How to Grow a Must-Read Newsletter (Lessons from The Hustle)
Learn the strategies that took The Hustle from scrappy startup to multi-million-dollar acquisition—and use them to build a loyal following for your brand.
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TL;DR 👓
The Hustle didn’t become a must-read newsletter by accident—it’s built on smart, repeatable tactics. From crafting irresistible headlines to hooking readers with every line, there’s a method to the madness. Steal their playbook to write content that keeps people coming back and grow your brand one killer email at a time. Ready to hustle-fy your writing?
How to Grow a Must-Read Newsletter (Lessons from The Hustle)
It's 7:05am. My phone beeps.
Another annoying email notification. Probably some work drama.
But instead of the usual groan, I feel a spark of excitement. Why?
Because it's The Hustle, and I know I’m in for a treat.
But, how did a newsletter become the first thing millions reach for with their morning coffee?
It's not magic—it's method.
Today, we’re going to dissect The Hustle’s playbook to see what you, as a founder or marketer, can steal to level up your brand’s reach and engagement.
Stick around.
Here’s what I’ll cover:
Why The Hustle Is a Big Deal
The Hustle's Backstory
Stealing The Hustle's Playbook
Case Study: How a Month of Sludge Went Viral
Your 7-Day Hustle-fy Your Writing Plan
Final Thoughts
But First, Why The Hustle Is a Big Deal
0 to 500k subscribers in just 4 years
2.5m+ subscribers as of 2024
Average open rate of 40% (industry average: 17%)
Click-through rates consistently above 10% (industry average: 2.6%)
Acquired by HubSpot in 2021 for $27 million
Oh, and their early sign-up page?
It was copywriting gold.
The Hustle's Backstory
It started as Hustle Con, an entrepreneurial conference brainchild of Sam Parr after he sold his previous Hot Dog Stand business (Yea I said a Hot Dog Stand).
To get people in seats, Sam whipped up a newsletter—and people couldn’t get enough.
So he went all in.
What started as a niche newsletter in 2016 quickly became a daily must-read on everything from tech to culture.
This wasn’t luck—it was strategy.
Word-of-mouth led to buzz, smart partnerships, and then paid media.
Subscriber counts skyrocketed, open rates soared, and Sam built a killer team to scale and monetise.
HubSpot took notice, snapping it up in 2021 for a cool $27M.)
From Hotdogs to Hot Takes
So, how did Sam Parr go from selling hotdogs in Nashville to running a media empire that HubSpot just had to have?
Simple: He didn’t stumble on success—he built it, word by word, newsletter by newsletter.
And guess what? You can steal their playbook.
These are the exact strategies that turned a kitchen-table (actually, they used a door as their first table) operation into a multi-million-dollar acquisition.
Let’s break it down, Hustle-style.
Your First Impression Matters
Remember when your mom said first impressions count? She wasn’t lying.
In copywriting, your headline is your handshake.
It’s your shot to make them fall in love at first sight.
The Hustle’s move?
Write 25 headlines. Yes, 25.
The first 10 will be obvious. The next 10 will be weird. The last 5? Gold.
Here’s one that hit home:
"What Happened When I Went 30 Days Without Food."
I’d imagine the flow might have been something like:
Headline #1: "Man Drinks Soylent for 30 Days"
Headline #15: "I Replaced Food with Sci-Fi Sludge for a Month"
Headline #25: "I Ditched Food for 30 Days. My Body Hated Me, But My Bank Account Didn't"
Why it works:
Curiosity + Controversy + Personal stake = Irresistible click
That’s The Hustle magic.
The Slippery Slope is What Keeps 'Em Hooked
Ever wonder why you can't stop scrolling through the Hustle?
Two words: Slippery slope.
Each sentence should make the reader crave the next.
It's the "just one more episode" of writing.
Common examples include:
"Here’s the deal:"
"But wait, there’s more:"
"Let me explain:"
"That’s not all:"
Try this: End each paragraph with a mini-cliffhanger. Like this one, where I'll tell you the secret to making your writing addictive. But first...
Use phrases like "but first" or "let me tell you this before we dive in." Keep your readers on their toes, craving more.
It’s like those TikTok clips that cut off just before the big reveal (you know the ones).
Keep It Simple, Stupid
The Hustle writes at a 6th to 8th-grade level.
Not because their readers are simple, but because simplicity is powerful.
The New York Times writes at a 9th-grade level.
