How And When To Build A Paid Newsletter

We have talked about paid newsletters in other deep dives, but have never done a full exclusive case study on how and when you should be launching one.

While I have made it pretty clear that I don't love paid newsletters as a Newsletter Business Model, there are some unique situations that can make it the best path.

Here are a few of those situations:

1. You are in a niche that isn't ideal for selling digital products.
2. You want the writing to be the product and have no interest in earning more by creating products and/or providing services.
3. You are the absolute go-to thought leader in a specific niche and fall into one of the other two categories.

Among these situations I think there are A LOT of people that find themselves in the first category, which makes the paid newsletter model a great way to not only have something to sell your audience, but also something that creates recurring revenue.

Bonus Note: This allows niches that would otherwise have to build around a Media Brand Newsletter model to diversify their income away from strictly being sponsorship oriented. 

We've seen in other deep dives like The Ultimate Guide To Newsletter Types and Styles (scroll to the final section of it), and How To Add A Sponsorship Section To Your Newsletter that sponsorships are not always an ideal business model - and many people go in thinking they make far more than they actually do.

In the first deep dive I mentioned there I quoted Marketing Max of Growth Daily talking about Sam Parr (Founder of The Hustle):

"It's funny because I did so much homework Q4 of last year, listening to every podcast, and the one thing I keep thinking about a lot these days is how Sam Parr said 'If I started another newsletter there would be no ads, it would be other ways of monetizing'...you know, just because ad sales suck".

"Ad sales" in this case is Max referring to sponsorship sales.

As we know, sponsorships not only take a ton of volume (lots of subscribers, and daily emails) to earn from, but also require you to still be in an ideal niche (with high CPMs) and eventually go out and actually fill those slots.

But, before we get too far into the weeds here, let's start making our way into some case studies.

In this one I'll be breaking down awesome creators like: 

• Nicolas Cole
• Dr. Julie Gurner
• Lenny Rachitsky
• Kevin Van Trump
• Heather Cox Richardson

We've seen a few of these creators in other deep dives, but now I will be going into more depth on their specific [paid newsletter] offers, and the "why and how" of them being a good fit for their specific brand.

Quick Timeout:  What Are We Actually Covering Here?

I will NOT be breaking down the specific content style of each of these newsletters and the main focus will be their niche, how they make money with a paid newsletter, and why it's a good fit for them.

 The Van Trump Report

I would be doing you a disservice if I didn't talk about Kevin Van Trump and his paid newsletter: The Van Trump Report.

I want to preface this section by stating that Kevin is absolutely an anomaly here, and the main takeaway I want you to get is: A paid newsletter can be extremely lucrative in different niches if you are the #1 GO-TO authority.

That said, let me share some quick stats: Kevin said they have between 30-40K subscribers paying $60 per month (or $600 a year).

Which is over $20 MILLION dollars per year if you didn't immediately do that math.

Oh, and the best part?

Other than Kevin (and his wife and son helping out), he only has one employee.

$20 million a year, and one employee...🤯

📬 How Does The Van Trump Paid Newsletter Work?

Van Trump is the only newsletter in this deep dive that doesn't have a free version of his newsletter leading into the paid version of the newsletter.

He's an anomaly in multiple different ways.

His newsletter has grown via Trade Shows and referrals.

He's the best at what he does, and he offers a 30 day free trial knowing that he'll be able to convert farmers with the value he provides.

The image above shows what you get with the daily paid newsletter.

Bonus Note: Kevin Van Trump still writes his newsletter. He has ONE employee that helps put together some other resources, but still writes the newsletter every single day.

(You'll see a trend here with some of these paid newsletter writers/creators. They LOVE writing their newsletter.)

 Letters from an American

Next up we have Heather Cox Richardson's amazing daily newsletter: Letters from an American.

Richardson is a professor of American History at Boston College and has been teaching (and writing) about history for over 30 years now.

Back in 2019 she didn't even know what a newsletter was. A graduate student told her she should start one and she said "What the f**k is a newsletter!?" 😂

Now she has the largest following on Substack with 1.5 million subscribers.

Richardson may be another example of an anomaly among newsletter creators/writers, but she is also another perfect example of being the go-to authority within a niche.

