How Stratechery founder Ben Thompson built a one-person newsletter that generates about $3 million and became the envy of journalists
Stratechery founder Ben ThompsonStratechery
Thompson's daily newsletter is beloved in Silicon Valley. By one estimate, his solo enterprise will make more than $3 m...

How Stratechery founder Ben Thompson built a one-person newsletter that generates about $3 million and became the envy of journalists

Thompson's daily newsletter is beloved in Silicon Valley. By one estimate, his solo enterprise will make more than $3 m...
  • Founded in 2013, Ben Thompson's $120-a-year Stratechery newsletter is beloved by tech executives and venture capitalists in Silicon Valley and reaches subscribers in more than 80 countries.
  • By one estimate, Thompson's solo-media enterprise is expected to generate more than $3 million in revenue this year.
  • Yet as a raft of big-name writes leave their jobs to start their own newsletters via the "pivot to Substack" trend, Thompson's success will be difficult — if not impossible — to replicate.

Primarily working out of Taipei, Taiwan, Ben Thompson sits some six thousand miles away from his adoring fanbase of techies in California.

His Stratechery newsletter reaches subscribers in more than 80 countries, but his most rabid readership is in Silicon Valley where has built a large following of tech executives and venture capitalists including Upfront Ventures' Mark Suster and Facebook top brass Andrew Bosworth. The co-founders of newsletter platform Substack even cite Thompson as the inspiration for starting their business.

Thompson's prolific daily analysis covers the intersection of technology, business and society and digs into companies ranging from Apple to Zendesk. Often accompanied by hand-drawn doodles, Thompson's missives are focused around catchy concepts like "aggregation theory" and "disruption theory."

Thompson has said one of his favorite published pieces was a 2013 take on what his "intellectual hero" Clayton Christensen, the late academic who came up with the business theory of "disruptive innovation," got wrong.

For $120 a year, or $12 a month, subscribers get access to the daily update and its archive of articles. Fans can also pay $5 a month or $50 a year to subscribe to the "Dithering" podcast, which he co-hosts with John Gruber, author of the popular tech blog Daring Fireball. Thompson also pumps out one free article a week to lure in potential new members. By one unofficial estimate, Thompson's newsletter is on track to rake in over $3 million this year.

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Thompson is perhaps an unlikely leader of the solo newsletter pack. By contrast to the recent raft of writers leaving salaried journalism jobs to create their own individual media empires — Casey Newton from the Verge, Matt Taibbi from Rolling Stone, Emily Atkin from The New Republic, to name a few — Thompson has never been on the masthead of a newspaper or magazine.

The "ethics statement" on his site says he hasn't taken "consulting or speaking arrangements" with the companies he covers since 2016. And unlike many big-name tech thinkers, he rarely schmoozes on the conference circuit.

"He's found this perfect spot in between [sectors] where he has a refreshing outside perspective," said media analyst and Stratechery subscriber Thomas Baekdal.

Thompson rarely grants interviews, and declined to participate in this article.

"I have been fascinated by the technology industry from a young age, and feel very fortunate that the same forces I am interested in writing about have also made my business possible," Thompson emailed. "While I am honored that you are interested in writing about Stratechery, my focus continues to be on the arguments and analysis, not publicity for myself."

Thompson may well be one of the most lucrative one-man newsletter outfits, but as other writers flee their salaried jobs to start their own, they'll find his success hard — if not impossible — to replicate.

From humble beginnings to a newsletter nobleman

Born in Michigan and raised in what he has described as a blue-collar upbringing in Wisconsin, Thompson graduated with a BS in political science from the University of Wisconsin-Madison, where he contributed to The Badger Herald student newspaper.

He went on to spend six years teaching English in Taiwan, where Thompson met his wife. They now have two children.

He gained an MBA from Northwestern's Kellogg School of Management, focused on marketing and strategy, and an MEM in design and innovation, and many of his bigger-picture themes are rooted in business school concepts.

