Newsletter Skill

Most newsletters are forgettable. Subscribers open them once, skim the first paragraph, delete.

The newsletters that build loyal audiences—and businesses—do something different. They have a format readers can rely on. A voice that's recognizable. Content worth opening.

This skill helps you create newsletters people actually look forward to.

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The core job

Transform your content, curation, or ideas into publication-ready newsletters that:

• Get opened (subject line + sender reputation)
• Get read (hook + scannability)
• Get remembered (voice + value)
• Get shared (insight worth passing on)

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First: What type of newsletter?

Different formats serve different purposes. Pick your archetype:

1. Deep-Dive / Framework (Lenny Rachitsky style)

Best for: Expertise, thought leadership, premium positioning Frequency: Weekly Length: 1,500-3,000 words Revenue: Premium subscriptions ($15-30/month)

One topic explored thoroughly. Original frameworks. Actionable templates.

2. News Briefing (Morning Brew / Finimize style)

Best for: Daily habit formation, broad audience, ad revenue Frequency: Daily or 3x/week Length: 500-1,000 words Revenue: Sponsorships, ads

Quick hits on what happened. Scannable. Gets you up to speed in 5 minutes.

3. Curated Links + Commentary (Ben's Bites style)

Best for: Niche expertise, building in public, creator economy Frequency: Daily or weekly Length: 500-1,500 words Revenue: Affiliate, sponsorships, community

Hand-picked links with your take on why each matters.

4. Personal Essay / Reflection (Sahil Bloom style)

Best for: Personal brand, philosophy, coaching/courses Frequency: Weekly Length: 1,000-2,000 words Revenue: Courses, coaching, premium tier

Themed reflections with frameworks for life/work improvement.

5. Startup/Builder Updates (Greg Isenberg style)

Best for: Founder audience, community building, deal flow Frequency: Weekly Length: 800-1,500 words Revenue: Community, advisory, investments

Ideas, observations, and frameworks from the building trenches.

6. Irreverent News + Stories (The Hustle style)

Best for: Broad business audience, entertainment + education Frequency: Daily Length: 800-1,200 words Revenue: Sponsorships, subscriptions

News told through narrative with personality and humor.

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Format Templates

Template 1: Deep-Dive Framework Newsletter

SUBJECT LINE: [Specific question or problem] — [Hint at framework]

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[PERSONAL OPENER - 2-3 sentences]
Brief personal context or why this topic is on your mind.

[THE QUESTION - Bold]
**[State the exact question you're answering]**

[CONTEXT - 1-2 paragraphs]
Why this matters. What's at stake. Who this is for.

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## [FRAMEWORK NAME]

[Framework intro - 2-3 sentences explaining what it is]

### [Component 1]
[Explanation + example]

### [Component 2]
[Explanation + example]

### [Component 3]
[Explanation + example]

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## How to Apply This

[Specific steps or implementation guidance]

1. [Step 1 with detail]
2. [Step 2 with detail]
3. [Step 3 with detail]

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## Template / Checklist

[Downloadable or copy-paste resource]

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## The Bottom Line

[2-3 sentence summary of key insight]

[SIGN-OFF]
[Your name]

P.S. [Personal note, question for readers, or CTA]

Example from Lenny Rachitsky:

"How do you make good decisions in situations where you lack perfect information? This question came from three different readers this month, so let me share the frameworks I actually use..."

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Template 2: News Briefing Newsletter

SUBJECT LINE: [Day/Date]: [Hook about biggest story]

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[LOGO/HEADER]

[ONE-LINE HOOK]
Today: [Teaser of what's inside]

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## MARKETS
[Brief market data if relevant to your niche]
↑ [Metric 1] | ↓ [Metric 2] | → [Metric 3]

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## TODAY'S TOP STORIES

### [STORY 1 HEADLINE - Intriguing, not straight news]

[2-3 sentence explanation of what happened]

**Why it matters:** [1-2 sentences on implications]

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### [STORY 2 HEADLINE]

[2-3 sentence explanation]

**The bottom line:** [1 sentence takeaway]

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### [STORY 3 HEADLINE]

[2-3 sentence explanation]

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## QUICK HITS
• [One-liner news item 1]
• [One-liner news item 2]
• [One-liner news item 3]

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## [SIGNATURE SECTION - Quiz, poll, or engagement hook]

[Question or interactive element]

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[FOOTER with social links, referral program]

Morning Brew voice markers:

• Humor in unexpected places
• Pop culture references
• Relatable analogies ("It's like if Netflix and your credit card had a baby...")
• Bold the surprising part of each story

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Template 3: Curated Links + Commentary

SUBJECT LINE: [Number] things worth your time: [Hook topic]

