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Lessons from a Badass Writer Who Sold His Newsletter for $17.2 Million

by | Jul 19, 2021 | Money

Email is older than most content creators on Youtube driving Lambos.

Making money through email seems obvious. It’s easy to think email is done to death. The revolution that Substack created is lost on most. Substack didn’t make email newsletters relevant again.


Substack gave content creators the ability to build an audience and own their audience’s data. See, conventional content platforms use the label “follower.” Follower simply means, ‘sorry champ, you don’t get the audience’s data.’ *Does sad face*

While going down the email rabbit hole on Twitter, I came across Sam Parr. Sam made email relevant again before Substack. He started an email newsletter called “The Hustle” for people who love business, with a whopping 50% open rate.

It’s an accident he even rediscovered the power of email in the first place.

The accidental conference that made $60,000

Sam moved to San Fran in 2012. He spent a lot of time around tech startups. That led him to run a conference called “Hustle Con.” To promote the event he sent emails to a group of people about the speakers. Those emails got people to his event. The event made a $60,000 profit. All of it was the result of the emails Sam sent. That’s when his love affair with email reignited.

Email has been reincarnated

Anyone who says email’s dying is on drugs or stupid — Sam Parr

Email is back from the dead. Even Bill Gates is on board. Yay! Sam changed my thoughts about email.

He says email is more useful than social media or website views. Emailing 1000 people is better than 100,000 people coming to your website. Why? Email builds a relationship with a subscriber that transcends the one-night stand of a lonely ‘view.’

Finding an audience for free to get to the first 150,000 subscribers

Sam grew The Hustle newsletter to 150,000 email subscribers in year one. All of that growth came from daily blogging. He wrote anywhere from 1–5 articles per day. Those articles got shared on both Reddit and HackerNews.

These are the rules Sam lived by to get those subscribers. Copy them.

  • Publish at least one article per day. None of this works if you don’t write on a consistent basis. That’s the brutal truth.
  • Use free social media platforms to distribute your content.
  • Work out what sort of subscribers you’re trying to attract. Then go where those subscribers hang out. If it’s gamers, then go to Twitch. If it’s Bitcoiners, then go to the subreddit on the topic. If it’s writers, then take a look at a few writing newsletters.
  • Alternate between long-form and short-form content.
  • Leverage Twitter. It’s an old platform but it still has a huge audience you can tap into as a content creator. I’m on it daily.
  • Go all-in on one or two growth channels. Sam chose HackerNews and Reddit. Find the two platforms where your kind of people hang out and go there. Then go deep. Publish a lot and play the long game.

The Romeo and Juliet relationship of a one-year commitment

Sam just kept slapping me across the face with his email wisdom.

The Hustle is a free email newsletter. There’s a paid newsletter his company offered, too, called “Trends.” The subscription began at $299 for one year. To differentiate the newsletter he added case studies and a membership community. There was no other length of subscription available that was less than a year.

This takes guts.

This model gets rid of the pretenders and the wannabes and attracts the right kind of customer. If you’re not willing to get into bed with Sam’s company for a year, then you could simply stay on the free Hustle newsletter. It taught Sam the power of the subscription model. Instead of falling into the ads trap that traditional business news relied on, he created a different category.

Takeaway: If you create a newsletter, why not demand a long-term commitment?

This is the secret to a kickass newsletter

I knew there had to be more to Sam’s success than sending emails via a one-year subscription and promoting it on Reddit and HackerNews. There is.

A distinct voice.

Sam’s newsletter stands out because he obsessed over the voice of his words in the early days. I learned the same lesson from writing for seven years in my undies from outback Australia.

A lot of content sounds generic, especially newsletters. The voice you write in helps you gain subscribers faster. What’s the best voice? Yours. Not imitating some other mate down the road.

Sam lives by two content philosophies:

  1. Write like you speak.
  2. Make every single piece of writing entertaining or educational.

Later, Sam created a style guide for his newsletter when training others to write content. “These are the words we will use. These are the words we won’t use,” he said in an interview. I took his advice. I wrote an entire Apple notes page with words I love. I scatter these words through most of my stories so it feels and reads like me — not like the outrage clickbaiter ruining people’s lives by saying America is going to collapse.

Too many emails are boring to open. All you have to do is be interesting and do the opposite of everybody else to build an audience faster.

The weird idea to explode email subscriber growth

Ambassadors. Wait, what the heck is that? Ahhhhh labels. There are subscribers, obviously. Then there are those who want to do more than read emails. I call them superfans.

By dividing up email subscribers into two categories, Sam’s newsletter experiment took another wild turn. He created an ambassador program. Ambassadors refer subscribers and get t-shirts, tickets to events, and stickers for being great mates.

Sam also uses ambassadors to test ideas with.

I do the same with my superfans who have their own segment in my ConvertKit. Superfans and ambassadors let you fail and continue to kiss your gorgeous feet. Normal readers aren’t so forgiving. I’ve certainly been given a few backhanders by strangers on email.