Thompson spent a relatively short time actually working in the tech industry that he writes about so prolifically, first as an intern at Apple University in Cupertino, then as a product manager on Microsoft's Windows app team in Redmond, Washington, for about two years. He founded Stratechery in 2013, while employed as a growth engineer for WordPress.com owner Automattic.

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Thompson was relatively unknown on the tech and strategy scene when renowned tech blogger John Gruber — who Thompson has said was one of the inspirations to start Stratechery — gave one of his posts ("Apple Rejects Google Now; EU to Investigate") a shoutout on the Daring Fireball blog.

"I went from 500 to 1,500 Twitter followers in a day," said Thompson in a Q&A on the tech website ProductHunt three years ago. Stratechery's paid-for daily update newsletter was introduced the following year; the annual price was increased from $100 to $120 in 2019.

A vital weapon in the Silicon Valley toolkit

Some Stratechery subscribers say the newsletter and the vast archive of content have not only become part of their daily morning routine, but fundamental to the way they do and think about business.

Keith Rabois, the famed venture capitalist, claims to have been one of the first "three to 50" people to sign up to Stratechery and has met Thompson in person "a few times" over the years. The newsletter, Rabois said, has shifted his perspective on subjects like net neutrality, where Thompson took a more nuanced view to much of Silicon Valley.

How Stratechery founder Ben Thompson built a one-person newsletter that generates about $3 million and became the envy of journalists
Founders Fund General Partner Keith Rabois.Steve Jennings/Getty Images
Rabois, currently general partner at Founders Fund, said he filters prospective interview candidates based on whether or not they read the newsletter.
It shows you're intellectually bankrupt if you're not reading it. – Keith Rabois

In venture and tech, "it shows you're intellectually bankrupt if you're not reading it," said Rabois during a Zoom video call with Business Insider. "You really cannot compete if you can't understand the concepts described in Stratechery."

When Rabois was single, he'd even send Stratechery articles to his dates.

But, he added with an impish grin, "It was more successful with my chiefs of staff."

Calling out the 'Kool-Aid'

Not everyone has their flag planted firmly in Thompson's camp.

In an October blog post "Ben Thompson's 'Stratechery' Smart, but a little too much Kool-Aid," Tim Wu, Columbia Law School professor and author of the books "The Master Switch" and the "The Attention Merchants," questioned Thompson's record and expertise in writing on antitrust.

"Stated simply, I'd say he's inducing his readers to drink too much of his 'aggregation theory' Kool-Aid, as opposed to encouraging them to think more broadly or read more deeply to understand a slightly messier reality than he presents," wrote Wu.

How Stratechery founder Ben Thompson built a one-person newsletter that generates about $3 million and became the envy of journalists
Tim Wu, the tech expert popularly known for coining the term "network neutrality."AP Photo/Mike Groll

Thompson coined the phrase "aggregation theory" as a framework to describe how the internet giants have dominated and disrupted their industries. Aggregators — which Thompson says include Netflix, Uber, Google and Airbnb — share three common characteristics. 1) They have a direct relationship with users. 2) They incur no marginal costs for serving users. 3) They can be described as "demand-drive multi-sided networks with decreasing acquisition costs."

Thompson responded to Wu with a blog post of his own, critiquing some of Wu's arguments and disagreeing with the "caricature" that he applies his aggregation theory to everything to boost the brand.

Not entirely convinced, Wu replied with a "Part 2," asserting once again that while Thompson's work is insightful for understanding tech business models, "when it comes to antitrust, it is on much shakier ground."

Thompson didn't continue the back and forth.

Wu told Business Insider over email that while he enjoyed the exchange overall, he was surprised by how "fanboy loyal" the Stratechery army of followers is to Thompson, judging by some of the responses he received on Twitter.

"It felt as if I'd dared criticize World of Warcraft, or dared question the church of aggregationology," said Wu.

Thompson himself admits he's not infallible. He recently stated on Twitter his aim "is to get stuff right in the long run, which usually entails some degree of getting it wrong in the short run and subsequently changing course."

