Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we talk about what happened to trust—why it’s gone, where it went, and whether it can be rebuilt. We go from the 1990s paranoia about driver’s licenses to today’s AI-powered pendants that record everything, from the erosion of open internet ideals to the rise of app store monopolies. We compare Apple’s branding collapse to meme coin absurdity, reflect on the fallout from 2008, and wrestle with whether open source and individual agency can still offer an exit ramp. Sam Altman, Trump, China, and the App Store all make appearances.

Check out this GPT we trained on the conversation

Timestamps

00:45 Stewart Alsop II on the evolution of driver's licenses, digital identity, and government ID.
03:31 Discussing the Limitless Pendant: real-time transcription, unmet expectations, and the "Life Log" concept.
09:06 From "vaporware" announcements to today's premature product releases in the tech and AI space.
11:26 Apple Intelligence as a case study in how tech companies can damage long-built consumer trust.
18:47 How the iPhone's App Store model fundamentally created walled gardens and changed the open internet.
22:36 Revisiting the "Evernet" thesis: the implications of persistent, high-speed internet connectivity.
35:33 The argument that declining trust in US institutions predates and influenced the social media explosion.
44:56 Exploring whether open-source AI offers a decentralized alternative to trust issues with big tech AI.
51:18 Delving into the origins of the Evernet thesis (circa 2008-2009) and its relevance today for cloud storage and enterprise.

Key Insights

1. The Privacy Shift: We've journeyed from a 90s-era paranoia about government surveillance surrounding things like driver's licenses to an age where personal data is constantly captured and processed by AI, often through devices like the Limitless Pendant. This marks a significant societal recalibration of privacy expectations and acceptance of ubiquitous recording.
2. From Vaporware to Premature Release: The tech industry's historical issue with "vaporware"—products announced far ahead of actual delivery—has largely inverted. Now, particularly in the AI sector, companies frequently release products in a nascent state, effectively making early adopters beta testers and risking an initial erosion of trust.
3. Trust as the Core Commodity: Echoing Steve Jobs' philosophy, brand strength is fundamentally built on trust, which is earned through positive experiences and diminished by negative ones. Current trends, such as Apple's "Apple Intelligence" announcement perceived as overpromising, and the broader rush to market with unfinished AI, are actively damaging this crucial trust with consumers.
4. The iPhone's Internet Reformation: The introduction of the iPhone, and specifically its App Store ecosystem, represented a pivotal moment that reshaped the internet. It guided users away from the open web and into curated "walled gardens," granting platform owners like Apple considerable control and arguably curtailing the initial promise of a completely open internet.
5. The Evernet Manifested: My "Evernet" thesis, predicting persistent, high-speed internet connectivity across all devices, has largely become our reality. This constant connection is the bedrock of modern cloud services, social media, and our digital interactions, but it also facilitates the continuous data flow central to current privacy and trust dilemmas.
6. Pre-Existing Institutional Distrust: The decline in public trust towards institutions like government and mainstream media was a trend already in motion before the rise of social media. This pre-existing skepticism may have actually fueled social media's explosive growth, as these platforms emerged in an environment where traditional authorities were already losing credibility.
7. AI: A Localized Path to Trust?: While large, centralized AI models from major corporations might perpetuate existing trust issues, there's a glimmer of hope in open-source AI and locally-run applications. Empowering individuals to build, customize, and control their own AI tools could foster a more personal and reliable form of trust and utility, independent of big tech.
8. The Challenge of Relevancy in Rapid Change: The breathtaking pace of technological advancement, especially in AI, makes it incredibly difficult for individuals to stay informed and for companies to remain relevant. This dynamic often leads to a concentration of attention on a few dominant platforms, like ChatGPT, even as innovative alternatives struggle for visibility.