The simple math behind it

There are roughly 4,000 ambassadors of The Hustle at last count. The average ambassador refers around 25 people. This accounts for roughly 15% of Sam’s newsletter’s growth. Word of mouth is nothing new. Neither is referral programs. Sam simply took a proven model and applied it to email newsletters before anybody else did.

Lame stickers don’t just make 5-year-olds happy

Who knew stickers were a powerful way to build an email newsletter. I wouldn’t think adults cared about stickers. Although, there are so many places you can place a sticker — laptop, fridge, motorbike, bicycle, kid’s lunch box.

After you refer 10 people to Sam’s newsletter, you get a sticker in your letterbox. They even have a fulfillment center to handle all the sticker excitement. After you refer 25 people, a t-shirt lands on your doorstep. Then when you refer 50 people, you get a hoodie which really enforces the “Hustle” lifestyle of working in startups that they’re promoting.

Takeaway: Low-cost physical items create memories for subscribers. It’s not the cost. It’s the effort it takes to mail stuff that is appreciated and makes people want to share your amazing newsletter.

You don’t need to use Substack, ConvertKit or Ghost

Wait, what?

I spent so much time trying to find Sam’s dirty little secret: the email platform he used to build his newsletter. I expected to find a ghost in his computer or a bright orange Substack sticker quietly hiding on his laptop. Nope.

Sam got his team to build their own software to run the newsletter. He wanted full control and didn’t want to share any of the revenue with any software company, the greedy bugger! Joking.

If you got friends in tech then this is definitely an option. It will save you paying 10% on every subscription to Substack.

I personally love ConvertKit for emails. I even emailed the founder, Nathan Barry, and confessed my undying love for his software. He rejected my request to ‘hook up’ via email — can’t blame the dude really, as an email relationship between Australia and America could be destined for failure.

If your goal is to start an email newsletter then don’t get romantic. The software you use won’t make your newsletter a raging success. How you think about differentiating your newsletter will.

A painful truth for content creators

When asked what content creators should do if they want to follow in his footsteps, the answer made my eyes bleed.

Build an email audience as soon as possible.

You’ve heard it a hundred times. You’ll hear it a hundred more. An email list is how you own your audience. Otherwise, platforms like Facebook will simply take advantage of your content and use it to sell their ads. Over time, as you get addicted to their audience drug, they’ll show your content to fewer and fewer people so Zucks can buy another one of his neighbor’s homes.

You’re good enough to build an email list. Set up a landing page. Offer a free eBook, or course, or checklist. Politely ask for the email address. Winning.

Losing email subscribers equals massive success

There’s a formula for Sam’s very high email open rate of 50%. I did not know this trick at all. I’m willing to bet you won’t either.

You’ve got to lose email subscribers to be successful with a newsletter.

Why? This is how Sam explains it.

  • You have 100 people on your email list.
  • 60 subscribers open your emails every day.
  • Then, let’s say you add another 100 people who never open them.
  • Now, those 60 people who did open your emails won’t see them as often.
  • Your emails will end up in people’s email spam box.

This all comes down to email deliverability. When there are people who don’t open your emails on your list and love them, they signal to email services like Gmail that your emails suck big time. So what does Gmail do?

Gmail starts putting your emails in people’s spam box. They don’t tell you. You can’t see your subscriber’s email inbox. Silently, behind the scenes, email software companies are ruining your newsletter without you knowing.

The solution to fight back at email providers

The Hustle is a daily newsletter. When Sam’s subscribers stop opening emails for 30 days, they send a friendly email saying “we’re you’d go buddy?”

If there is no response then the subscriber is deleted from the newsletter automatically, to boost the email deliverability of the subscribers who are frothing at the mouth for their words.

Takeaway: send emails to people who open them. Delete subscribers who don’t open your emails, so the email deliverability stays high, and your emails don’t end up in spam boxes to die a horrible death.

Why don’t we copy Sam Parr?

There are a lot of content creators reading this article I’m sure. I’ve procrastinated on going all-in on newsletters for years. I couldn’t work out why. Sam wiped the smile of my potty mouth.

The thing that holds them [us] back is fear of launching — Sam Parr

That’s right. We’re afraid our newsletter is going to suck, but it won’t if we follow Sam’s advice. Silence your fear and launch your own newsletter. Make your own category like Sam did.

Stamp your view of the world all over your newsletter. That’s how you rise to the top and find an audience.

Sam Parr became a badass newsletter writer as a result of his hard work blogging every day. The Hustle Newsletter he created sold for $17.2 million to Hubspot. The journey Sam went on taught many content creators like me that email is a powerful medium when you use it right.

Newsletters aren’t dead. Newsletters haven’t reached saturation point. No, newsletter is just another dumb label. A newsletter is simply an email.

Turn your blog posts, stories, and articles into emails. Don’t waste the audience’s time. Promote your content on free social media platforms to find people who want to be inspired by your view of the world. Most of all, have fun creating and learning.

We’re all just figuring shit out as we go. That’s what Sam did and he rediscovered the power of email after decades of abuse, then pocketed millions of dollars doing the thing everybody laughed at.

Start sending kickass emails if you’re a content creator. It can change your life.

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