Newsletter Growth Case Study: From 0 to 50k Subscribers in 20 Months

by 
Harry Dry

Founder of Marketing Examples Harry Dry became a success seemingly overnight. With no formal training to speak of, Harry embarked on a journey of trial, error, and luck. 

Today, Harry’s marketing case studies and unique, actionable content have been read by more than one million people, and his newsletter has over 50,000 subscribers.

As a guest on Wynter Games 4, Harry walked us through his tips for growing a newsletter of your own. 

Grow a newsletter with views and conversions 

To grow a newsletter, you need two things to happen. 

  1. People need to see your work 
  2. People need to convert (sign up)

We’ll dig into how Harry worked to get his content out into the world, and what he did after that to improve his own newsletter conversion rate so more people would sign up to his email list

1. Get people to see your work 

When Harry left his full-time job to test the marketing waters, no one was visiting his Marketing Examples website. 

So he started to seek out all of the various places that marketers congregate online - the places he calls the marketing “watering holes.” 

This included platforms like Twitter, Facebook groups, LinkedIn, Designer News, Indie Hackers, and Slack groups, reddit forums.

Since traffic wasn’t coming to his website, Harry figured he’d bring the content directly to them.  

“I thought to myself, no one's reading my website at the moment. So what about if I could somehow take my articles, my content, and share them where there's loads of marketers buzzing around,” Harry said. 

Experiment with social platforms 

For Harry, bringing his content to these marketing hubs meant more than dropping a link and calling it a day.

He wanted to both help them and impress his fellow marketers. This meant thinking about things more imaginatively.

“It’s not rocket science. Essentially, I like to say people are busy. So you've got to wow them where they're already at,” Harry said.

Harry would tailor his articles to each of the platforms in question, and plug his newsletter at the end of each post. 

As his success grew on the first platforms he tried, he experimented with others. Slowly but surely, the email subscriptions started ticking up. 

Showcase image-based content 

Much of Harry’s content was image-based, thanks to his skills with graphic design and his focus on showing rather than telling.

“The beautiful thing about images is that you can kind of share them anywhere, because all platforms are really suited to images,” Harry said. 

Below is one of Harry’s popular articles on copywriting, which illustrates the engaging nature of his visual posts. 

Focus on value

Once Harry began to get more traction with his sharing strategy, a pattern started to emerge. He realized that there are three things you need to do to ensure your content makes an impact.

  1. Create value
  2. Transfer value
  3. Store value


Value is created by coming up with helpful content that benefits your audience. Value is then transferred to different vehicles such as your article and your website.

Finally, value is stored within the hands of your email subscribers.  

Why build a newsletter?

If social media distribution is so popular on its own, what’s the point of attracting newsletter subscribers in the first place?

“Let's say someone comes to Marketing Examples. Chances are they'll probably forget about it, and probably won't return. But if you can capture them as an email subscriber, then you've got that direct line into them whenever you like, really,” Harry said. 

When you reach an audience on Twitter, you don’t truly own that audience - Twitter does.

And if something changes or the algorithm is updated, you could face a major setback. In contrast, your email subscribers are 100% yours. 

Promotion versus sharing 

Harry doesn’t deny that he’s done his fair share of self-promotion. But he has always done it in a way, where he delivers as much value as possible.

“I think that the best self - promoters aren’t really self-promoters. So I took the time to become more or less a genuine member of all the communities I was sharing my content in,” Harry said.

That means that he spent time doling out valuable advice on platforms like Indie Hackers.

He would share a link to his website, but he would also share many other helpful resources and tips in the same breath. 

“I like to say that content promotion is a positive-sum game. I think if you help other people out...then they'll help you out.

You can't just force your stuff down people's throats. That's not really how it works,” said Harry. 

To be truly successful, you need to inspire a true conversation. 

2. Get people to convert 

We’ve covered some best practices for getting your work out into the world. Now, we’ll move on to Harry’s tips for converting your visitors into newsletter subscribers.

Imagine that you have a website that gets 10,000 hits a week.

