authors like travel writer Rolf Potts, investor Kamal Ravikant, and stoic Ryan Holiday.

Indeed, he’s actually a co-author of at least two of Holiday’s books.

So if everyone wants to write a story about how Tim Ferriss or Ryan Holiday became best-sellers, the path taken by most of your competitors will be to either…

Do a lot of Googling, and rehash other pieces or…
Try to contact the authors for (yet another) interview

An option that’d set you apart would be to reach out to people like Stephen.

Tim and Ryan are practically impossible to contact because of the volume of inbound they get. Stephen’s Gmail address is listed right on his Publisher’s Marketplace profile.

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I think my old company, The Hustle provides an interesting example of how this works in practice.

Our main competitor was Morning Brew, and if you subscribe to both The Hustle and Brew, and a few other similar newsletters, what you’ll find is that maybe 40-60% of their daily coverage overlaps.

They report on the same stories, share the same links.

Why? Because everyone’s pulling from the same few information sources.

Running a multi-million dollar daily newsletter is all about efficiencies. Over time, each writer finds their favorite sources – a few places they’re guaranteed to find the stories readers want – and there are only a handful of those.

Then there was the Sunday Story.

The Sunday edition of The Hustle was refined by Zachary Crocket, and it sprang from his desire to do more in-depth, long-form coverage of business stories that were further off the beaten path. Things like…

You can’t just Google these kinds of things. That’s why they’re so interesting.

Zack spent his time combing through old newspapers, absorbing the comments in very niche Facebook groups, or rifling through long-forgotten boxes in the dark corners of museum archives.

Almost as a rule, he tried to avoid talking to big, well-known names. Instead preferring the people who were deep in the trenches, had lots of experience, and almost zero attention.

He wrote what no one else could because he looked where no one else would.

And he (read, “we”) were rewarded for it. The pieces were insanely popular. To this day, it’s common to surf Hacker News and see one of the old Sunday Stories from years ago trending on the front page again.

When you write what no one else can, people want to share.

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I know I promised you my own personal method for finding these kinds of interesting employees in a company, so here it is…

I like LinkedIn.

When I’m deconstructing a company, I start by reading a few interviews with the founders to plot the growth over time, along with any other major milestones.

I chart it so I can see any major turning points. For example…

Then, I search LinkedIn for everyone who’s worked at a place, or was hired around major turning points in a company, and manually plot their…

Name
Title
Department (Editorial, Sales, Operations, etc.)
Start/End Dates

…in a spreadsheet.

There’s probably a way to do this automatically with robots or VAs or something, but I do it manually because I find it gives me a much better feel for each person’s actual relationship with a company.

For example, on LinkedIn, someone may say they were CMO of a company for just three months, and if you take that data at face value, you may think something very bad must have happened for a company to hire and lose such an important role in so short a time.

But when you look closer, you see that this person was a sophomore in college at the time, that the company was just a month old, and that actually, it wasn’t so much an executive hire as it was kids trying to get something off the ground.

That sort of thing happens a lot when you study startups, and that’s why I do it manually.

At any rate, if you do this, what you’re left with is a map that shows how a company grew over time – where their hiring priorities were, and by extension, the major challenges or opportunities they were facing at any given point, as well as the people who played pivotal roles in their success.

It’s not perfect. Some people don’t keep their LinkedIn up to date. But it’s directionally accurate, and enough to give you the kind of look into a company you won’t typically find on TechCrunch.

Once you have that, there are two things you can do:

Sleuthing: I plug names of lesser-known key employees into Google and Spotify to see if they’ve talked about their work publicly at all – often, they have.
Consulting: A lot of people are happy to give you an hour of their time after they leave a company, and for $100 or so, you can learn things the original employer paid thousands to understand.

You don’t need many. In fact, most the time, all it takes is one name, and from there, you can find your way to the rest.

That’s the beauty of focusing on people – they have such rich context. A ten-minute chat can save you hours of research.

And so I’ll leave you with one more little tip I got from Zach when we worked together – something small that’s had a big impact on my work.

When finishing an interview, one of the last questions he always asked was, “Who else do you think I should talk to about this?”

It’s small. But you wouldn’t believe what comes from that.

Why I Unfollowed Everyone In The Newsletter Space

By Ethan

On February 4, 2024

In Newsletters, Writing

Recently, for the first time, I noticed daily stories making their way through the newsletter community on Twitter.

