Start a Newsletter Business with AI PART 1 – Why start a newsletter?


Obviously this is a cool one for me because, as you know, I run a newsletter.

What newsletter? Well, the one you’re reading silly! 😋 

Additionally, I work on the business side of newsletters too and know how the “money side” works. I’ll go into that a bit more later in the week when we talk monetization.

What is a newsletter business?

Newsletters are curated email publications that provide subscribers with regular updates, insights, and valuable content on specific topics of interest.

Importantly newsletters are NOT the email marketing you get from companies that you interact with.

You know the type – you buy some nails at Home Depot and they send you emails for years about their Thanksgiving offers.

We’re NOT talking about that. Those are company newsletters that a marketing a business.

Instead we’re talking about newsletters that ARE the business. The business is in writing, publishing and growing and audience. And then monetising that audience. It’s a subtle but important difference.

Some successful examples of newsletters run as businesses include Morning Brew, a daily business newsletter that provides concise and engaging summaries of the latest news and trends in the business world. Morning Brew sold for $75m.

Another example is Milk Road, a newsletter that focuses on web3 and crypto and was sold for 8 figures just 10 months after starting.

Both of these newsletters have managed to attract a large and dedicated subscriber base by consistently delivering high-quality content that meets the needs and interests of their target audience.

Why is the newsletter business exciting?

They have gained significant popularity in recent years due to their ability to deliver personalized and relevant information directly to subscribers’ inboxes.

This is a huge deal for advertisers recently because Meta/Google advertising rates are increasing whilst tracking of results (because of privacy laws and things like the iOS 14 update) is becoming harder and harder.

Entering the newsletter business as a writer is exciting right now because it offers significant financial opportunities.

Newsletters can generate income through various channels such as paid subs, sponsorship, affiliate marketing, and advertising.

One newer revenue source recommending other newsletters. You know that the people reading your newsletter like newsletters. And you know what subjects you like. So by simply recommending other newsletters you can make ~$1-2/referred subscriber. Pretty cool!

Additionally, as newsletters allow for direct communication with subscribers, writers can build a loyal and engaged audience, which can further enhance their earning potential through partnerships, collaborations, and even book deals. Once you have an audience the sky is really the limit.

The potential for financial success in the newsletter business is high, making it an enticing venture for writers.

OK what about AI?

Newsletters have been around for years but they are particularly exciting right now because of the advances in AI that we’ve seen this year.

AI is particularly valuable for

  • curating content from your topic
  • idea generation
  • newsletter outlines
  • drafting your newsletter
  • editing and correcting your newsletter
  • social media to promote your articles
  • and more

You could set up an AI to automatically generate a whole newsletter. It would basically find other quality sources in your subject area and rewrite/compile them into a newsletter.

That’s not what we’re going to focus on, even if it sounds very appealing.

Why not?

It’s not a sustainable business model.

If it’s that easy lots of other entrepreneurs will enter the market and do exactly the same thing.

Supply will rise, demand will stay the same.

The value of the pure AI generated newsletters will fall to zero.

Instead we’re going to utilise AI alongside our own creativity to make something unique enough to stand out whilst still not being a full time job.


Structure of the week

These guides are no-holds-barred, full walkthroughs of the steps you need to take.

Setting up a new business and adding an income steam is not easy. It’s not meant to be easy.

But you follow along and ACT (rather than just read) and you’ll have the basic foundations of a newsletter business in place.

In brief here’s the week:

Part 1: Understanding Newsletters

Part 2: Setting up your newsletter

Part 3: Content Creation with AI – Part 1

Part 4: Content Creation with AI – Part 2 & Audience Building

Part 5: Monetization: Advertising and Sponsorships

I’ve intentionally split this guide up over five emails so you have a handful of actions to do daily.

At the end of the process this will be compiled into a (short) book.

Connect with me on Twitter and let me know how it’s going.

Let’s get started:

Understanding Newsletters and Niche Selection

We’ve covered a lot of “theory” above so today’s actions are more limited.

1. Identify Your Interests and Skills

We’re going to borrow and adapt a prompt we’ve used before :

As a brainstorming assistant, generate a list of 50 potential newsletter niches based on my interests in [insert interests here] combined with my skills [insert skills here]

The goal is to come up with unique and engaging content niche that combine these interests and skills. 

