Case Study – How The Hustle’s Daily Newsletter Uses Storytelling to Captivate Their Audience

It’s not every day that a small group of people comes together to form a startup that competes with the likes of big names like Bloomberg, Forbes or the NY Times.

But that’s precisely what media company, The Hustle, sought out to do.

With big aspirations of becoming a top media business-related news source, The Hustle had their work cut out for them.

However, five months after their launch, they had gained over 100K loyal fans.

How did they manage this?

While quite a bit of strategy lends itself to their continued success, the foundation they’ve built their entire company on is none other than email marketing.

Specifically, a daily email newsletter.

The Hustle newsletter:  A case for effective storytelling in emails

When most of us think of a newsletter, chances are you’re underwhelmed, and that’s to be expected.

While there are a few newsletters you always open, the majority of what floods your inbox is often so repetitive in form and content that we roll our eyes and send it straight to the trash.

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The Hustle Daily email is not that type of newsletter. To their target audience, their emails are anything but dry and dull.

Today, their newsletter has more than 2+ million hungry, happy email contacts and they show no signs of losing the level of loyalty they’ve acquired.

So it may be a slight understatement to say that The Hustle has mastered the science of a successful newsletter.

No matter what niche you’re in, the process they use to create their newsletter is one every business can customize and use in their email marketing efforts.

In this case study, I’ll be breaking down some of the core building blocks in that process and giving you key takeaways that you can start testing your emails today.

Where to start: Customers and competitors

Before the team at The Hustle writes even a single letter of content, they start with a single question:

“What does a 20-something college graduate male interested in business and technology world want and need to read?”

This question guides 100% of their editorial decisions because this is who their readers are and what interests them.

Would this person be interested in buying a Beanie Baby?

Uh, no.

But would this person like to know what he can learn from matching human behavior to business the way the frenzied Beanie Baby Bubble of 99’ did?

You bet he would.

Understanding who they’re addressing allows for a focused content process while leaving room for some outstanding creativity.

But, just having a customer avatar isn’t all they use to create this content baseline.

The team also keeps close tabs on their competitors content. 

Knowing their target contact makes it easier to figure out where they’re currently hanging out.

For The Hustle, that would be places like Wall Street Journal, Forbes, and Business Insider. And since these are all top media sites, they also have significant social followings.

By going to Twitter and Facebook to see what their competitors have published The Hustle gets a leg up in knowing what content and topics are relevant in the minds of their readers.

Granted, your audience and competitors may not be the same as The Hustle’s, but the way they find their content’s starting point is something you can and should follow.

Takeaways For You

  • Know Your Customer. I know, I know. It seems like everywhere you turn, someone somewhere is telling you this. But that’s because it’s so fundamental and yet poorly executed.
  • Research Your Competitors. Once you know who your customers are you should also figure out where they hangout online. Is there a blog or content channel they’re always on? What about Facebook groups or social media channels? Dig into the data you find to see if your buyer persona matches what you’re finding on competitor channels.
  • Establish A Content Vetting Process. The Hustle starts with one question. If the topic they’re considering doesn’t match up, it gets tossed on the digital fire. To decide what to put in your newsletter, you can do something similar by asking one or more questions that fit your business, goals, and audience.

Now, let’s take a look at three examples of the daily newsletters from The Hustle to see what else we can learn.

Email 1. Mickey Mouse is pissed

No doubt, part of The Hustle’s success with email marketing is their ability to write headline copy that gets you to open up.

The “Mickey Mouse is pissed” headline does this well thanks to one key factor:

It triggers an emotion and sparks curiosity. 



While that sounds simple in theory, being able to pull this off, again and again, takes time and a lot of practice.

For this headline, the emotion they are trying to provoke is one of surprise.

When you think of Mickey Mouse, you would never connect the word “pissed” with a mouse from the Happiest Place on Earth. Reading a headline that places the two together will quickly get you wondering what’s going on with poor old Mickey and prompts you to open and read it.

Once you do, you’ll see the story behind the headline unfold.

Right away, the first headline in the email settles your curiosity.

Then, below that (see the highlighted part), you’ll notice they use some seemingly unusual phrasing.

Calling the referenced conglomerate “cuckoo for Cocoa Puffs” isn’t something you would see Bloomberg doing, and that’s why I love it.

This subtle phrasing is genius because the email isn’t addressing a 60-year-old man living in the California suburbs driving a $75,000 car.

No. It’s speaking to a younger millennial fresh out of college living with five roommates who is probably eating a bowl of cereal as they’re reading the email.

By using words and phrases this demographic relates better to, the entire email becomes more relatable.

