Sam was tired and sunburnt. Again.
It was the summer of 2012, and Sam Parr’s hot dog stand had just sold its last smokie.
He’d spent the whole day on a hot Nashville sidewalk shouting “Alllllll beeeeeeef!” and having conversations with strangers in 99-degree heat.
It’s wild to think that only a few years later, he’d gather 300 strangers and a dozen tech founders at a live conference and make $40k in profit.
And this little conference was the launch pad for one of the world’s biggest newsletters.
This is how Sam Parr built The Hustle to 2m subscribers and an 8-figure business.
The Growth Timeline of The Hustle
Let’s take a look at the growth timeline to see how Sam grew The Hustle and the major inflection points.
I’ve left out his social media accounts because they quite honestly pale in comparison to The Hustle’s subscriber counts.
Before we dive deeper into how Sam Parr grew The Hustle, let’s quickly run through the main ways The Hustle was making money while Sam was running things.
A final note before jumping in:
We should mention that Sam had a co-founder for The Hustle named John Havel. John isn’t mentioned much in interviews or in media, so it’s difficult to extract how much involvement he had in the day-to-day operations of The Hustle. But from interviews and from John’s LinkedIn profile, it looks like he joined Sam as a cofounder in 2015—after the first HustleCon, but before The Hustle was a newsletter.
For the sake of ease, we will simply refer to Sam in this deep dive, as he’s been the very public face of the brand.
How The Hustle Makes Money
HustleCon
The Hustle was funded in the beginning by Sam’s live events he called HustleCon.
The first HustleCon event in 2014 made $40k in profit (and don’t worry, we’ll get way more into the weeds with how Sam built this event later).
But HustleCon wasn’t just a profit grab — it was the launching pad for TheHustle.com’s blog and eventually, the newsletter.
HustleCon was a one-day event that made money by ticket sales from attendees who’d come listen to tech founders sharing experiences and stories of building their startups.
The first HustleCon brought 300 strangers together in one room for a day. The last one in 2019 brought in over 2,500 people.
Here’s a breakdown of figures over the 6 years Sam and his team ran HustleCon (2014-2019).
It’s safe to estimate that the HustleCon events brought in over $2m in total revenue throughout the 6 years the annual event took place.
Profit margins over the first two events were significant. Even more, Sam has said in interviews that he never lost money on his conferences. He was able to make a profit from the beginning because he was super frugal and wouldn’t spend money on “stupid shit” (his words, not ours).
Ads & Sponsorships
The HustleCon events made money on sponsorships, but those only happened once a year. That’s a really spikey cash flow situation. Not ideal.
So Sam launched TheHustle.com as a blog website in 2015. And while they didn’t profit off of web traffic at the time, it did spawn the idea of launching a newsletter and helped grow their email list.
That email list is where The Hustle ended up making their millions: newsletter ads.
The Hustle was making $15m annually before it was sold to Hubspot in 2021. And a large percentage of that revenue was thanks to ad sales.
Trends.co
While newsletter ads and sponsorships paid well, Sam discovered an idea for a subscription product.
Recurring subscription revenue was coveted in the tech space, and while looking for ideas, Sam would share some research he was putting together for companies.
He’d share it with his team and friends, and they had told him how awesome that information was. And they wanted more of it.
That tipped Sam off that this could actually be the product: a report on fast-growing business trends. In 2019, The Hustle did a presale for Trends, which brought in $30,000 in one day.
Fun fact: Chenell was a day one member of Trends, back when it was free.
Then they did an official launch with an annual subscription price of $300/year (no monthly price option).
The launch converted 4,000 paying subscribers. Some quick napkin math tells me that’s $1.2m. Whoa.
It is reported that Trends had more than 10,000 paying subscribers before selling The Hustle to Hubspot. (source)
Sadly, Hubspot sunsetted Trends in 2024.
The Growth Levers of The Hustle
Alright, let’s jump into the growth side of things.
