Entrepreneur: Ben Thompson

Biz: Stratechery

Tilt: Analysis of strategy and business of tech and media

Scene: Newsletter (44K), podcasts, X (238.7K)

Snack Bites: 

  • Ben Thompson launched the newsletter in 2013 and a paid version in 2014, which allowed him to quit his traditional job.
  • In 2017, the founders of Substack cited Ben’s business as the inspiration for the online platform that helps writers publish, sell, and manage their newsletters.
  • Fortune cited Ben as No. 3 on its inaugural Creator 25 list, estimating the newsletter brought in over $3M in revenue in 2020. In 2023, that estimate has risen to over $5M a year.

Why We Stan: We are impressed by Ben’s commitment to his ethics, which he outlines in detail. It’s a strong indicator of how much he respects his audience and the trust they place in him.

The Story of Ben Thompson

In 2013, Ben Thompson launched his Stratechery newsletter and made it his full-time job a year later.

He saw a fresh content tilt, as he explained in his welcome article: “There are lots of (great!) sites that cover the day-to-day. And there are some fantastic writers who divine what it all means. 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? How does this translate to normals?”

In 2017, his successful newsletter-as-a-business model inspired Chris Best and Hamish McKenzie to found Substack. Ben explains in this Vox article, “Yes, making content worth taking out your credit card is hard, but cobbling together the services you need to service the business is a pain.

Ben was No. 3 on the debut Fortune’s Creator 25 list, where it estimated Stratechery brought in over $3M in revenue in 2020.

Stratechery analyzes the strategy and business side of technology and media, and the impact of tech on society. Weekly articles are free. Stratechery Plus subscribers who pay $12 a month or $120 a year receive the Daily Updates newsletter three times a week. They also gain access to Stratechery Interviews and the Sharp Tech, Sharp China, Dithering, and Greatest of All Talk podcasts.

Before becoming a full-time content entrepreneur, Ben had interned at Apple and worked at Microsoft and Automattic. As he explains on his site, his work focused on strategy, developer relations, and marketing for Apple University, Windows, and WordPress.com.

According to Stratechery’s website, the New York Times calls it “one of the most interesting sources of analysis on any subject.” Subscribers from over 85 countries include tech industry executives, venture capitalists, investors, and others interested in how the internet is changing everything.

Establishing firm boundaries

Ben works hard to operate as an independent media business, publishing a detailed ethics statement on his site. Here are some excerpts:

My goal is to be a truly independent analyst, a commitment that is about more than just not having an employer. To wit:

  • I am not paid by any company for any opinion I post on Stratechery or in any public forum, including podcasts and Twitter.
  • I do not hold individual stocks in any company I write about. I do hold various 401k and IRA accounts that invest in a wide-ranging basket of stocks, over which I have no control. I have one angel investment in a startup founded by a personal friend in a field I do not cover.
  • I pay for all of my own travel and expenses when I attend company events.

… In addition, as of 2016, I do not take consulting or speaking arrangements with companies I cover (before that date I spoke at Google once, and did one-off consulting projects with Atlassian, Okta, and Dropbox; in all cases the fees I charged were a very small percentage of my overall income, and I disclosed my activity the next time I wrote about the relevant companies). 

Subscriptions are the vast majority of my income; this is purposeful on my part as I want my incentives to be aligned with my readers’.

Growing a content business success

Over the years, he has simplified his subscription rates. As the Blockbuster Blueprint analysis notes, the paid launch plans included three options – $50 a year for community access, $100 for community and posts, and $300 a year for a community, posts, and calls. He simplified the program to a single annual fee and pulled back from the community as he didn’t enjoy that work as much as crafting the articles.

The 2023 Blockbuster Blueprint analysis estimates Stratechery has about over 40K paid subscribers, which would translate to over $5M a year.

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About the author

Ann regularly combines words and strategy for B2B, B2C, and nonprofits, continuing to live up to her high school nickname, Editor Ann. An IABC Communicator of the Year and founder of G Force Communication, Ann coaches and trains professionals in all things content. Connect with her on LinkedIn and Twitter.