Business. News. Media. Unsubscribe.
A couple of years ago I was approached by a client struggling to convert traffic into email subscribers. So I decided to research businesses which rely wholeheartedly on their ability to convert traffic to subs: newsletter and media businesses.
This taught me a valuable lesson: consider who relies heavily on the element you are trying to improve and study them (not just your competitors). For example, if your content thumbnails are poor look at the top YouTube creators. If prospects aren’t completing lead capture forms, look at insurance and comparison sites.
Today we’re focusing on five newsletter brands with combined subscribers totalling over ten million. These are the big dogs.
But you don’t have to be running a newsletter business to get value from today’s breakdown. If you have an email list or opt-in of any kind, there’s a lot to digest.
Enjoy,
— Robbie
The Hustle & theSkimm
When you think of brands pioneering a space, theSkimm comes to mind. The brand was launched in 2012; email newsletters didn’t exist and they certainly weren’t a business. Weisberg and Zakin launched theSkimm as a daily newsletter for millennial women. The business was acquired by Ziff Davis for ~$30M in 2025.
The Hustle followed suit a few years later. What started as an expo soon became a newsletter for the tech bros and founders of Silicon Valley. Sam Parr (founder) sold The Hustle to HubSpot for ~$27M in 2021.
All this to say, these two businesses know how to generate subscribers. So let’s get into the copywriting used to turn lurkers into readers. Both these brands take a similar approach to their subscribe forms. No flash, no pomp.

Unique Selling Point (USP): The Hustle does a really good job of highlighting the brand’s tone-of-voice (TOV) in the headline alone–Boring Isn’t Our Business. Boring is turned into a noun (nominalisation) to keep the copy concise.
This is also immediate objection handling. Before the reader has time to think “business newsletters are so boring” you’ve overcome that hurdle.
Frequency: both brands share the frequency early on so you know exactly what you’re signing up for. The Hustle is “daily” and theSkimm is “every morning”. Seems minor but newsletter businesses live and die on subscriber quality and engagement.
Yes, you want tons of people to subscribe. But you want the right people to subscribe. If they’re not looking for a daily newsletter they’ll disengage and drag your performance metrics down. Not worth it.
Target Audience: neither of these brands specify a target audience for their newsletters, which is unusual but not a surprise given their brand positioning.
The Skimm is a 92% female audience. The logo is a silhouette of a woman. The traffic they’re driving from ads and socials will already be selected within their demographic. The Hustle has no target audience, per se.
The audience is anybody interested in business news that “isn’t boring”. Calling out an audience would only serve to alienate potential subscribers.
Value Proposition: this is the main takeaway from these two subscribe forms. Both brands have a very clear value proposition (the unique benefit of subscribing):
→ “Unconventional business news”
→ “Prepares your for your day in minutes”
This is your differentiator. This is the value your readers get in return for sharing their personal information with you. Inbox’s are valuable. You have to earn the right.
Morning Brew
Morning Brew is one of the only major newsletter businesses with a dedicated subscriber page still in place. Most drop the page when they reach terminal velocity–it’s better to send people to your heavily populated home page.
Before Morning Brew, the brand was called Market Corner. The original idea was to provide business news to college students that moved away from the dry and dense tone of traditional media. It worked. The business launched in 2015 and was acquired in 2020 for $75 million.