Similar to the way national news has a handful of daily stories that all the channels cover, the newsletter industry is now big enough and has enough people talking about it that my feed was filling up with different takes on the same topic every day.

One day, it was, “Beehiiv or Sparkloop?” The next, “Are we in a newsletter bubble?” Or perhaps, “Can you really call creators business owners?” Etc., etc., etc…

It reminded me of this quote from Hemingway:

“Writers should work alone. They should see each other only after their work is done, and not too often then. Otherwise they become like writers in New York. All angleworms in a bottle, trying to derive knowledge and nourishment from their own contact and from the bottle…”
Green Hills of Africa

That book is one of my favorites, by the way. I’m convinced you can learn everything worth knowing about writing by just studying that one your entire career.

Anyways, I realized I was spending too much time in the bottle, and it was affecting what I thought I should write about. It was also making me feel less relevant if I didn’t comment on the topic of the day.

Of course, any time spent focusing on today’s “thing” is time you don’t get to spend making something that lasts a long, long time. And that’s a problem.

So I unfollowed everyone, on Twitter at least.

I do still read their long-form stuff, either via their blogs or newsletters, and this has two important benefits over social media:

First, it’s long form. They’re usually exploring an idea in much more detail, and you’re absorbing more deeply.

But second, and perhaps more importantly, you’re taking each person on their own, rather than as a chorus. And the difference between those two things is the difference between signal and noise.

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

By Ethan

On February 2, 2024

In Case Study, Newsletters

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.

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:

The Idea-Reality Gap

By Ethan

On August 12, 2023

In Uncategorized

I found a new framework I love for thinking about speed and how it relates to work.

In this video, Alex Hormozi is talking about overcoming procrastination and says that one of his company’s core values is, “speed is king.” You’d be excused for rolling your eyes – a lot of companies say stuff like that to justify a frantic culture and inability to prioritize. It gets old.

But he takes it in a different direction.

“It’s not what a lot of people think,” he says. “It’s not about being impatient. It’s not about trying to get a hundred things done. It’s about knowing how to get things done that matter…”

Here’s framework I love: He goes on to define power as the gap between thoughts becoming reality.

So an all-powerful, omnipotent being would think things into reality immediately, and at the other end of the spectrum you’d have someone who was completely powerless – unable to turn a thought into reality no matter how much time they were given.

We are typically somewhere in between, and (ideally) should be working our way left on that line.

I love this because it seems both simple and universally true. Across all times, and in all situations, the person with the most power is the one who is able to transform their ideas into reality the fastest. And over the course of your career, a way to measure progress or mastery in your craft is to assess whether you’re moving left on this scale.

I also like it because it puts useful guardrails on the old adage of “move fast and break things.”

“Speed isn’t doing things fast,” Hormozi says. “It’s basically just not being distracted by other shit that doesn’t matter. It’s being able to prioritize.”

Which brings me to the last reason I love this framework – it lends so much more weight to the importance of prioritizing, avoiding multi-tasking, and saying “no” to more.

Multi-Tasking Drains Your Power

I’ve been studying manufacturing recently. It’s a field that values precise thinking, and out of necessity, they’ve gotten good at analyzing systems, looking for bottlenecks, and removing them – something more knowledge-work companies should learn from.

One of the key thinkers in the space was a man named Dr. Eliyahu Goldratt who came up with something called The Theory of Constraints.

One of the keys to that theory is the idea that multi-tasking is bad. He liked to show this using the example below:

Imagine you have 3 projects that need to get done, and you can do them either sequentially, or you can multi-task between them. Depending on your choice, your timeline will look like one of these.

On its own, this graphic does a great job showing two things:

Multi-tasking significantly delays any individual project’s completion, which is a problem because the work isn’t useful until it’s done.
Because you incur a slight switching cost every time you change focus, all three projects ultimately take longer to finish overall.

But when we layer on Hormozi’s idea-to-reality principle, we see that what’s really going on here is that multi-tasking is tangibly decreasing your power. It’s moving your further to the right on the idea-reality line.

A lot of people talk about the importance of focus, or of being able to say no. But ~~they~~ I still say yes to too much. Focus feels like a nice-to-have. The first thing on the chopping block when things get tough.

But power? No one in their right mind would knowingly undermine their own power, or the power of the organization they work for.

This applies to both big-picture projects, and the way you spend your time day-to-day, hour-to-hour.

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.