But first a quick caveat: this is not an exhaustive list. Sam and his team did a lot of things to grow The Hustle. But these are the most well-documented levers I found, and the ones I also found the most intriguing.
📢 1. Live Events. Sam never meant to start a newsletter. He launched a conference long before The Hustle was hitting millions of inboxes.
🦠 2. Viral Content & Blogging Strategy. Using Reddit and other sources of inspiration, Sam was able to figure out what worked to get viral views and leveraged strong headlines to drive clicks, opens, and traffic.
📈 3. Paid Growth. This was a pivotal growth strategy for The Hustle, but they didn’t even think about paying for subscribers until they’d reached a certain subscriber milestone.
✍️ 4. Copywriting & Sales Psychology. Growth comes down to persuasion. Sam realized this early on with his hot dog stand. But he put in the work to hone his copywriting skills to understand how to attract and keep online attention.
💪 5. Brute-Force Networking & Partnerships. Sam didn’t wait for people to come to him. He couldn’t afford to wait. So he brute-forced his network and his first hires.
1. Live Events 📢
The Hustle didn’t start as a newsletter. As we mentioned above, it started as an event. Here’s how it went down.
From Launch to $40k Profit in 7 Weeks
It was early 2014, and Sam and cofounder John Havel had recently sold an app called Bunk (it was like “Tinder for finding roommates”). The newfound cash gave Sam time to figure out what he wanted to do next. Since he had just sold an app, he wanted to learn more about the tech entrepreneur scene.
And who better to learn from than successful tech founders, right? But Sam knew calling them and asking to “pick their brain” wasn’t a good strategy.
He had a better idea:
→ Get a bunch of tech founders in one building to share their knowledge with a large audience of eager 20- and 30-somethings.
How did he come up with this event? Well, he didn’t.
Sam met a guy named Eric Bahn during the process of selling Bunk. Eric had actually organized the first even HustleCon in 2013 and Sam attended.
After that, Sam wanted in. He knew he could make it even better.
They went much harder on this second event and started running a content marketing playbook around it.
It was a one-day event where Sam would sell tickets and sponsorships—all while learning valuable lessons from these tech founders.
Turns out you can have your cake and eat it too.
Sam not only pulled it off, he did so in a matter of 7 weeks. In less than 2 months, he sold 400 tickets, booked notable guest speakers, and sold 7 conference sponsorship packages.
That is INSANE.
You have to appreciate Sam’s hustle (pun!) and persistence to pull off this event. Had it failed, The Hustle as we know it may never have existed.
But it didn’t fail. The opposite, actually.
They made $19.25k in sponsorships + ~$37k in ticket sales. At the end of it, he walked away with over $40,000 in profits (here’s his revenue & expenses breakdown).
Oh, and he didn’t even pay any of the speakers. More on that later.
The $40k in profit was great.
But the biggest “profit” was the proof of concept for HustleCon as a business, along with the email list they’d built on the back of it.
The Email List Saved The Conference
Sam knew he needed email to sell tickets. So he created a Mailchimp account and got to work.
Sam had learned how to create effective email drip sequences (shoutout to Neville Medhora’s Autoresponder Kourse). So he wrote and scheduled out a 12-email sequence based on the bios of the speakers he’d booked for HustleCon.
But he still had to get people ONTO his email list.
To do that, he used those speaker bios as mini blog posts that he shared on
- Hacker News
- Facebook groups
- Growth Hacker
- Inbound.org
Sam also asked the speakers themselves to share the posts written about them to their audiences.
He also gave away 50 tickets to influencers with large Facebook audiences in exchange that they’d share the event and landing page.
All of this helped sell out HustleCon in 2014, and was the beginning of what The Hustle’s email list is today.
Sidenote: The Hustle launched on Mailchimp. But not long after launching, Sam realized the risk of relying on someone else’s software to build his media empire. So he hired a developer to build out an ESP (email service provider) in-house! They had the foresight to create proprietary software and de-risk their operations and costs. Just another example of how Sam thinks and operates differently than most.
