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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode of Deep Questions, Cal Newport explores the rise of paid newsletter platforms like Substack through the lens of economist Paul Krugman's successful transition from the New York Times to his own newsletter. (02:00) Newport analyzes whether paid newsletters can replace traditional print media by examining key metrics around subscriber numbers, revenue potential, and market size. The episode reveals that while Substack has created meaningful income opportunities for writers, the ecosystem remains relatively small compared to traditional media at its peak.
Cal Newport is a computer science professor at Georgetown University and bestselling author of books including "Deep Work" and "Slow Productivity." He hosts the Deep Questions podcast and writes extensively about productivity, technology's impact on society, and the pursuit of meaningful work in an increasingly distracted world.
Newport's research reveals that only about 34 newsletters on Substack have reached the 500,000+ subscriber level that generates million-dollar annual revenues. (17:02) While this represents significant success for individual writers, it demonstrates that newsletter platforms haven't yet scaled to match traditional media's peak employment levels. The analysis shows approximately 500-1,000 writers making a substantial living ($150,000+ annually) from newsletters, compared to tens of thousands who worked in traditional newspapers. This suggests that while newsletters can provide viable alternatives for talented writers, they won't dramatically expand the total number of people who can make a living from journalism.
Newport's viral advice on reducing phone usage centers on addressing the underlying psychological void that drives excessive screen time. (55:58) His experiment with 1,600 people revealed that those who successfully avoided social media for 30 days were the ones who aggressively pursued alternative activities and interests, rather than just "white-knuckling" their way through abstinence. The key insight is that phones often serve as a way to "paper over the void" created by unmet potential, misalignment with values, and life's inherent difficulties. Simply removing the phone without addressing what it was helping you avoid leads to failure.
Using Krugman as a case study, Newport demonstrates that successful newsletter writers can earn between $1.2-4+ million annually. (07:48) With 505,000 subscribers and assuming a 3-10% conversion rate to paid subscriptions at $7/month, the math shows substantial earning potential. This revenue model often exceeds what writers could earn at traditional publications, explaining why established journalists are making the transition. However, building such an audience requires consistent daily publishing and substantial existing credibility or expertise.
Newport argues that readers can more effectively assess and adjust for bias when consuming content from individual newsletter writers compared to large media institutions. (40:22) When engaging with someone like Paul Krugman, readers understand his political perspective and can filter his insights accordingly. This contrasts with institutional media that claims neutrality while operating with clear biases, leading to declining trust. Individual writers who are transparent about their viewpoints allow readers to apply appropriate skepticism while still benefiting from their expertise and analysis.
The greatest threat to the newsletter economy isn't the model itself but dependence on a single platform like Substack. (45:48) Newport warns of "enshittification" - the tendency for platforms to initially provide value to build an audience, then shift focus toward maximizing revenue in ways that degrade user experience. If Substack prioritizes becoming a billion-dollar company over serving writers and readers, it could transform from a publishing tool into an attention-grabbing distraction platform. The solution requires developing open-source or independent alternatives that maintain low friction for writers while avoiding single-platform dependence.