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Hey [First Name] 👋

[1-2 sentence personal opener - what you've been thinking about]

Here's what caught my attention this week:

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## 🔥 The Big One

**[Link Title](URL)**

[2-3 sentences on why this matters and your take]

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## 📚 Worth Reading

**[Link 1 Title](URL)**
[1-2 sentence commentary]

**[Link 2 Title](URL)**
[1-2 sentence commentary]

**[Link 3 Title](URL)**
[1-2 sentence commentary]

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## 🛠️ Tools & Resources

**[Tool Name](URL)** — [What it does + your opinion]

**[Tool Name](URL)** — [What it does + your opinion]

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## 💭 One Thing I'm Thinking About

[Personal reflection or question - 2-3 sentences]

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That's it for this week. Hit reply if anything resonated.

[Your name]

Ben's Bites voice markers:

• Genuine enthusiasm (not performative)
• "I found this and thought you'd like it" energy
• Commentary adds value beyond the link
• Organized by type (reading, tools, news)

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Template 4: Personal Essay / Reflection

SUBJECT LINE: [Philosophical hook or contrarian take]

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[OPENING HOOK - Story, observation, or provocative statement]
[2-4 sentences that create intrigue]

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## [THE CORE IDEA]

[State your thesis clearly - 1-2 sentences]

[Expand on why you believe this - personal experience or observation]

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## The Framework

[Present your mental model or framework]

**[Element 1]:** [Explanation]

**[Element 2]:** [Explanation]

**[Element 3]:** [Explanation]

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## Questions to Ask Yourself

1. [Reflection question]
2. [Reflection question]
3. [Reflection question]

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## The Takeaway

[1-2 sentence distillation of core insight]

[PERSONAL SIGN-OFF]
[Your name]

P.S. [Often includes a template download or resource]

Sahil Bloom voice markers:

• Opens with philosophical hook or life observation
• Frameworks have memorable names
• Includes reflection questions for reader
• Warm but substantive tone

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Template 5: Builder/Startup Update

SUBJECT LINE: [Contrarian observation or "here's what I'm seeing"]

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Look...

[Personal observation or realization that hooks - 2-3 sentences]

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## The Idea

[Present a concept, framework, or trend you're seeing]

Here's what's working:

**[Pattern 1]** — [Real example with company name]

**[Pattern 2]** — [Real example with company name]

**[Pattern 3]** — [Real example with company name]

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## Why This Matters Now

[Context on why timing matters - market shifts, technology changes, etc.]

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## How to Think About This

[Your framework or mental model for the opportunity]

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## What I'm Doing About It

[Personal application - your projects, investments, experiments]

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If you're building in this space, I want to hear about it. Reply to this email.

[Your name]

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📍 [Event or community plug]
🎙️ [Podcast or content plug]

Greg Isenberg voice markers:

• "Look..." opener
• Peer-to-peer energy, not guru
• Real company examples, named
• Building in public transparency
• Community-focused CTAs

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Template 6: Irreverent News + Story

SUBJECT LINE: [Unexpected angle on news + emoji]

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[HOOK HEADLINE - Surprising juxtaposition or question]

[Opening anecdote that humanizes the story - 3-4 sentences]

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**What happened:** [Factual summary in 2-3 sentences]

**Why it's weird:** [The angle that makes this interesting]

**The bigger picture:** [Business implication]

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## Also Worth Knowing

**[Story 2 Headline]**
[Brief summary with personality]

**[Story 3 Headline]**
[Brief summary with personality]

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## The Number of the Day

**[Surprising statistic]**

[1-2 sentence context on why it matters]

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## One More Thing

[Lighter item, meme-worthy moment, or unexpected angle]

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See you tomorrow,
[Editor nickname] 🦊

The Hustle voice markers:

• Irreverent but not trying too hard
• Headlines that create curiosity
• "Why it's weird" — finds the surprising angle
• Editor nicknames/personalities
• Pop culture and meme fluency

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Voice & Tone Guide

The Newsletter Voice Spectrum

FORMAL ←————————|————————→ CASUAL
             Newsletter sweet spot
                    ↓
         Professional but personable
         Smart friend, not professor
         Opinions with reasoning
         Direct, not corporate

Voice Principles

1. Write like you talk (but tighter) Read it out loud. If you wouldn't say it, don't write it.

2. Have opinions "I think X because Y" beats "Some experts say X while others say Y."

3. Be specific Not "recently" → "Last Tuesday" Not "a lot" → "47%" Not "a company" → "Notion"

4. Show your work Not "this is important" → "I spent 3 hours on this because..."

5. Admit uncertainty "I'm not sure but..." builds more trust than fake confidence.

Words That Kill Newsletters

Avoid:

• "In today's edition..."
• "This week we'll explore..."
• "Without further ado..."
• "It goes without saying..."
• Corporate jargon (leverage, synergy, ecosystem)
• Excessive exclamation marks!!!

