AI & Automation
Personas
SaaS & Startup
Time to ROI
Medium-term (3-6 months)
I used to think LinkedIn newsletters were just fancy blog posts with a subscribe button. Then I watched a SaaS founder build 5K subscribers in 3 months while their competitor with "better" content sat at 200 subscribers.
The difference? One followed every newsletter best practice guide on the internet. The other treated their newsletter like a personal conversation with their ideal customer.
Most startup founders approach LinkedIn newsletters backwards. They focus on polished content and growth hacks when they should be focusing on one thing: sounding like an actual person solving real problems their audience faces every day.
After working with multiple SaaS startups on their growth strategies, I've seen what actually works for customizing LinkedIn newsletters that convert readers into customers. Here's what you'll learn:
Why most startup newsletters fail (and it's not what you think)
The "founder voice" framework that builds trust faster than any marketing copy
How to structure content that feels personal but scales professionally
The metrics that actually matter for SaaS newsletter growth
Real examples of startups winning with contrarian newsletter approaches
Industry Reality
What the "experts" tell you about LinkedIn newsletters
Walk into any marketing conference or scroll through LinkedIn, and you'll hear the same newsletter advice repeated like gospel:
Post consistently - Pick a schedule and stick to it religiously
Use growth hacks - Collaborate with other creators, cross-promote, tag influencers
Create valuable content - Share industry insights, tips, and "thought leadership"
Optimize for engagement - Ask questions, use polls, encourage comments
Build authority - Position yourself as the expert in your niche
This advice isn't wrong, but it's incomplete. It's the same generic framework that works for established thought leaders with existing audiences. But when you're a startup founder with 47 LinkedIn connections, this approach puts you in direct competition with people who've been building audiences for years.
The problem with following conventional newsletter wisdom is that you end up sounding like everyone else. Your content becomes indistinguishable from the dozens of other startup newsletters talking about "scaling," "growth hacking," and "disruption."
Most founders spend months creating content that technically checks all the "best practices" boxes but fails to convert because it lacks the one thing that actually matters: a unique perspective rooted in real experience.
The conventional approach treats newsletters like content marketing when they should be treated like relationship building. There's a fundamental difference between broadcasting information and having a conversation.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
When I started working with SaaS founders on their content strategy, I noticed a pattern. The ones with the most "professional" looking newsletters had the worst conversion rates. Meanwhile, founders who wrote like they were texting a friend were building engaged communities that actually bought their products.
The breakthrough came when working with a B2B SaaS client who was struggling with user acquisition. Their marketing team had been running a LinkedIn newsletter for six months, following every best practice guide they could find. Professional layout, industry insights, consistent posting schedule. The result? 150 subscribers and zero attributed deals.
That's when I realized something: their founder's personal LinkedIn posts were getting more engagement than their newsletter. His posts were raw, honest, and specific. He'd share failures, behind-the-scenes struggles, and contrarian takes on industry trends. People actually commented and started conversations.
The newsletter, by contrast, read like it was written by a marketing committee. Generic insights, polished prose, zero personality. It was professionally boring.
This disconnect made me question everything I thought I knew about newsletter strategy. If the founder's personal voice was resonating, why wasn't the newsletter? The answer was simple: they'd stripped away everything that made his perspective unique in favor of "best practices."
Most startups make this same mistake. They hire writers or follow templates that turn their unique founder insights into generic business content. The very thing that makes them worth following - their specific experience building their specific product for their specific market - gets lost in translation.
Here's my playbook
What I ended up doing and the results.
Instead of starting with content templates, I started with a simple question: What would this newsletter look like if it was just the founder talking to their ideal customer?
The approach I developed breaks every conventional newsletter rule, but it works because it's built around authenticity instead of authority. Here's the framework:
The "I Did Something" Structure
Every newsletter starts with a real experience: "Last week I tried X" or "Yesterday a customer told me Y." Not industry analysis or thought leadership - actual things that happened in the business. This immediately differentiates the content because no one else can write about your specific experiences.
For the SaaS client, we restructured their newsletter around this principle. Instead of "5 Tips for Better User Onboarding," we wrote "Why Our New User Onboarding Failed (And What We Learned)." Instead of "The Future of B2B Sales," we shared "The Sales Call That Changed How We Think About Pricing."
