Writer Career Path #4: Newsletter Writer
An emerging career path for writers who have a lot to say about a specific topic.
Dear Writer,
So you want to be a Newsletter Writer?
Digital newsletters have been around for a long time—longer than most people realize. According to computerhistory.org, the very first newsletter online was published in 1977. It was called “EMMS; Electronic Mail and Message Systems: A twice monthly newsletter covering technology, user, product, and legislative trends in graphic, record, and microcomputer communications.” And it ran until 2001.
The newsletters that are successful today aren’t too different. They pick a specific topic. They make a promise to their readers. And they keep that promise, and explore that specific topic, week after week for a prolonged period of time. The scale of the Internet has grown. The technology has improved. But the value exchange between writer & reader is the same as it always was: “You give me your attention, and I give you information.”
However, it’s only been in the past few years that earning a full-time living writing & publishing a weekly (or monthly, or daily) newsletter has become a viable (even lucrative) way to earn a living. That’s because the predominant business model for newsletters has always been to monetize the “attention” and run ads. But in the late 2010s, technology platforms like Stripe (to accept payments) and Substack (to easily paywall content) lowered the barrier to entry and unlocked a new business model for everyday writers & creators:
Paid subscriptions.
Here is how I classify the differences between free & paid newsletters:
Free Newsletters: A free newsletter is the engine that powers a larger business. Ads are rarely the only revenue stream. These writers/creators also monetize by selling digital products like eBooks and courses, as well as services like coaching programs, consulting packages, etc. The free newsletter is the entry point to these other monetization vehicles.
Paid Newsletters: A paid newsletter is the business itself. Readers pay for access to the content—making the paid newsletter sort of like an evergreen eBook that gets more valuable over time (and you never want to stop reading). These writers/creators may monetize in other ways too, but their paid newsletter is their core business.
For the sake of clarity, I am going to categorize “free newsletters” as a piece of the Writerpreneur career path—because this is the predominant engine that powers all their other businesses. Whereas the Newsletter Writer career path, and being able to charge for access to your content, is a completely different game.
Anyone can start a free newsletter.
But not everyone’s free newsletter has the potential to go paid.
The Art Of Newsletter Writing
The paid newsletter category was pioneered by the The Agora, a publishing company founded in 1978 by Bill Bonner. You don’t need to know much about Agora except that it is the largest publishing company you’ve never heard of—with 13 US-based subsidiaries, 9 non-US based subsidiaries, and 120+ paid newsletters that lead to hundreds of different products and services. It’s a privately held company so financials aren’t public, but it’s estimated that Agora does anywhere from $500 million to $1 billion in yearly revenue.
Agora’s sweet spot is finding industry experts, positioning them as thought leaders in their industry, and then helping them launch niche paid newsletters to “scale their insights”—specifically in the category of Finance.
And it all can be distilled down to one very simple equation:
Industry Expert + Unique Point of View = Successful Paid Newsletter
Today, this “winning combination” can be seen everywhere in our now digital-first Creator Economy.
Almost every single top paid newsletter on Substack—the company that has provided the tools for any writer or creator to now paywall their content and deliver it via email—is by a writer (or team of writers) with some sort of credibility in their chosen niche + a unique perspective on that niche topic.
Let’s break both of these parts down so you have a firm understanding of why this winning combination is so important in the world of paid newsletters:
Part A: The Credibility
Credibility is subjective, and largely in the eyes of the beholder.
For example: for the first 5 years of my career writing on the Internet, the badge of credibility I leveraged (over and over again) was that I was a Top Writer on Quora. Did anyone know what that meant? Not really. Back in 2014 and 2015, Quora was a little-known social Question & Answer website. Being a Top Writer was a far cry from being a New York Times best-selling author or columnist for The New Yorker. And yet, it didn’t matter. Every podcast I went on, or anytime some other blogger referenced my work, they would introduce me as “Nicolas Cole, a Top Writer on Quora.”
You do not need to be Oprah Winfrey or Tony Robbins to start a paid newsletter. All the reader needs is a small bit of context as to why they should listen to you—and that reason could be something as simple as: “Because I’ve done it” or “because I’ve lived it” or “because I’ve read 100 books on it.”
Your credibility could literally be anything:
“I have a degree in this topic.”
“I have built a company in this industry.”
“I have worked for companies in this industry.”
“I have written a book about this topic” or “I was/am a columnist for a major publication where I frequently write about this topic.”
