2026.09.24 | Substack | META | Stratechery: Profiling Zuckerberg
原标题：An Interview with Colossus EIC Jeremy Stern About Profiling Mark Zuckerberg (Stratechery Interview 9-24-2026)
Thursday, September 24, 2026
Good morning,
This week’s Stratechery Interview is with Colossus Editor-in-Chief Jeremy Stern. Stern is, in my estimation, the best profile writer working today. That is no small praise: as Stern notes, the profile is one of the critical American contributions to literature; that Stern focuses on tech and business is equally critical, given that these are the drivers of culture.
Last week Stern published a fascinating profile of Meta CEO Mark Zuckerberg. This was, in full disclosure, a profile I participated in with an off-the-record interview. I did it because I appreciated the way that Stern had treated his previous subjects, most notably his profile of Palmer Luckey, which was Stern’s first.
That particular profile wasn’t that long ago, which is interesting in its own right. I was very interested to learn more about Stern’s fascinating background and circuitous route to his current career, which included an extended tour of duty as an explosive ordnance disposal officer in the U.S. Army. We talk about his career path, his shift to profile writing, and why someone like Zuckerberg would sit down with him. Then, we give a brief overview of his other profiles, including Scott Wu, Shyam Sankar, Josh Kushner, Neil Mehta, and Jake Sullivan. We also touch on Colossus and its attempt to bring back the best of American magazine culture.
As a reminder, all Stratechery content, including interviews, is available as a podcast; click the link at the top of this email to add Stratechery to your podcast player.
On to the Interview:
An Interview with Colossus EIC Jeremy Stern About Profiling Mark Zuckerberg
This interview is lightly edited for clarity.
Topics:
Background | Writing Advice | Palmer Luckey | Mark Zuckerberg | Colossus
Background
Jeremy Stern, welcome to Stratechery.
JS: Thanks for having me, Ben.
You are, I think it is safe to say, and relatively rapidly, the preeminent profile writer in tech. You just dropped an incredible profile of Mark Zuckerberg, which I want to dive into in a bit. For now, however, I get to turn the tables on you and profile you, if only for a few minutes. What is your background? If I’m writing a Jeremy Stern story and opening by recounting a conversation with your parents, which is how you opened the Mark Zuckerberg story, where am I and what do they say?
JS: Yeah, it reminds me of this, there’s this great David Foster Wallace essay where he describes writers as natural lurkers and starers and watchers, and that they covet this image of themselves as witnesses, and that the thing that they’re most terrified of in the world is being watched by other people.
I know, I didn’t tell you I was going to ask this question, so I sprung it on you.
JS: I really stumbled into this by accident in the last couple of years. I’ve been writing for a while, all my previous writing had to do with American politics and German politics and foreign policy. I spent a while in the Army, the U.S. Army, and in the State Department, and I wrote about some of that stuff.
Just wait. We’re going back to your parents, because I want to get to the Army stuff, I want to get to the foreign policy stuff, because I actually think it’s incredibly fascinating, you would actually make an interesting profile subject. So let’s go back. Where did you grow up? And you obviously didn’t start out as a writer. So what was your goal?
JS: I grew up in LA, I went to college — I split college between Kenyon College in Ohio and Saint Petersburg State University in Russia.
Right. And you studied Russian history, right?
JS: I did, yeah. I studied Russian language and literature.
And what was it? Did you get assigned Crime and Punishment in high school and you were hooked, or how did you end up there?
JS: It was actually — I went to Kenyon because the Kenyon Review, it had this storied English department, and I thought I wanted to be an English major. And then I did so badly in high school Spanish that I didn’t place out of the language requirement that they had for freshman year at college so I was obligated to take one year of a foreign language. I just decided — I hated languages, and so I would just go for something that sounded zany and weird, and I chose Russian and then it’s one of those things where it changed my life. The professor who ran the department became probably the biggest person in my life up until that point, she’s an incredible teacher and mentor, she convinced me to go to Russia for a semester, which I then extended to a year, which I then extended to a year and a half.
What gripped you about it?
JS: I ended up not taking a single English course, I think, while I was there, because that need I had was totally satisfied by these Russian literature courses.
So to your question, yeah, we read all the great 19th century Russian novels, I was really hooked on that, I loved the language, a lot of the TV we would watch in class — watching TV in a foreign language is a good way to absorb it and figure out the colloquial usages of the language — was all these Soviet children’s cartoons and then we progressed to the Soviet family sitcoms and then the more esoteric and abstract stuff. I just got totally hooked on it and I went to Russia in 2009, 2010, which was probably the last time that things felt quasi-hopeful in the country.
Right. You got there just in time.
JS: It was delusional at the time to think that, but no one knew that, right? And certainly no one in Russia really had a grasp on that.
