Improving Content Quality in Newsletters

Why do some newsletters get 50% open rates… while others get ignored? I studied 100+ top-performing newsletters, and found 6 things they all do differently: 1. Crystal-clear positioning Readers don’t subscribe because they like you. They subscribe because you help them solve a specific problem. Examples: • Lenny’s Newsletter: Product management career advice for PMs, by PMs • The Generalist: Tech and investment insights for senior tech & investing professionals Clear positioning = higher open rates, stronger loyalty, and better monetization. 2. Killer subject lines High-performing ones tend to be: • Curiosity-driven: “The weird growth hack most creators miss” • Benefit-focused: “5 frameworks to double your freelance rates” • Personal: “I lost $10K building my first product” • Timely: “New LinkedIn algorithm changes (June 2024)” ❌ "Your daily business update..." ✅ "Apple just killed an entire industry..." Pro tip: Write 5–7 subject lines. Pick the strongest. Never settle for your first draft. 3. Strong hooks You have 3 seconds to convince readers they made the right choice opening your email. The best newsletter hooks: • Speak to a specific pain point • Make a bold, unexpected claim • Start with a mini-story • Ask a thought-provoking question Example from Justin Welsh: "We live in a world that's obsessed with certificates, diplomas, and structured learning. The kind of learning that's neatly packaged into college degrees or training programs. But what if the traditional ways that we've approached learning and education, especially in business, are flawed? 4. Use a simple structure This 5-part structure keeps things fast + focused: • What's the main problem readers face? • What's the common (but flawed) fix? • Why doesn't it work? • What's a better solution? • What's one action they can take today? I write newsletters in 45 minutes using this. Without it? 3+ hours staring at a blank screen. 5. Scannable formatting People don’t read, they skim. Make it easy: • Short paragraphs • Subheaders that tell a story • Bullet points • Bold key takeaways 6. They edit ruthlessly After writing: • Cut 20% of the words • Ensure the writing follows the what-why-how structure (what it is? why it’s important? how it can help the reader?) • Read it aloud to catch awkward phrasing • Read on a different device when editing (laptop → phone) 3 common mistakes to avoid: 1. The "Me, Me, Me" Newsletter Successful newsletters focus relentlessly on the reader's problems, not the writer's wins. Every issue should answer "What's in it for me?" 2. Breaking News (Instead of Breaking It Down) Focus on the “so what?”, not the headline. How does this news apply to your readers? What should they do about it? 3. Publishing Without Purpose Every issue should educate, inspire, or persuade. If it doesn’t, rework it.

We had a beautiful customer newsletter... and no one cared. Up until the end of 2023, we had a highly designed version of the newsletter. It looked great, but it took a ton of time to pull together. Every send required custom images, specific copy lengths, and with no real guardrails on content, we tried to include ✨everything.✨ And it did… fine. But not fine enough to warrant the time it required and no clear strategy, so we stopped doing it. This year, I relaunched our customer newsletter — and doubled our engagement score and click-through rates. Here's the 4 steps I took to do it: 1️⃣ I redefined the purpose. The newsletter needed to be a valuable touchpoint for account managers — something that kept customers informed and encouraged them to explore more of the Lattice ecosystem through features, events, and content. Not salesy. 2️⃣ I scrapped the overly designed template and went plain-text. The emails now come directly from Account Owners (because who’s Kerry Wheeler anyways?). 3️⃣ We segmented our customers into three key groups and tailor content to each one based on what’s most relevant to them. 4️⃣ I implemented strong content guardrails. Every send now includes just two of the most relevant product updates, events, and resources — and it must be actionable today (no “coming soon” teasers). The results? Open rates held steady at ~50%, but engagement took off. Click-through rates more than doubled, and we’ve heard great feedback from both customers and AMs on how the newsletter has kept them informed and engaged.