Use instead:

• Jump straight into content
• "Here's what I found..."
• "The short version:"
• Conversational transitions

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Subject Line Formulas

What Works

1. Specific + Curiosity

"The $47K email mistake (and how to avoid it)"

2. Question they're asking themselves

"Should you raise prices in a recession?"

3. Contrarian take

"Why I stopped using [popular tool]"

4. Number + Specificity

"7 newsletter formats that actually work"

5. Direct value proposition

"The framework I use for every product decision"

What Doesn't Work

• Clickbait that doesn't deliver
• ALL CAPS
• [NEWSLETTER NAME] in subject
• Vague ("This week's update")
• Too clever (sacrifices clarity)

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Scannability Checklist

Before sending, verify:

[ ] Headers break content every 200-300 words
[ ] Bold text marks key insights (not everything)
[ ] Short paragraphs (1-3 sentences max)
[ ] Bullet points for lists of 3+
[ ] White space between sections
[ ] Mobile-friendly (preview on phone)
[ ] One clear CTA (not five)
[ ] Above-fold content hooks reader

The 30% Rule

Highlighted/bold text should be <30% of total text. More than that, nothing stands out.

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Hook Patterns

Pattern 1: The Direct Question

"How do you make decisions when you don't have enough data?"

Pattern 2: The Contrarian Statement

"Most SEO advice is wrong. Here's what actually works."

Pattern 3: The Personal Story

"Last week I made a $40K mistake. Let me tell you about it."

Pattern 4: The Surprising Stat

"73% of newsletters get deleted unread. Here's why yours won't."

Pattern 5: The Observation

"I noticed something weird in my analytics..."

Pattern 6: The Promise

"By the end of this email, you'll know exactly how to..."

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Curation vs. Original Content

When to Curate

• You're covering a fast-moving space (AI, news)
• Your value is taste/filtering (too much content exists)
• You're building daily habit (can't write 2000 words/day)

When to Create Original

• You have unique expertise or access
• You're building premium/paid tier
• You want stronger differentiation

The Hybrid (Best for Most)

70% Original insight/commentary
30% Curated links with your take

OR

1 Deep original piece
+ 3-5 curated links with commentary

Never: Link dump without commentary. That's RSS, not a newsletter.

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The Newsletter Creation Workflow

Step 1: Gather

• What happened this week in your space?
• What did you learn/create/notice?
• What questions are readers asking?
• What links are worth sharing?

Step 2: Select

• Pick 1 main topic (deep dive) OR 3-5 items (roundup)
• Ask: "Would I forward this to a friend?"
• Cut anything that's "fine but not great"

Step 3: Structure

• Choose your template
• Outline before writing
• Front-load the best stuff

Step 4: Write

• Hook first (spend 25% of time here)
• Get the draft down fast
• Add personality in editing

Step 5: Polish

• Read out loud
• Cut 20% (newsletters are always too long)
• Check scannability
• Mobile preview

Step 6: Send

• Best times: Tuesday-Thursday, 6-10am local
• Subject line A/B test if possible
• Personal preview to yourself first

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Best-in-Class Examples to Study

Newsletter	Type	What to Learn
Lenny Rachitsky	Deep-Dive	Framework presentation, credibility anchoring
Morning Brew	News Briefing	Voice, scannability, referral program
Ben's Bites	Curated + Commentary	Curation that adds value
Sahil Bloom	Personal Essay	Reflection frameworks, templates
Greg Isenberg	Builder Updates	Peer energy, real examples
The Hustle	Irreverent News	Personality, unexpected angles
Finimize	Financial Briefing	"Key takeaways" format
The Rundown AI	AI News	Business implications framing
boringmarketer	Marketing	Contrarian takes, systems thinking

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How This Connects to Other Skills

Input from:

• brand-voice → Ensures newsletter voice matches overall brand
• keyword-research → Identifies topics your audience searches for
• positioning-angles → Provides contrarian angles for content

Uses:

• direct-response-copy → For CTAs and conversion elements
• seo-content → When repurposing newsletter into blog posts

The flow:

1. brand-voice defines how newsletter should sound
2. keyword-research or audience questions suggest topics
3. newsletter creates the edition
4. Content repurposed for SEO or social

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The Test

Before hitting send, ask:

1. Would I open this? (Subject line test)
2. Would I read past the first paragraph? (Hook test)
3. Would I remember this tomorrow? (Value test)
4. Would I forward this to a colleague? (Share test)
5. Does this sound like me, not a committee? (Voice test)

If any answer is no, revise before sending.