HustleCon: Part 2
HustleCon in 2014 was a wild success.
So Sam and his small team went to work to plan the 2015 event. First, they made it bigger and better: More speakers. Bigger venue.
Then they 3x’d the ticket price ($300/ea).
Then they sold 600 tickets—1.5x more tickets than 2014.
You probably won’t be surprised to learn that HustleCon 2015 also sold out—and made even more money.
And once again, the 2015 event helped grow the early stages of The Hustle’s email list.
While I personally wouldn’t recommend running a conference with the goal of building a newsletter, it worked out really well for Sam (even if unintentionally).
He told Eric Siu in an interview that they never lost money on any events. Sam offered this advice for anyone interested in launching a conference:
- Spend as little as possible until you start making money on tickets and sponsorships
- Don’t spend money on stupid stuff—at least not until you’re getting cash flow
Sam and The Hustle went on to do annual HustleCon events until the 2020 pandemic shut down live events. Their 2019 event would be the final HustleCon.
2. Viral Content & Blogging Strategy 🦠
Sam got The Hustle to 100k subscribers in under a year.
And he did it 100% organically—meaning zero paid ads or co-reg campaigns. That’s almost unheard of now.
But before The Hustle was a newsletter, it was just a website.
Sam and his small team took their HustleCon earnings (~$250k) along with a small investment round of $250k and launched TheHustle.co in July 2015 (check out this launch video).
And not long after launch, they were driving nearly 1m monthly visitors to TheHustle.co.
But what the hell was it?
Sam believed most content online sucked.
Buzzfeed and Upworthy were click-baiting millions of people on Facebook with “shallow, meaningless articles that were treating their readers like a bunch of morons.”
Sam had been blogging since 2013. After taking Neville Medhora’s Copywriting Course—along with reading a bunch of books on writing—he’d gotten pretty good at writing viral content.
He began to master not only headlines but writing articles that people would click on and share with their friends.
For example…
They wrote an article on an experiment where one of their writers lived on Soylent for 30 days.
They wrote another article about microdosing LSD for a month straight.
Then they ran an experiment to see if they could “publish” a best-selling Kindle book to try and prove how corrupt and flawed Amazon’s digital book system was. (Harlequin Romance threatened legal action so they took that article down. Bummer.)
Reverse Engineering Content Ideas
Sam’s content drove so many views because he knew how to create viral content. But where did these great ideas come from?
In a talk he gave at Craft & Commerce in 2022, Sam shared the exact processes he used every day to “mine” for ideas at The Hustle.
One of the best places for content ideas was Reddit. Sam and his team would scour Subreddits and find the most popular posts in those communities. Then, they’d look for the comments with the most replies or upvotes to find untapped opportunities.
Sam says the comments section is where the gold is. It’s where the unanswered questions live.
So Sam and his team would concoct experiments to answer the questions, or they’d do the research to find the answers.
Posting Relentlessly
Sam would post his blog articles everywhere. Like—every.where.
He’d get articles to go viral on Hacker News, Reddit, and Indie Hackers. He’d also reach out to other relevant blog sites to get The Hustle articles featured as guest posts.
Sam was relentless in getting as many eyes on his content as possible. This was a huge factor in their early growth.
But so was his prolific publishing habit.
10 Articles Per Week, By Sam and His Alter Egos
Sam understood that success was a recipe of quantity + quality.
So when he wasn’t scouring Reddit for ideas, he was writing articles.
The Hustle published 10 articles every week. That’s 2 articles per weekday.
One quality article a week isn’t easy.
One quality article per day is really hard.
But Sam was doubling that.
And still going viral and growing exponentially.
But despite being the only writer at The Hustle, Sam didn’t want people to think he was running a tiny, one-man operation.
