🎯 10 Best Newsletter Ads This Week (May 30-Jun 5)

Welcome back to another edition of Newsletter Ad Vault.

If you’re new here, every Thursday I break down 10 winning newsletter ads and explain exactly how you can mimic them for your own campaigns.

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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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 Deep View

Time running: 67 days

Why this works:

This billboard format from The Deep View stops people mid-scroll because it’s completely unexpected.

Your brain isn’t used to seeing highway billboards in social feeds, so it creates a pattern interrupt that forces attention. 

I’ve run tests with standard, “normal-looking” ads versus formats like this, and the more “unusual” ones always get higher CTRs.

Fear-based headlines are also great because people are more motivated to avoid loss than gain something new. 

How to apply this concept:

• Use formats that don’t belong in social feeds. Billboards, receipts, sticky notes, and others work well because they break scrolling patterns.

• Start your ad copy with what people are afraid of losing or missing out on, then position your newsletter as the solution.

• Try listing exactly three benefits. I’ve tested this extensively and three seems to be the sweet spot for most successful newsletters.

2. The Money Maniac

Time running: 132 days

Why this works:

It’s simple: people nowadays trust information that doesn’t feel like conventional advertising. This ChatGPT format looks like genuine advice someone discovered, not a company trying to sell something.

The “secrets Wall Street won’t tell you” creates an enemy, which is strong positioning. When there’s a “villain” keeping information from you, the newsletter becomes the hero helping you fight back. 

Also, they give away three genuinely solid investing insights right in the ad. This adds that trust element and proves they know what they’re talking about before asking for your email.

How to apply this concept:

• Disguise your ads to look like screenshots from apps your audience already uses. ChatGPT, Google searches, emails, and text conversations all work well.

• Create an “us vs them” story where the big institutions in your niche are the bad guys hiding information from regular people.

• Give away enough value in your ad to prove credibility, but save the best insights for subscribers only.

3. Mark Manson

Time running: 339 days

Why this works:

Authority sells newsletters faster than anything else. When someone already knows you and trusts you, the ad becomes simple social proof instead of persuasion.

Most newsletter creators overthink their ads when they can just focus on building authority first. The million subscribers number and the eye-catching book title do all the heavy lifting here.

I also like the behind-the-scenes photo because it feels natural and personal, like you’re seeing the world through the eyes of a successful author.

How to apply this concept:

• Lead your ad copy with your biggest credibility marker (book sales, podcast downloads, or whatever else that proves you know your stuff).

• Let social proof numbers carry the weight instead of over-explaining your value proposition.

• If your newsletter isn’t your main claim to credibility, position it as a secondary proof point. Here, “bestselling author who also writes a newsletter” works better than “newsletter writer who also wrote a book.”

📧 RECOMMENDATIONS

3 Newsletters to Inspire Your Own

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.

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

4. Wall Street Oasis

Time running: 196 days

Why this works:

The Notes app format will always remove sales resistance because it looks like personal advice. When something appears helpful first and promotional second, people don’t put their guard up.

I see way too many newsletter ads lead with “Subscribe to my newsletter!” instead of leading with value.

And that specific testimonial works well because it promises a specific workplace advantage. It’s not just knowledge, it’s a competitive edge, which is what ambitious people want.

How to apply this concept:

• Structure your ads to look like helpful advice that happens to mention your newsletter.

• Find testimonials that describe social or professional advantages instead of just outcomes of learning.

• Combine a tiny time commitment with massive subscriber numbers if you have them. This eliminates effort and credibility concerns at the same time.

5. Ravenwood Writing Academy

Time running: 72 days

Why this works:

Memes work in ads when they perfectly capture the audience’s current emotional state.

Freelance writers constantly worry about finding good clients, and this Pikachu face represents that moment of pleasant surprise when they find one.

The format itself does half the work here because their audience lives online and immediately recognizes the reference.

The before/after structure also creates a clear transformation story. I’ve always seen that people don’t really subscribe to newsletters; they subscribe to become a better version of themselves.

