Category: How-To

How The Hustle And Others Maximize Email Signups

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 Hustle1440, and Chartr, and can boil the learnings down to 4 areas:

  1. The Five Basic Email Captures Common To Newsletter Sites
  2. A Universal Framework For Newsletter C2A’s
  3. The Importance Of Customized Interactions
  4. 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:

  1. Above The Fold
  2. Footer
  3. Nav Bar
  4. In-Content
  5. 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…

  1. In-Content Forms
  2. 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:

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.

How To (Actually) Make Money Writing Online

From 2020 to 2023, I helped run a multi-million dollar newsletter called Trends, which is the sister-publication of another even bigger newsletter called The Hustle.

While there, I had the chance not only to see behind the scenes of a successful media company, but also to help literally write the book on how 7-figure newsletters make money, interviewing leaders at other major publications like Axios, Buzzfeed, The New Yorker, Morning Brew, Motley Fool, Washington Post, and more.

I’ve also talked to lots of people you’ve never heard of, who still make 6- to 8-figures each year on their writing.

Do you want to know what they all have in common? It’s NOT a big audience, a fancy website, or even very good writing.

The people who make the most money from their writing understand one simple business model…

…Oh, and by the way, this works for different kinds of media too. Podcasters, TikTok-ers, Instagram influencers, and more – the ones that make money all do it by adhering to the same simple framework.

Here it is – there are three ways to make money from media:

  1. Free products: Monetized via ads and affiliate deals
  2. Low-cost products: Known as “front end” products, these are typically $100 or less (cheap enough to be an impulse buy) and designed to reach large audiences.
  3. High-price products: Known as “back end” products, these are typically $500 and up (can go all the way up into the many thousands of dollars). Because of their price, they’re often designed for much more narrow audiences.

That’s it.

Anyone who’s making serious money is doing it through one or more of those 3 levers, whether they realize it or not.

And that’s the problem – big companies understand that this is how the model works, but a lot of smaller creators or media startups don’t realize that this is the game they’re playing. They feel like they’re taking shots in the dark.

On their own, any of the three can be a multi-million dollar business. You can also mix and match them. For example, 1440 makes money from ads alone, The Browser has both free and low-cost subscriptions, whereas The Motley Fool uses all three.

Once you understand how these pieces fit together, you’ll have a much easier time deciding what to create, and when.

I like to think of it as a bullseye.

Here’s how it works…

Each ring of the bullseye represents one of the three monetization methods (free, front-end, and back-end).

The size of the circle correlates to the breadth of the audience that you can capture with that product. The depth speaks to how detailed and specific your content has to be at each stage.

Let’s break down each…

Free Products

When I say “free products” I’m talking about media properties you run that your audience can access for free.

For writers, this is primarily free newsletters and blogs. But it can also be free YouTube channels, podcasts, Twitter accounts, etc. – really anywhere you can build an audience and place ads.

To keep things simple, let’s just use the example of a free email newsletter.

Your free publication represents the outer ring of your bullseye. It will always be your biggest audience because it has the lowest barrier to entry. There’s no cost, and people don’t need to love you to subscribe. They just need to be somewhat interested in your work.

Because of the broad reach, the content will be fairly broad too. You can typically cover several different topics if you want, and the depth of coverage doesn’t have to be super deep.

There are two ways this free audience can make you money:

  1. Showing them ads & affiliate deals
  2. Selling your paid (front- and/or back-end) products to them

Important: When it comes to your free audience, bigger doesn’t always mean better.

I’ve seen publications with 1k highly targeted subscribers make 6-figures a year. The Newsette did more revenue with 500k readers than Morning Brew did with over a million.

The key is understanding what makes an audience valuable. There are three factors that contribute:

  1. Size: How big is the audience?
  2. Trust: Are they taking action based on what you say?
  3. Budget: How much do they have to spend?

You basically need two of the three for a valuable audience. Of those, No. 3 is the most important, since it dictates everything else (e.g. the kinds of advertisers you can work with, the products you can create/sell, etc.).

But if you have any two, you’re ready to start monetizing a free publication.

Affiliate ads are typically the easiest place to start. Or you can sell direct advertising to brands, or develop paid products for your audience to buy. Speaking of, let’s take a look at those…

The Basics of Paid Media Products

There are two types of paid media products – front end and back end.