So he created fictional writers: Sidd Finch, Steph Whitfield, and Steve Garcia.
Sam still wrote articles as Sam Parr, but he’d use these “alter egos” for different types of stories. He even created LinkedIn profiles for them.
Lexi Grant questioned Sam’s ethics in an interview: “So a critic or cynic would say you made shit up, then, to grow the audience.”
But Sam defended himself.
Yes, he used made-up characters to pen the stories. But he based what he wrote on his opinions, real-life experiences (his own and others), and experiments. The content was real, but the authors weren’t.
Was he catfishing his audience? Maybe.
But Sam felt it was necessary for the business. Regardless, whether it worked or not isn’t up for debate. And whether you agree with it or not, there’s no denying The Hustle took off like a rocket ship.
And Sam’s alter-ego pseudonyms were part of it.
3. Paid Growth via Facebook Ads
There is limited information on how Sam grew The Hustle with Facebook ads in the early days.
What Sam has shared is that they didn’t start using any paid growth (ie. Facebook ads) until they had reached 250k subscribers organically.
And this was really smart.
Instead of doing it right away, Sam could learn who their subscribers were, how much money they were making per subscriber, and what the lifetime value of a subscriber (LTV) was. It also helped him figure out his pay-back period for a subscriber at various CPA costs.
Sam bragged he knew those numbers “like crazy.”
And that’s pretty important if you get into the paid acquisition game: when you’re armed with the right info, you can create campaigns that speak to your target audience while paying for clicks that grow your base and maintain profitability.
It’s a pretty basic but highly effective flywheel:
The Hustle launched Trends (their paid product) in 2019.
Sam shared they were spending $50k per month on ads to acquire subscribers for Trends. You can be assured they wouldn’t have been spending that much money unless their numbers were dialed in.
Here’s an example of the FB ads they were running:
4. Copywriting & Sales Psychology
Long before The Hustle, Sam sold hot dogs. From a hot dog cart. On the hot summer streets of Nashville.
His hot dog stands were called Southern Sam’s: Weiner’s as Big as a Baby’s Arm. He got really good at getting attention and talking to people.
When Sam tweeted about his hot dog stand, people wanted more. So he shared this Twitter thread:
The experience taught him the foundations of business. But it was hard work and didn’t scale well.
So when he discovered copywriting, he had an epiphany:
“Copywriting is just salesmanship on paper that could scale to an infinity (sic) amount of people.” — Sam Parr
In-person conversations from a hot dog stand are one-to-one. But online conversations are one-to-infinity.
Making Copywork Work For You
Sam studied copywriting obsessively. He calls it his “unfair advantage.”
He got so obsessed that he locked himself in a room for 2 hours every day for 6 months to get really, really good at copywriting—and writing in general.
What did he do during those 2 hours? Sam did copywork.
Copywork is an old technique even Ben Franklin used to get better at writing. Sam explains it in more detail here—and he even built a course called CopyThat 100% focused on teaching copywork.
Safe to say… this skill has paid off for him. Writing was the foundation for The Hustle.
And Sam leaned heavily on copywriting to:
- write the emails that promoted and sold out HustleCon
- increase email opens with powerful subject lines
- write unignorable headlines for his blog articles (that attracted 1M monthly visitors)
- drive higher CTRs for their newsletter advertisements (which is critical in rebooking sponsors)
So when it came time to launch The Hustle’s paid product, Trends, Sam once again leaned on his copywriting skills. He threw some words on a Gumroad page and drove $30k in presales.
Yes, he had a large audience to pitch.
But he wouldn’t have sold $30k with weak writing chops. And on the flip side, he could’ve sold even more if his copywriting skills were even better.
The bottom line: copywriting is good for growth, which is good for the bottom line.
5. Brute-Forcing Your Network
There’s one consistent, unignorable theme in Sam’s story.
He is really good at finding the right people for the job—and then convincing them to help him.
He’s brute-forced his network to a large degree.