How to apply this concept:

• Use meme formats only when they perfectly match your audience’s emotional experience. Forcing it can backfire badly.

• Mention the transformation your newsletter creates, not just the information it provides.

• Make the required effort of reading your newsletter so small it feels silly to scroll past.

6. The Rundown

Time running: 226 days

Why this works:

Twitter-style ads like this from The Rundown blend in with regular posts, so people are more likely to read them. It feels familiar, not promotional, and that makes a big difference. 

The three-step structure here works because it feels like a complete system. Most people want actionable plans, not information dumps.

“Stop wasting time, sign up, learn daily” also gives the audience a clear path forward instead of leaving them wondering what to do next.

How to apply this concept:

• Mimic social platforms exactly: same fonts, colors, and layouts.

• Present your newsletter as step two in a bigger life improvement plan, not as the headline. Start with what your audience is currently doing wrong to grab their attention.

• Use short and specific timeframes to make end results feel concrete/achievable.

7. Junkbondinvest

Time running: 139 days

Why this works:

Checkboxes trigger completion bias – people want to finish lists once they start them. Seeing that green checkmark makes people feel like they’ve started something, so they naturally want to keep going down the list.

One of the biggest challenges when creating ads is finding ways to get people to read them in full, and this neat psychological trick can help. 

“Expert-level” filtering is also smart because it attracts serious people who’ll actually engage with your content.

I’ve seen many newsletter operators try to appeal to everyone and end up with subscribers who never open emails.

How to apply this concept:

• Use checkboxes in your ad creative to make people want to complete an action.

• Position your content as advanced to attract engaged subscribers rather than trying to please everyone.

• Acknowledge what people are currently doing (scrolling) first to create awareness and an immediate connection.

🎬 VIDEO ADS

8. The Attention Seeker

Time running: 262 days

Why this works:

This almost “reluctant” endorsement from The Attention Seeker feels trustworthy, as if a close friend were talking to you. 

Her casual and slightly annoyed tone removes all sales pressure, which is exactly why it works so well.

The chaotic and imperfect delivery also makes it memorable in a feed full of rinse-and-repeat ads. Generic ads blend together in people’s minds, while something raw and unpredictable sticks out.

How to apply this concept:

• Have spokespeople (or do it yourself) present your product reluctantly or sarcastically. It creates a refreshing break from the hard-sell tone people are used to.

• Embrace mistakes and imperfections in video content because they create authenticity that perfect production can’t match.

• Let personality shine through instead of that corporate spokesperson mode that gets repetitive over time.

9. Upworthy

Time running: 308 days

Why this works:

The mountain scenery here creates another instant mood shift from typical doom-scrolling.

Most news makes people feel stressed, so this visual immediately sets the stage for Upworthy to be the peaceful alternative.

What’s really smart is keeping “Tired of regular news?” on screen the entire time. It’s a constant reminder of the pain point while the narrator talks about uplifting content. 

Most video ads let people forget why they started watching, but this keeps the problem front and center.

How to apply this concept:

• Use calming visuals that differ from the negative emotions your audience currently feels.

• Keep your main pain point visible throughout your entire video ad so people remember why they need your solution.

• Encourage your audience as they listen to your ad. Lines like “restore your faith in humanity” inspire hope and reinforce the positive change your content offers.

10. Intern Insider

Time running: 139 days

Why this works:

Every college student dreams about that “holy cow, we actually did it” moment.

Watching Dwight and Michael from The Office celebrate is hilarious because it’s exactly how dramatic landing something good feels at 20. 

The casual “me and bro” language hits perfectly with what their audience is used to seeing. It feels like it’s coming from a friend who genuinely gets the struggle.

Plus, references from The Office are always gold with college students; they probably binged the entire series during finals week.

How to apply this concept:

• Use memes in your video ads that show the main emotional payoff your audience wants.

• If you only highlight one outcome in your ad creative, make sure it’s the one your audience craves the most.

• Use references in your ads that your target demographic recognizes and connects with.

👋 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.

That’s all for this week! See you next Thursday with more breakdowns and templates.

– 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!