Thanks for tuning into Tech Stuff.
If you don't recognize my voice, my name is Oz Voloshian and I'm here because the inimitable Jonathan Strickland has passed the baton to Cara Price and myself to host Tech Stuff. The show will remain your home for all things tech, and all the old episodes will remain available in this feed. Thanks for listening. Welcome to Tech Stuff.
I'm oz Voloshian and I'm care Price.
It's Wednesday, which means it's time for a deep dive conversation with a fascinating person in and around tech. Were thrilled to bring you a conversation with Jessica Lesson. She is the CEO of The Information, which is a media company based in San Francisco that covers the tech industry. Because just two days after the inauguration, one of the stories I find most personally fascinating is the alliance for now between MAGA and the tech Bros. And it's obviously
clearest in Elon Musk. Have you seen that video of him and DJT dancing right away?
It's fantastic.
This is the robot dance they're both doing on Newye's Eve at mar Lago.
My first thought when I was watching it was who's better thing?
That is Trump's dance And you see Elon starting and then you see Trump kind of shooting him at Lance, being like, slow down, br that's my dance. But of course it's not just Elon his currying favor with the new president. Up and down Silicon Valley, there's this rush to cozy up to Trump. And eight years ago there was this amazing moment where Trump summoned all the tech CEOs to Trump Tower in Manhattan right before he was
inaugurated to kind of show them who was boss. And now all these stories about tension between Trump and tech, and now it couldn't be more different. And the coziness between Silicon Valley and Trump seems to be getting, you know, cozier and cozier.
Yes, it's incredible to it's it's almost as incredible as Mark Zuckerberg's fashion transformation.
Well, I want to get to the fashion choices too.
I found just one of the most striking things an outside observer of technology is Mark Zuckerberg's physical transformation. I mean, from the hoodie wearing character of the social network to a mixed martial artist who also released his own t shirt line, which have Latin sayings printed on them. He wore on recently that said out Zuck out Nihil. How's your Latin Cara?
Not good enough?
I had to google it too, But it means all Zuck or all nothing.
I don't even know what that means.
Well, I think it means he's a big guy.
Before that, I want to note that Jessica has this kind of interesting personal connection to Mark Zuckerberg. The co host of her podcast, which is called The More or Less Podcast, was at Harvard with Mark Zuckerberg and went on to be VP of Product at Facebook. That co host, Sam Lesson, is also Jessica's husband. Finally, if I couldn't have imagined being closer to my podcast host than you and I are but stranger things but more seriously, and
we've got She got a listener email about this. Mark Zuckerberg suspended the fact checking program at Meta and at Facebook, which sewed, frankly.
Quite a lot of horror.
He also added to the board of Meta Dana White, the founder of UFC and a very close confidante of Trump. And so one of the things I really wanted to talk to Jessica about is what's going on with Mark Zuckerberg, how much of this kind of change is driven by personality, and how much of it is driven by kind of opportunism and wanting to appeal to the new power center in the US.
So I'm excited to get the inside scoop. Jessica was originally a tech reporter for The Wall Street Journal who was covering Silicon Valley from New York City before she moved west to Silicon Valley and eventually started her own site called The Information.
The clues in the name very much, so it's.
The sort of mainline source for news on technology.
I heard Jessica on the Daily Beast podcast, which is hosted by Joanna Coles, who's a friend and a mental and advisor of mine. And Joanna and Jessica and Samantha Bee were talking about this idea of the revenge of the Nerds, and I thought I was just irresistible. So I wrote to Jessica, who greed to sit down for
tech stuff. I really enjoyed your conversation with Joanna and sam Bee, and you use this very entertaining phrase, the revenge of the Nerds, and I was wondering if there was like a single moment or a dinner or a tweet, or an outfit or an image or something that really sort of brought that moment home to you.