The first example is how Sam convinced an executive producer of the A&E show American Pickers to hire him after recognizing him on the street.
Sam went on to work for American Pickers. This got him into the hot dog stand business, where he got friends and acquaintances to work for him at his stand.
This theme is carried throughout Sam’s story.
He brute-forced a live event to happen (HustleCon) by cold emailing and phoning tech founders over and over—and convincing them to come speak for free! He even convinced friends to help him with the event.
Brute-Force Hiring “Talented Weirdos”
The first handful of hires at The Hustle were either friends he reached out to or people Sam emailed directly to apply.
Sam said in an interview he looks for a mixture of talent and “weirdo”:
“I hire weirdos. I look for people who are not only skilled in their craft, but also have unique perspectives and a genuine passion for their work.”
When he spots these talented “weirdos”, he seizes the chance to hire them.
That’s how he got talents like Steph Smith, Alex Garcia, and Trung Phan to work for The Hustle. He saw Steph’s personal website and blog post called “To Be Great, Just Be Good Consistently.” He was so impressed that he cold-DM’d her.
But Steph told him she was a Product Manager, not a professional writer.
But Sam was unrelenting. He convinced her, “You’re already doing it as a hobby, I’ll just pay you money to do it.”
Steph has since left The Hustle post-Hubspot acquisition and has gone on to run a podcast for a16z.
Other notable hires who worked for Sam at The Hustle include:
- Adam Ryan, cofounder & CEO of Workweek
- Brad Wolverton, former Senior Director at Hubspot
- Ethan Brooks, founder of Austin Business Review
- Matt McGarry, founder of GrowLetter & Newsletter Marketing Summit
- Zachary Crockett, podcast host for Freakonomics
Sam was savvy at spotting uniquely talented “weirdos”, and skilled at convincing them to work for him.
Push Networking
You’ve heard of Push vs. Pull Marketing?
Well, Sam is a Push networker. He’s not afraid to pick up the phone and ask. And all this despite being a self-proclaimed introvert. (Even us introverts are running out of excuses!)
Sam is never nervous to ask questions, even ones that might be taboo: When he was younger, he’d ask his friends’ parents how much money they made.
“You can’t be too proud, most people are too worried about looking silly,” Sam says.
Asking tough and meaningful questions will get you to stand out. It won’t always work, but if nothing else, you’ll be memorable.
Sam also learned from Ben Franklin (again) to always ask for a tiny favor first. If someone is willing to do you a tiny favor, they’re more likely to do you a larger favor later on. So Sam would ask for small favors from people, and this helped him find the right people to build a business and newsletter around early on much more efficiently.
How You Can Replicate Sam Parr’s Success
Write content people can’t ignore. Viral, shareable content built The Hustle’s initial email list from a few thousand to 250k subscribers, all before Sam paid for growth. A solid lead magnet or podcast appearance might get you a head start with growth. But if you focus on creating valuable, irresistible content, growth will be a lot easier.
Leverage events to build an early audience. Again, I’m not suggesting you start a live, in-person conference to grow your newsletter (though I won’t stop you from trying). But start with an online event, webinar, or workshop to get new subscribers onto your list. Justin Moore ran dozens of digital events before launching his first in-person conference. Bonus points if you can collaborate with a brand sponsor and/or charge for the workshop.
Know your numbers before scaling paid growth. The key to paid acquisition isn’t just spending and high-converting ads—it’s knowing LTV, CAC, and the payback period. And remember, Sam didn’t start scaling with paid ads until The Hustle had reached 250k subscribers. It’s a marathon, not a sprint.
Shoutout to Dylan for putting this deep dive together 👏
If you liked this, you might enjoy the two deep dives I wrote on Lenny Rachitsky:
- Lenny’s overall growth story and how he built his first 350k subscribers. He just hit 1,000,000 recently.
- A more specific deep dive into Lenny’s paid newsletter.