So this was this period where [Vladimir] Putin was the prime minister, technically, not the president — [Dmitry] Medvedev was, and it seemed like capitalism was transforming the country, you could point to the four-hour lines at the Burger King in Moscow. And so I had an incredible time, St. Petersburg is an amazing city, I lived with a Russian family for most of it, I had a Russian girlfriend, it was just amazing. And then, obviously, it’s extremely sad what happened, 2014 was the last time I was there, right before the invasion of Crimea.
What would [Fyodor] Dostoevsky have to say about AI and effective altruism?
JS: You probably have a better opinion on this than I do. Have you read Demons) recently?
I’ve not recently — it’s been years. But whenever someone says they’re into Russia, I just assume the avenue is the exact avenue where I, and probably lots of people, got nerd-sniped by — you read Crime and Punishment or you read Demons or something long, and you’re like, “This is unbelievable, this is awesome.”
JS: Yeah, exactly. I also haven’t read it in a long time, and I definitely haven’t read it since I found out that people in San Francisco are obsessed with this book. But I always — I was not, I mean, I love The Brothers Karamazov, but I was never a big Dostoevsky fan relative to [Leo] Tolstoy and [Anton] Chekhov.
Got it. That’s always the divide, isn’t it?
JS: It is.
Which one is your favorite? I was Dostoevsky — that was my favorite. But I guess we’ll have a bit of a sparring session.
JS: Okay, yeah. So that suggests you’re edgier and a little cooler, like you’d prefer the Rolling Stones to the Beatles or something.
I’m a Beatles guy, actually. Huh, that’s interesting, I didn’t know that was the way — that’s the way it lined up. But yes, sorry, we’re getting sidetracked, no channeling 19th century Russian authors and takes on AI?
JS: No, I don’t think so. I mean, I’ve tried to read a lot of what people consider to be the Silicon Valley canon and some of it I love and some of it I have a really hard time getting through. But no, I haven’t revisited any Russian literature since the AI moment.
So you leave college after studying Russian and living in Russia — did you go straight to the U.S. military then?
JS: I spent a year in Washington first, working at The American Interest magazine. This was Francis Fukuyama‘s magazine back then, it’s since folded, after I think 2017 or 2018. But it was an American political quarterly and that’s where I learned how to do copy editing and editing and a little bit of writing on my own. But it was mostly cool just to spend time around him. And Walter Russell Mead was my boss there — the historian who writes for the Wall Street Journal, Adam Garfinkle was the editor.
Well, I’ll jump in right there, actually, I was going to ask about Walter Russell Mead at the end. He wrote what is on my Mount Rushmore of the single most important pieces to understanding American politics, which is The Jacksonian Tradition and that was back in 1999, and it feels like it was written in 2015 during Trump’s first run for presidency, it’s incredible. And I’m curious — what’s it like doing a podcast with him every week, and what’s his current view on the state of the world?
JS: Walter gave me my first full-time job out of college, I was his staff writer, and I was, I think, the first research assistant on the book that ended up not coming out until a couple of years ago, about American foreign policy in the Middle East, basically.
But Walter was just an absolutely unbelievable teacher and mentor and boss and part of what he would do is — I’d contribute, me and a couple of other people, we’d contribute to the blog that he was maintaining at The American Interest at the time called Via Media, which is basically news coverage and so we’d hang out at his apartment in Queens, in Jackson Heights, we’d split time between there and DC, and we’d write three- to eight-hundred-word blog posts in the morning and then he’d make us go around in a circle and read them, and he would tear them to shreds. We were like 21, 22 and he would just point out all the logical fallacies and the ways that the prose was terrible and how we didn’t know anything and it was a terrifying experience, but it was probably the most formative experience I had as a writer.
He then, as he is now, was one of the most prescient analysts of American history and American politics and yeah, it is crazy how much of the Jacksonian stuff has come true in the last ten years.
It’s incredible. It always feels like it was part one of a series, and we never got parts two, three, and four. So let him know — I’m waiting for the Hamiltonian tradition piece, I’m waiting for the Jeffersonian tradition piece, we need all of them. Anyhow, you work for him, he’s tearing your pieces to shreds to the extent that you’re like, “I need to go defuse bombs” — what was the shift here?
JS: (laughing) That mostly came from — I don’t know if you have experience of DC, but at least my experience was most of the people I met were journalists, people who worked at think tanks, staffers on the Hill, maybe some people who worked in the Obama administration at the time and I kind of saw where your life could go if you move to DC and you never leave and it was increasingly unappealing to me and I got a little worried. I could see it happening to me easily and so I could retroactively come up with a justification for joining the Army that has to do with patriotism and a desire to serve, all of which was true, but also what was true is I was 22 and I was kind of impulsive, and I wanted to do something that sounded really adventurous.
So you just enlisted, you were just a grunt.
JS: I went to a mall and I enlisted, I had a track to go to officer candidate school, but I had to go to basic training first, because I didn’t go to ROTC or West Point or anything like that. So yeah, I went to regular basic training with all the other 17- and 18-year-olds.