“I have experienced this topic first-hand.”
Etc.
The analogy I like to use here is: imagine you’re at a dinner party and overhear someone talking about real estate. You walk over, drink in hand, and say, “I’m actually thinking of buying my first rental property.” Their eyes light up and all of a sudden they start telling you all sorts of things you should do, mistakes to avoid, tips to find a good tenant, etc. They’re so helpful! But you’re curious… “How do you know all of this?”
That’s when they say, “Oh, I’ve been buying rental properties for 5 years. I have over 50 units now.”
You now perceive them to be a trusted source of information.
They don’t need to be the most successful real estate entrepreneur in the world. They don’t need to be a best-selling author or influencer with a gazillion followers. All you needed to know was that they had done the thing they are now telling you how to do.
Part B: The Unique POV
Everyone loves to put all the emphasis on "The Credibility,” but the truth is, it’s the part of lesser importance.
It matters, but not nearly as much as Part B: The Unique POV.
Credibility, in and of itself, is a leading indicator. It’s based on the past and what you’ve done “historically.” But leading indicators aren’t always trustworthy signals of the future. Just because someone has built a successful company doesn’t mean their forthcoming book is going to be any good; just because someone has built and exited one startup doesn’t mean their next startup is going to achieve the same outcome; and just because someone went to a good school, worked a high-paying job, or received an award doesn’t mean they are going to do great things in their future. (We all know that kid from high school who got straight A’s and scored well on their SAT/ACT and now works an average job.)
Your Unique POV is the opposite: it’s a lagging indicator of your future success. It takes time for readers to get introduced to your perspectives and insights. Which means someone with “more credibility” might get more attention or approval in the short term (your mom probably pointed to that kid getting straight A’s in high school and said, “He’s going to do great things in life!”), but if your Unique POV is compelling, helpful, and valuable, you will lap them in terms of output once that quality is recognized by more and more people.
Which is the entire “art” of newsletter writing.
Case Study: Stratechery by Ben Thompson
A great example of how these two pieces—Credibility & Unique POV—work together is Stratechery, a paid newsletter about the technology industry by Ben Thompson.
Ben’s bio reads: “I’ve worked previously at Apple (interned), Microsoft, and Automattic, where I focused on strategy, developer relations, and marketing for Apple University, Windows, and WordPress.com. I attended undergrad at the University of Wisconsin, received an MBA from Kellogg School of Management with a focus on strategy and marketing, and an MEM from McCormick Engineering school in Design and Innovation with a focus on human-centered design.”
Now, how many people are there in the world like Ben? How many people have an MBA and have worked at a big technology company at some point in their careers?
Half a million? A million people?
The point is: Ben’s credibility isn’t what made Stratechery into the success story that it is today. Ben’s credibility was mostly a formality—a “checkmark” in the reader’s brain to make sure he was a somewhat trusted source of information.
What made Stratechery successful was Ben’s Unique POV and his ability to provide detailed, thoughtful analyses on the technology industry—something a lot of people with MBAs like to believe they can do, but either can’t or don’t prioritize in their busy careers. His research is thorough. His takeaways aren’t conventional wisdom. And his insights, to the right readers, are invaluable.
Today, it’s estimated Stratechery does over $3,000,000 in yearly revenue from paying subscribers alone.
That’s a whole lot more than most people with MBAs make working at large tech companies!
The Newsletter Writer Career Path
Newsletters have no social hierarchy.
Anyone can start a newsletter—including your mom, dad, uncle, or college roommate.
Which is why, of all the career paths, becoming a Newsletter Writer (even if it’s paid) is fairly low status. Ben Thompson earns more from Stratechery each year than most Pulitzer Prize-winning novelists earn over their entire careers—and yet he is significantly lesser-known.
But what paid newsletters lack in status, they more than make up for in financial upside:
It’s significantly easier to earn $100,000+ per year with a paid newsletter than writing and selling books.
Paid newsletters are subscription revenue, whereas books and other products are one-off revenue—making your business more defensible and your income more predictable.
And with a paid newsletter, your library of content becomes more valuable over time—increasing the likelihood of new readers wanting to subscribe, which creates a flywheel for growth.
So, while becoming a Newsletter Writer probably isn’t going to get you mainstream notoriety, when executed correctly your paid newsletter can become the ultimate lifestyle business.
Here’s what the career path looks like:
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