how i would fix Pomp’s flagship newsletter: The Pomp Letter
good morning media folks ☀️
When you think about shifts from media to personalities, Anthony Pompliano is one of the first people that come to mind. He’s built an incredibly successful business and has been a supporter of crypto (specifically Bitcoin) before it became mainstream.
He was also at the forefront of building a media company around one person... not a brand. He has nearly 300k email subscribers and his newsletter continues to grow... including paid subscribers and a growing podcast.
But the editorial and content have gone pretty downhill over the last year. Tons of link dumping, podcast and YouTube video promotions, and not very much evergreen editorial... and frankly it feels thrown together last minute.
Look at the difference between a newsletter in 2020 and 2024:
2024:
2020:
Now this happens. Priorities change, people change... and businesses change.
I’m not saying it’s a bad newsletter. I’m just saying that it’s gone away from its roots. So today we will talk about how I would fix it: from design, monetization, content strategy, voice, and how he can engage his community better.
a quick bit about The Pomp Letter
Pomp started his newsletter in 2018. And the sole purpose was to demystify Bitcoin and its applications. The primary motivation was to make complex financial information more accessible and easier for a broad audience to understand. He initially used it to clarify his thoughts, but then it took off. Reaching nearly 30M readers annually. And his audience started boasting legendary investors, CEOs, and the average retail investor.
The content was superb because it focused on recent trends, insights from private conversations with industry leaders, and Pomp’s perspectives on navigating the Bitcoin landscape.
But in 2024 he announced an expansion into traditional finance which was a head-scratcher. He’s consistently been against Wall Street over the years. Now the expansion doesn’t necessarily involve The Pomp Letter... he decided to launch a new newsletter called Opening Bell Daily. Which I understand... growth happens. But it’s affected the content and the direction of his flagship newsletter. And has deviated from the original mission.
starting with design
His newsletter runs on Substack. And Substack is very limited in what you can do with design. You can’t really customize what you’re newsletter looks like compared to other platforms. But you can fix the small details that can make the newsletter feel cleaner and more aesthetically pleasing.
First, we will start by adding a new header image. One that creates more brand awareness for each newsletter. Each header image will be customized based on what the newsletter will be about, giving each newsletter some personality.
new header image:
The next thing we will do is fix the dimension on the Podcast plug. It feels fractured, and the dimensions aren’t clean, making it look awkward in the newsletter.
here’s what the old version looks like:
here’s what the new version would look like:
monetization
There is so much great real estate that we can use to drive paid users and support Ad products.
If you look at the blurb to drive paid users, it’s not interesting and doesn’t tell me or make me want to pay for the newsletter.
You could make it more enticing by adding some newsletter issues that you might have missed by only subscribing to the free newsletter. Here, in this case, we will add some social proof to increase conversions and get people to click on this.
here’s the old version:
here’s the new version:
We have to remember that the free newsletter is top of the funnel and the prime driver of paid subscribers. So we need to treat it as such.
Next, we need to stop link dumping. ASAP. It hurts deliverability, doesn’t create a great Advertising experience, and is a deterrent for clicks. Instead of highlighting every single podcast sponsor we’ve ever had, we can highlight a few and write some strong Ad copy to increase conversion.
The preference here is to highlight one sponsor for each newsletter. The reason you want to do this is you don’t want to create choice paralysis. People may click, but they probably won’t buy when you have too many options.
I usually use 3 pillars for my Ad copy:
- audience interest - writing ad copy based on survey and demographic data from your audience
- getting personal - telling your personal experiences with products, using storytelling to form the Ad
- social proof - using your reader's experience in the Ad copy, to create a sense of community around the product
build community
This is one of the biggest mistakes newsletters make. They don’t engage their readership. I’ll never understand why because it’s so easy. And Substack has a commenting feature designed for this. Pomp gets some comments, but it doesn’t look like he replies much and doesn’t initiate too much conversation. And it’s got spam all over.
The way we can approach this is by creating blurbs to initiate some form of conversation. About the topic, readers' opinions, and more.
This is one of the easiest ways to get people to sign up for paid. He may already do this for his paid subscribers, but doing this for your free subscribers can result in some serious cash.
And he can do it for advertisers too. Things like “Hey! Curious if anyone has used XXX product before. Comment and let me know your thoughts.” And boom. Now you have some social proof for your next Ad with that product.
here’s what an Ad looks like now:
here’s what it could look like:
editorial & voice
Right now, his newsletter feels thrown together, last minute, is often shorter, and talks at you not with you. That’s far and away different from the way he used to present his editorial. In this case, his past editorial was great. It felt like a 1:1 conversation, and that Pomp was in a coffee shop sharing a conversation with you.
I would go back to his old style. His current style is dull. And it’s probably hurting his engagement numbers (open rates, clicks, etc...)
I understand that long-form content is tough to consume, but if you have a voice already, you don’t want it to drown out too much by using AI generators or cookie-cutter copy. You can tell it’s not “write like you speak” language.
And this part is so important because again, this is the top of the funnel and the most important driver for revenue (the free newsletter). Just because it’s free, you can’t neglect it because it’s what got you here today.
The point here is to be audience-centric. Newsletters forget that there's a person on the other side of the computer and it should still be treated that way no matter how big you get.
Small thoughtful tweaks can make all the difference.
see you soon,
shaan
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