5 Vital Insights on How to Write a Newsletter Successfully With Harry Dry

In a revealing conversation with David Perell, Harry Dry breaks down the intricate mechanics behind his highly successful newsletter.
With engagement rates that stand out even among newsletters with 100,000+ subscribers, Harry’s approach offers valuable insights for anyone looking to master the art of newsletter writing.

Understanding the Newsletter Format

It’s less about the news and more about the letter.

This fundamental principle shapes Harry’s entire approach.

While blogs, tweets, and social media posts each serve their purpose, a newsletter creates an intimate connection with readers through its letter-like format.

The Importance of the Opening

Harry’s newsletter openings are masterclasses in scene-setting.
Here’s a sample introduction he shared:

Hey, it’s Harry. It’s 3:47 a.m. I’m in the Big Smoke alone, laptop, green tea, looking at the whiteboard like a dozy dog.
Six words on it, five with lines through. Intro glares at me, I glare back—the final horcrux. Sip some tea. Is this any good? I don’t know. My tea tastes cold. I should press send.

This introduction demonstrates several key principles:

• Time and place anchoring (3:47 a.m., Big Smoke/London)
• Immediate scene-setting (laptop, green tea, whiteboard)
• Vulnerability and authenticity (questioning if it’s good enough)
• Creating a sense of immediacy (“fresh bread warm to touch”)
  

The Three Foundational Pillars

1. The Rule of Five

Harry’s newsletters maintain a consistent structure:

• Exactly five examples per newsletter
• No more, no less
• Creates a dense, valuable package of information
• Helps readers know what to expect
• Forces quality and curation
  

2. The Power of Conflict

Every example in Harry’s newsletter contains inherent conflict.
Types include:

Before and After:

• Shows transformation
• Highlights improvement
• Demonstrates progress
  

Problem and Solution:

• Identifies pain points
• Presents clear resolutions
• Shows practical application
  

Contrasting Approaches: Using the Loom example:

• Traditional screen recorder positioning: “We’re an easy-to-use screen recorder”
• Loom’s revolutionary positioning: “Remote communication sucks, and we’re fixing it”
• Result: “They’re now worth more than that whole screen recorder bucket combined”
  

3. The Two-Line Paragraph Rule

Since March 2021, Harry hasn’t written a paragraph longer than two lines.
This strict rule serves multiple purposes:

Readability:

Short paragraphs are like monkey bars—they’re easy to swing between.

Focus:

• Forces clarity of thought
• Eliminates unnecessary complexity
• Makes mobile reading easier
  

Quality Control:

If I write a sentence which is a paragraph which is three liners long, there’s a good chance I’m not explaining myself as well as I should be.

The Science of Simple Writing

Kaplan’s Law of Words

The fundamental principle:

Any words that aren’t working for you are working against you.

Harry’s extension:

You aren’t taking Kaplan’s Law of words seriously enough.

This applies to both words and ideas:

• The strength of an idea is inversely proportional to its scope
• Single-focus messaging often outperforms broader approaches
• Example: “We make jeans” vs. “We sell jeans and t-shirts and socks and have dressing rooms”
  

The Burrito Principle

A good paragraph is like a burrito—you should be able to throw it to you and you should be able to catch it and it shouldn’t come apart in the air.

Characteristics of a “burrito-worthy” paragraph:

• Internally coherent
• Self-contained yet connected
• Each sentence essential to the whole
• Removes anything that doesn’t strengthen the core message
  

The Multiple Versions Technique

Harry’s writing process involves:

1. Writing initial version
2. Copying and pasting
3. Rewriting with tweaks
4. Repeating 4-5 times
5. Comparing versions

Benefits:

• Allows for experimentation
• Provides options for feedback
• Makes editing more concrete
• Enables better collaboration
  

Structural Frameworks

The Power of Division

Harry breaks down complex topics into manageable parts:

• Copywriting becomes: Who, What, How
• Growth becomes: First 100, Next 99,900
• Ideas become: Problem, Solution
  

The 1971 “That’s Interesting” Framework

Two key approaches:

1. Take multiple things people think are different, show how they’re one
2. Take one thing, show how it’s actually two
   

Example Application:

• Growing readership isn’t one challenge
• It’s two distinct phases:
  1. Getting the first 100 readers (things that don’t scale)
  2. Getting the next 99,900 (momentum)

Real-World Application: The Loom Case Study

Harry breaks down Loom’s successful positioning shift:

Original Position (Screen Recorder Bucket):

• Feature-focused: “Easy to use screen recorder”
• Competitive with other screen recording tools
• Limited market potential
  

New Position (Remote Communication Revolution):

• Problem-focused: “Remote communication sucks”
• Solution-oriented: “Introducing async video messaging”
• Pain point targeting: “No one likes long Zoom calls”
• Value proposition: “Emails are too impersonal”
  

Result: Category leadership and increased valuation

The Quality Bar Principle

A mentor’s advice to David encapsulates the challenge of maintaining excellence:

There’s two things that if you do, you will be insanely successful:

1. Learn how to have a high quality bar
2. Never let the high quality bar fall

The mentor emphasized:

• It sounds simple but isn’t
• People will get angry
• Some will become anxious
• Others will stop working with you
• But maintaining quality standards leads to exceptional results
  

Practical Implementation Tips on How to Write a Newsletter

1. For Openings:
   • Look out your window
   • Notice specific details
   • Ground the reader in time and place
   • Share authentic moments
     
2. For Structure:
   • Start with clear divisions
   • Use parallel construction
   • Create clear frameworks
   • Maintain consistent patterns
     
3. For Writing:
   • Write multiple versions
   • Keep paragraphs tight
   • Remove unnecessary words
   • Test coherence regularly
     
4. For Quality:
   • Set high standards
   • Maintain them consistently
   • Accept the challenges
   • Focus on long-term results
     

Conclusion

Harry’s approach to newsletter writing combines technical precision with authentic connection.

His methods demonstrate that great writing isn’t about natural talent—it’s about deliberate practice, careful structure, and unwavering commitment to quality.

The success of his newsletter proves that readers value:

• Authentic voice
• Clear structure
• Consistent quality
• Engaging conflict
• Simple presentation
  

By following these principles and maintaining high standards, writers can create newsletters that don’t just get opened—they get read, shared, and remembered.

Every word should work for you, every paragraph should hold together, and every newsletter should feel like a letter to a friend.

(Source: “How I Write” podcast with David Perell featuring Harry Dry)