Of those 10k people, 1% of them are signing up for your newsletter, equalling a total of 100 signups per week. 


If you want to increase that conversion rate to 300 signups per week, Harry says you have two options.

  • Option 1: You can increase your website traffic by 300%, using advertising and SEO tactics. This could take years. 
  • Option 2: You can improve the conversion rate of your existing traffic by 3%. 

For many websites, Harry believes that option two can be accomplished as quickly as one day, if you optimize your site properly.

He knows that’s possible, because it happened with his own website (more on that below).

Optimize your signup language 

The first step to getting more join the newsletter mailing list is to create an enticing signup message.

You need to do something out of the ordinary that makes people want to subscribe. 

“The mistake you see all the time is a B2B or any company has this little, like email thing on their website. And it's like, ‘subscribe for updates,’ or ‘subscribe to our newsletter.’

But there's no real purpose behind it. So adding this purpose is the first way of increasing that number,” Harry said.

The example below shows what many people say, versus what you should say: 


The difference is clear. The first example of signup language is vague, while the second has a sense of purpose and passion. 

Fast way to grow your email list

Another example of this comes from Patch.com.

Originally, the Patch website had a generic CTA urging visitors to ‘subscribe to the newsletter.’ 

When you update that to read: ‘Stop killing your plants: Sign up to our free houseplant parenting course,’ you have a more interesting proposition that functions almost like a lead magnet. 


Back in the day, Harry’s subscribe message was like the one on the left, and no one was subscribing. 

When Harry tweaked his own bland signup language as shown below, the results were instant.

“Honestly, just that one tweak [led to] 1% to 3% overnight,” he said.  


Make it easy for people to subscribe

In addition to eye-catching signup copy, you need to make sure that your audience can signup easily.

On Harry’s own website, there are four ways to sign up for the newsletter. You’re never more than one click away from being able to sign up.

You can: 

  • Sign up at the fixed navigation bar at the top of the site
  • Sign up at the end of each article
  • Sign up via a pop-up which comes up after about 60 seconds
  • Sign up at the dedicated subscribe page

Write amazing content 

“I'd be lying if I said that content wasn't really the key behind all this,” said Harry.  

Good content means that:

  • You get more eyes on your content (because you’ll see more organic sharing)
  • You get improved conversion (because a great article will convince readers to sign up)

While there is no magic formula for content and no one-size-fits-all recipe for success, Harry believes that quality is greater than quantity.

“One thing I realized is that the return you can get from one great piece far outweighs the return from say 20 pieces which are kind of okay,” he said.  

Amazing content takes time

Harry’s approach to creating amazing content isn’t easy to replicate.

That’s because he routinely spends weeks working on just one piece of content - something that a traditional employer would never allow. 

“Managers might say, Hey, we've got to get this out. We've got to get this out by Tuesday. And it's got to have these keywords and, you know, get on it. That's not really giving you the fuel to actually write great content,” said Harry.  

If you can’t take Harry’s approach, the answer lies in doing the best you can, with the resources and employer support that you have. 

Creating loops between content

The final key to Harry’s conversion puzzle is creating what he calls “loops” between his content channels. 

For instance, once he began to get traction on Twitter, he uses that exposure to springboard readers to his newsletter.

Within his newsletter, he introduced readers to the fact that he had created a LinkedIn presence. 

Cross-promoting content

“That's how I kind of kickstarted my LinkedIn groove, is everyone from the newsletter would come to LinkedIn.

And then on LinkedIn, I'm sharing the slide shows and then at the end of that, ‘Hey you, come to the newsletter,’” Harry said.

“And then when I launched my Instagram, I think I probably put it in an email and said ‘Hey, I've just launched an Instagram page where I'm going to share slideshows, if that's your chosen platform.’

So you kind of kickstart that, and it's connecting these things together.

You can kind of create a bit of a web.” 

We hope that with Harry’s insights and real life email list building case study, you’re ready to spin up a successful newsletter of your own. 

Watch Harry talk about newsletters here. 

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