Episode #30: From InfoWorld to x.com: The Patterns That Repeat

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation winds through a rich mix of personal history, editorial philosophy, and the evolution of tech—from getting fired (twice) to putting Steve Jobs on the cover of Inc. in 1981, from the impact of VisiCalc on Apple II adoption to the deeper meaning of what it means to be an editor. Alongside reflections on the newsletter era, the internet boom, and the looming AI shift, there’s a core thread about editing as a form of pattern recognition and meaning-making.

Check out this GPT we trained on the conversation!

Timestamps

00:00 Welcome to the Stewart Squared Podcast

00:21 Writing a Book with AI

00:57 First Time Getting Fired

02:12 Conflict at Bank Magazine

04:43 Steve Jobs and the Apple II

10:40 Transition to Boston Computer Society

15:06 Starting a Newsletter

19:06 The Role of an Editor

25:20 Discovering Personal Computers

27:25 The Early Days of Apple II

28:11 The Magic of Spreadsheets

29:20 AI and Business: A Modern Parallel

31:42 The Rise and Fall of Tech Giants

34:56 The Dot-Com Boom and Bust

43:16 The Evolution of Online Banking

48:06 The Future of AI and Technology

52:12 Conclusion and Upcoming Topics

Key Insights

1. Getting fired can be formative, not just traumatic: The episode opens with a reflection on the first time Stewart Alsop was fired, tracing how a power struggle with an inexperienced editor-in-chief led to his dismissal from Inc. Magazine. Rather than framing it solely as a failure, he acknowledges how it pushed him toward more independent paths, including editing a user group magazine for free and eventually launching his own influential newsletter. The act of being fired becomes a recurring milestone that reorients his career.
2. Editing is about structure, clarity, and coherence at multiple levels: Stewart distinguishes between different kinds of editing—line editing, copy editing, and the editorial vision that shapes an entire publication. He credits a mentor at Marine Business magazine for teaching him foundational principles: every article needs a premise, development, and conclusion. These ideas anchor the episode’s broader conversation about what editing means, especially as they consider how to transform podcast transcripts into a book.
3. VisiCalc transformed the personal computer from hobbyist gadget to business tool: The story of how business people began taking personal computing seriously centers on the spreadsheet. VisiCalc, running on the Apple II, created a breakthrough moment because it solved a real problem for professionals. Stewart recalls buying an Apple II, struggling to set it up, and then being captivated by the power and immediacy of the software—a turning point not just for him but for the industry.
4. Newsletters became a medium for synthesis and pattern recognition: After his second firing, this time from InfoWorld, Stewart decided he was done working for others. Inspired by Ben Rosen and later Esther Dyson, he launched his own newsletter to track trends in tech. This format allowed him to highlight weak signals, identify inflection points, and say things others weren’t yet seeing. Pattern recognition became not only a skill but a way of establishing voice and authority.
5. Much of the AI hype echoes the dot-com boom, but with faster cycles: Drawing on past experience, Stewart compares today’s AI investment frenzy to the speculative fervor of the late '90s internet bubble. He notes how large sums of money are pouring into companies, many of which may not survive. The key difference, perhaps, is the acceleration—developments like DeepSeek’s low-cost LLM could rapidly undercut many players, triggering what he calls an “AI apocalypse.”
6. Protocols, not platforms, may be the real legacy of AI and internet revolutions: Stewart emphasizes how lasting impact often lies not in individual companies but in underlying infrastructure. The protocols established during the internet’s early years—HTTP, domains, security layers—continue to define it. Similarly, he predicts AI will leave behind layers like markdown, JSON, and new personal-device-level architectures that quietly shape future interaction, regardless of which companies survive.
7. The editor’s job is to see things before others do and say them clearly: Whether in print, newsletters, or now AI-facilitated writing, Stewart frames editing as the disciplined practice of saying what others are only beginning to sense. His credibility was built not on data alone but on intuition grounded in experience, allowing him to make bold claims that time later affirmed. Editing, then, becomes both a craft and a mode of perception—shaping not just texts but how trends are named and understood.