Publishing more content does not always strengthen a marketing strategy. In some cases, it can quietly weaken it. During a period of rapid content expansion, one marketing team adopted the familiar “more is better” approach. Blogs were published more frequently, posts went out daily across multiple channels, and hitting the content calendar became a point of pride. On the surface, the operation looked productive. But over time, engagement began to flatten. Messaging started to drift. Strong ideas were pushed out before they were fully developed. Speed created the impression of efficiency, but it came at a cost. When volume becomes the primary goal, quality often fades into the background. And when quality declines, trust tends to follow. Buyers can quickly sense the difference between content created to fill a schedule and content designed to deliver meaningful insight. Platforms and algorithms recognize that difference as well. Depth, clarity, and coherence consistently outperform frequency. The pressure to move faster is real for modern marketing teams. But sustainable growth rarely comes from activity alone. It comes from authority, and authority requires intention. Sometimes the most strategic decision is not to publish more, but to slow down, refine ideas, and raise the standard. The latest newsletter explores this shift in depth and examines why rushed content often undermines long-term marketing performance.

Internal newsletters get a bad rap because most of them are terrible. I'm talking about those corporate updates that everyone immediately deletes. The ones that feel like someone's checking a box rather than actually trying to connect with their team. But here's the thing: when done right, internal newsletters can transform your company culture, especially for remote teams. Brittany Zerr breaks this down perfectly in her latest article about how we started The Hundy P Gazette at Kick Point Inc. two years ago, and it's genuinely become something our team looks forward to reading. The secret? Make it 80% fun and 20% important updates. Include recipe recommendations, pet photos, Taylor Swift fan theories (thanks Liz!), and yes, even silly polls. When people actually want to read your newsletter, they'll stick around for the boring but necessary stuff too. What I love most is how it humanizes everyone. These small connections make such a difference when you're all working from different screens. Brittany makes a great point about using Notion instead of fancy email templates because it keeps things casual and lets people comment directly. It feels more like a conversation than a corporate broadcast. The best advice from her article? Start small, make it easy for people to contribute, and don't overthink it. Your first edition will probably suck, but that's okay. Focus on getting your team's personality to shine through. #RemoteWork #CompanyCulture #InternalCommunication

I write newsletters for the CEO of a $100M company. Here’re 3 uncommon hacks I use to *always* nail their voice: 1/ Style Guide One of the first things I do when I start working with a client: I ask if they have an internal document describing their writing style & voice. Now, if they don’t have one (most people don’t), here’s what I do: I ask them for 3-5 pieces of content they’ve written themselves & are very proud of. Then, I use my proprietary AI prompts to analyze their writing & create a style guide for them. By creating this asset upfront, I save myself dozens of hours worth of future edits. And I make sure my clients are always excited to read the emails we’re creating. 2/ Transcripts 90% of the newsletter content I write for this client actually comes from their YouTube channel. And not just the topics - but even the “words.” The way I think about it is: Every YouTube video they’ve created is a “pre-approved” piece of content. So whenever I’m working on an email, I always get the transcript of the video I sourced the topic from. Then, I use that as my outline - and try to make the least amount of tweaks possible (from a “voice” perspective). That way, I can minimize the risk of “deviating” from their voice even more. (You can also use this technique if your client has a podcast, by the way.) 3/ Claude Projects Last year I started creating a dedicated Claude project for each client I work with. And it’s been ridiculously helpful. Inside each project, I upload: • The style guide I mentioned earlier • A PDF of my client’s LinkedIn profile • A PDF version of all their landing pages • A prompt with any additional context needed • As many “approved” writing samples as possible And by feeding all this data to the AI model upfront, the quality of the output increases 100x. Basically, it’s like having a writing assistant who not only knows everything about my client… But also knows exactly how to write in their voice. Needless to say, I use these projects to streamline almost every part of the writing process: • Coming up with topics • Outlining the newsletters • Extracting content from transcripts • Brainstorming subject line & PS variations And it’s 1 of the big reasons I can work with this client while also having so many other things going on. And that’s it! Found this helpful? Let me know below which hack was your favorite.