Still, a successful hit rate doesn't hurt.

"I've come to put Ben into the category of someone who has been mostly right over time, which given the amount of content he generates is pretty remarkable," said Frank Shaw, corporate vice president of communications at Microsoft.

Can Thompson's success be replicated?

Those following the Substack gold rush might see the newsletter route as an easy way for an established journalist to make a living by going solo — or at the very least, shedding the baggage and overhead of a traditional publisher.

Substack's most popular paid newsletter, The Dispatch, a conservative news organization founded by Jonah Goldberg, Steve Hayes, and Toby Stock, told TechCrunch in March it was on track to generate more than $1 million in revenue this year from its $100-a-year subscription, which offers access to newsletters, events and conference calls with its team.

Almost all of Thompson's income is derived from his subscribers, according to his Ethics page. He last publicly disclosed his newsletter subscriber numbers in January 2015, when he said Stratechery had 2,000 paid memberships. Germany based product manager and tech blogger Andreas Steggman extrapolated that Stratechery would have just over 26,000 paying subscribers as of May this year.

This somewhat correlates with a datapoint that used to be publicly available on the The Stratechery Forum — for which each paying subscriber is automatically assigned a username — which stated in February there were 25,189 members.

How Stratechery founder Ben Thompson built a one-person newsletter that generates about $3 million and became the envy of journalists
An estimate of Stratechery's active subscriber growth.Andreas Stegmann

Factoring in Dithering — the co-hosts estimated the podcast had 6,000 subscribers in June this year — Stegmann estimated Thompson would be on track to generate more than $3 million in revenue in 2020. Thompson has never got in touch to confirm or correct the figure, Stegmann said.

Stratechery benefits from having a clearly defined focus in tech analysis and an audience that is more than willing and able to pay for information they think might give them an edge at work.

"It's the cheapest course in any business school in the world," said Business Insider alum and former Recode editor-in-chief Dan Frommer, a Stratechery subscribe. He cites Stratechery as an inspiration for his own business, The New Consumer, a website and newsletter about the intersection of technology and consumer brands. It is monetized entirely through paid memberships that start at $200 a year, or $60 a quarter.

"I saw Ben Thompson and I said, 'OK, this model makes sense'," said Frommer. "I don't need to be Ben, I just want a model that works for me and the math is simple: Get a couple thousand people to pay you a couple hundred dollars a year and you're in good shape."

Plus, Thompson's appeal extends beyond tech — not least as he mostly writes about large public companies.

"Anyone at a mutual funds manager, or a hedge fund, if they can get a tiny nugget of insight that they wouldn't get from a piece of sell-side research, they only need to read one insightful line in three years in order for [their Stratechery subscription] to pay for itself," said Axios chief financial correspondent and Stratechery reader Felix Salmon.

But anyone looking to mirror Thompson's success will be entering a crowded and competitive space while facing the prospect of newsletter fatigue. Take Alex Bazin, a UK-based technology strategist. Aside from a subscription to National Geographic magazine, Stratechery is the only other written content pays to read.

"I know with Stratechery that I get some work-related value out of it and some personal value and though I don't expense it, I think it's [a justifiable expense]," said Bazin. "That's going to be the tough thing for everyone following [with other subscription newsletters]: For the average consumer, how many subscriptions are they going to be prepared to pay for?"

Thompson's distinctive voice and personal touch are also key to his appeal.

"His voice is utterly unique. I don't know if the model itself works for things that are in competitive fields — sport, finance, tech — without a very unique voice," said Rabois. "Lots of people cover sports, but there's only one Bill Simmons."

Successful newsletter entrepreneurs have to build a community of members who not only find them valuable enough to pay for, but also want them to succeed and grow, according to Frommer.

"I do not think it's the future of business for everyone," he said. "It is for certain people who have the ability to create excellent differentiated content who want to run all aspects of the business, which also includes operations, and legal, and customer service and — by the way — you'd be alarmed how many people's credit card number changes every year."