The difference between them is their cost, as well as the depth, specificity, and value of the content you create. We’ll look at the particulars of each below.

For now, just know that both can be sold on either a one-off or subscription basis. The main benefits of subscriptions are that they create recurring revenue for your business, and they can scale in a way that other media can’t. But they also typically require you to continue creating new content over time, which can be tough. You’ve got to weigh your ability to do that when thinking about how to structure your offer.

Front End Products

The so-called “front end” products are paid products that are typically priced in the $50-$100 price range – cheap enough to be an impulse buy.

Most often, these are something like a short course, downloadable guide, or paid newsletter. But they can be other things too – a book you sell, images you license, even subscription apps or software. The distinguishing feature is that the price is in that impulse zone under $100.

Because they’re paid, the potential audience is narrower than your free product. But because the price is somewhat low, the aim is typically to reach several thousand customers (at minimum).

The content also tends to be more in-depth than whatever’s provided at the free level.

For example, at The Hustle, our writers reported on tech and business news every day in quick, pithy pieces (typically 150-250 words). That was the free newsletter. Our paid newsletter, Trends, offered deeper coverage specifically focused on emerging business opportunities for startup founders (usually in a longer format, and with much more data, insights, etc.)

Millions of people could subscribe to The Hustle because they enjoyed general business coverage. But Trends was for a narrower group that wanted to go deeper – people actively trying to build businesses.

In a similar way, your front-end product will be a paid solution that you know a sub-set of your free audience is interested in.

There are two big mistakes people make with front-end products:

1) Pricing: People often price these willy-nilly. For example, at Trends, we priced the subscription at $300 for the year because we didn’t know any better.

That price point is kind of a no man’s land – you don’t know if you’d earn more by dropping the price (going after a bigger audience) or increasing it. So stick to $100 or less on your front-end product unless your audience is big enough to do proper A/B tests.

2) Value Prop: The bigger problem people face is not getting clear on the value prop. SO many creators offer a “paid” tier which is just more of the same kind of content they give away for free. It often goes something like this…

“Welcome to my newsletter. You’re on the free plan, which is just one email per week. But if you sign up for my patreon, you’ll get two emails per week, plus access to the archive.”

DONT do this.

The problem here is that you’re not really offering anything unique to the reader. Just more of the same. If they do sign up for the paid subscription, they’re often only doing it because they like you as a personality, and that’s not a sustainable way to do business.

Instead, use your relationship with your free audience to figure out what their main frustrations and pain points are (the valuable ones you can solve), then solve those with your paid products.

Back End Products

Much more specific, much deeper coverage, and much more expensive.

Back end products typically start at $500-$1000 and can go up into the many thousands of dollars per year.

How, you ask?

Well, back-end products are typically very focused on value creation. Think insider-business know-how, or industry data. They can even be high-end consulting packages, or expensive live events.

What ties them all together is that they’re typically focused on helping customers make money, save money, or save time. That’s why they command a high price.

For example, James Altucher has several back-end newsletter subscriptions that run $4-$5k+ each year. They’re focused on specific stock trading strategies he’s developed, and the allure for buyers is that one great trade can return many times what the newsletter costs them.

In a different example, Industry Dive licenses content to other companies for thousands of dollars a year. They also have custom research services they offer. Companies know they’re saving tens- or even hundreds of thousands of dollars not having to create the content themselves, and they believe it’ll help them attract more customers, so they’re willing to pay.

Your back end products will always have the narrowest audiences, so it’s important to price them high enough that they can make money with relatively few subscribers (often <1% of whatever your free audience is).

Pulling It All Together

Generally speaking, your free product sells your front-end, and your front-end sells the back-end, so that the whole system is set up to attract free readers and gradually convert the most dedicated ones to high-paying customers.

You can have multiple free, front- and back-end products if you like.

The most important thing is to know that you’re not obligated to have any of them. This model is a choose-your-own adventure.

For a long time, Morning Brew did tens-of-millions with just free products. On the other end of the spectrum, someone like Kevin VanTrump makes millions on just a paid newsletter about corn and soy (there’s a free trial, but no permanently free subscription).

