Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation orbits around the mechanics and ethics of digital walled gardens, from YouTube’s curated algorithms to Meta’s domination of social platforms like Threads and Instagram. The Stewarts reflect on relevance in tech, the decline of platforms like Quora, the ascent of Substack, and the meaning of audience ownership in a fractured media landscape. They explore marketing not as manipulation but as a hunt for shared value, and weigh the implications of spam, AI's blind spots, and even political messaging strategies.

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Timestamps

00:00 — The Stewarts kick off with the challenge of visibility on YouTube and the mechanics behind algorithmic promotion and walled gardens.
05:00 — Discussion turns to how platforms like Facebook and YouTube suppress outlinks and shape behavior through censorship and user tracking.
10:00 — The Stewarts reflect on relevance and platform decay, contrasting the early value of Quora with its decline, and mentioning Substack’s quality audience.
15:00 — They examine creator economics, Substack’s success, and Medium’s struggle, linking this to media independence and monetization.
20:00 — Stewart Alsop proposes rebranding the marketing funnel as a treasure hunt, and the conversation shifts to email ownership and the organic vs. algorithmic divide.
25:00 — Focus moves to political marketing, television vs. social media, and how figures like Trump and AOC capture attention in different ways.
30:00 — They debate comedy as commentary, with references to John Oliver, Tim Dillon, and media adaptation for Gen Z.
35:00 — Technical glitches lead to reflections on technological failure, AI limitations, and the unreliability of platforms like Riverside.

Key Insights

1. Walled gardens have evolved from closed systems to algorithmically enforced ecosystems. Platforms like Facebook and YouTube no longer block external links outright but diminish their visibility, incentivizing creators to remain within the ecosystem and discouraging discovery beyond the walls.
2. Relevance, not just reach, defines a platform's influence. The conversation underscores that staying relevant—having cultural and intellectual weight—matters more than raw user metrics. Platforms like Quora and Medium became irrelevant not because of numbers but because they lost the attention of valuable contributors.
3. Substack's success lies in empowering creators with ownership. Unlike social media platforms that act as intermediaries, Substack allows writers to maintain control over their audience via email lists, representing a shift toward sustainable, direct creator economies.
4. The attention economy is shaped by who participates and why. Stewart Alsop notes how the quality of engagement on platforms like Quora diminished as the user base shifted. It’s not just about numbers, but about the intellectual and creative caliber of the audience and contributors.
5. Marketing is most powerful when it becomes a form of truth-seeking. Describing it as a “treasure hunt,” the episode reframes marketing from funnel-based conversion tactics to the search for authentic connection—finding the people who genuinely care and resonate with the message.
6. AI, for all its promise, still stumbles on basic functions. Frustrations with email spam and time zone confusion reveal the disconnect between AI’s perceived intelligence and its actual utility, raising broader questions about how technological competence is defined.
7. The generational exchange brings a layered understanding of media and culture. The podcast’s value lies in the dynamic between a millennial and a baby boomer navigating old and new paradigms—offering both context and critique, rather than conclusions.