In this episode of Acquired, Ben Gilbert and David Rosenthal interview Ben Thompson, the founder of Stratechery, on the eve of its 10-year anniversary. They delve into the history, strategy, and evolution of Stratechery, from its humble beginnings as "some guy in Taiwan with no access" to a powerhouse influencing the technology industry's conversations at the highest levels.
The interview starts by acknowledging Ben Thompson's early beginnings, starting multiple blogs, building a back catalog to establish credibility. Ben emphasizes the importance of consistency and regularity in content creation for subscription-based businesses. He believes that subscribers are paying for the promise of consistent, high-quality content, not just individual articles or episodes. This approach allows creators to fund their work upfront, rather than speculatively bidding for money through microtransactions or advertising.
Ben shares his experience working at Microsoft and Apple, and how it influenced his understanding of company culture and strategy. He notes that culture can be a powerful tool for coordination, but also a constraint when companies need to change direction. He reveals his initial motivations for starting Stratechery, driven by a desire to analyze the intersection of strategy and technology, a gap he perceived in the market. He discusses his decision to pursue a subscription-based model, inspired by John Gruber's Daring Fireball and made possible by the emergence of Stripe, but also feeling there was an unscalable sponsored-post advertising market to get into.
The conversation moves to the early days of Stratechery, including the initial struggles with the website, the decision to deliver content via email, and the eventual breakthrough when John Gruber linked to the site, which dramatically increased traffic and awareness. Ben explains his strategy of maximizing revenue per user through subscriptions and building a loyal audience. He also stresses the importance of building a strong brand and standing out from the crowd, criticizing Substack's lack of visual distinctiveness.
Ben addresses the limitations of relying on social media for growth, particularly the decline in the organic reach of links on Twitter. He discusses his decision to expand into podcasting, which he sees as a natural extension of Stratechery's mission to make content as accessible as possible. He acknowledges that podcasting may have slowed down subscriber growth but has been beneficial for churn management. Ben explains his strategy of bundling Stratechery with other podcasts, such as Dithering and Sharp Tech, to increase the value of a subscription.
The conversation shifts to aggregation theory, a business framework developed by Ben Thompson. He reflects on the timing of writing a book on aggregation theory and acknowledges the potential for his analysis to become outdated. He shares his views on Meta, arguing that the company is broadly on the right track, despite the challenges posed by Apple's privacy changes and the metaverse initiatives. Ben offers his insights into the strategies of TSMC and Amazon.
Ben concludes by reiterating his passion for creating economic opportunities through the internet and expressed his gratitude for the success of Stratechery and the freedom it has given him. He acknowledged there would be challenges, but was hopeful that the next decade would lead to bigger and better things.