Episode #96: From Steve Jobs to AI: The Stories That Never Became Data

In this episode of Stewart Squared, Stewart Alsop III sits down with his father, Stewart Alsop II, for a wide-ranging conversation that moves from a heartfelt tribute to the late Brent Schlender — legendary tech journalist and author of Becoming Steve Jobs — through the history and philosophy of journalism, the concept of the fourth estate, and what it meant to cover Silicon Valley's biggest names up close. The two also dig into Cold War history, Russia's ambiguous relationship with the West, the Alsop family's own journalism legacy, and how AI is reshaping the way we think about memory, personal data, and the historical record. For more on Brent Schlender's work, check out his book Becoming Steve Jobs and Stewart Alsop II's Substack obituary for Brent, where he also shared the iconic Fortune magazine cover featuring Steve Jobs and Bill Gates together.

Timestamps

0:00 Brent’s memorial and the jet lag opening, then into who Brent was and his role in tech journalism
5:00 Brent’s journalism background, friendship with major tech figures, and the idea of the three Steves in Steve Jobs’ story
10:00 Why journalists usually stay objective, what the fourth estate means, and how the press acts as a check on power
15:00 The press, patriotism, Cold War context, CIA tensions, and how journalists like Stuart and his uncle navigated American loyalty
20:00 McCarthyism, fear, false accusations, and how brave reporting protected people and challenged demagoguery
25:00 Russia as part West / East, Christianity, borders of identity, and the discussion shifting into Russian history
30:00 Soviet-era travel, tech speeches, old-school publishing, and the problem of reconstructing the past without a digital trail
35:00 History vs. journalism, archives, memory, and why preserving records matters for telling the story later
40:00 Brent’s memorial memories, the Steve Jobs book, and how Brent’s work shaped the industry through insight and relationships

Key Insights

1. Brent Schlender stood apart from most journalists because he became genuinely close friends with the people he covered — Steve Jobs, Bill Gates, Larry Ellison — and that access gave him a depth of understanding that produced what many consider the definitive Jobs biography, Becoming Steve Jobs.
2. The fourth estate originated during the French Revolution as a check on the clergy, nobility, and commoners, and evolved in America into a press that sits outside the three branches of government — a concept that only became formalized after the 1920s, largely sparked by Upton Sinclair's exposé of the meatpacking industry.
3. The Alsop brothers — Stewart's grandfather and great-uncle — built their journalistic credibility by taking on Joe McCarthy at the height of his power, which gave them enough reputational armor to withstand the later revelation that they had been informally debriefing the CIA after foreign trips.
4. Russia is neither fully Western nor Eastern — it spans eleven time zones, was shaped by Mongol rule, replaced the Tsar with communism, and at one point sent quiet diplomatic signals about wanting to join NATO, not as a junior member but as a great power on par with the US and China.
5. AI can only build a picture of you from the digital trail you've left behind — and for anyone whose active years predate Gmail, that trail barely exists, making tools like the digital twin app Sentience far less useful for older generations.
6. Journalism and history are fundamentally different disciplines: journalists capture the present moment, while historians piece together the past from whatever fragmentary records survived — a challenge that becomes vivid when trying to reconstruct what Stewart Alsop II actually said in a speech he gave in Soviet-era Moscow.
7. The rationalist movement around figures like Eliezer Yudkowsky, which helped seed effective altruism and shapes thinking at places like Anthropic, may be strong on the technical mechanics of AI but weak on understanding how AI will actually play out in a human world — because humans are not, and have never been, purely rational actors.