She also has no interest in monetizing with sponsorships and other products, and LOVES writing the newsletter - so this model is perfect for her.

Chenell Basilio of Growth In Reverse shares: 

"Heather does not accept sponsorships or brand partnerships, yet from my estimates, she’s pulling in over $1 million per month."

Chenell goes on to break down some earning calculations like this:

• $1 Million a MONTH from Substack paid subscribers.
• Around $200,000 a year as a Professor at Boston.
• $50,000-$100,000 PER speaking event each year.

It's think it's safe to say she's likely not teaching for the money at this point (which Chenell agreed with in her breakdown as well).

📬 How Does Richardson's Paid Newsletter Work?

For this we're going to specifically focus on the $1 million a month from Substack subscribers (for obvious reasons).

Heather's paid newsletter model works like this:

1. Free Daily Newsletter and Podcast
2. $5 A Month (or $50 a Year) for Subscriber-Only Posts, Full Archive, and the ability to Post Comments and Join The Community.

So Chenell's breakdown is working under the assumption that out of 1.5 million free subscribers, if Richardson has even 200,000 paying $5 a month, she's earning $1 million a month.

And yes, you're reading that right and it's not a typo. A million a MONTH.

📬 How Does Richardson Convert Subscribers To Paid?

While Van Trump doesn't have a free newsletter that he uses to drive paid subscribers; every single other newsletter on this list DOES have a free version of their newsletter that allows people to subscriber and get value that leads them to sign up for the paid version.

Richardson writes her daily newsletter and shares the podcast version for free (among with some other resources), and then on her site you'll find a couple small CTAs asking if you'd like to "Upgrade To Paid".

The only other CTA you'll really find to upgrade is if you go to comment on the newsletter you'll be told that you must be a paid member to share your thoughts and join in the conversation; which is probably one of Richardson's strongest CTAs.

Note: As with Kevin Van Trump, Richardson is the one writing her daily newsletter. In this case SHE is the authority. Her subscribers pay to read more and interact with HER.

 Lenny's Newsletter

Next up on our list we have Lenny Rachitsky's newsletter (named very appropriately): Lenny's Newsletter.

Lenny's Newsletter is a great example of a niche and creator that likely could have monetized with digital products and services, but instead went the paid newsletter route that essentially functions as though it's a paid community you may see run by another creator (that doesn't have a paid newsletter).

I'll explain more of what I mean below, but I do also want to mention the fact that Lenny also monetizes with sponsors and a paid job board, but the main focus of this deep dive will be how he runs the paid newsletter.

📬 How Does Lenny's Paid Newsletter Work?

As you can see in the image above, Lenny's paid newsletter is a community.

Lenny charges $15 a month (or $150 a year) for:

• Every issue of the newsletter.
• Access to a private Slack community.
• Access to a curated selection of coaches, resources, deals and more.

And if we also base it on his description in the image above (the bullets I listed were taken from his Substack "Upgrade To Paid" page) Lenny adds:

"Within the community, you’ll find: 

Frank conversations about product, growth, and career 

Book clubs, mentorship programs, live AMAs, and hands-on workshops

Monthly community meetups across five continents and dozens of countries."

Which is probably giving you a pretty good explanation as to why I compare it to a regular paid community you may see from another creator who isn't framing it as a paid newsletter.

A LOT is going into Lenny's upgraded "Paid Newsletter".

📬 How Does Lenny Convert Subscribers To Paid?

Lenny has the same CTAs on his site as Richardson being that they're both on Substack (ie: "Upgrade To Paid" after you're a free subscriber), but he also uses a couple other tactics that aren't hard pushes, but still very effective.

Lenny first has the simple one: the "Community" tab on the menu bar that goes to the page I have shown in the image above and gives a better example of what you'll get when you sign up.

Lenny also drops some small CTAs in his free newsletter, but not quite often, and instead allows his paid newsletter to do the selling. 

Each week Lenny has a "Subscriber-Only Edition" which is for paid subscribers.

Free subscribers can still read a portion of it (they get a teaser that still provides value), but if they want to continue reading and finish the article they get a CTA to upgrade.