The Takeaways

  • Write Headlines To Trigger An Emotion. If you’re not a seasoned copywriter, this can be tricky to master. Thankfully, there are tools to help you practice. To get started, spend about half or more of your time writing headlines and the rest writing your email. (Yes, headlines are that important!) Headline Analyzer by CoSchedule is an excellent tool for testing emotion within your headlines.
    And when triggering an emotion, target ones that convert the best:

    1. Shock and awe
    2. Fear
    3. Curiosity
    4. Laughter
  • Use Words and Phrases Your Audience Can Relate To. This will vary from business to business so to get a better grasp on this, you can do the following:
    1. Send out a survey via email to your list. Try to collect insights like age, education level, business interests and what keeps them up at night.
    2. Put the results through TagCrowd. This tool will tell you if any repetitive words are being used by your audience.
    3. Copy and paste the repetitive words or phrases into a Google Doc. Keep this on hand when you’re writing emails and season those words or phrases into your content.

Email 2. Time is apparently different for rich people

Here we see another excellent example of curiosity in the headline. This technique — also called The Curiosity Gap — is a practice of teasing a reader with intriguing news without giving away the answer.

The only way they can bridge their knowledge gap is to open up your email. With this newsletter and the previous one, that connection is through a news story.

The Hustle newsletter is unique because they send highly-digestible pieces of business news each day.

However, storytelling is a way to stay ingrained in the minds of your readers, so it’s worth using whenever possible.

The Takeaways

  • Test The Curiosity Gap In The Subject Line. I say “test” because this may not work as well for your business as it would another. But how does one write using the Curiosity Gap?
    Take some advice directly from The Hustle’s content team:

    “The best way to write a curiosity gap headline is to act like a tabloid newspaper editor — tease out the most interesting, compelling, frightening aspect of the story and use that to lead the reader into clicking.”

    Experiment with a few emails and then check your email analytics. If you get more opens but also increase hard bounces, then you may be straying from what your audience wants. Or you may be under-delivering in your email copy and need to test better content overall. If open rates go up and hard bounces go down, then you may be on to something.

  • Don’t Just Relate Information, Tell A Story. For The Hustle, their emails also double as blog content. The email shown above also had two other stories included, and all of them link back to their blog.

    For you, perhaps test a short newsletter series that focus on stories, or place an entire blog post within your newsletter and link it to your site. Keep an eye on email analytics to get a better idea of how this style is working out for your email marketing efforts.

Email 3. Arrested on Coke charges

In this email you’ll notice a change.

While the other examples focused on written content and a few stories, this email contains only one long story and uses a bunch of images.

This is a smart move.

Too much of the same thing will bore anyone. (Unless of course it’s coffee.) By shuffling format and style from time to time, your audience is less likely to tire of your content.

Also, notice that each of these emails has some content other than stories.

For example, every newsletter contains a “This email is brought to you by X Sponsor,” and ends with an ad from that sponsor.

Some emails even contain affiliate links for other products.

I bring this up because sometimes we are afraid to be promotional. We don’t want to ask too much or put too much in front of our audience out of fear they will be irritated.

But, you’ll never know what is too much until you’ve tested the waters.

Your email list is made up of your buyers so don’t be afraid to sell to them.

The Takeaways

  • Play With Newsletter Length And Style. Shake things up from time to time. The Hustle has a few different styles for their newsletter that they’ve found that works for them. You can test a various styles and formats that work well for you. If you’re not much of a designer, then you can buy templates for your dedicated email marketing service. Here at Sendlane, we offer both email marketing templates and a drag-and-drop template builder to give you more flexibility in designing a style that works for you.
  • Use Images. They’re You’re Friend. Every email from The Hustle has at least one image in their opening message. While you don’t need to put your image in the same place, you should try including at least one relevant image, screenshot or video in your emails. You could test linking the image to your blog or whatever else makes sense to see if that helps with click-throughs.
  • A Newsletter Can Be Promotional. Ask for social shares. Places links back to your blog content. Sell ad space within your content. Promote an affiliate, or your service or product. The Hustle does all of these in their newsletter, and if you’re delivering exceptional quality content, your audience will likely not care about you seasoning your emails with an ask or promotion every other email or so.

A regular email newsletter can be anything but ordinary

As we’ve seen from the The Hustle’s emails — daily newsletters don’t have to be boring.

You can find a style that fits your voice and business goals while using it to grow revenue by trying out various promotions in your email.

Finding the best layout, voice and process will take time, but with some testing, you can discover a style that’s all you and something your audience will come to love.

Kristen Dahlberg

Content Manager at Sendlane
As a member of the Sendlane content marketing team, Kristen focuses on everything from organization to content curation and process improvement. She enjoys variety and the challenge of learning the best way to accomplish each new goal.

Outside of work, Kristen spends as much time as possible at the beach, soaking up the San Diego sunshine!
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