Great question. I think it's really more a shift in communication style among leaders here in Silicon Valley, who, yes, could somewhat be stereotyped as nerds, although the industry has certainly grown beyond that, but a real kind of flex in their communication, often using social media. And I think
Elon must is obviously a trendsetter here. Mark Zuckerberg is part of the picture, and you know it's clear that this kind of go direct to share their message, wearing their luxury fashion clothing and so forth, is really the vibe shift in tech right now. And I do think it's been building, and I think Elon's kind of over the topness, outrageousness, whatever you would call it, has given kind of cover and shifted the window, and many other CEOs are following.
I mean, you've been at this since two thousand and five, right, originally the Journal and then founding Information. Where would you say that like sort of vibe shift if you had to pinpoint in a moment in time, when did it kind of start to coalesce.
You know, right now, in a micro sense, we are in this moment fueled by the Trump election. I think one of the big questions in twenty twenty five will be will it continue or which direction will it go? If you zoom out a little bit more, I think, particularly as it relates to politics, tech had been a
little more defensive over the last four plus years. I mean, the vibe was very much a very tense relationship with Washington, with regulators, with the press, and I think broadly a lot of companies kind of not that they didn't rattle cages, but they tried not to rattle cages in a sense because there's a lot at stake, and the regulatory pressures were very real with the cases and finds they were getting hit with, and so it was sort of like, don't poke your head out too much and draw attention.
And so I think prior to this very new period, we were in a little bit of apologizing defending we in the industry, and this is a reaction to that. But I think everything is a reaction to the thing before it.
You have been a reporter and an editor and found an incredible media company covering this space, but you're also part of the world, I guess. I mean through your through your marriage with Sam and social relationships with some of these figures. Is that a kind of complicating factor or a bonus or sometimes one sometimes the other.
I mean, how do you kind of navigate that?
I mean, every journalist has a personal life, and I'm no different. But I don't feel at all that I'm part of, you know, that world of the elite Silicon Valley CEOs in any way. I mean, I think, you know, the information has been scrutinizing the technology business now for more than eleven years, and I think that's firmly where
my reputation is. Although I hope that as a founder, I have experience in what it's like to build a company, and so that helps inform the storylines we go after the questions we ask.
I think sometimes as this feeling from the Silicon Valley folks that like journalists the enemies and don't understand them and all these things. You know, you obviously come from from the same point of coverage in terms of speaking truth of power, but also you know how to slip into that register. I suppose in terms of how to communicate.
There are some commonalities. I mean, sometimes you can get a source to build a relationship by talking about, you know, some recruiting challenge you're having that mirrors some recruiting challenge they're having. But you know, I think there's no doubt in people's minds, you know what the purpose of the information is and what our mission is to be the most authoritative publication covering this industry. But it does also help to have known and covered as a reporter people over a long time.
Let's start with it with Mark Zuckerberg because in a sense, the esthetic transition of Mark Zuckerberg for me as an outsider, has been one of the clearest indicators that like, something is going on. So and can you just describe for people who haven't been sort of following his personal appearance for the last sort of five years, what's changed and what it may say about meta and the wider industry.
Yeah, it's I mean, I think it's in interesting a part because Mark has talked about it. I don't know that I have great insights into the choices that he's made from a fashion perspective, but I think what's clear is that he's leaning in to being himself and I think that also feels very elon. Elon that you see on Twitter is you could be having a dinner conversation with him and these would be the things he's saying, and he's not censoring himself. And I don't think Mark is censoring himself.
And so when it comes to when it comes to something on the top of censorship, like you know, the removal of the fact checking function of Facebook, I mean, do you view that as sort of Mark being himself and feeling unconstrained, or do you view it more as a kind of gesture towards the new political elite.
I think it's both, I really do. I think from the earliest days of Facebook, Mark was talking about free expression. He has given many speeches about and pushed back on on things he is deemed censorship. There's obviously a period in the whole Internet where many platforms went in the direction of moderating more and more and more under pressure from regulators in the media, and I think Mark seesed a political opening in a moment to get back to
where he has always thought the company should be. What happens next is anybody's guests, right, I mean, I think having made the decision to do this, he's definitely striking the notes of mentioning Elaw and giving him shout outs, attacking some of the same enemies that President Trump has attacked, so making something out of this moment. But I don't
think he pivoted to Curry favor. He's very consistently been very uncomfortable with the direction a lot of these platforms have gone in moderating and even as a journalist, I think it's very complicated.