Amazing. So why ordnance? Why is that the particular specialty you developed?
JS: You’ve got the regular Army, which is the big, vanilla units and I think life in those units is maximally miserable, because these are the units that fight for funding the most and have the most Congressional oversight and are most down the line with grooming standards and uniforms and all that kind of stuff, and I started meeting people from the special operations branch, and they seemed more well-funded, a little freer to just live their own lives and conduct training and missions in the ways they saw fit. That seemed really appealing to me, but I knew I would be terrible at infantry, I was not a door kicker, so I was not going to be a Green Beret. That left either explosive ordnance disposal, which is bomb disposal, IEDs, or flying helicopters. I hate helicopters, I have a fear of helicopters, so bombs it was.
There you go. So how many tours did you do? You did like five tours, is that right, over six years?
JS: I went to five countries, but it was mostly during 2017 and 2018. So by that time, it was an interesting period, because Iraq was over and Afghanistan was basically over, I don’t want to overstate that, because I know people were still getting injured and killed at that point. But really the big thing that was happening was Syria at the time. But they were all — it was a pretty small presence, there were all these temporary missions, so we mostly just rotated throughout CENTCOM to a bunch of different countries.
Writing Advice
As you look back, is that just an interesting chapter in your life that’s fun to come up in bar stories, or is there a thread that you can draw from defusing bombs to arguably journalistically throwing them?
JS: I guess one thing would be — I’m just now hitting the point in my life where people younger than me are asking me for advice on becoming a writer for the first time, it’s never happened to me before, and so I’ve been thinking a little bit about this, which has a connection to the Army, which is basically — if you’re reasonably smart, you can learn the thing that you care about in a reasonable period of time and with writing, I feel like you probably either have the gene or you don’t, but it just requires a lot of practice, it’s like practicing your scales. The thing that you can’t just practice your way into is — it just helps to have an interesting life and to lead an interesting life.
This is why I was excited about this interview. I think you get that from your profiles. But then it’s like, no, actually, I wasn’t joking about the profile about you. We’re already literally traveling around the world, and we haven’t even gotten to any of the pieces you’ve written yet.
JS: It is true that a lot of people get stuck in this trap of they major in creative writing, and then you go to graduate school for creative writing, and then after that you apply to creative writing fellowships, and then at age 29 you write a memoir about your life as a professional creative writing student or whatever. Journalism definitely has a version of this, which is you study English or political science, you go to Columbia Journalism School, you get a job at the New York Times covering national politics, and through your lens as a professional grad student.
I think it just helps to, instead of doing all that — I think I was well-served by spending college in rural Ohio and in Russia, joining the Army, serving in the State Department overseas, and then I moved home. I got married, I have three kids, we bought a house, I’m building a startup, which is Colossus, dealing with the problems of my aging parents — all of which is really fucking stressful, but at least it allows you to maintain a relationship to reality that I think does benefit your writing. The more Army-specific version of that would be that one of the benefits of joining the military is you just get to work with and get really close to Americans that you never would have met otherwise.
Oh man, this is such an important point. I think it applies to your experience point in general, you don’t need to be having crazy experiences now, it’s the fact that you have had them that gives you just broader context, a broader lens for the rest of your life. And the point about — you don’t need to be normal, or as it were, live amongst everyday Americans, but to have actually experienced it in a very tangible and real way, and not just as flyover country or whatever it might be. Again, just the contrast you drew to the student who takes a gazillion creative writing courses and wants to write about U.S. politics. It’s like, on what basis?
JS: Right, exactly. First of all, it’s just fun, it’s enjoyable, it makes you happy, I think. But also, in terms of down-the-line professional and life benefits, you meet people who are very, very different from who you are and you have to, in order to work together and make sure that everyone stays alive, you have to figure out what they want, what their ambitions are, what brings out the best in who they are, and basically figure out how do you give that to them so that they want to follow you.
It’s really good practice and I think it’s probably why — I don’t know if this is literally true, but it’s people’s general sense that once you no longer had conscription in the United States, once you no longer had political leaders who had served in the military, the quality of political leadership declined somewhat. If that is true, I think probably a lot of it has to do with — you figure out people, mostly working-class and poor people in America, and you figure out how to work with them and how to make their careers work for them and give them what they want and that’s just very good life experience.
Palmer Luckey
Yeah. I want to start with actually the Palmer Luckey profile. That was really, I think, the one that put you on the map — was that the first real big profile you did? I tried to go through all your history of writing, and before that it was all a lot of just news coverage and analysis. Like you mentioned, you wrote about Germany, you wrote about U.S. national defense things, tell me about that profile and how it came about.
JS: Yeah, I’d never written a profile of anyone, I think, before that. I’d written one about the national security advisor at the time, but that was not with his participation, it was just kind of an opinion thing. So that was the first time I’d reached out to someone and asked if he’d be interested in sitting for a piece.
