Stewart Squared
Episode #96: From Steve Jobs to AI: The Stories That Never Became Data
- AI & Agents
- Argentina & Latin America
- Brent Schlender
- Silicon Valley
- Wall Street Journal
- Fortune magazine
- Steve Jobs
- Bill Gates
- Larry Ellison
- Tokyo bureau chief
Listen
Download MP3About this episode
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
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
Episode transcript
Everyone is wrong about AI but if you know the history of technology, you can be wrong and still be right.
I know the history since I started in technology with the personal computer in 1980. So listen in while we explore what is true about AI.
Welcome to the Stuart Squared podcast. Got another great episode today. My, father is now, what is it called, when you teleported, from Tokyo to Healdsburg, California. I forget why you're there, but, we can talk about that too. But, welcome to the show. What did you learn on the airplane over
on the airplane? That's, that's a tough, tough thing. I flew from Osaka to San Francisco Wednesday night, and spent two days in San Francisco and then two days up here in Healdsburg. and the reason for that is Lorna had a celebration of life for her, husband Brent. past last December octamer. Excuse me. And the, So that was a lot of, a lot of people saying great things about Brent and the, So, I mean I am so jet lagged, who wouldn't ask me what I'd learned anywhere because I'm like, well
let's, let's talk about Brent. Who was Brent for our listeners? Of course I'm aware of Brent because I stayed at his house. and who, who is Brent and what did he mean for the PC industry?
So any regular listener will know that I've been around a long time. and I first met Brent when he moved to the Bay Area, San Francisco bay area in 1986 or seven, somewhere in there, which is shortly after I started my newsletter in 1985. and you know, I hadn't started producing a conference yet. Well, the first one was in the fall of 87. and so I was considered a pundit and he, his job was to report on Silicon Valley. He was the Wall Street Journal bureau chief for Silicon Valley and traditions going on. Today there's still a bureau chief and a team of people that cover Silicon Valley for the Journal. so he reached out and we got to know each other. Brent was particularly good, and this is really after he moved to Fortune, because he did, I don't have the years quite right, but he moved to Tokyo and became the Tokyo bureau chief for Fortune magazine. And you probably won't remember this, but your sister Natalie went over there for several weeks, and hung out in their apartment, in Tokyo, which is part of the reason that she's out of deathless fondness for Japan. the That was 92 and So you were like seven. Seven. Yeah. so anyway, so Brent, the thing he was particularly good at is that he would interview big mucky bucks in the business. Bill Gates, Larry Ellison, Steve Jobs, et cetera, Andy Grove, and he'd end up being friends with them, which is not typical. Usually reporters don't make friends with the people they interview. and he particularly got to know Steve Jobs. and when Steve was in the hospital, Brent went and visited him. And then later when Brent was in the hospital, Steve came and visited him. And ultimately he spent X number of years working for Fortune. He moved from Tokyo back to Silicon Valley. I kept working for Fortune and So he had ended up writing a book called Becoming Steve Jobs. And in my humble opinion it's the best Steve Jobs book. because it. He he had interviewed Steve so many times. He had all these tapes of his interviews. So he went through the tapes of interviews and developed this thesis that there were three Steves. The first Steve was the bad boy who ran Apple, before he got fired. Then the second Steve was the one that ran next which failed, kind of failed but Apple ended up buying it. And then the third Steve was, when he came back as CEO of Apple in 98 I think it was, and you know, which led to the iPhone and so on and so forth. So the third Steve was actually incredibly self aware and developed an approach to management which persists to this day even though he ended up dying. Now was.
Your first full transcript is free. After that, an email opens every transcript in the index — a list of readers we can write to, not a guest book.