Note: Lenny writes a lot of his own newsletter and also hosts his podcast, but also has guest writers come in and share their expertise for subscriber-only editions, really ramping up the value that can be provided in specific sub-niches Lenny talks about.

This works extremely well considering Lenny is not only writing as a thought leader, but also teaching in an extremely broad niche that allows him to bring in other experts and increase the value he can provide through collaboration.

 Ultra Successful

Ultra Successful is Dr. Julie Gurner's newsletter helping people become top performers.

I might be a bit biased here because I'm a massive Billions fan, and right in her social bios she writes: "Compared to Wendy Rhoades of Billions via WSJ." ... but I promise this one is incredible.

While this is yet another example of a paid newsletter being ideal for thought leaders who can become the go-to authority in their specific niche - it is also a great breakdown of taking different approaches to the free to paid model when launching a paid newsletter.

Dr. Gurner is also a great example of someone who is also able to sell high ticket coaching (and other products/services), but loves allowing her writing to be the product.

Dr. Gurner has over 28,000 subscribers right now, and likely converts between 5-8% of them (a good conversion is around 3-5%, but I'm boosting Dr. Gurner up a bit just based on her raving fan-base), which would have her earning over $300,000 a year from paid subscribers.

📬 How Does Dr. Gurner's Paid Newsletter Work?

Dr. Gurner's paid newsletter is either $9.99 a month or $115 a year.

Which essentially makes it a no-brainer considering the coaching she does with top performers costs $8,000 per month.

Here's what you get with her paid newsletter:

1. Weekly deep dives and personal challenges designed to help you level up your mindset, strategy and performance.
2. Exclusive Q&As with Dr. Gurner.
3. Access to the entire Ultra Successful archive.

And I'm telling you right now: If you want to level up your life, Dr. Gurner's paid newsletter is the way to do it.

Yet another newsletter from this list that over-delivers on value relative to the price point.

📬 How Does Dr. Gurner Convert Subscribers To Paid?

Dr. Gurner DOES have a free version of the newsletter, but it is MUCH different than the paid version, and MUCH shorter.

• She sends out "Thoughts Of The Week" which are "Quick Hits" as she calls them, and essentially wraps up and curates some of her top content and things she's thinking about and/or discussing the previous week.
• She also sends out "4 Minute Focus" which is a 4 minute audio newsletter where she discusses one of her past deep dives and gives some additional insights into it.

This is a big CTA, as she talks about the ways she covered the topic in the paid deep dive, and links to it for her audience to get a chance to sign up for paid and get access.

And while she has the regular Substack "Upgrade To Paid" CTAs, of course, I also saw her add a very large CTA recently that I want to add to this list.

On June 24th she shared "The Life-Changing Benefits of Being Boring. [From the Archive - Now with Voiceover]", which she shared:

To celebrate the growth of this incredible community, we are unlocking one of my favorite posts from the archive, “The Life-Changing Benefits of Being Boring,” to be permanently free and launching our first-ever (and potentially only) summer sale, so you can get an additional 15% off your annual subscription to Ultra Successful for the next week only.

If you’re on the fence about upgrading to the paid version of Ultra Successful, this is a great opportunity to test it out for yourself. Dive into the edition below, set aside time to do the weekly challenge, and show up for yourself. This work is rarely glamorous or easy, but — as you’ll read in the edition below — it’s certainly worth it. If you want to listen, click here or scroll to the bottom of the post to tune in.

The reason I want to highlight this is because you CAN add CTAs and discounts for your paid newsletter the same way you would with other digital products and services, and this brings us right into our next newsletter which we'll see even more of this.

Final Note: Dr. Julie Gurner is THE authority. So she is the on we're hearing from with her newsletter and 4 minute audios. She is writing the newsletter, it's coming from her voice, and that's why we pay for it. 

 Write With AI

The next newsletter on our list is Nicolas Cole and Dickie Bush's AI newsletter: Write With AI.

I really love this example because Nicolas Cole and Dickie Bush have made millions of dollars with "regular" newsletters, but now make over $200,000 a year with their Write With AI newsletter that is built around a paid model.