Combine where they naturally intersect but do not force combinations. Please avoid overly wide niches. 

Sit down with a pen and paper (I know, medieval!) and sketch out your interests and skills.

Why paper? It’s easier to avoid self editing.

Just go nuts and get as much down on paper as possible. We’ll let ChatGPT do the sorting.

If something falls under interest and skills add it to both. This is normal. What we are interested in we tend to do more. And doing it more makes us skilled at it.

Prompt Output 💬

In this example I inputted

[interests] = AI, productivity, writing, board games, video games, weightlifting, cycling, entrepreneurship

[skills] = systems thinking, writing, AI, endurance sports, entrepreneurship, business strategy

Add more if you can, the more the better.

These are the first 20 of 50.

Keep generating and copy/paste the ones that you like.

When you have ~10 ideas that sound good to you (based on your interests and skills) feed them back into ChatGPT and tell it that these are your favourites and to generate more ideas based of those.

2. Identify money niches

Combining interests and skills is a first step.

But this is a business. We need to make sure that the newsletter we create can also generate an income.

Therefore we need a third variable: a good market!

Here’s the next prompt:

As a marketing strategist analyse this list of newsletter business ideas. This business involves creating a newsletter, building an audience and then monetising the audience through advertising and sponsorships.
Analyse them by these factors: total market size(+), value of subscribers(+) and competition(-). Score each factor out of 100 and use this to create a composite total score of 300 for the attractiveness of the newsletter business idea. 
Sort all entries by their composite score, highest composite score at the top then descending. Present results in tabular form.

Prompt Output 💬

Here’s my ranking using ideas from the previous step.

Use this ranking to start to filter out ideas that have no obvious market. Lots of mine have solid market potential but this is a function of the interests and skills I put in.

Generally though the big three markets will be the winners here:

  • Money
  • Health
  • Relationships

If you can nail something into one of these big three you’re generally going in the right direction.

3. Research other newsletters

Once you’ve honed in on your rough niche we want to see what the current newsletter landscape is like.

Don’t worry about having totally nailed the niche yet. Honestly, it’s going to shift and adapt as you get going and work out what your readers want. You just need to know the topic.

Here’s the prompt:

Give me a list of newsletters that cover the topic of [copy/paste whole title, description]

Copy in the whole name and description that ChatGPT generated. For instance” “AI Driven Entrepreneurship: Future-Proofing Your Business”

This will give ChatGPT as much context as possible.

Prompt Output 💬

Using the prompt “Give me a list of newsletters that cover the topic of AI Driven Entrepreneurship: Future-Proofing Your Business”

Warning: this is a case when ChatGPT’s learning period comes into play. This is a decent list but AI (which is the topic entered into ChatGPT) has exploded since September 2021, the end of ChatGPT’s training period.

If you have access to Claude2 (currently UK and US only) use this tool instead because it’s training period is up to 2023. It’s free.

Here’s Claude2’s output:

If that’s not an option head to as a good place to run research.

Once you’ve got the newsletters go ahead and subscribe to them all! You need to see what they are writing about.

We’ll be referring to their content in future parts of this guide.

4. Absorb Matt McGarry’s wisdom

Not an AI prompt but potentially the most important action today.

Subscribe to this newsletter:

Newsletter OperatorHow to grow and monetize your newsletter.Subscribe

Why? It’s run by Matt McGarry who is THE newsletter guy. He talks about how to grow and monetise a newsletter and is basically the best in the biz.

If you are serious about making a profitable newsletter business his emails are gold-dust – it’s all actionable and tested advice.

Pulling it together

That’s everything for today.

It’s been a theory heavy day rather because I needed to outline what exactly a newsletter business is and what we’re going to be working towards over the next week.

There will be more actions in the next 4 steps, don’t worry!

Over the next few days we’re going to cover the four remaining steps:

Part 1: Understanding Newsletters and AI Tools

Part 2: Setting up your newsletter

Part 3: Content Creation with AI – Part 1

Part 4: Content Creation with AI – Part 2 & Audience Building

Part 5: Monetization: Advertising and Sponsorships

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