Writing Captivating Newsletters

Don't try to sound smart. Try to be useful. 3 years ago, I deleted my most "impressive" newsletter. 2,000 words. Multiple frameworks. Industry jargon everywhere. 14 drafts. It felt "professional." It felt "high-level." It felt wrong. That week, a CEO guest spoke to me before our podcast: "You know why I listen to your show? Because you make things simple." Then she paused. "But your newsletter... sometimes I need a dictionary." That changed everything. I opened my analytics that night. The pattern was clear: My "smartest" content performed worst. My simplest advice spread fastest. I had been: • Writing to impress peers • Stacking jargon on jargon • Trying to sound "intellectual" • Hiding behind complexity So I started over. New rules: 1. Write like I talk 2. No words I wouldn't use at dinner 3. Every piece needs a clear "do this" Example: Before: "Contemporary market dynamics necessitate strategic pivots in content optimization." After: "Test what works. Double down on what people love." That decision? It built my entire business: • The podcast grew exponentially • The newsletter became my main lead generator • Sponsorship deals rolled in • Speaking opportunities opened up Best feedback I get: "Used your advice. Landed the client." "Finally, someone who makes this simple." "Implemented this today. It worked." The truth about expertise: • Rookies hide behind jargon • Veterans embrace simplicity • Masters focus on impact This philosophy drives everything: • How I write • How I speak • How I teach • How I coach Because here's what I learned: Value beats vocabulary. Always. 3 questions before publishing: 1. Would my mom get this? 2. Can someone use this today? 3. Did I remove all the fluff? Remember: Your audience's success is your scorecard. Not your vocabulary. Today? That decision to choose simplicity over sophistication was worth millions. But more importantly: It actually helped people. // Agree? Simple or complex content - which actually helps you more? Share below. #ContentCreation #Podcasting #Writing #ValueFirst

Traditional email marketing is dead... And no, it wasn’t AI that killed it. It was inbox fatigue. We’re done with bland promos and one-way blasts. Now? We want to be entertained, educated, emotionally hooked. The best brands today don’t just send emails, they build experiences in your inbox. Here are 2 new types of email strategy that actually work: 1. Email as Entertainment: Let’s talk about NUDE PROJECT. They send chaos, in the best way possible. Their emails read like a group chat meets underground zine: chaotic storylines, Gen Z memes, interactive graphics, and cliffhangers. You’re not just reading, you’re part of the ride. It’s unpredictable, unfiltered, and totally them. ➡️Result? Passive followers turn into die-hard fans, eagerly waiting for the next episode. 2. Email as Education Now look at Gohar World. They’ve turned email into a museum. Every send is a beautifully crafted experience: whimsical guides, historical nuggets, product stories, and curated “world-building” moments. They’re not selling they’re storytelling. ➡️The goal isn’t conversion. It’s context. Because context creates curiosity. And curiosity builds desire. 🚫 The old “10% OFF, BUY NOW” formula? Dead. The new inbox? Story-first. Weird. Human. Visually rich. Emotionally sticky. Drop your fav newsletter below #EmailMarketing #NewsletterStrategy #BrandStorytelling #GrowthMarketing #DigitalInnovation #RetentionMarketing

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!

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.

