How Ben Thompson Got 40,000+ Paid Newsletter Subscribers
Author’s Note: Before watching today’s video, I recommend reading the post first so you can get the most from the video lesson.
Ben Thompson started his $12/month, one-man newsletter, Stratechery, in 2014. Today, he has an estimated 40,000+ subscribers. Doing the math, this means that he’s likely:
Making $5M+ per year
To create four posts per week
Earning ~$28,000 per post
Which makes him the most financially successful article writer in the world!
I subscribed to Thompson’s newsletter in 2015, and I’ve been reading it religiously ever since. Thompson is the #1 inspiration for me launching this newsletter, and I’m not alone. The founders of Substack say that Thompson was a major inspiration for the original idea.
Thompson has done surprisingly few interviews about his newsletter model, so this clip and the larger interview in which it appears is a rare treat from him.
He has a lot of amazing strategies we can all learn from, but I think this clip holds the biggest one…
Thompson’s Video Lesson Contains The Holy Grail For Creating High-Quantity, High-Quality Content
There are two schools of thought when it comes to creating content:
Adherents to quantity first think it’s good because it:
Builds a habit for your audience to view your content.
Gets you more traction on newsfeed algorithms that want more content.
Helps you get faster at creating content through repetition.
Helps you avoid perfectionism.
Keeps you top of mind with your audience.
Helps you maximize luck (ie - something unexpected becomes a hit).
Adherents to quality first make the case that quality is good because it:
Helps you gain traction. What’s the value of consistency if no one reads you?
Helps you leave a legacy and not just add to the noise on the Internet.
Helps you create viral blockbuster hits that create true fans.
Helps you improve faster, because you’re constantly pushing the limits of your skills rather than hitting a plateau from doing the same thing over and over.
Each side trashes the other.
Quality people accuse quantity people of creating mediocre content and running on a hamster wheel just to stay relevant.
Quantity people accuse quality people of being perfectionists who don’t publish enough.
One of the things that make Thompson unique is that he creates high-quantity and high-quality content. Put differently, he’s able to create four posts per week (quantity) while creating content that’s so good that tens of thousands of people pay him (quality).
Thus, he’s able to get the best of both worlds. He’s found the holy grail…
This is a big deal, because there is typically a tradeoff between quantity and quality. The more time you spend on any one post, the less time you have for other posts.
Today, I break down Thompson’s video lesson so that you too can create high-quantity, high-quality content. I’m also going to share my hard-won lessons on the topic.
With that said…
Here’s Today’s Game Plan
Case Study: I break down Thompson’s career to give context to his strategy.
Video Clip Breakdown: I break down what Thompson says in the clip and leave you with four key takeaways:
Key #1: Learn the most useful and universal mental models in order to become an “instant genius”.
Key #2: Use mental models in three ways in order to write 3x more (for paid subscribers).
Key #3: Update your mental models by disproving them in order to become smarter and more trusted (for paid subscribers).
Key #4: Create short posts as you research your longform articles (for paid subscribers).
But, before I jump in, it’s worth giving you a little more context on Thompson’s journey…
Case Study: Ben Thompson’s Journey To Success
Born 1979-ish (estimated)
Polymath. Thompson has been passionate about writing, technology, and business for his whole adult life.
Multiple Masters Degrees. He earned an MBA and MEM (Master’s in Engineering Management) from Northwestern University.
Writing Experience. He wrote for his school newspaper and had a tiny blog he gave up on.
Work Experience. He interned at Apple University, worked at Microsoft, and worked at Automattic.
Stratechery Newsletter History
Founded Stratechery in March (see first post).
Worked on Stratechery part-time while working for Automattic (company behind Wordpress).
Saw the opportunity. Describing the hole in strategic analysis of tech news at the time, Thompson said the following when he launched: “There are lots of (great!) sites that cover the day-to-day [of tech]. But I think there might be a niche for context. What is the historical angle on today’s news? What is happening on the business side? Where is value being created?”
Blog was free for readers (Automattic had a strict no second income policy).
Publishing schedule. Published two posts per week. The reason he kept the output low is that when he transitioned to the paid version, he wanted to make sure that the paid subscribers would get more posts than free subscribers.
February: Launched Exponent.fm podcast to do a weekly podcast convo about that week’s posts.
April: Quit Automattic, went full-time into Stratechery, and launched a paid version of the website.
Email Newsletter: Because he had to stitch together all of the tech, it was buggy. Thus, the initial paid subscribers couldn’t log in. Therefore, he sent the first post to all of the paying subscribers via email. Email ended up working great, and he kept it. Thus Stratechery actually became an email newsletter by accident.