I didn’t even really have an idea in my mind that it was going to be a profile yet, I just wanted to talk to Palmer and the way a lot of these profiles come about — the way this one certainly did — was I began with a thing that I was interested in. I was interested in the thing first, and then I wanted to go find the best person to almost use as an excuse to explore the thing.
So in the case of Palmer, after October 7th in Israel, one of the interesting things about it was Israel had what was then considered to be the most advanced fourth-generation hybrid warfare, AI-powered military infrastructure — smart fences and drones and satellites and underground sensors and all this stuff — that was just assumed to have so much technological overmatch that they would deter anything like October 7th from happening. And October 7th happens, and it happens with people on paragliders and with construction equipment and so one of the things I was thinking about in the aftermath of that was how much of the defense tech stuff is actually bullshit. Or if it’s legitimate, how far away are we from it actually working? Because it seems like there’s a big gap in that.
And so Palmer was someone I’d been vaguely aware of. I think Anduril started in about 2017, something like that, which is when I was deployed, so I’d heard a little bit about them, and I knew he was also the guy who invented the Oculus, but that was kind of all I knew. And then I went looking, reading about him and watching him on podcasts and stuff and he’s a very interesting, animated guy, but still at that point—
Of all the people to do your first profile on, it’s hard to pick a more fascinating one.
JS: Yeah. So this was early 2024, so he was already kind of a legend and icon within tech, but people like my mom had not heard of him yet, he wasn’t on 60 Minutes or whatever, so it was also good timing, I think the piece came out something like August of 2024.
So anyway, I just went to Palmer with the intention of trying to explore that question and then anytime you interview someone, it’s like this whole galaxy opens up. Each person’s life is like a whole universe and so I’d had in mind this kind of 3,000-word piece about defense technology based on an interview with Palmer, which turned into a 15,000-word story about basically his entire life.
Then afterwards, you’re like, “actually, I’m pretty good at this”? What was the — like, you are the profile guy now, you mentioned a very short amount of time, but I’ll just say from my perspective, you talked to me for this Mark Zuckerberg piece and I pointed to that Palmer Luckey profile, I’m like, “Yeah, I’m skeptical to talk to a fair number of folks, but I’ll talk to you”. Did it happen overnight?
JS: Part of it was that I’d been working at Tablet Magazine. I left to come to Colossus, which was started by Patrick O’Shaughnessy, and we’re building the business together, and I liked the idea of a business-and-investing-and-technology magazine that was primarily focused on long-form magazine journalism.
This is one of my favorite genres of writing, my old colleague David Samuels likes to say that long-form magazine writing is America’s only indigenous form of writing — as distinct from the novel or poetry or theater or whatever, long-form magazine writing belongs in the American vernacular and a lot of America’s best writers had some mastery over it. So I liked the idea of bringing that to bear on business and technology, where, outside of you and a few others, I think the quality of prose is not in overabundant supply — so to try to bring some literary or cinematic ambition to these pieces.
Colossus publishes a lot of non-profile type writing, but the profiles tend to get the most attention and it’s just one of those things where, for the first year, most of our assignments were outbound requests — we were approaching people asking if we could interview them, now we’re getting over 50% inbound.
I’m curious about this — how to write a profile. I appreciate you being kind to me and saying I’m not a total loser as far as writing, but we are both writers, but it feels like an entirely different language. I’m writing a diary in some respects — I’m writing every day, sort of updating my views, this is like you’re writing a set piece. So let’s use the Mark Zuckerberg profile as an example. How long was this in the works? From idea to actually working on it to actually writing it. Is this like a book project?
JS: Well, first of all, you have the most precious thing in writing, and every writer wants it for themselves, which is a voice, I could go into the middle of any Ben Thompson piece and I know who wrote it, I know it’s you. That is probably the hardest thing to achieve in any type of writing. So if I could have anything, it would be that.
It was interesting, they reached out originally. From the Palmer piece, Zuckerberg was the villain of that piece, the big villain, and I’d reached out to him to provide a comment, I told him what the piece was going to be about, and he ended up providing one in the piece that was really interesting. I haven’t gone back and looked at it, but my memory of it was that it was kind of 90% corporate speak, and then the last 10% of it, he seemed to be providing an apology to Palmer. For anybody who doesn’t know, he basically fired, or didn’t block the firing of, Palmer after 2016, after Palmer had donated to a pro-Trump political group. I thought that was interesting and then Palmer, I think, read it the same way.
Well, I think he said at the end, “I hope we can find ways to work together in the future, I’m glad an entrepreneur of his caliber is working on these things”. It was a very gracious statement.
JS: Exactly. And especially for him and someone in his position, it was as close to a public apology as he was going to get, which I think really surprised Palmer and I think it served to reconnect them and patch up their relationship. So I was a little bit surprised when I heard from them, but I guess maybe not so surprised, knowing that they’d kind of made things OK.