I spent 10+ hours learning to write stronger calls to action this week. 14 concepts I plan to use: 👉 1. Call to Action vs. Call to Value A call to action is for people ready to buy - keep it as simple as possible. A call to value reminds the prospect of the great outcome they're going to get. 👉 2. Use the phrase "I want to ____" in your button or link copy. Fill in the blank with a desired outcome. THIS: "I want to grow my business" NOT: "Download it now" 👉 3. Use the word "show" THIS: "Show me outfits I'll love" NOT: "Sign up now" That's a real example where the change resulted in 123% more clicks. 👉 4. Use first person language on buttons. THIS: "I want to double my revenue" NOT: "Double your revenue" 👉 5. Think of links as a door. People don't know what's on the other side so it's scary to click. Make it less scary for them. 👉 6. Focus on ONE action. Don't compete with your own CTA by making multiple asks. 👉 7. Lead with action verbs. THIS: "Unlock your marketing potential and download our free strategy guide" NOT: "Download our guide" 👉 8. Use an "If" statement. Weave a specific problem and solution into your CTA. Example: "If you're ready to maximize your profit and grow to 50k months working part-time hours, book a call with me to discuss what next steps would look like for you." 👉 9. Avoid generic phrases. Your CTA should work even if there was no other copy around it. Don't settle for "Click here," "Download now," "Submit," etc. 👉 10. Avoid hesitant language. Be more confident than "Let me know if you want it" or "If you need me..." 👉 11. No jargon or vague language. Address a specific problem using language your target audience uses. Don't say stuff like: "If you want to live your best life and step into your full potential..." 👉 12. No negative language. THIS: "Are you ready to lose 10-25 pounds of that menopause weight?" NOT: "Are you struggling to lose weight with menopause?" 👉 13. Write your CTA before you write anything else. It gives you a north star to guide the rest of your writing. 👉 14. Make sure your CTA includes two things: ✅ Why they should act ✅ Why they should do it NOW Want more useful tips like these? This week on LinkedIn I'll share: • How I turn newsletter subscribers into buyers • A formula you can use to strengthen your niche • How I'm growing my LinkedIn following 👉 Follow me and hit the 🔔 at the top right of my profile to turn on notifications so you don't miss those posts. Thanks for your interest!

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.

Newsletter operators are leaving $10,000+ on the table every month by ignoring SEO. Let’s change that with this step-by-step plan. Most newsletter owners waste time chasing broad, competitive keywords, ignoring niche topics their audience cares about, skipping optimized landing pages, and writing random blogs with no clear CTAs. The result? A lot of irrelevant traffic that doesn’t convert. Here’s what works instead: Step 1: Master High-Intent Keywords High-intent traffic is gold. These readers are primed to engage or subscribe. Skip the vanity metrics (traffic for traffic’s sake) and go for keywords that signal real interest. Identify terms directly related to your audience’s problems or goals (AI funding updates, top marketing strategies for SaaS startups). Avoid generic terms with high Keyword Difficulty (marketing newsletters) and instead pursue lower competition, long-tail keywords with clear intent (marketing newsletters for small agencies). Run a competitor analysis to see what queries they’re ranking for and find gaps where you can provide better answers. Prioritize questions your audience asks (how to grow SaaS revenue, latest AI industry funding) to attract high-quality traffic. 2. Build Landing Pages for Core Topics Create pages for each niche, with clear CTAs and unique selling points (weekly AI insights, exclusive SaaS trends). Test direct vs. FOMO-driven copy to maximize conversions. 3. Publish Evergreen Content Write detailed, long-form posts that stay relevant (2024 SaaS growth strategies, top AI tools for startups). Refresh them with new data and add CTAs to capture leads. 4. Create Lead Magnets Offer high-value resources (newsletter ROI calculators, 2024 AI trends reports) and gate them behind email signups. Promote them across blog posts and landing pages. 5. Repurpose Newsletter Content Turn your newsletter into SEO assets: blog posts, comparison articles (best SaaS newsletters), and video scripts. Link them back to landing pages to boost authority. 6. Write Comparison Articles Help readers make decisions with “best of” posts and guides (best AI newsletters in 2024). Include pricing, value, and strong CTAs like “Subscribe now for similar insights.” 7. Optimize Technical SEO Boost search visibility with FAQ schema, mobile-friendly pages, fast site speed, and keyword-rich meta titles. Fix broken links and optimize for technical issues quarterly. 8. Expand Content Formats Turn top-performing content into videos, podcasts, and social media posts (this week’s biggest AI funding news, SaaS growth tips). Use platforms like TikTok and LinkedIn for extra reach. 9. Build Topic Clusters Organize content into hubs (ultimate guide to SaaS newsletters) and link supporting posts (growth strategies, funding news) to establish authority and improve rankings. 10. Focus on Conversions Traffic is only valuable if it converts. Use bold CTAs (Join 15,000 founders getting actionable SaaS tips) and retargeting ads.