A really robust media company, like Motley Fool or Agora might look something like this…

When you know how the model works, you can pick the pieces you want and spend less time guessing.

Wrapping Up

So that’s it.

Obviously, there’s a lot more that could be said about the nitty gritty of pricing, growth, content strategy, technology, and more.

But you now know the model used by all media companies to thrive.

Dive deeper into this site for case studies that show this model in action.

A Mistake I Made

Back in the spring of 2021, I published a Twitter thread about some research I’d done on 7-figure newsletter companies.

I had been lucky to get unprecidented access to leaders in that industry, and over the course of about six months, I’d boiled down the business model in a way no one had really shared up to that point.

Newsletters were very popular, and the tweet spread fast.

A friend at the time recommended that I publish another thread. And another, and another. One a day for the next 30 days or so, in order to ride the wave, build my Twitter following, and establish my name as a go-to resource in the field.

It would have been easy enough. I had 500+ pages of edited insights, plus hundreds more in interview transcripts, P&Ls, and more.

In about twenty minutes, I wrote an outline of what the publication schedule would look like.

The first few days went well, I was stacking followers like never before. But then two things happened:

  1. I hit a day where I didn’t feel like writing, and
  2. I worried, “What if I run out of things to say?”

That was two years ago, and in a lot of ways, my career went on pause that day.

I’ve continued to work (a lot). And learn. And publish in other places.

But my personal audience-growth (especially on that topic) mostly stalled, and I still haven’t worked my way through that original list of 30 threads. And now I think that was a mistake.

Giving in to number one is always a mistake. Any pro knows that.

But number two was more complex.

Because in a weird way, it became a self-fulfilling prophecy. I was worried about running out of things to say. So I didn’t say anything. And the effect was the same, except now, my research isn’t out in the world working for me like it could. And I’m also sort of stuck, because I can’t possibly move on to anything new until I get this out in the world.

Don’t feel too bad for me. The last two years have been fun.

But the lesson is an important one: It is both selfish and self-destructive to hold back your ideas just to make them last longer.

If I were giving advice to my younger self, I’d say, “Do the opposite.”

Share a little more than you think you can sustain.

Not only will that help strengthen your creativity muscle. But staying out at the leading edge of your content ideas will help ensure that you can continue to evolve and reinvent yourself as the situation demands. Whether that’s because the industry changed, or because you find something you’re more interested in.

This game, of audience building and idea-sharing for money – it’s all about movement. You need to stay moving. Stay curious. Stay publishing.

As in life, stagnance is death.

How to (Really) Pack for the Appalachian Trail — A Look at My Gear After One Month of Hiking

2020 UPDATE: It’s been almost half a decade since I originally wrote this piece, and it’s been viewed thousands of times since then. I sat down this year and did a complete review, updating info and links as I went. Virtually all of it has held up to the test of time, and all these years (and miles) later there’s nothing I’d add. The only thing that may seem outdated is the technology I carried to run my business remotely while hiking the trail (iPad Air2 and iPhone 4S). But all the rest holds up and AWOL is still making the best damn guidebooks on the planet. 

Best of luck on your adventure…

Cheaper Than Knee Surgery

“You know, my first time out I learned two things,” a man by the name of Hatchet told me as our cookstoves simmered in camp, “If you buy wrong you buy twice, and expensive gear is cheaper than knee surgery.”

He was certainly one who’d know. He’d been given the trail-name Hatchet because he began the Appalachian Trail with—among other things—a hatchet, a five-man tent, two hundred-foot lengths of rope, heavy-duty combat fatigues, a lantern, a flashlight, and a headlamp.

This scenario is way more common than you’d think, even among experienced hikers. I spent many weekends backpacking as a kid, and used to sell equipment for a living. And yet, when I spent a month retracing Bill Bryson’s footsteps on the Appalachian Trail, I still brought almost twenty pounds too much.

The excess weight is killer on the knees, and replacing gear with lighter, more-effective versions is a pain on the wallet. So to help you avoid both I offer a comprehensive guide to my final gear load out.

This is not the stuff I started with, but the stuff I ended with and as such I think it’s a much more useful representation of what a long-distance hike really requires.

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