Mark Zuckerberg
But the basic course of it was, earlier this year, we just decided to have lunch, talk completely off the record, just to say hi and talk about what’s on our minds and see if this was something we wanted to do. At that point I was still feeling a little skeptical, it felt like he’s been under a microscope for 20 years, he’s probably one of the most overexposed human beings who’s ever lived, I’ve never been particularly interested in Meta’s business or its apps, at least compared to a lot of other stuff. So I wasn’t particularly motivated by it at the start.
But then we spoke and he seemed pretty earnest to me and it was clear that they had a very big year coming up and part of what — when I reached out to you to ask you about some stuff, part of what I did have in mind that was interesting was, I did remember during a lot of the craziness between 2016 and 2020, I just had these images that were still imprinted in my memory of him being subpoenaed and there being enormous government pressure for censorship on social media. When a lot of his competitors like Google and YouTube and Twitter just caved immediately, he did hold out longer than the others did and he did end up caving at a certain point, but he held out longer, and the attempts to go after him were a lot more vicious than I think they were for a lot of the other CEOs.
I was just kind of interested in talking to him about that period in time and then, same thing with Palmer — that was the thing that I was interested in to start, and then once you start talking to people and thinking about them and talking to their friends and their family and their coworkers and former colleagues and all that, again, a whole universe opens up.
How many people did you talk to again?
JS: It was almost 40 over the course of about five to six months.
So why does someone like Mark Zuckerberg — you mentioned they reached out. What do subjects get from a profile? And again, you’re relatively recent to doing this, but what’s your perception of it? What’s the upside? Is it vanity? Is it they want to land a message? What’s your take?
JS: It’s hard, I try to mostly write about people who are not as famous and overexposed as he is, that was kind of a first for me. So usually when it’s someone who’s not particularly well-known, especially outside of business and tech, I think sometimes what they want is a fair shake, or an opportunity to get their message out, to become better known or a lot of times, if it’s someone who just hasn’t done a lot of press before, they kind of just don’t — they’re not familiar with the reasons they should say no to a profile.
What are the reasons they should say no?
JS: Well, I think you have to pick your profiler and the institution behind them.
If you pick an institution full of literary critical writing students, they want to do some critical writing.
JS: Right, exactly. I am always amazed at the number of people who spend so much time railing against the New York Times and then sit for a profile with them every couple of years, because they can’t, I think, resist the logo and the brand, you want to be able to tell your mom that you got profiled in the New York Times.
I think the dangers and the pitfalls are usually — it’s sometimes less the individual writer and more the institution behind them, if you know that the editors are just not going to let a negative piece about person A or a positive piece about person B fly — and it’s easy to find out which institutions won’t let it fly — then it’s going to be hard to get any kind of accurate, fair understanding of the person.
But I think with Colossus, what we try to do is — we’re generally very pro-business, pro-tech, we’ll be very critical when we think it’s called for, and we just want to tell the truth as we understand it without coming to it from a place with any kind of partisan agenda.
I want to ask you more about Colossus and the business in a little bit. But I think maybe this will be your last interview of this cycle, I’m not sure, you’ve thought about Mark Zuckerberg and Facebook a lot, you mentioned it wasn’t top of mind before, I’m sure you’re eager to not think about it anymore. But when you look back at what you wrote, which everyone should read — obviously I’ll link to the profile, I’ll link to all your profiles throughout this interview — what is your high-level takeaway? Did it end up being what you expected, or was it surprising in ways you didn’t foresee?
JS: It’s very intimidating to answer this question with you asking it, you’ve thought much more about Meta and Mark than I have.
But that makes it more interesting. I’ve been in the weeds with this company. I see this company as — my colleague John Gruber, who I record Dithering with, he writes a blog called Daring Fireball. He was there for Apple, he writes about Apple, I think he started it a couple years after the iPod, then the iPhone comes along, that is the company that he grew up with. They grew up together, they’re still associated, most of our episodes on Dithering are about Apple, because that’s sort of John’s specialty. It’s always an interesting company, that’s kind of my outlet to talk about Apple.
The equivalent for me, I’ve always said, is Facebook and Meta. They started 2006, 2007. Stratechery started in 2013, but right after the IPO, in the middle of the nadir, as everyone’s like, “They missed mobile, all this is going wrong”, and I feel my development as an analyst, in terms of understanding advertising business models, understanding new trends, AI, all the controversies, Aggregation Theory, all this sort of stuff — that’s like my partner company in many respects. So I’m actually interested, I appreciate your point like, “Who am I to tell Ben what I think?”, but that also means I’m fascinated about someone who didn’t care and came in from the outside, and what surprised you about the entire thing.