And yet when it comes to like the Elon version of free speech and the Mark Zuckerberg version of free speech, most generous feel very ucomfortable.
So it's a strange kind of paradox.
What I know is a journalist is a we have to fight for the value of professional journalism. Social media is not going to reveal the things that companies want hidden. It's not going to tell you that the Chinese government owns a direct stake in byte dance and scrutinize what's happening to us users data things that are in the
public's interest. And right now, especially in Silicon Valley, the discourse is so toxic around it that tech folks hate journalists and journalists hate tech folks, and there's sort of no room to say what if These are both important pieces of the information ecosystem. Now, of course, how we combat the misinformation that can spread very quickly on social media's a tremendous problem, but I think that is outside what any one company can necessarily do.
When we come back, we'll hear about the rise of Christianity in Silicon Valley.
It's funny you mentioned this last four years of the tech industry having to be very careful around the administration obviously Lena Khan and the FTC and stuff. But rewind eight years and there was that famous moment where Trump, like the school principle, summoned all of the unruly tech CEOs to Trump Tower, basically to Flex's authority. And the coverage at the time was all around how much tension
there was between Trump and the tech community. How did that change so dramatically in the last eight years.
Yeah. I think over the last four years, in particular, the relationship between the tech industry and the Biden administration really beyond soured, I would say, and on multiple fronts, from crypto to just anti trust to AI regulation, things that have become very press issues for the industry. Washington
and the industry was really not seeing eyed eye. So I think you had a group of tech leaders receptive for a different approach, and Trump, either because he believed it or was opportunistic, really effectively positioned himself as an alternative to that and someone who would not take the same approach on blocking the smallest of acquisitions companies wanted
to do and so forth. And this was really crystallized when markind Recent and Ben Horowitz, who had been staunch supporters of the Democratic Party announced and we broke in the information we're going to endorse Trump, And I think they outlined their thinking very clearly, I mean from their point of view, and it was really how on so many topics they thought it was existential around things for
AI to have a different approach. So the industry was never it wasn't cozy with Trump the first time around this time, it seems, you know, in many cases and not at all, there's an attempt to forge an alliance and see more alignment. But it is so early and I think it's very safe to say that the relationship will be a bumpy one.
Yeah.
I think there was a story from Maggie Haeman that Trump has already started to kind of comment that Elon's around a lot.
Do you have any intel on the unfolding of that relationship.
I don't. I mean from what I hear, there is a friendship there, so I have every reason to sort of believe that. But yes, And one question I have is, obviously you have a lot of technology leaders really sort of bragging about how frequently they're in mar A Lago talking about their influence. I mean Mark in recent recently went on a podcast, said he spent fifty percent of his time since the election involved in some way on
the new administration. I also imagine there are a lot of people in Washington and politicians who might be somewhat skeptical, right, but you still have two different worlds clashing and colliding here. Time will tell. You'll also undoubtedly have reporters and folks trying to make something of friction because that's a good story. I mean, that's a problem with the press these days. So I think we'll see, you know, what are the
policies that come out, what are the appointments. Obviously, in terms of appointments and tech figures who are playing direct roles in the administration, there are quite a few, so I think we just have to watch it unfold.
I wonder if in a sense Trump's approach himself with something of a revelation or point of inspiration in terms of how he effectively sidestepped the media and created his fan base and used that political leverage, and whether that's something that leaders and say they can value have kind of consciously emulated, or whether it's just something which kind of happened at the same time.
