How to recreate Jaisal Rathee’s profitable newsletter playbook to grow and sell newsletters FAST


Growing newsletters are hard work. Many burn out trying to keep up with content creation hamster wheel. That’s why choosing a good niche topic is key. Read my hard-earned lessons about newsletters on X here.

Today we will look at someone who’s done this well. In fact, he’s launched over 10 newsletters and collected over 30,000 subscribers in his newsletter network. He is a serial entrepreneur with 9 exits, at least 5 of which were newsletters.

In this article, you will learn what a newsletter flywheel is, and the mistake you should avoid when designing your content to avoid burn out.

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What you will learn

  • How to create a newsletter structure so that you can operate multiple newsletters at once without burning out
  • Why offering free marketing for his readers is a smart move
  • The one thing you need to maximize inbound sponsorship leads so you never have to chase for sponsors again.
  • How Jaisal Rathee gets his first 1000 subscribers
  • How to skip the painful 0 to 1000 subscribers phase when building multiple newsletters

Who is Jaisal Rathee?

Jaisal Rathee is a newsletter operator with a network of successful newsletters in the startup, business, and tech niches, reaching an audience of over 30,000 subscribers. 

Some of his newsletters are:

  1. Insanely Useful Websites: This was one of his first newsletters launched as a fun weekend side-project. It grew to 5,000 subscribers in a few months. He sold it with less than 5k subscribers after running it for 8 months to another successful newsletter operator, Michael Houck.
  2. 12,000 subscribers. Sold.
  3. Tiny Startups: His current startup
  4. Buy Sell Startups: His current startup
  5. Insanely Cool Tools: Sold

Needless to say, if you are interested in building a newsletter for your startup or your personal brand. Jaisal Rathee is someone you want to learn from.

His secret newsletter flywheel

A flywheel is a circular process that grows itself. The more interesting content you create and share, the more people subscribe. As these subscribers engage and share your content, it attracts even more subscribers, making the whole process stronger and more effective over time.

  1. His subscribers are his product – All his newsletters are directory sites with a mailing list attached. Every time someone adds their product or startup to his directory, they get added to his subscriber list. I’ll show you why this is clever and examples of how it looks like.
  2. His subscribers are his sponsors – Unlike other newsletter operators who have to work on writing and getting sponsors separately, Jaisal’s niche selection strategy helps him merge both process into one.
  3. He doesn’t get attached to his products – He sees himself as a serial micro startup founder in the business of launching, growing and exiting startups. Unlike other newsletter operators like Michael Houck who is all in on one newsletter (his newsletter is named after himself), Jaisal’s newsletters are always for available for sale.
  4. His first 1000 subscribers is a grind – Like everyone else, this part is a grind. I will share his tactics on growth.
  5. He never has to starts from zero again – This is his most clever tactic. After going from zero to one for his first newsletter, he created a strategy to never start from zero again. You will learn how he does this effectively.

Lets look at each in detail:

1. His subscribers are his also product

Remember the saying “if the product is free for you to use, YOU are the product?”

In Jaisal’s case, all of his newsletters are structured as billboards for indie makers and founders. Tiny Startups is a directory of small startups, Buy Sell Startups is a directory of startups available for sale. Each has its own mailing lists that updates its subscribers on new listings.

Anyone can submit their product on his directories. For free.

Newsletter flywheel - Free directory listing
Anyone can add their startup to the directory for free by clicking “Submit Startup”

If you’re wondering what his business model is offering a free billboard to founders, here’s what he gains every time someone adds their product to his directory:

  • He gets free content for his directory and newsletter (“new startup added!”)
  • He gets a new subscriber to his email list (they are auto-enrolled to his mailing list)

In other words, anyone who submitted their startups or tools to his website are giving Jaisal free content and free subscriber count in exchange for marketing their tools.

p/s: if you are worried about auto-enrolling subscribers, as far as I can tell, you just need explicit consent when they submit their startup to comply with privacy regulations.

Newsletter flywheel - auto subscribed
Submitting my startup and joining his newsletter at the same time

But wait, it gets better…

2. His subscribers are also his sponsors

If you are a “traditional” newsletter writer like me, you will likely struggle to balance the time it takes to write content and the time it takes to find sponsors. Both process takes ages with little to no synergy.

You’ve already seen how Jaisal gets free content from his subscribers.

Now you will learn how he barely spends any time finding sponsors either.

