How One Founder Made $1M+ After Fixing These 5 Newsletter Mistakes

PLUS: Bonus tips and pro moves

Author

Tommy Mandia
March 07, 2025 • Estimated Reading Time: 5 minutes

Hey Advisors, it's Tommy.

Today, we're diving into the $1M+ newsletter strategy that transformed one founder's business after 18 months of making $0.

In today's issue:

  • Why most newsletters fail to generate revenue (even with large audiences)

  • The 5 critical mistakes costing you subscribers and sales

  • How to build a "value ladder" that turns readers into customers

  • My newsletter monetization timeline that you can implement today

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STRATEGY
An in-depth analysis

I recently spoke with Chris who added $1M+ to his business with his newsletter.

But here's the kicker - in the first 18 months, he made $0.

Zero. Zilch. Nada.

When I asked him why, his answer stopped me in my tracks.

"I was making all the classic newsletter mistakes without even knowing it."

Sounds familiar?

You're not alone.

Most founders spend hours crafting newsletters that never convert.

The worst part?

They leave money on the table month after month.

Let me share what this founder learned the hard way, so you don't have to.

5 Newsletter Mistakes Costing You Money (And How To Fix Them)

1. Prioritizing growth over retention

Most people obsess over subscriber count while ignoring their existing audience.

Fix it: Calculate your "subscriber value" by multiplying open rates by subscriber count.

Then focus on improving that number by sending content your readers actually want.

Try this: Survey your top 20% most engaged subscribers and ask them exactly what they want to learn.

2. Creating content on a rigid schedule without measuring impact

Sending newsletters "just because it's Tuesday" is madness.

Fix it: Track these 3 key metrics for each newsletter:

  • Reply rate (aim for at least 0,5-1% of opens)

  • Click-through rate on your CTA (not total CTA)

  • Direct attribution to sales

Bonus tip: After sending, wait 24h hours before checking analytics

Use this data to plan your next 4 newsletters.

3. Outsourcing your voice too early

Your newsletter is often the most intimate touchpoint with customers.

Fix it: Create a document with examples of: writing style, phrases you use, and topics you never discuss.

This becomes your style guide when you eventually hire help.

Quick test: Can a loyal reader tell if you wrote something or someone else did? If not, your voice isn't defined enough yet.

4. Assuming B2B content must be formal and dry

Business owners are people too.

I know, crazy right?

They don't magically prefer boring content when they're at work.

Fix it: Write exactly how you speak.

Read your newsletter out loud before sending. If it sounds stiff or you stumble while reading, rewrite it.

Pro move: Record yourself talking through your main points. Then, transcribe and edit that instead of writing from scratch.

5. Trying to monetize too early

Building trust comes before building revenue.

Fix it: Create a simple "value ladder" for your newsletter:

  • First 90 days: Focus solely on delivering unexpected value

  • Days 90-180: Introduce soft mentions of your services/products

  • After 180 days: Start direct offers to your most engaged readers

Success metric: When readers start asking how they can work with you instead of you telling them.

What about Chris then?

Once he fixed these 5 issues, his newsletter started generating $83,000 per month.

The best part? He didn't need more subscribers. He just needed to serve his existing ones better.

What newsletter mistake have you been making? Hit reply and let me know - I read every response.

Building alongside you,

Tommy

In case you ever need it, here are 3 ways I can help you:

That's it for this week!

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See you soon,

Tommy - founder at NewsLaunch.co