I think so the relationship between what now is so not affectionately dubbed the legacy media by tech leaders and the tech industry has gotten quite poor in a sense. I mean, I think you have a lot of media outlets who have just been out to get the tech industry, who have pursued stories based solely on the sort of agenda that they have to show a particular thing. And so I think in that respect you have some tech
leaders who are sort of rightfully miffed. At the same time, there's been a lot of very fair, tough journalism of growing businesses that are having extraordinary impacts on the world, and powerful people don't much like the scrutiny. So you had a situation where there was a lot of animosity so absolutely, a figure like Elon who literally bought a very important communication platform to subvert the media is inspiring
to the enemies of the press for sure. Now, of course, the fact that these leaders then go on and lie about the media and create all sorts of animals toward it that isn't deserved is also problematic.
When you think think into the future, when people kind of write the history of this next chapter of Silicon Valley, what do you think I'd write about Elon Musk and how will they describe his influence on the on the culture of the whole industry.
I think the story is still being written, honestly. I mean, I think from a perspective of a leader being emulated by others, the impact is real. I mean, I think you can see from Sam Altman all the way down. You know, you used to just be the CEO of one company. Now everyone wants to run four or five because Elon does. You know, you used to give your interviews and now you just tweet at your enemies and until they buckle. So that's clear. Obviously Elon has built
and is building some incredible businesses. You know, it seems to me that he's trying to fashion himself as shaping political opinion culture you know, around the world, and that seems awfully audacious, perhaps as audacious is going to Mars. And so what's interesting though in this is a little bit meta, so to speak. But like Elon, the cult of people around him will always celebrate him. I think people are choosing to believe what they want to believe and to vilify or celebrate who they want to.
Is this stuff with the alternative foot doutsge Land thing, the AfD in Germany making anyone in the valley uncomfortable? I mean, this seems to be like crossing yet another rubicon in terms of the company.
Yeah, I think everyone here is a little bit uncomfortable, But there's also the He's going to send us to Mars. I say this too much, but everything just it feels like the pendulum swinging in these days, it's swinging faster and more furiously. And so to be in the role of a journalist kind of standing by and watching is fascinating and I think it actually is a bit hard to predict at this moment because so much is at play.
I remember when I used to work for Charlie Rose, a producer many years ago, and we came to Silicon Valley to do some interviews in like twenty ten, I think, and like one of the interviews was at Facebook with Mark and Cheryl, and it was like such a traveling from New York. It felt like going to this like flip flops, T shirts, green juice, like liberal enclave. And now it's like completely in a very very short period
of time in grand scheme of things flipped. But there's been some very interesting reporting in the information this feature that you ran on the rise of Christianity in the Silicon Valley, which I found super interesting because it speaks to a kind of cultural conservatism that maybe also had something to do with what we're talking about.
Yeah, this was a wonderful story in our weekend section about the rise of Christianity in tech and really fueled by I mean figures like Peter Teal who have long been very religious but it being more open about it, who have anti christ seminars and so on and so forth, and it's definitely something to watch. The industry now is so big that certainly doesn't speak for the entire industry, but it's emerged as a pocket that's quite strong. You have people going to meet founders by hearing them preach
and then going up to them. So, I mean, based on our surveys of our subscribers with the information, you still have the majority of tech workers voting for Kamala Harris to be clear, right, But there's a very loud group that's not and I think they're you know, they're winning some more followers and they'll probably win some more too. But what's so interesting is they also have the largest
megaphones in society right now. So and maybe the lesson here isn't Maybe what's different is there's nothing exceptional about the tech industry right now. The tech industry is now business. It's grown up, it's big, it reflects lots of different things, and so it votes less as a block so to speak on all of these issues. And you know, I'm not sure that's good or bad actually, but it's interesting and we'll have some.
Consequences when we come back how it all started. Jessica talks about why she felt big tech needed the information.
You wrote a piece last year in the Atlantic.
It was a stark warning to other media companies not to partner with AI companies. Essentially, even though funny enough, the Atlantic was one of the you know trailblazers.