In fact, in a recent interview with Newsletter Circle, Jaisal shared that ALL of his sponsors are inbound leads.

His newsletter example – Tiny Startups

Tiny Startups’ target audience is solo founders running tiny startups.

We already know that they are:

  • His source of content – they submit their startup details to his directory and emails
  • His subscribers – they read about startup stories of other founders

    Now we also know that they are:
  • His sponsors – They likely built tools or startups and want to pay to market those to other founders. All he needs to do is add a call to action at the bottom of his emails to reach them.
Newsletter flywheel - sponsors (2)

The reason this works is because he picked a newsletter niche where his readers and his sponsors are the same audience.

Let’s compare that his older website niche where this wasn’t the case.

For Pitch Bear, his readers and his sponsors are 2 different audiences:

  • His readers: the founders who want this database
  • His sponsors: the investors listed on this directory.

    Both have different interests and needs. Simply adding a call to action at the bottom of the emails likely won’t work as well.


By aligning his product to only serve a single audience who are also his sponsors (customers), Jaisal effectively cuts his workload down in half.

3. He doesn’t get attached to his products

I will explain why he is able to be detached to his products in a second.

For now, let’s look at his track record selling his newsletters.

  • Insanely Useful Websites: Sold Aug 2022 (8 months of launch at 5k subscribers)
  • Daily Dose of Startups: Sold July 2023
  • Internet Is Beautiful: Sold in Nov 2023
  • Startups FYI: Sold Dec 2023 (8 months post launch)

In short, he is a newsletter operator who launch, grow and sell micro digital businesses. As of the date of writing he has sold 9 startups and are working on another 3.

4. His first 1000 subscribers is a grind (like everyone else)

Growing from ground zero is hard.

Most of his audience are founders, which means platforms like Twitter, Product Hunt, Indie Hackers, and Reddit are great for him.

Newsletter flywheel - Launch

Aside from the strategies he talked about in the interview snippet above, you should also collaborate with other newsletter operators to cross promote each others’ content. This is exactly wheat he suggested I do when I first started Juicy Ideas.

Newsletter flywheel - collaboration advise

Lesson: If you are new to running newsletters, collaborate with similar sized newsletters until you get your first 5000 subscribers.

5. He never has to starts from zero again.

It gets easier once you get past your first few thousand subscribers.

So why does Jaisal keep selling his newsletter after that and start a new newsletter? Isn’t it insane to want to start grinding from zero again?

This is what I thought until I read Jaisal’s response to this interview question.

Newsletter flywheel - Launch (2)

It took me a while to figure out how he did it.

Here’s my guess:

  1. He gets his first 1000 subscribers the usual way through sweat and tears as described above
  2. He launches a second newsletter in the same niche
  3. He uses his first newsletter to cross-promote his second newsletter
  4. He sells his first newsletter and launches a third newsletter
  5. Now he uses his second newsletter to cross-promote his third newsletter
  6. And so on

He effectively pushes his subscribers from one newsletter to the next and continue to grow his newsletter network without ever having to start from zero again.

You can see this tactic in action here:

Newsletter flywheel - cross recommendations
All of these are his newsletters: Startups FYI, Insanely Useful Website, Daily Dose of Startups, Insanely Cool Tools and Buy Sell Startups. They cross-promote each other.

Lesson: Running multiple newsletters within a single niche is a clever way to extract maximum value from your subscribers.

Juicy ideas to replicate success

  • Start newsletters where your readers are your sponsors. By aligning both audiences you eliminate hours spent hunting for sponsors after writing each issue and can attract inbound sponsorship leads from your email footer.
  • Run multiple newsletters within a single niche. You can cross-promote your newsletters to extract maximum value from your subscribers. Each newsletter is an asset you can sell.
  • Don’t be afraid to sell your newsletter. Remember, cross-pollinating your newsletters can help you avoid the 0 to 1000 subscribers grind. And if you do have to start from 0 again, don’t forget to collaborate with other newsletter operators.

What’s next

In a future issue, I will reverse-engineer Marc Louvion’s 5 day idea to MVP launch strategy based on his launch of ZenVoice he live streamed over YouTube.

If you haven’t already, sign up to get notified when a new issue of Juicy Ideas drop!

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Each week, we will reverse engineer the growth and distribution strategies used by top indie makers to grow their startups past $100k annual revenue. Subscribe so you don’t miss the latest issues!