In this episode of Stewart Squared, Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation on the frustrations of modern UI/UX, Microsoft’s struggles with spam and AI adoption, Google’s approach to knowledge management, and the broader lessons of technological hype cycles from fiber optics to GPT-5. Together they explore how big companies evolve from serving programmers to serving enterprises, touch on the role of regulatory capture in shaping user experiences, and recall stories of early email, Hotmail, AOL, and long-distance calls in the 1960s. Along the way, they connect today’s debates on monopolies, Bitcoin, and satellite internet with personal anecdotes from their family history and reporting trips to Moscow.

Check out this GPT we trained on the conversation

Timestamps

00:00 UI/UX frustration, Microsoft spam vs Gmail; scam email triggers rant on filtering and usability.
05:00 Admin controls, external IT friction; Google Drive knowledge management and closed-by-default files.
10:00 Bitter lesson, compute at scale; GPT-5 hype, model consolidation, tokens and cost signals.
15:00 Consumer UI simplicity vs programmer leverage; Bitcoin early-adopter edge; Coinbase code alerts.
20:00 Regulatory capture thesis—Microsoft, Coinbase, Palantir; too big to fail, users sidelined, startup opening.
25:00 Monopoly talk: Netflix, Apple App Store; success metrics and venture-scale outcomes.
30:00 Microsoft arc: programmers → enterprise; MS Basic, MS-DOS/Seattle DOS, IBM; latency woes on the call.
35:00 Starlink Mini portability, power limits; satellite iPhone messaging; T-Mobile, Globalstar arrangements.
40:00 Email history: AOL, CompuServe, Hotmail/Yahoo; Gmail scale; Outlook/Office 365 vs Edge/Safari.
45:00 NEA standardizing on Windows, regrets; Riverside recording hiccups; early Gmail usernames, scale effects.
50:00 1963 operator calls, injury story; Moscow reporting trips; Khrushchev–Nixon Kitchen Debate context.

Key Insights

1. Stewart Alsop and Stewart Alsop II opened with frustrations around UI/UX and how even industry leaders like Microsoft fail to implement effective AI for basic tasks like spam filtering. Gmail adapts instantly to user feedback, while Microsoft’s Exchange requires convoluted admin settings, leaving everyday users powerless.
2. Their discussion shifted to Google’s knowledge management problems, highlighting how file access defaults in Google Drive create needless barriers. Both observed that corporate bureaucracy shapes user experience more than technology itself, reflecting how large firms prioritize control over usability.
3. The “bitter lesson” by Richard Sutton framed the conversation on AI. The Stewarts compared today’s trillion-dollar GPU investments to the fiber optic overbuilding of the 1990s—misguided methods that still laid crucial foundations. They questioned whether GPT-5’s consolidation into one model was a sign of efficiency or hype masking economic strain.
4. A key theme was programmer leverage. They noted that programmers who mastered Bitcoin early became “post-economic,” while non-programmers remained locked out. This reinforced their point that tech often empowers a small, technically literate class while excluding ordinary users.
5. They critiqued regulatory capture, suggesting Microsoft, Coinbase, and Palantir thrive not by delighting users but by embedding themselves with governments. Once companies become too big to fail, their true customers shift from individuals to institutions, and user needs fade from priority.
6. The episode revisited Microsoft’s history, from buying Seattle DOS to serving programmers and then enterprises. They argued that companies inevitably drift away from their original users, though some, like Microsoft through its OpenAI partnership, manage to stay relevant despite this drift.
7. Finally, they wove in communications history—from AOL and Hotmail to Gmail’s dominance, and even back to 1960s operator calls when family news was relayed across continents with constant dropped connections. These stories framed the present as just one phase in a longer evolution of technology mediating human connection.