What I learned from Harry Dry about growing a newsletter

Harry Dry managed to grow his newsletter from zero to 19k subscribers in just one year.

I spent 5 hours studying how he did it.

Here’s everything I learned.

The Origin Story

Harry started without an audience and no connections.

As everyone knows, the first 100 subs are the hardest.

To overcome this initial hurdle he used a smart hacks: a compelling origin story.

Harry published a blog post that tells the story of how he tried to build a dating site for Kanye West fans.

While the dating site ultimately failed, the story went viral and put him on the map.

After reading The Kanye Story every reader has some picture of what kind of a person Harry is:

A hustler who’s able to think outside the box.

Establishing these attributes through a story is 10x more effective than putting them into your Twitter bio.

Copy and tweak

Harry does not have years of experience working in the marketing industry.

So how is he able to put out so much great marketing content?

In his own words:

“None of my ideas are original. I’m just always looking out for that next thing to copy.”

Many of his posts are clearly inspired by well-known sources.

But he does a great job at distilling the best parts and reassembles them in interesting ways.

(And always gives credit).

Now while Harry obviously has a great taste for picking topics that resonate, he doesn’t stop there.

He also uses the following tricks to set his content up for success.

  • Short paragraphs (<-> threads)
  • Visuals
  • Personality

Short paragraphs

When you copy any of Harry’s posts into Twitter, you get a perfect thread.

This is of course not an accident.

  • Tweet-long paragraphs keep readers engaged.
  • And he in fact shares all of his longer posts as threads on Twitter.


My estimate is that Harry spends 70%+ of his time creating visuals for his content.

Most posts have an image/text ratio above 50%.

His visuals are always Steve Schoger style quick tips.

(See what I did there?)


  • Click on any post on Harry’s site Marketing Examples.
  • Read the first paragraph.

You’ll immediately understand that this isn’t some SEO-optimized junk.

The content he puts out is something you won’t get from someone paid per word or by the hour.

Harry’s personality and enthusiasm shine through in every paragraph

Most writers are insecure and try to sound overly professional.

Harry writes like he talks.

He uses phrases like “Phew!” and ends his posts with his catchphrase “Over and out — Harry”.

All of these elements reinforce the personal brand Harry introduced in his origin story:

He’s a smart young hustler who freely shares his learnings.

As a result, he has hundreds of superfans rooting for him.

Now let’s get a bit more technical.

Great content, even if it’s perfectly formatted and enriched with engaging visuals is not enough.

You still have to work hard to get the word out and convert readers into subscribers.

Here’s what worked for Harry.

Distribute your content

Harry posts his content in all the places where marketers typically hang out.

  • He posts the link at Hacker News and in slack groups.
  • He posts the whole article on sites like Reddit and Indiehackers
  • He posts individual tips on Facebook Image

Tweak your titles

One smart trick he uses is to tweak the title for each audience.

However, the only way to learn how to do this is to look at the top posts on each platform until you develop some intuition.

Always be amplifying

Most people have just a bunch of social share buttons below their posts.

Harry instead always publishes each post also as a tweet thread and then asks readers specifically to share this thread.

This is smart for two reasons:

  • It makes it very easy on the reader. They don’t have to think about how and where to share the article.
  • There is a compound effect and chances that the thread goes viral are maximized.

Moreover it’s smart to bundle the energy on Twitter since this is where he (like many people) is seeing the biggest returns.

Exit intent popups

Like any sane marketer, Harry asks readers at the end of each post and thread to join his email list.

But incredibly, 50% of his total sign-ups are via exit intent popups.

People are already in the process of leaving the site. So there’s nothing really to lose by asking them to sign up to the newsletter and a lot to gain.

Launch content like startups

Harry creates megaposts and then does a big launch:

  • His Twitter Inspiration Handbook got 600+ upvotes on Product Hunt
  • His Copywriting Examples even ended up as #1 Product of the Week

This def added thousands of subs to his list.

Quick Wins

f you sign up for Harry’s newsletter, he immediately sends you an autoresponder sequence with the best actionable tips from his site.

Giving new readers small, quick wins like this is one of the best tricks to get them psyched to keep hearing from you.

Written on August 7, 2022

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