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  • 📌 Build a $300K/yr Paid Newsletter in Just 18 Months

📌 Build a $300K/yr Paid Newsletter in Just 18 Months

Hey, great to see you!👋

Each week, I break down standout newsletters with smart strategies + ready to use templates, all in under 4 minutes.

Today’s issue is about one of the most real and practical authors I’ve met online.

Backstory

You’ve likely heard of Nicolas Cole and Dickie Bush. Top writers and entrepreneurs.

They have mastered the art of turning words into money. With multiple digital products and paid newsletters, Cole & Dickie have honed a formula for success.

What's in it for you?

1. The paid newsletter model you can use.

2. Free vs. paid content.

3. Ready-to-go templates to start your own paid newsletter.​​

Content

Can every newsletter go paid?

No—but here are two that can:

1. Researched Curation

People pay for well-researched, curated content with a unique take.

2. Original Thinking

Readers pay for direct access to your expertise.

But a good idea isn’t enough.

1. Evergreen Content

It should remain valuable over time

Like a book that wants to read forever (Cole’s analogy)

2. Tangible Deliverables

Offer content that feels more like a product, not just words

(e.g., reports, templates, case studies).

3. Clear Outcomes

No vague promises.

Focus on results like “writing prompts that boost email sales”.

4. Value-Based Pricing

Show clear benefits—saving time, money, or making money.

Ex. Compare a $100/month yoga membership with two visits at $50 each.

Your newsletter offers unlimited resources for only $15/month.

It provides ongoing value at a much lower cost.

How often do you need to publish?

Publish one free and one paid newsletter per week for optimal growth.

- Free content attracts subscribers.

- Paid content is a product that delivers value to justify the fee.

Adjust the frequency based on topic urgency and content volume:

- Urgent topics (e.g., investments) may need daily updates.

- Less urgent topics (e.g., marketing tips) work well with weekly or bi-weekly updates.

- More content per issue requires lower frequency.

Deliverability

Cole’s email strategy focuses on simplicity.

A clean landing page with clear value propositions & strong social proof.

A solid welcome email builds credibility.

It keeps the sign-up process straightforward and

subtly introduces products with a soft sell.

What can you do to improve deliverability if you just started?

Use a 4-step sign-up flow

1. Landing page

2. Survey

3. Thank-you page

4. Welcome email

Need more info about the sign-up flow?

Still have questions? Just reply to this email, and I’ll be happy to help!

Growth

Cole & Dickie have strong social media presence and top entrepreneur reputations.

That allows them to rely solely on organic growth.

No ads or fancy funnels - just consistent content on X and LinkedIn.

From Nov '23 to Aug '24, they grew from 20K (~1K paid) to 45K subs (~1.5K paid).

1. Promote each product on different channels to avoid confusing your audience.

Newsletter on X, PGA course on LinkedIn, Ship 30 for 30 course on YT.

2. Post daily short-form content on X to drive traffic to their free newsletter.

Once subscribers are on the list, they’re informed about the paid newsletter.

3. 20% of traffic comes from Substack’s community feature.

There readers engage, comment, and share recommendations.

4. Upsell free readers with a paywall before the most valuable content (cliffhanger).

This creates FOMO to encourage upgrading.

5. Add CTAs in your free newsletter to prompt readers to share or refer to it.

Monetization

The paid version of Writing with AI is priced at CAD 28/month.

The annual subscription is 18% off.

Subscribers get exclusive posts, AI prompts, and access to workshops.

Their strategy combines niche expertise and tangible deliverables.

Your 2 criteria for paid newsletter success:

1. Give yourself 5-6 months to see the trend.

2. If it works, you could be generating $5-10K/mo.

If not, you can exit and cover some expenses.

And remember, exiting isn’t a failure - it’s a valuable experience.

P.S. Oh, and..

I hope you found value here.

If so, please forward this to 2 friends who might benefit as well - sign up here.

P.P.S.

Questions about newsletter growth, monetization, or other how-to topics?

Reply to this email or connect with me on LinkedIn.