Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation weaves through the evolution of media, venture capital’s long shadow over technology, and how editorial instincts have (or haven’t) adapted to the pace of software. Stewart Alsop II brings firsthand insight into the early days of digital publishing and the structural mismatches that still shape newsrooms and tech companies alike. Topics range from John Doerr’s influence on startup thinking to the archival black holes created by neglected knowledge systems.

Check out this GPT we trained on the conversation!

Timestamps

00:00 - Opening riff on the confusion between Stewart Alsop Sr., Jr., and III; transition into how legacy media handles its own memory poorly, with a few anecdotes about lost archives and disappearing links.

05:00 - Discussion around venture capital’s influence on media and tech—John Doerr’s role in shaping the “scale or die” mindset, and how that clashed with journalistic values.

10:00 - Breakdown of editorial vs. engineering tension—why newsrooms and product teams often talk past each other, and what gets lost in that misalignment.

15:00 - Stories from early digital publishing: CMS nightmares, how print workflows were just ported online without rethinking them, and the inertia that followed.

20:00 - Exploration of archival decay—missing metadata, broken URLs, and the business implications of failing to preserve intellectual assets. Some sharp takes on institutional amnesia.

25:00 - Pivots to AI and vector databases—what they might enable for content rediscovery, and the risks of relying on tech without editorial intent or context.

30:00 - Richer dive into organizational knowledge and ownership—who controls information, how roles are shifting, and why institutional memory needs its own champion.

35:00 - Personal experiences with failed knowledge systems—both in media and tech startups. Reflection on how internal culture shapes what gets remembered.

40:00 - Pushback on “move fast and break things”—how speed has damaged continuity in publishing, and the cost of constantly reinventing without reflection.

45:00 - Final threads on building more durable systems: not just technology, but incentives, rituals, and cross-functional collaboration to prevent forgetting by design.

Let me know if you want a more granular breakdown or direct pull-quotes from any specific section.

Key Insights

1. Media organizations often suffer from institutional amnesia. One recurring theme is how publishing companies, especially legacy ones, lose track of their own intellectual assets—past reporting, editorial strategies, or even technological decisions—because they lack durable knowledge systems. This isn’t just a storage issue; it’s a strategic failure that hampers innovation and continuity.
2. Venture capital has reshaped the expectations of both media and tech. Alsop II emphasizes how figures like John Doerr didn’t just fund companies—they pushed a worldview where scale, speed, and disruption became non-negotiable. That logic infiltrated newsrooms too, especially when tech-driven platforms began to dictate the pace and form of publishing.
3. Editorial and engineering cultures have long been misaligned. This tension plays out in product development cycles, CMS design, and decision-making about what constitutes “valuable” content. While journalists prioritize nuance and context, engineers often optimize for efficiency and metrics. Without meaningful bridges, both sides end up frustrated—and organizational progress stalls.
4. Digital publishing inherited many of print’s blind spots. The episode explores how early online media failed to rethink fundamental workflows. Rather than redesigning around the capabilities of the web, many companies simply transferred print-era thinking into a browser. That inertia led to clunky archives, rigid hierarchies, and missed opportunities for interactivity or reader engagement.
5. Archival neglect is a systemic risk, not just a technical oversight. The guest shares examples of entire swaths of reporting being lost due to poor metadata, broken links, or obsolete formats. These failures reflect a deeper undervaluing of historical continuity—when organizations treat content as ephemeral, they erase not just stories but lessons learned.
6. AI and vector databases could offer a partial corrective—but only if used intentionally. There’s a sense that the new wave of tools might help media companies rediscover and recontextualize their archives. But without clear editorial frameworks, even the most advanced systems risk amplifying existing biases or simply surfacing the loudest content.
7. There’s a growing need to rethink who “owns” knowledge in a media org. As roles shift—product managers gaining influence, data scientists becoming gatekeepers—editorial authority is increasingly fragmented. This episode makes the case for more integrated, cross-functional stewardship of institutional knowledge, where content, context, and infrastructure aren’t siloed off from one another.