Yeah, there were higher ups there who were not happy with the timing of those two things, but kudos to them for not interfering because I didn't know that at the time. I still think these deals are very dangerous and for a lot of reasons. I think fundamental technology companies and news and information companies are not in the
same business. They're not aligned. There may be particular partnerships or getting more eyeballs on journalism, things like that, but the history of these partnerships is that they've n did very, very poorly, and that news organizations have diverted time, resources, attention focus to placating these partners who, at the end of the day change their strategy, don't do what they say they're going to do, not because they're evil, but because they're not news organizations. So we saw this with
social media publishers rush to make content for Facebook. Facebook change its priorities. You can see this down the line, the same as true Google. You know, it's so important that as news organizations we control our own destiny, that we don't align with tech companies, but that we use tech to better reach our audiences and in particular. These partnerships also sought to remove sort of legal issues around news content and other content that these models were trained on.
And will the New York Times case be heard this this year and twenty five times.
I don't know, but I am cheering them on because I think to just say, let's wait a second, maybe there is a partnership, Maybe we can come up with fair value for this, but we're not there yet. I think takes tremendous courage and so yeah, to strike these deals when there is no product, there is no business model. It's just not possible at this point. And also there's always you have to read the fine print of them. You know, there's some headline grabbing numbers, but a huge
portion of the payouts are in open AI credits. So it's not even that you know, these newsrooms are getting cash and so forth.
It's a classic will invest in your company but not in cash.
I mean that's not You're just explaining the whole SaaS enterprise cloud ecosystem there. So we need to let this play out and come up with the right framework and then build the right partnership soft products that actually exist and have users.
And just have question on Sam Oltman.
Why back in two thousand and five did you want to cover him when nobody else did And how have you seen him change or not change in the intervening twenty years.
Well, I'd like to say there was some grand plan, but I was really, you know, the young reporter scrounging for stories. And I was actually a tech reporter based in New York. And at the time, all of the journals tech reporting was out in Silicon Valley, and they got to cover Google, and they got to cover all Yahoo, a big story back in the day, and I was left. I mean, scrounging is not inaccurate, and so everyone who
got in my inbox got a follow up. But what I remember from that was also at the time, the Wall Street Journal didn't write much about startups. I believe there was a rule that, you know, the paper wouldn't write about a deal less than a billion dollars or something that in a very of antiquated way of looking I think at business and what was happening. And so you know, I think my editor rolled his eyes when
I was talking about this mobile thing. And what Alman's app was was it was a friend finder, so you could see your friend's location, and obviously that raised a number of questions around privacy and phones weren't really being used in that way before with those apps. And so I think the way I got my editors interested was hooking it to a partnership with AT and T that
the app was doing. And then also Sam had gone to Washington to talk about legislation around mobile privacy that he wanted to advocate for, and I remember he offered me this his like documents that he was, you know, sharing with senators or so on. And I think I had a light bulb go off about two years ago when there were a bunch of headlines if Sam was again going to Washington with his thick binder of proposals
on how to regulate AI. And I think there's a savviness to Sam to try and get ahead of the narrative and shape it that was there kind of twenty years ago. There was also a savviness, you know, to working with a reporter to get coverage in a paper that really was not super friendly or interested in startups, which he worked with me to do. So I guess the story, the story published, story published it.
So you had the first byline in any major press.
Yeah.
I mean maybe there was some tech Crunch articles or whatever existed back in the day, but I think it's quite telling. And as a business reporter, I really enjoyed watching people, you know, operate for a very long time. I think you can learn a lot.
Why did you leave the Journal to start the Information.