JS: Yeah, I guess the biggest thing would be, I came into it feeling very conflicted about what Meta’s actual products are. Feeling like probably, on net, they’re harmful to society, but not really having a well-thought-through opinion on that. And I think what I came out with was — I could still believe that social media was a mistake, in the same way that perhaps smartphones were a mistake or the Internet was a mistake, but to blame Zuckerberg personally for everything that people hate about modernity is really kind of insane. But it’s clear why we do it, and why we’ve been doing it for ten years — because it’s very appealing, this idea that if you could only martyrize him, then we can wash all of our sins from the last 25 years away because it allows us to absolve ourselves of individual and collective responsibility for actually living with these technologies.
One of the most fascinating things is Peter Thiel is very famous for loving René Girard, and given that Peter Thiel was still on the board at this point, the extent to which Facebook did not perceive that they were a Girardian scapegoat, I don’t know how no one connected the dots here, I was kind of losing my mind at the time.
JS: Yeah. What else would it take?
You sort of reference this in the article — post-2016, brewing civil war on the Democratic side between the New York Times writing about emails and Hillary Clinton never — I’m still waiting to bring my daughter to the Hillary Clinton campaign in Wisconsin, which I was waiting all fall to do, and she never showed up — and then the Obama sort of wing, “Oh, let’s all blame Facebook”. It’s like, Facebook — they just didn’t see what was happening to them.
JS: Yeah, that is really fascinating. So yeah, I think there was a lot of that. And then also, I think, if I disliked him before starting on this piece and before meeting him, it was just a general impression that among rapacious capitalists, he seemed to be the biggest rapacious capitalist. After going through this whole experience — and it was an interesting year to be doing it — I think actually what I appreciate about him a little more now is he does seem to be more in the just tradition of classic American industrialists and businessmen and I appreciate that ideologically, even if I don’t agree with his core beliefs about a lot of the stuff that he makes — that he is ideologically unconfused and coherent in a way that I think a lot of his peers, like Sam Altman and [Dario [Amodei], are not. So I came to appreciate him just more as a business figure than as a technologist, especially as the ideological fights around AI and effective altruism and all of this are spinning out of control.
How did you arrive on the opening with his parents, talking about what he was like as a kid, and closing with talking to Priscilla and what his daughter is like?
JS: So the ending I tortured myself about for a long time, and I experimented with other endings, the intro I knew was going to be my intro within the first five minutes of talking to his parents, because — first of all, I never expected to have the opportunity to talk to them in the first place, they don’t do things like this very often, and they haven’t in a long time. And you always wonder about people like this — are their family members also media trained, because they’ve also been living with this for 20 years? I saw that maybe they are in a certain sense, but it didn’t come off that way at all. They reminded me immediately of my family. A bunch of readers have told me that they enjoyed the fact that the parents were bickering during the interview, which had never occurred to me — not while they were speaking to me, not while I was reading the transcript, not while I was writing the piece.
It came across in a charming way, not in a like they were arguing, but in a like, “She doesn’t really get technology”, sort of thing, I cracked up at that.
JS: Yeah. I’ve been thinking in the last week, like, I might just experience the sound of bickering Jewish parents as white noise — but I think it was mostly because they were really open about the difficulties of your son being Mark Zuckerberg, which I thought was really interesting. And then his mother, one of the questions I asked was something along the lines of, “Do you wish he’d just stopped doing this and would do something else with the rest of his life?”, and she gave what I thought was a very moving and profound answer. And that question kind of became the heart of the piece, it’s like, “Why is he still doing this?”, and then, at the very end, Priscilla kind of gives her own answer to that question, so it tied it up nicely.
It was beautiful, that’s why I’m surprised to hear the ending was torturous, because it matched perfectly the beginning, it was really brilliant writing, it’s an excellent piece, everyone should go read it. I could spend, as you know, I could talk about Meta and Mark Zuckerberg for a very long time.
Profile Accounting
I’m going to do a quick hit of some of the other profiles that you’ve written, and this is going to be difficult, we have not too much time left. Give me your high-level takeaway — what do you remember about that and what’s going to stick with you — and then we’ll just bounce through them. I’m going to go in roughly the order you’ve written them. So before Mark Zuckerberg, you’re going to go with Scott Wu.
JS: The thing that first interested me in Scott was — again, this was around the time when the unlikability of all the major AI figures was first becoming a big deal, not just in tech, but also in American culture and society and politics and it began with the question of, “I wonder if there is a major AI figure, or plausibly a future major AI figure, who’s actually not this hateable, who’s actually really likable and humanist, and is just as big of a nerd as all these other people, but actually seems pretty grounded”. And I talked to a lot of people, Scott’s name was one that came up a lot, and I thought he totally delivered.
Yeah, of course, I’ve met him before, he’s the nicest guy in the world, so it was a great choice.
JS: Yeah, exactly.
Shyam Sankar, the CTO of Palantir, co-founder, who I’ve interviewed on Stratechery previously, but I should probably give more context on who these people are in case people don’t know.