To dive slightly deeper into what I mean by that is: They also have newsletters that are more of the typical "Creator Newsletter" Business Model we learn about in my deep dives; making millions with digital products and coaching like eBooks, courses, cohorts, and even evergreen group coaching.

But their Write With AI newsletter is built around letting the writing do the selling and being the product itself, and it is proving to be extremely lucrative for them.

Quick Note: Cole and Bush may have been able to turn this into a more Creator or even Hybrid Newsletter business model, but the model they went with allows for the selling to be much more hands-off and in turn be a bit of a side project for them.

📬 How Does The Write With AI Paid Newsletter Work?

One thing you're going to notice with the Write With AI newsletter is that it's similar to Lenny's Newsletter in the sense that the "paid" portion could also essentially be considered digital products as well (which is what I was alluding to just before this section).

Here's what you get when you upgrade to paid:

1. Subscriber-Only Posts and Full Archive
2. Free access to ChatGPT and AI Writing Paid Workshops ($1000 Value)
3. Instant access to our entire ChatGPT Prompt Vault ($5000 Value)

As you can tell by the way I added the values and phrasing of the perks you get, this is a copy-paste from how Cole and Bush are describing it for their audience.

📬 How Does Write With AI Convert Subscribers To Paid?

Cole and Dickie already have massive followings in the writing space that allow them to funnel organic traffic to this newsletter, so they don't have to put a massive focus on repurposing their content and running an absolutely invaluable free version of the newsletter, BUT, I really like the way they use some of their CTAs.

If you look back to the list of items you get by upgrading to paid, you can see they are tacking on bonuses that are outside the realm of their paid newsletter (which is similar to Lenny).

This is already a bonus, but then they also have more CTAs to help convert.

They send out a free version of the newsletter a few times a month, providing value and also adding occasional CTAs to not only sell the paid portion of their newsletter, but also other courses that they sell from their personal brands (like Ship 30 For 30, for example).

Then, on top of this, they also have their "Products" tab on their menu bar that brings up the page I'm showing in the image above.

Their "Products" are past paid newsletters that are breaking down specific topics in depth that their audience can click into, get a short teaser of, and then decide to subscribe for if they're like.

I think, again similar to Lenny's Community Tab, this is one of the more powerful CTAs they are using to convert free subscribers to paid subscribers.

 Should You Launch A Paid Newsletter?

This is the point where we decide whether or not a paid newsletter is good for YOU.

For the larger percentage of you, the answer is probably no.

But there are the outliers that will be a perfect fit for a paid newsletter that need to know WHY and HOW they should be launching.

By now you should have a pretty good idea of the WHY you would want to start a newsletter, but we'll do a quick recap: 

• You are in a niche that isn't ideal for selling digital products.
  • Good examples of this would be Van Trump and Heather Cox Richardson.
• You want to let your writing be the main "product" and okay with potentially leaving money on the table by not focusing on selling digital products and services like eBooks, courses, cohorts, and coaching.
  • Good examples of this are Lenny, Dr. Gurner and Write With AI.
• You want to come in as a thought leader in your niche and either of the top two apply.

And you should also be walking away with a bit of knowledge about HOW to start your paid newsletter, but we'll also do a quick recap there as well: 

• You can let the writing be the product.
  • A good example of this are both Heather Cox Richardson who simply offers access to commenting and community, and Dr. Gurner who locks the paid aspect entirely and gives overwhelming value behind the pay wall.
  • Note: The one exception here is that Dr. Gurner also throws in bonus Q&As.
• You can build on the paid version of the newsletter as though it was a "regular" digital product like a community or other digital products.
  • A good example of this is Lenny's community and Write With AI's product attachments to the paid addition(s).

All of the newsletters I mentioned above (with the exception of maybe Van Trump who may be just too much of an outlier) are a great place to start if you're looking to do a deeper dive into how they structure their newsletter content and make it flow with their paid version.

You'll find that each one of them has their own flow, and (as we saw above), their own way of making it an offer their audience will want to purchase.

At the end of the day (as I teach with most other things when building our freedom businesses) it's going to come down to:

• YOUR niche/obsession.
• YOUR ideal media type.
• YOUR preferred offer stack.