For two reasons. The first was I was very frustrated with how technology was being coveredwere including the Journal. This was twenty thirteen when I left, and there was a lot of hype around companies. It was a lot of putting founders on the cover of magazines, and to me, all of these businesses were going to be very important
businesses and needed to be understood as businesses. They're financials, you know, so on and so forth, and I just thought there wasn't a rigor to covering the tech industry, and even internally the journal. I'd reach out to a colleague to try and collaborate on the story and they'd sort of dismiss So I'm not a tech reporter. That's what those people out there do. And so I thought that was just a huge missing opportunity because I know business leaders are very smart and they were seeing tech
upend their businesses and they wanted to go deeper. The second piece was business model. Back then, the line of thinking was that if you're a big publication, you had to chase what Google and Facebook were chasing with ad dollars and go for traffic. The rise of digital advertising cause publishers to go crazy for traffic, and what that did is obvious. It meant we were catering to huge
audiences that we weren't going deep. We were focused on live blogging announcements instead of doing investigative reporting, and we weren't playing to our superpowers. And so I knew that for the industry to have a really successful and sustainable digital future, digital subscriptions had to be more than an afterthought. They had to be the kind of true north. And no one really believed me. I mean even when we launched,
everyone laughed. And eleven years later, you can't name a publisher that doesn't have a digital paywall or subscription, or.
An executive Silicon Valley who doesn't pay for the information.
We've got a fair number of them, shall we say. But also, you know, more than half our readership is outside of Silicon Valley. Actually, so there is a growing group. But Yeah, it was really those things. It was a commitment to the business model and really the type of coverage that inspired me.
Jessica, thank you so much.
I really really appreciate you taking the time and enjoyed the conversation.
Thanks as me too.
One of the things that I found most interesting about this interview is this shift that seems to be happening, vibe shift, major vibe shift in Silicon Valley. The fact that when Biden came into office, the attitude towards Silicon Valley was very different than its feels right now.
Yeah, and Biden hired as his FTC chair Federal Trade Commission Lena Kahan, who's actually somebody that you and I somewhat know. She was on our previous podcast, Sleepwalkers, and as a very young Yale law student, she wrote a paper called Amazon's Antitrust Paradox, and this was basically a broadside against the tech industry and how previous frameworks of anti trust enforcement weren't appropriate to dealing with monopolistic practices
in tech. And she became kind of a hero in the tech regulation sphere and then became like in her thirties chair of the FTC and basically made it her business to make the tech companies lives more difficult.
And actually, something really crazy is happening right now, which is that Lena Kahan is siding with Elon Musk on what issue, on the issue of sam Altman transferring open ai from a nonprofit to a for profit into this sort of as they said on Puck Mega Unicorn. Wow, and you know Elon is not about it at all.
Well, I mean it's interesting. Obviously OpenAI is transitioning or hoping Samilton's trying to transition it from you know, safety.
Focus not for profit to for profit.
But OpenAI and Microsoft are so closely connected that I can kind of understand why, you know, Lina Khan's anti monopolistic practices spidery senses are tingling here.
The last thing I wanted to bring up was an article that I read in the New York Times that Maggie Haberman wrote about Elon's physical positioning near the White House. Yeah, and just to imagine in the Biden administration that like the owner of a mega technology company would have office space so close to the executive branch. Is such a
departure from twenty twenty. I mean, both of you look at Lena Khan as the head of the FTC, but also just in terms of the relationship between the executive branch and Silicon Valley and how they were sort of at odds, like especially when we were even reporting on Sleepwalkers, Like there's real technoskepticism and an interest in regulating AI and understanding its effects on the American public. And now it's like let's play.
But by the way, I mean, Biden was close to various executives, Jeffrey Katzenberg being one, much of Hollywood. Hollywood picked Biden, the tech industry picked Trump.
It's true who.
Won, who has money, That's who won. That's who won. That's it for tech Stuff Today. This episode was produced by Victoria Dominguez, Lizzie Jacobs, and Eliza Dennis. It was executive produced by me Kara Price, os Vaalahan and Kate Osborne for Kaleidoscope and Katrina Norvell for iHeart Podcasts. Our engineer is Charles de Montebello at CDM Studios. Kyle Murdoch wrote our theme song.
Join us on Friday for tech Stuff's the Week in Tech. We'll run through our favorite headlines, talk with our friends at four or for media and try to tackle a question, when did the PayPal mafia become a thing.
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