JS: That one kind of got back to this question of, there’s been something like $200 billion in venture capital poured into defense tech in the last several years and I think there’s a somewhat plausible scenario where all of that ends in a giant sucking sound. I kind of wanted to get to the heart of what this whole defense tech ecosystem is really about, both ideologically, but also what is the kind of political project that they see themselves as being a part of that’s longer than just the current administration.
Palantir is different because it’s just software, they’re not making hardware like Anduril, but I thought that was an interesting exploration of — the piece is really about Shyam’s life, but it got into a bit of, how can you justify a multiple like Palantir’s when they’re just selling software to the government? And the piece got into a lot of that.
What was interesting about Palantir is, right now you mentioned that large number and that potentially sucking sound, but Palantir came along and raised money at a time when there was no perception that there was a lot of money there, and I think it’s a fascinating company because you had to be a true believer all along and those are the sort of companies that I think do end up being different, because even as they get large and successful and the stock goes to the moon, the residue of that level of commitment and belief that was required to be there from the beginning — which, by the way, you do get from Meta too, I think. You reference this in the piece, the aspect of, in the end, Zuckerberg’s always right, that is their biggest strength and their biggest weakness and you see a similar dynamic with Palantir.
JS: Yeah, definitely. That’s interesting.
Josh Kushner — new Lakers owner, Josh Kushner, also largest funder of OpenAI outside of Microsoft, Thrive Capital, kind of an entire new generation of VC, also somewhat related to President Trump.
JS: This one had a weirder origin story, which is basically just — I had this long-standing interest in the Kushners that dated back to before 2016, when I was just kind of vaguely aware of who Jared was, but it was mostly the father, I can’t even remember how I first came across them. But there was just this Kennedy-esque story of this one New Jersey real estate principality that was built within one generation from the unimaginable destruction and loss of the family, which was in the Holocaust in Eastern Europe.
I was already very interested in them and then Jared, obviously, over the last ten years has become one of the more covered people in the country, and I was kind of vaguely aware that he had this younger brother who was considered by a lot of people to be maybe the savviest VC, but he didn’t do a lot of press — he didn’t do any press — and that he was the biggest investor in OpenAI. And so it was hitting every element of my interests.
It also came at a time — and this theme saturates a lot of the pieces I write — but at the time, I was especially concerned with this idea that American national identity has been coming apart in all the ways people are familiar with over the last ten years, and that the glue that keeps that identity together was coming apart. A big result of that is that people keep basically saying the American dream doesn’t exist, it’s a failure, it’s a lie, it’s propaganda, and I like unearthing these stories that demonstrate that, whatever its shortcomings, which we’re all very familiar with, the fairytale version of the American dream is, in some ways, an animating truth. The story of the Kushner grandparents coming up to what Josh is doing today, I thought was an important example of that.
Yeah it’s a very fascinating family. Both brothers — I’ve had a chance to meet both — are very impressive in person, so it’s very good stuff. Neil Mehta — give me the take on that one. Greenoaks Capital, long history in China, kind of almost the opposite end of the spectrum, same end of the spectrum because it’s a VC world, but very opposite end in other respects.
JS: Yeah, that was similar to the Scott Wu one, but it was just more personal to me. I came to Colossus from Tablet, this was my first foray into the VC world, and my general impression was just that, as a type of person, I just didn’t like venture capitalists, I thought they were full of shit and really annoying and I didn’t understand why they thought that the rest of us were interested in their health tips or book recommendations or their political opinions or whatever. Just as a class of people, found them extremely irritating.
So it was a similar thing where I was just asking a lot of smart people, “Who’s the guy who just understands that he is not the main character, and who’s super smart, and who actually means it when he talks about all the VC tropes — like conviction and being highly concentrated and being a founder’s best friend and all the other stuff that I find incredibly annoying to hear from most VCs?”, it was like, “Who’s the guy who’s the real deal?”, and Neil’s name kept coming up.
It just so happened that there was something interesting about him, which is he basically absented himself from the model companies. He was just convinced that OpenAI and Anthropic and these companies — he was very bullish on the technology, but pretty bearish on the business models. But he had just recently made this half-billion-dollar investment into Safe Superintelligence, the Ilya Sutskever venture, which I thought was interesting.
That is a repeated story, I think, in venture capital. You mentioned in passing the first profile you did — you didn’t get the cooperation. I’m assuming you’re referring to Jake Sullivan.
JS: Yes, that’s right.
Colossus
I’m curious — this sort of gets to the shift in what you’ve done. You were writing news and analysis, and you write a third-party profile of the National Security Advisor and then you shift into actually talking to the people, in cooperation with them. As you think about your role and what the job of a profile writer is, what is the extent of, “I have a view on this and this is going to be the angle, to say what I think”, versus, “I’m going to discover and see what comes out”? Has that shifted in your mind over time?