Three plans: Thompson originally launched with three plans—$50/year (community), $100/year (community + posts), and $300/year (community + posts + calls) per year. He would later simplify things to just the $100/year plan. He stopped doing the calls because they weren’t scalable, but because they were higher ticket, they were a critical revenue source for him at first. He stopped investing so deeply in the community, because he didn’t enjoy it as much as the posts.
Publishing schedule. Two free articles per week / Five paid posts per week.
October: On track to make a 6-figure salary based on monthly recurring revenue.
November: Passes 1,000 subscribers seven months after launching the paid newsletter.
February: Reaches 2,000 paying subscribers ($200,000+ per year).
Publishing schedule: Settles on 4 posts per week (1 free + 3 for paying subscribers only) format, which was more sustainable for him to produce than five per week.
Starting around 2020, Thompson jumped into podcasts.
He turned all of his posts into an audio podcast that he reads. In an interview, he said that about 50% of subscribers now listen to his content rather than read it.
More recently, he added several other podcasts (Dithering, Sharp China, Greatest Of All Talk) as an additional benefit for Stratechery paid subscribers, and he increased the monthly membership price from $10/month to $12/month.
With that context set, let’s break down Thompson’s video lesson…
Video Breakdown: 4 Keys To Ben Thompson’s High-Output, High-Quality Writing
SECTION SUMMARY Key #1: Learn the most useful and universal mental models in order to become an “instant genius” Key #2: Use mental models in three ways in order to write 3x more (for paid subscribers) Key #3: Update your mental models by disproving them in order to become smarter and more trusted (for paid subscribers) Key #4: Create short posts as you research your longform articles (for paid subscribers)
Key #1: Learn the most useful and universal mental models in order to become an “instant genius”
The first sentence of the clip says a lot…
I have this model of the world. [Articles] pass through the model.
Later in the clip, the interviewer summarizes what Thompson says about mental models…
So Ben, it sounds like your process is:
1. You have a great memory
2. You remember all these facts
3. You have a bunch of existing frameworks in place of how you think about things.
So you're able to pass any news as it comes through, or any strategic decision that happens, through those frameworks, and [you're] able to operate pretty quickly, and you ruminate on a bunch of different ideas and build on top [of them] to come to things like Aggregation Theory as you sort of are noodling them.
In other words, Thompson has spent years consciously collecting, creating, and stress-testing mental models of how the technology business works.
This is one of his secret weapons.
Because he has these refined mental models of the world, he can look at the same technology news as everyone else and have a different and valuable perspective.
Mental models are frameworks that explain the cause-and-effect relationships of how a specific domain works. The more accurate our model of a domain is, the more efficiently and effectively we can:
Predict the future.
We all unconsciously carry around mental models. For example, if I asked you to close your eyes and walk to the kitchen from where you are, you could, because you already have a mental model of your house in your head. Similarly, we also carry around conceptual mental models of our industry.
Even just one really powerful mental model can make our entire career. And Thompson has a few models that he consistently goes back to over and over in order to explain the technology industry:
Aggregation Theory (model he created)
The Law of Conservation of Attractive Profits
Quantity vs Quality Takeaway: The beauty of mental models (and timeless knowledge in general) is that while it may take you years to learn, it only takes you seconds to recall and minutes to explain to someone else. And you can use it forever. This provides one explanation of how Thompson is able to get both quantity and quality. He invested time into learning key mental models and created a system to recall what he learned. Now, he can reuse that knowledge rapidly over and over again.
Personal Story: I learned about the power of mental models in 2014. In 2015, I wrote How One Life Hack From A Self-Made Billionaire Leads To Exceptional Success on Forbes to summarize my lessons learned. In 2018, I came to the conclusion that learning the most useful and universal mental models was one of the best things I could do for my future career as a thought leader. So, I created the Mental Model Club in order to go deep on one new mental model every month.
Having a large basket of mental models is one of the things that has given me the confidence to create this newsletter. More specifically, I’m confident that for every video clip I find, I can extract useful and nonobvious insights because of my past mental model collecting.
Spend a lot of time learning the most useful and universal mental models. I made a list of some of the most useful and universal mental models in This Is Exactly How You Should Train Yourself To Be Smarter [Infographic]. Thompson spent years before Stratechery being super passionate about, going to school in, and working in technology, business, journalism, and engineering. This gave him a unique mix of mental models.
Develop a system to memorize and store what you learn. Thompson’s blog serves each of these purposes. By writing down his thoughts, he not only creates a permanent store of his thoughts that he can reference in the future, he also leverages the power of the Explanation Effect, which improves his memory.