Social Proof & Credibility: Morning Brew’s headline is a masterclass in showcasing the authority and scale of the brand. What they’re really saying is; over four million people like you are reading our newsletter so it must be valuable.
We’re social animals and whether you like or not, we follow the herd. Also notice how they say “professionals” not “people” or “subscribers”. This allows for self-selection. If you identify as a professional, you opt-in to the brand’s target audience.
Brand Voice: Much like The Hustle, Morning Brew does a great job of highlighting the brand’s voice to prospective readers–“important business news, with a hint of wit and humor”. What they’re really saying is: we only tell you the business news that’s actually worth reading, and we deliver it in a way that’s entertaining and easy to digest.
A brand’s voice is important. It’s a self-selection filter. We identify with brand’s that align with our personal style (or the style we wish to attain). If you’re a suit-wearing, straight-laced business man who loves the Wall Street Journal, maybe Morning Brew isn’t for you. They don’t need to say it. The brand does the heavy lifting.
Value Proposition: Morning Brew’s value proposition is a strong example of making the audience the subject of the copy and painting a visual picture. We want a resource that feels like a superpower–something that makes us feel like we’re getting a head start on the day: “Start your day informed, knowledgeable, and ready to go.”.
The Milk Road
The Milk Road is a wild story: launched by Shaan Puri and Ben Levy (already successful founders) in January 2022 and acquired ten months later for somewhere in the ballpark of $5-10 million. One key difference with The Milk Road is the heavy focus on paid acquisition straight out the gate–this newsletter was a purpose built rocket.
But the brand and copy is probably the best of the bunch. Let’s get into it.

Transformation: with just six words you’re shown the journey that a standard subscriber can expect from the newsletter. You can expect to transform from an everyday person to a smart investor. The Milk Road takes you A to B. Sold.
“Everyday People” is immediate objection handling. Most people are turned off by investing or finance topics because they’re dry and confusing. The objection is handled before you can say “but I don’t know anything about crypto or investing”. This isn’t for experts. It’s for everyday people. And you’ll become an expert.
The subheading is also transformative: “today’s opportunity for tomorrow’s wealth”. The parallel structure makes it nice to read and the payoff is clear—wealth.
One thing they don’t disclose (which the others share) is the number of subscribers. Instead they opted for “#1 Newsletter for Everyday Investors”. I’m sure they’ve A/B tested this and opted for the highest converting copy. If it ain’t broke, don’t fix it.
1440: Daily Digest
1440’s Daily Digest is a slightly unique newsletter in that they have no niche or category. The business was founded to go a mile wide and inch-deep. Most newsletter do the opposite. And the copy reflects this.

Education > Entertainment: 1440 are much more direct in their delivery. It’s an education-focused newsletter, not entertainment. Readers can expect a fact-driven briefing to learn and stay informed. Daily. No fluff.
Audience: 1440 don’t specify who their newsletter is for, but it’s shared with “millions of curious minds”. Which I love. This is a clever way to get people to self-select as a potential reader. What they’re really saying is: if you don’t read 1440, maybe you’re just not that curious. Who wants to be seen as not curious? Sold.
Social Proof: this is the section they do better than anybody else. Firstly, photos. We love photos because they’re visual and real. These aren’t subscribers or numbers on a screen. They’re real people just like me.
Secondly, specific numbers. There’s a ton of research to suggest specific numbers are seen as more believable than rounded numbers. And in this case, 4,664,935 looks way bigger than 4M+. When the number is not particularly impressive, round it off.
A Quick Caveat
There’s one important point that needs to be covered: all of these newsletters generate millions of dollars in revenue and are incredibly successful.
These brands are not on the starting line and what they are doing today may be very different from what they did in the early days. And in most cases, the brands you see now are unrecognisable from the initial idea.
But these companies spend hundreds of thousands of dollars every month to ensure their copy and conversion rates are optimised. So what they are doing is working. My suggestion is: learn from the best and test for yourself.
These are the main things to ask yourself:
Have we defined the audience? (eg. curious minds, professionals)
Have we explained the value? (eg. stay informed, become a smart investor)
What’s the frequency? (eg. daily, weekly, every morning)
Have we shared social proof? (eg. read by 120,452 marketers)
TL;DR
Study brands reliant on the element you wish to improve
Have a clear value proposition: why should they give you their email?
Clarity wins: confused prospects don’t buy (or subscribe)
We offer comprehensive, private copywriting audits for businesses like yours. We uncover where you’re leaking revenue and offer copy-edits to improve conversions.
(audits cover landing pages, websites, email sequences etc).