JS: It’s definitely always dependent on the writer and on what you can kind of get from the interviews. I generally feel, with some exceptions — the Scott Wu one would be one — but I generally feel like I want to present very extreme circumstances and opinions, without ever showing my hand completely as to which are the ones that I think belong to me. So I don’t like telling people how to feel, but I like giving them a range of things to feel so that’s why I’ll generally try to make some of these profiles feel like you’re reading a short story or a novel or watching a film, but then when you get to the end of it, it’s not totally clear what the author thinks. I don’t always succeed, but that’s usually what I’m going after.
The exceptions can be if, in the course of the interviews, the person tells you something they really shouldn’t have told you, and it breaks a lot of news, and that becomes the story. But otherwise, if it’s really just more about trying to figure out who the human being is behind this public persona, it’ll usually be the former.
So you’re able to do this, you mentioned Colossus, Patrick O’Shaughnessy started this. Tell me, you’re the editor-in-chief, what’s the vision here? Is there a business model? Is this a, “We think there needs to be a platform for these sorts of long-form stories and we’ll figure the rest out as we go”? What happened, you wrote about Palmer Luckey and Patrick just reached out and was like, “You want to do this full time”?
JS: Yeah, basically. There was a long stretch of time — a number of months — where we were just talking first before we ended up actually agreeing to it. But it began with Patrick’s podcast, Invest Like the Best, that then became a podcast network, which includes David Senra’s Founders and some other shows. And then toward the end of 2024, Patrick and some other folks at Colossus decided to do a print magazine with one issue, 1,500 copies, no plan for anything, and those copies sold out really quickly, mostly among the podcast listeners.
I think he felt like, “Okay, we just want someone to come in and be the EIC of all of this” — of the magazine and the podcast network, and I’d been working at a magazine. He liked the Palmer profile, we share similar instincts and aesthetic judgments for what these things should look and feel and sound like and we both just liked the idea of bringing that kind of 1960s Esquire, 1950s New Yorker prose aesthetic to bear on business and technology.
My own interest in it came simply from the fact that I don’t think it’s true that in every era, business people and technologists are the most interesting, interdisciplinary, salient figures in culture. Maybe in the 1940s and ’50s it was physicists or people who worked in the national security bureaucracy, in the 1960s and ’70s it was novelists and musicians and filmmakers, and on and on. Right now I think it happens to be people in business and tech and it wasn’t always the case, and it probably won’t always be the case, but it is right now, so writing about these people is an opportunity to explore some larger phenomena happening in America. So Colossus is now a full quarterly print magazine.
And it’s the print magazine. That’s what you actually sell, right? Everything online is free?
JS: There’s a print magazine that has some of the online content and some print-only content and so that’s a subscription model, but you’ll be pleased to hear that Colossus as a whole is supported by advertising, which we’re very proud of and not ashamed of.
I’m pro-advertising!
JS: Yeah, exactly. The ceiling on interest in the print product is probably relatively low, but the fact that we’ve broken even on the print product by itself after 18 months is great. The business is doing really well, and we have a core group of sponsors that we love working with and otherwise, we just publish at whatever cadence we want, we’re kind of shocked about how well it’s done in only a year-and-a-half.
Final question. Do you believe in the Great Man theory of history?
JS: I somehow was never prepared for this question, but I probably should have been. Obviously there’s a lot more gray area than the two sides allow for, but if I had to pick, I would say yes, definitely. I come down on the side of individual people in certain circumstances do end up changing the course of history, and the word “great” in “great man” encompasses both people who bring unimaginable destruction, as well as good things, and all the canonical examples, I think, are the right ones. It is hard to imagine that the Second World War would have taken that course without Hitler, and it’s also hard to imagine the Western alliance being preserved without Churchill, or whatever you want to pick.
It’s funny, because I think this came up — there was some phrase or paragraph in the Zuckerberg profile where it’s like, this is actually a person that historians will talk about, there’s not actually that many people that are like that and it’s fascinating because it’s in tension with your takeaway of talking to him, that this is a good guy, blaming him for all of social media’s issues and impacts is maybe not completely fair. And yet at the same time, that is the price, that’s the price of being the great man. Of course you need the circumstances, of course it needs to be right place, right time. But someone has to actually do it. And that’s, I guess, part of the takeaway I got from your piece.
JS: Right, exactly. I think that was probably one of the takeaways I had, which was — if at any point in your life you were envious or jealous of him or someone in his position because of the money or the power or the fame or whatever, you do come away from interactions with him, or maybe people like him in general — and at least I come away feeling like, “Thank God that’s not my life, I would not want that life”. But that is the price of, as I think I said in the piece, I do think people will still be writing about him and what he did a hundred years from now.
Well, Jeremy Stern, you had an interesting life, which I loved to hear about, and I was happy to talk about it with you for an hour. Thank you for coming on.
JS: Thanks Ben.
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