If I had to build my 60,000+ subscriber newsletter again from scratch today Here’s the 6 things I’d do ⬇️ Story time: starting my newsletter I went against a lot of best practices and yet I grew to 60,000 subscribers and over $180k in sponsor revenue in year 2. Sharing my tips below… ➡️ 1. The 50 Subject Line test Most newsletters fail because they pick a topic they *should* talk about and not something they are passionate about talking about. If you can’t write the newsletter for a year, you won’t see significant money. Sit down and write 50 subject lines about all the things you’d want to write about. Then categorize them and figure out who would benefit from those. ➡️ 2. Th 10 person survey I’d next find 10 people who fit that description and ask if you could send the first few newsletters to them for feedback. This gets you into the rhythm of producing while ensuring your format resonates. ➡️ 3. The 6 month test Once you’ve received feedback, I’d commit to a 6 month test of one format. Most newsletters fail because they simply can’t stay consistent. Sponsors and subscribers are looking for stability. Build the muscle of showing up. ➡️ 4. The 90/10 sales rule Most of you are starting a newsletter as a sales vehicle to your products…. And that’s OK but I’m starting to see newsletters that don’t add any value. They just sell. Focus on 90% value. 10% sales. This increases your referrals because no one refers commercials but they do refer documentaries. ➡️ 5. Network effects There are two network effects I’d focus on right from the beginning: - who do I know that reaches my audience on social? - who do I know that reaches my audience via email? Find 5 people in both cohorts who is just a few steps ahead of you and ask for a shoutout in exchange for a dedicated promotion of their product when you hit 10,000 subscribers. Here’s a sample script to steal: Hey ______! I love your content about X helping Y achieve Z. 6 months ago I started a newsletter helping those same people solve the following pain points: - pain point - pain point - pain point I’m now confident in the format, value and feedback I’ve received and looking to partner with a few people to help cross promote each other’s content. I know I’m a few steps behind you so I’d do a promo now and then again when I hit 10k as part of my 10k celebration! Here’s the copy for the promotion so you can see what (newsletter) is all about: Insert Promo copy Let me know what you think! Appreciate you, Name ➡️ 6. Inject yourself Many newsletters miss the opportunity to build emotional connection with their audience. Ways to build connection: - images - life updates - stories Those are the 6 things I’d do if I was starting my newsletter again today from scratch before I ever touched paid marketing. Let me know what you think!

How to write a 700-word newsletter without boring people to death? Most people think you need big or innovative ideas. But no: Your ideas matter less than the structure of your writing. Crazy but true: Tiny ideas can get more attention than the big stuff. It’s the structure that matters. First, figure out why your newsletter matters to your reader: → What (tiny) problem do you solve? → Which (tiny) aim do you help achieve? → Which burning question do you answer? Next, make each element of your newsletter contribute to that one content goal: → A subject line to get attention → A pre-header to up the curiosity → Opening lines that invite readers in → 3 or 4 sections to explain your solution → A final paragraph that encourages & inspires action → A P.S. to sell I’ve been structuring newsletters, blog posts, book chapters, and course lessons like this for over 12 years. And this seems crazy to me: 1,132 people have continued reading my work for over 10 (ten!!!!) years. Wow. They've stayed engaged week after week, year after year. It works for me, too: Using a proven framework helps me tap into creativity, sharpen my thinking, and write faster. Win-win. Human content wins. 💜

It’s not that people aren’t using email marketing and automation. It’s that they aren’t using it well. Usecase: Onboarding Wrong way -> Nearly every B2B product has an onboarding flow. Sometimes from their marketing tool, sometimes from their CS tool, and nearly always it’s generic, unhuman, and not segmented. Better way -> Over the last decade, working with countless lifecycle teams, here is what I have found elevates an onboarding sequence and increases activation… - Stick to no more than 3-4 emails in the first 2 weeks - Audit your whole lifecycle flow to make sure they aren’t getting 4 standard onboarding emails, and another 2 triggered emails based on having not put in their CC yet and another 2 emails from sales. - Have your onboarding come from a person, not just the brand generically. name@domain.com will inbox better and get more engagement than team@, support@ etc. - Set expectations. In that first email let them know the core things that will help them be successful and to expect emails around those. Let them know the "when" - Don’t make them dig. What’s not helpful is the “If you have questions about setting up your first XYZ, here is the help doc” and they get linked to a 50 page monstrosity. Instead, link them to a specific video (that is up to date!) that walks them through step by step. Usecase: Newsletter Wrong way -> You send a newsletter that reshares your favorite blog article or social media post. You figure, if I have a good message, why not distribute it in more spots? Better way -> You want every channel to have a unique reason to go there. A better way is to have your social posts tease the value, and then the newsletter can expand on it. Or you take your great blog content and get a dozen experts to weigh in and make the newsletter send that. Other best practices…. - Use a personal name and company in the send-from name. “Casey at ActiveCampaign” for example. And have a unique tone of voice. All the top newsletters in B2B from Growth Unhinged, to Scaling SaaS to ProducTea come from an individual perspective, not the generic brand. - In terms of value of engagement, think opens < clicks < page views < replies. Replies are the gold standard that will get you into the primary folder and build relationships. - Have a clear purpose. Your customer newsletter is very likely different from your lead newsletter. Provide unique information and perspective. - Set expectations in a welcome email. The best newsletters do three things really well when you sign up… 1) Give you a recap of exactly when you will hear from them and what about “We message you on Fridays at 8AM PST about a usecase of a brand that scaled with SEO to their first $1m ARR”. 2) Give them content they can engage with immediately on your blog or elsewhere. 3) ask a targeted question to drive more engagement. What other applications of email marketing would you love to optimize in your business? I am happy to add insights in a future post.