The Conversation Tone Framework
I developed a simple test: if you wouldn't say it in person, don't write it. This meant replacing phrases like "leverage synergies" with "make things work better together." Instead of "optimizing conversion funnels," we talked about "helping more people actually use the product."
The founder started writing like he was explaining his business to a friend at a coffee shop. Contractions, casual language, admitting when things didn't work. The result? Comments increased by 400% and people started reaching out directly.
The Problems-First Content Strategy
Instead of leading with solutions, we led with problems. Real problems the founder was dealing with, problems customers were facing, problems the industry wasn't talking about. This approach works because it's easier to relate to someone's struggles than their successes.
One newsletter that went viral was titled "Why Our Biggest Customer Almost Quit (And It Wasn't About the Product)." It got 50 comments and generated three qualified leads because it addressed a problem every SaaS founder fears but rarely discusses openly.
The Behind-the-Scenes Approach
We made transparency a competitive advantage. While competitors shared polished case studies, we shared messy reality. Failed experiments, tough conversations with investors, features that customers hated. This built trust faster than any marketing copy could.
The key insight: People don't follow perfect companies, they follow companies they can relate to. By showing the human side of building a business, the newsletter became less like marketing and more like mentorship.
Authenticity Over Authority
Position yourself as someone figuring it out, not someone who has it all figured out. Share failures alongside successes.
Problems Over Solutions
Lead with the messy reality of what you're dealing with. Solutions feel like sales pitches, problems feel like conversations.
Specific Over Generic
Write about your actual customers, your actual challenges, your actual experiments. Generic insights are forgettable.
Conversation Over Content
Write like you're talking to one person, not broadcasting to thousands. Use the tone you'd use explaining your business to a friend.
The results spoke for themselves. Within three months of implementing this approach:
Engagement metrics improved dramatically: Average comments per post went from 2-3 to 15-20. People weren't just liking content, they were starting conversations. Several newsletter readers became customers after engaging in comment discussions.
Quality of subscribers increased: Instead of attracting general "startup enthusiasts," the newsletter started attracting actual potential customers - other SaaS founders dealing with similar challenges. The audience became more targeted without any deliberate targeting efforts.
Direct business impact: The founder tracked at least 8 qualified leads directly from newsletter interactions over six months. More importantly, the newsletter became a relationship-building tool that made sales conversations easier.
Personal brand development: The founder's LinkedIn following grew organically as newsletter content was repurposed into posts. But more valuable than follower count was follower quality - investors, potential partners, and industry experts started engaging with his content.
The most unexpected result? The newsletter became easier to write. Instead of struggling to create "valuable content," the founder just documented what was already happening in the business. Content creation went from a weekly burden to a natural part of business reflection.
What I've learned and the mistakes I've made.
Sharing so you don't make them.
After implementing this approach across multiple SaaS startups, here are the key lessons that consistently emerge:
Your business is your content strategy: The best newsletter content comes from actually building and running your business, not from industry research or competitor analysis.
Specificity beats universality: Writing for "everyone in SaaS" reaches no one. Writing for "B2B SaaS founders struggling with enterprise sales" reaches exactly the right people.
Vulnerability builds trust faster than expertise: Sharing what you're learning builds stronger connections than sharing what you already know.
Comments matter more than subscribers: 100 engaged readers beat 1,000 passive ones. Focus on starting conversations, not collecting email addresses.
Your personal experience is unreplicable: Competitors can copy your features but they can't copy your specific journey and insights.
Consistency beats perfection: Publishing regularly with authentic voice trumps publishing occasionally with polished content.
The founder's voice is the startup's biggest differentiator: In crowded markets, personality and perspective matter more than product features.
The biggest mistake founders make is trying to sound like established companies instead of embracing their startup advantage: they're in the trenches, figuring things out in real-time, and their audience is going through the same journey.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS startups, implement this by:
Document weekly customer conversations and product iterations
Share specific metrics and experiments, not just high-level insights
Write about your actual tech stack, hiring challenges, and fundraising reality
Use your newsletter to test messaging before implementing in product or sales
For your Ecommerce store
For e-commerce businesses, customize by:
Share behind-the-scenes of product sourcing, inventory challenges, and customer feedback
Document seasonal trends, supplier relationships, and fulfillment experiments
Write about actual customer stories and how products solve real problems
Use newsletter to build community around your brand's mission and values