Don’t be the newsletter where every CTA says “Click here.” Here are six tactics you can use to improve those CTAs: ❶ Try the “Yes, and” approach — The reader’s just finished reading an email that they agree with — they’re already nodding their head “yes.” Now give them the CTA to have them take the next step: “Yes, I’ll support your work!” or “Yes, I believe in this mission!” ❷ Identify the value that readers care about most — There are a lot of things readers might value about your newsletter — this list can help you identify a few ideas — so mention those right in the CTA. For instance, if you’re selling a course or ebook designed to help readers overcome an obstacle, mention that here: “Let’s take the next step together!” or “Get the solutions you need!” ❸ Tie it back to a specific number — Let’s say you’re giving readers a special half-off discount. A great CTA might mention that: “Get 50% off now!” Or if you’re a non-profit offering matching funds, mention that in the CTA: “Triple your impact today!” ❹ Utilize two CTAs together — If there are multiple purchase options, try stacking two buttons on top of each other. An org driving donations might have one button with a link to donate monthly and another for one-time donations. A newsletter selling tickets to an event might have a button for general admission tickets and a VIP offer. ❺ Add an emoji or icon to the CTA — Don’t overdo it (too many 🚨🚨🚨 emojis might annoy readers), but an emoji that adds a bit more context could drive more clicks. You could also try adding something small, like an arrow emoji (→), as a reminder that there’s a next step. ❻ Adjust the design of the CTA — Test out different colors or button sizes to see if any make a difference. Or see what happens if you embed the CTA within a paragraph instead of using a button.

There are so many poorly done newsletters/email campaigns. As someone who turned an organization's newsletter w/ 15-20% open rates (quarterly) into two weekly newsletters each with consistently 65-70% open rate for years, I've learned a lot of lessons. Here's how to make your email something your audience can't wait to read: -Find the anti-pattern -5x value rule -Get over yourself, focus on delight -Trash compactor mindset -Only serve your fans What these mean: 1. Find the anti-pattern Figure out what your audience is craving for, that difference that would be so refreshing they would exhale when they learn about what you write. When I worked my first VC job, most VC fund newsletters were self-congratulatory announcements about portfolio company raises, investor press mentions, and occasionally a thoughtful piece. Pattern: Self-promotion in service of fund promotion. Anti-pattern: Zero self-promotion, only pure value given. Figure out what everybody does that is bad, and flip the script. 2. 5x value rule A lot of writers lack the humility to consider the fact that their idea/message/offer is simply just not as valuable as they think. When marketers/writers ask me for feedback, I tell them to consider what they think would be enough to get someone to care about their writing. Then 5x that bar. Make it so high a bar for value that it would be an "of course" decision for someone to read/respond/share about your stuff. 3. Get over yourself, focus on delight. It is obvious when newsletters are written with a KPI/explicit transactional goal in mind. Impress LPs to get them to invest. Convert those customers to subscribe for a plan. Get people to request meetings with you. If you provide delight in their experience of your product, the results will come. What would you do if you only want to make them as delighted as possible by your email every time they read it, without any conversion needed? Do that. The conversions will come. 4. Trash compactor mindset Remove the excess volume from your emails. I don't just mean concision in terms of length. Every marginal word you write should provide something of value - learning, insight, engagement, social proof, etc. If the next sentence doesn't raise or maintain the average value per word of your piece, don't include it. That might mean segment your audiences with different versions. Every sentence is a chance for the reader to lean in, or for them to rationalize why this is the last one of yours that they will read. 5. Only serve your fans. Don't try to get people onto your newsletter for subscriber-growth-sake. Every subscriber should be on your distribution because they make the active choice to become an audience member. If you had to describe what you write about and someone wouldn't automatically sign up, don't do it for them. Make something that will be shared word-of-mouth that will get them anyway. Opt-out list building does not make up for a low bar for content.