🎯 10 Best Newsletter Ads This Week (May 23-29)

Hey! Alex here. I’m back with another Thursday deep dive of newsletter ads that are absolutely killing it right now.

In today’s issue:

• 🎯 Newsletter ads that are crushing it right now (7 static + 3 video ads)

• 🧠 Simple breakdowns of why they work

• 🎨 Ready-to-use Canva templates to copy

• 📧 Newsletters to inspire your own

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It lets you recommend other newsletters to your new subscribers right after they sign up. When someone joins one and stays engaged, you get paid – usually $2-$5 per subscriber.

Here’s the link to sign up if you want to give it a try. It’s 100% free.

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📸 STATIC ADS

1. The Business Academy

Time running: 493 days

Why this works:

“We’ve purchased 21 companies” is the kind of statement that makes you stop scrolling right away. The Business Academy leads with massive credibility instead of making empty promises about what they’ll teach you.

Business acquisition is all about trust and proven track record, so the personal branding approach works great here.

What makes this even more effective is how they break down the exact value proposition.

They’re not just sharing random business tips. They’re offering the specific process they use to acquire cash-flow producing businesses, packaged into an easy weekly format.

This approach transforms complex, intimidating business strategy into something accessible and actionable.

How to apply this concept:

• Lead with your biggest, most impressive credential or result in the first line of your ad. Numbers work especially well because they’re concrete and hard to ignore.

• Frame your newsletter as giving away the “exact process” or “behind-the-scenes system” you actually use in your business or profession.

• Use personal branding when your own credibility is your strongest selling point. Put your face and name prominently in the ad to build that human connection.

2. The Street Sheet

Time running: 157 days

Why this works:

This meme perfectly captures the evolution from financial amateur to smart investor. The visual progression from tiny brain to large brain resonates because most people see themselves somewhere along that journey.

I also like how they list the common habits that keep people stuck with the “little brain” mentality.

I’ve found that progression-style ads tend to perform really well because they make people want to reach that final stage.

And with 5-minute shortcuts to “big brain” status, The Street Sheet makes that transformation feel both appealing and doable.

How to apply this concept:

• Use progression-style visuals that show the journey from where your audience is now to where they want to be. Meme formats work especially well for this.

• Position your newsletter as the bridge that helps people skip steps in their learning journey.

• Include specific time commitments like “5 minutes a day” to make the value proposition feel manageable and realistic.

3. 1440 Media

Time running: 164 days

Why this works:

The visual comparison here is brilliant. On one side, you see the chaotic mess of how most people consume news: social media, video feeds, search engines, and network news.

On the other side, there’s clean and organized 1440 branded content. It’s like showing someone a cluttered desk next to a perfectly organized workspace.

This ad works because it shows you exactly what the solution feels like visually. The contrast makes the proposition clear right away without requiring any explanation.

And I like how the “this is what separates the 1% who are well informed” positioning makes subscribers feel like they’re joining an exclusive group.

How to apply this concept:

• Create visual before-and-after comparisons that show the chaotic way people currently handle your topic vs. your organized solution.

• Make the benefit immediately obvious at a glance.

• Position your newsletter as the thing that separates high performers from everyone else. People always want to feel like they’re gaining an advantage others don’t have.

📧 RECOMMENDATIONS

Fresh Finds for Newsletter Creators

As a newsletter operator, I subscribe to tons of newsletters to get new ideas and inspiration.

Below are some great ones if you’re looking for inspiration from fast-growing newsletters:

• The Pen Pivot → Get psychology-backed secrets behind getting people to click, read, view, and engage with your content.

• I Will Teach You To Be Rich → Where 800k+ readers get actionable, no-BS advice on how to create a successful business and build a rich life without sacrificing the things they love.

• Write • Build • Scale with Sinem Günel → This helps you write confidently, build your audience, and scale your income, so you can make money doing what you love.

• Step By Step → No-fluff business advice from Chris Donnelly, who’s built and sold companies for 8–9 figures.

🔗 These are 1-click subscribe links – no email entry needed if you’re reading this in your inbox.

4. Austin Scholar

Time running: 55 days

Why this works:

I’ve always found the sticky note approach personal and authentic.

“Everyone said school was the only path. I took another one — and made it to Stanford.” This goes against the conventional wisdom about academic success in a way that generates huge curiosity. How can you make it to Stanford without focusing on school?

As big of a name as it is, simply mentioning Stanford in this context provides the proof that unconventional approaches can lead to prestigious outcomes.

And in my experience, this type of “everyone said X, but I did Y” positioning works very well when you have the credentials to back it up.

How to apply this concept:

• Use personal story formats that challenge widely accepted beliefs in your industry.

• Include prestigious outcomes or credentials that validate your different approach. This gives people confidence to trust your unconventional methods.

• Target people who are already questioning the status quo rather than trying to convince satisfied customers to change their ways.

5. The Dink Pickleball

Time running: 524 days

Why this works:

Simple and direct. “Want to get better at pickleball? You need to be subscribed to The Dink.”

There’s no fancy promises or complex value proposition here. Just clear statements that position The Dink as essential for anyone serious about improving their game.

The format breakdown works perfectly for their audience. Pickleball players want practical information they can use right away.