USA Today? 4th grade.
Why? Because simple writing hits harder.
Chuck the thesaurus. If you need one, you’re overcomplicating things.
Short sentences. Short paragraphs.
Think Hemingway, not your old English teacher.
Fancy words are like overpriced designer clothes—they might look impressive, but they're often uncomfortable and impractical.
Pro Tip: Edit your copy using Hemmingway app
The "Ugly Duckling" Draft Technique
First drafts are like first pancakes—usually a bit of a mess.
The Hustle embraces this.
Their strategy?
Write fast, write ugly.
Get it all out there, no filter.
It's like verbal vomit, but trust me, there are gems in that mess.
Just get something—anything—down on paper.
As Sam says, "Make your first draft horrible." Why?
Because once you start, the ideas will flow.
Pro Tip: Set a timer for 30 minutes and just write. No editing, no second-guessing. You'll be amazed at what emerges when you silence your inner critic.
The Incubation Period
Ever feel like your brain’s stuck on repeat, circling the same idea without getting anywhere?
That’s what we call "fixation," and it’s a creativity killer.
However I bet you’ve had a few genius idea while showering?
That’s no coincidence.
It’s called "forgetting fixation" and it’s crucial to creativity.
You let your mind take a breather, and boom—suddenly, those fresh ideas start flowing. After you’ve spewed out that first draft, walk away.
Take a stroll, grab a coffee, or yeah, hit the shower.
Let your brain marinate.
You’d be surprised at the gems it’ll dig up.
Editing Alchemy
This is where the real transformation happens.
The Hustle's editing process is brutal but effective.
Cut 50% of your first draft
Ensure every sentence propels the reader to the next
Start with a bang: Your first sentence should hit like a caffeine shot
Before: "I decided to try an experiment where I would consume only Soylent for 30 days to see what would happen."
After: "I replaced every meal with nutrient sludge for a month. My taste buds wept, but my wallet rejoiced."
Now that's an opener!
A Picture's Worth a Thousand Clicks
The Hustle doesn't just write—it paints.
With words and, yes, with actual images.
Remember the shirtless dude in the Soylent article?
Unnecessary? Perhaps.
Memorable? Absolutely.
Your mission: Find the unexpected visual for your next piece. If you're writing about finance, maybe it's a pig doing yoga. The quirkier, the better.
Case Study: How a Month of Sludge Went Viral
Remember that Soylent article? Half a million views. But why?
Intriguing premise (30 days of liquid food)
Personal stake (the writer's own body as a science experiment)
Controversial topic (replacing food with a tech solution)
Unexpected visuals (remember shirtless guy?)
The result?
A perfect storm of virality.
What Not to Do
Don't be afraid of controversy (but don't be needlessly offensive)
Avoid jargon like the plague
Never prioritise cleverness over clarity
Don't forget the call-to-action
Ready to Hustle-fy your writing?
Here's your 7-day plan:
Day 1: Write 25 headlines for your next piece
Day 2: Draft ugly for 30 minutes straight
Day 3: Craft a slippery slope paragraph
Day 4: Simplify a complex idea for a 12-year-old
Day 5: Find an unexpected image for your topic
Day 6: Handwrite your favorite piece of copy
Day 7: Put it all together in one brilliant piece
My Final Thoughts
So, what does all this look like in practice?
Well, The Hustle's article about living on Soylent for 30 days got half a million views.
Not too shabby, right?
Now, I know what you're thinking. "This sounds like a lot of work."
And you're right, it is.
But great copywriting doesn't happen by accident.
It's a craft, and like any craft, it takes practice.
Maybe your newsletter will be the next big thing. (Just remember us little people when you make it big, okay?)
Now, if you'll excuse me, I'm off to write 25 headlines for my next piece.
p.s. You can subscribe too the Hustle here
The Rabbit Hole - For the True Hustle Fans
Check out these hand-picked resources:
The Hustles first office (Originally Craiglist first office also)
Write Like a Master Without Complicated Lessons - Sam Parr
Sam Parr Copy writing Course:
If you want to take the next step and improve your copywriting you could take Sam’s copywriting course based on the concept of copy work “CopyThat - How to write irresistible copy (just like Ben Franklin“. It’s legit - I took it
The Hustle Timeline
The Hustle is the only 'company' newsletter I intentionally pickup every morning. I am glad that Hubspot invests in the newsletter to make it better rather than using the popular brand and subscriber count as a revenue tool.