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If there’s anyone who’s mastered the newsletter subscription business, it’s Ben Thompson. A business, technology, and media analyst whose career spans the likes of Apple, Microsoft, and WordPress developer Automattic, Thompson started his newsletter Stratechery in 2013 and has devoted himself to it full-time since 2014. His missives explore the strategy and business sides of media and tech, and consider their consequences—intended or otherwise—on society. The cadence of the newsletter is dictated by the nature of the reader’s subscribership. Weekly articles are free to read, whereas subscribers can pay $12 per month or $120 per year to receive Thompson’s “The Daily Update.” The model works. One unofficial estimate from December 2020 posits that Stratechery yielded over $3 million in revenue for that year. It has allowed Thompson to rely on the newsletter as his primary form of income while staying fiercely committed to his role as an independent analyst, per the “ethics statement” on his website. While Thompson is based in Taiwan, his ever-growing readership spans 85 countries and includes executives from the industries he’s analyzing, investors, venture capitalists, and countless others who eagerly await his broad explanations, granular deep dives, and interviews with power players in the spaces he covers. The founders of Substack have called Thompson an inspiration for the platform, and he is oft-cited by the New York Times, which has referred to him as “one of the most interesting sources of analysis on any subject.”

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