Also, mentioning “over 100k players (and pros)” and the “most-read newsletter in the sport,” adds huge credibility.

How to apply this concept:

• Sometimes, the most direct approach works best. If you’re already established in your niche, simply state that people need your newsletter to achieve their goals.

• Break down exactly what type of content you send and how often you send it. This sets clear expectations and helps people understand the value they’ll receive.

• Include both amateur and professional subscribers in your social proof to show that your content works for all skill levels.

6. MONEY

Time running: 111 days

Why this works:

Promising a simple solution to a major problem always grabs attention immediately, and Money does it perfectly here.

The yellow highlighting on key phrases “struggling financially,” “free newsletter,” and “invest smarter in 2025” guides the eye to the most important benefits.

I’ve seen this approach work well because it doesn’t assume that people are already interested in investing. Instead, it meets some people where they are (struggling financially) and offers a pathway to improvement.

The 250,000+ subscriber count also provides massive social proof that this actually works for real people.

How to apply this concept:

• Present your newsletter as a “life hack” or simple solution to a complex and widespread problem.

• Use strategic highlighting or color to emphasize the most compelling parts of your value proposition.

• Meet people where they currently are in their journey rather than where they want to be. Address their immediate pain points first.

7. Physician on FIRE

Time running: 149 days

Why this works:

Professional specificity is a powerful way to establish instant credibility.

Instead of generic financial advice, Physician on FIRE is offering insights tailored specifically for physicians. This makes the content feel relevant and valuable to their exact target audience.

Each reason builds a compelling case: exclusive financial insights for physicians, quick and actionable advice that saves time, and social proof from 30,000 other physicians.

The progression (personalization → efficiency → community) creates a complete value proposition.

How to apply this concept:

• Create profession-specific or niche-specific content that speaks directly to your audience’s unique situation and challenges.

• Structure your value proposition around multiple benefits that appeal to different motivations such as learning, time-saving, community, etc.

• Use subscriber numbers from your specific target audience rather than general numbers to create more relevant social proof.

🎬 VIDEO ADS

8. Mint Pillow

Time running: 251 days

Why this works:

Having someone on a podcast endorse your newsletter feels much more authentic than traditional advertising.

And it’s even better when they mention, “I’d go as far as saying it’s the #1 newsletter every hotel manager should be reading.” It carries the weight of a genuine recommendation rather than a paid promotion.

I really like the storytelling approach here. Instead of just listing features, the speaker shares a specific example: “Last week, I read how this one hotel is absolutely crushing Airbnb's in their local area.”

That gives potential subscribers a concrete idea of what they’ll learn and how it could help their business.

How to apply this concept:

• Partner with podcast hosts or influencers in your niche who can authentically recommend your newsletter based on their actual experience with it (or just mimic a podcast yourself).

• Use specific case studies or examples from recent issues to show the practical value subscribers receive.

• Position your newsletter as an essential read for professionals in your target industry.

9. The Imaging Wire

Time running: 188 days

Why this works:

This emoji-driven framework always makes complex information feel approachable and visually digestible. Instead of flooding radiologists with the heavy text they’re used to, The Imaging Wire breaks things down into simple highlights.

What makes this ad work is how they’ve structured it around the specific needs of busy radiologists. “Quick 5-min read” and “stay updated in your lunch break” acknowledge that they don’t have time to waste.

The 28k+ subscribers offer strong peer validation in a credibility-driven field. And with a radiology setup in the background, the ad instantly connects with its target audience.

How to apply this concept:

• Use emoji or icon-driven layouts to make information-heavy content feel more accessible and less intimidating to busy professionals.

• Structure your timing around your audience’s realistic schedule constraints. 

• Highlight subscriber numbers from the specific profession you’re targeting rather than general audience numbers for stronger social proof.

10. Jay Shetty

Time running: 80 days

Why this works:

The philosophical hook here draws you in with the promise of transformation. Jay Shetty has always positioned himself as someone who focuses on deep mindset shifts rather than generic self-help advice. 

What I find particularly effective is how he frames obstacles as potential wins waiting to happen.

The promise of “transformative insights plus exclusive podcast highlights” offers a mix of new content and handpicked snippets. And the calm, candle-lit visual matches the thoughtful tone of his brand.

How to apply this concept:

• Lead with thought-provoking questions that make people pause and consider new possibilities.

• Position yourself as a guide who helps people rethink challenges rather than someone who just provides general information or tips.

• Match your visual aesthetic to the emotional tone of your content. Peaceful and thoughtful visuals work well for personal development content.

👋 THAT’S A WRAP

Before you go, here are 3 ways we can help you

1. 🎯 Explore past winning ad breakdowns + templates on our website.

2. 🗂️ Grab the swipe file from this week’s newsletter ads – it includes all the ad descriptions, headlines, original images/videos, and landing pages they linked to.

3. 📧 Haven’t launched your newsletter yet? Try Beehiiv – it’s what we use, and honestly the best newsletter platform right now. They’re currently offering the first month FREE, plus 20% off for your next 3 months.

Hope these breakdowns inspire some fresh ideas for your next campaign. See you next week with another round of winning ads!

– Alex

P.S. If this email ends up in your Junk or Promotions folder, mark it as “Not Junk” or move it to your Primary inbox. That way, you won’t miss the next issue!