📊 Over the years of auditing thousands of email campaigns across various industries, I've noticed a concerning trend: The perpetual "sale spiral." 🌀 Companies are trapped in an endless cycle of discounting, each trying to outshout the other in increasingly crowded inboxes. Recently, I worked with a DTC brand whose open rates had declined over 30% over six months despite increasing their promotional frequency. Their customer lifetime value was dropping, and unsubscribe rates were climbing. The diagnosis? Discount fatigue. 😫 Here's what we implemented: We introduced what I call the "70/30 Value Rule" - 70% pure value content, 30% promotional. ⚖️ For the value portion, we created: ➜ Industry insight newsletters ➜ Behind-the-scenes glimpses into product development ➜ Customer success stories ➜ Actionable tips related to their product category ➜ Community spotlights The results after 90 days were compelling: ⭐ Open rates increased by 32% ⭐ Customer feedback emails jumped 215% ⭐ When promotional emails were sent, conversion rates improved by 28% ⭐ Unsubscribe rates dropped by 41% Key Learning: The most successful brands understand that email isn't just a sales channel—it's a relationship builder. By giving your audience "breathing room" between promotions, you create anticipation and trust that translates into stronger campaign performance when you do make offers. This approach requires patience and a shift in metrics. While immediate sales might dip initially, the long-term engagement metrics and customer lifetime value typically show significant improvement within 3-4 months. For companies looking to break free from the discount cycle, start small: Replace one promotional email per week with pure value content. Track not just opens and clicks, but also replies, shares, and sentiment. The data will speak for itself. Remember: In a world where everyone is shouting "BUY NOW," sometimes the most powerful message is simply "We're here to help."

Today marks 100 weeks of my newsletter. ~1,300 words each. 10K+ subscribers. 45% avg. open rate. All while running two businesses and trying to not sacrifice evenings and weekends. I don’t have a content calendar. Traditional advice tells you to plan everything, batch content, stick to rigid schedules. But life doesn’t follow content calendars. The problem is that inconsistency kills newsletters, but rigid planning kills creativity. So what’s the solution? In my case: AI. (Surprise!) Instead of forcing ideas when I need them, I try to capture them when they come. Instead of following a calendar, I use AI to turn messy thoughts into structured content. Instead of batch writing, I use AI to make each piece efficient enough to sustain weekly output. Here’s my 4-step system: 1/ Brain dump to outline in Claude Every newsletter starts with a brain dump. Text, often audio. A Claude project trained on my previous editions turns that into structure and explores different angles. 2/ 25-point checklist editor in ChatGPT Once the draft is out, this custom GPT makes sure I don’t fall too hard into teaching mode, catch technical errors, or miss grammar mistakes. Personal editor in my pocket. 3/ Title generation in ChatGPT A book is judged by its cover. Same with headlines. I frequently A/B test different approaches - numbers vs no numbers, short vs long headlines. This tells me what resonates most. 4/ Visual creation in ChatGPT Every newsletter needs some graphics. Thumbnails for social sharing or illustrations to get an idea across. Sometimes I draw something on paper and ask ChatGPT make it look good. Sometimes, I create flowcharts and turn them into Mermaid code. Sometimes just stock icons. Haven’t figured out the best setup yet. I use whatever works. With the help of AI, I can be consistent without being rigid. It doesn’t really replace a writer for me (I would never have hired one) but lets me express myself in a more scalable way. Scalability lever at work. Thanks to everyone who’s been reading, commenting, and replying. I read every email. You can find all previous editions and sign up for the next one using the link under my name. New edition every Friday. Oh, and if you’re a fan of my newsletter, there’s something exciting coming up this fall. Stay tuned!