[00:00:00] Jessica Lessin: 

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Media organizations have to not screw up. You have to earn it with every article, you have to earn it with every headline. 

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What worries me the most is when I see journalists who I think are more crusaders than reporters.

[00:00:11] Michael Eisenberg: 

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Why do you think that's selling your soul to the devil?

[00:00:12] Jessica Lessin: 

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We've seen what happens when quality news organizations take a quick buck from a tech company without thinking about how it is helping them build a sustainable business that serves their end user.

To build a news brand in this decade, you have to also build a community of people who really value your product and the experience that they get out of it. We don't get to launch a product and then tweak it and scale it. We have to launch our product every hour. We have to keep publishing.

[00:00:41] Michael Eisenberg: 

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What were you wrong about when you started The Information?

[00:00:43] Jessica Lessin: 

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Oh my God. So many things.

[00:00:48] Michael Eisenberg: 

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I am super excited to have Jessica Lessin on with me. This is the first time we've interviewed, or had on the podcast, the spouse, or someone even related to another podcast guest that we’ve had.

[00:00:58] Jessica Lessin: 

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Woohoo! We're the first couple. Love it.

[00:01:01] Michael Eisenberg: 

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There you go. I know Jessica for a long time. Actually, how did we meet? I don't even remember anymore.

[00:01:06] Jessica Lessin: 

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It may have been when I came to Israel more than a decade ago. And I know we came to Aleph, but I knew of you at least before then. But I think maybe that was the first time we met.

[00:01:19] Michael Eisenberg: 

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Yeah, I didn’t remember. So for those who don't know Jessica Lessin, she is the founder and CEO of The Information, which is probably, at this point, the most well-read, insightful news and analysis operation about Silicon Valley. It has a surprising readership that I hope we're going to get into. I keep running into people all over industrial America who read The Information.

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Jessica Lessin:

Awesome.

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Michael Eisenberg: 

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Part of what I wanted to get to–but why don't you tell everybody about your background, and I'll highlight what you're too bashful to say. 

[00:01:52] Jessica Lessin:

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Awesome. Well, I actually think you're catching me on our 11th anniversary. So 11 years ago, I was a reporter at the Wall Street Journal, covering Silicon Valley, and I was really concerned.

I was concerned that we weren't building a sustainable business model for quality journalism, that publications were very focused on traffic, and advertising, and trying to beat Google in the ad game instead of building meaningful relationships with our audience and making money from delivering something that was worth paying for.

[00:02:30] And I was also worried about how tech was covered. I actually edited the first article I think that was ever written about Facebook when I was at the Harvard Crimson. So I really saw the emergence of this whole category of company and business from very, very early on. And I saw at the time–this is more than 10 years ago–a lot of coverage that was chalking it up to, “Oh, what's the hype out there in Silicon Valley?” Or, “How much is this founder worth?”

And there was really, I thought, a lack of realizing that tech was transforming everything. Every industry was about to change, and a business leader needed to be following that as much as they needed to be following the stock market. And so I started The Information to do that, to build a subscription publication and community that was doing impactful work about journalism on tech companies, both scoops, and features, and data, and really to be that authority that I felt we needed to have–and to do it with a very simple, straightforward business model, 400 bucks a year, and to see where it took us. 

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And now, you know, we have an active, engaged audience of more than 700,000 global business leaders, and it's going pretty well.

But there are a lot of headwinds for news as well, which I'm sure we'll talk about.

[00:03:55] Michael Eisenberg: 

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Yeah. And before I dig into your subscription base, I want to point out to everyone that you were a reporter at the Wall Street Journal, I believe it was like for eight years, or something like that. Is that right?

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Jessica Lessin: 

That's right. 

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Michael Eisenberg: 

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And so you came out of traditional media, and before that came out what I would have called traditional media also, which is the Harvard Crimson. I myself was an editor of a college newspaper, and we always looked at the Harvard Crimson–

[00:04:16] Jessica Lessin: 

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Best job. Best job.

[00:04:19] Michael Eisenberg: 

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The Harvard Crimson and now, you know, Harvard–but we won't get into that right now, Harvard. 

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But I'm most interested in the following. There was no Substack. There were none of these people at the time really trashing mainstream media, which is what's gone on now. 

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Jessica Lessin: 

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Yeah. 

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Michael Eisenberg: 

And you talked about the prompt that you thought the coverage was shallow. But yet you kind of, I think you're the first actually, to kind of go out and leave mainstream media, and say, “Okay, I'm going to do this, with a subscription model, and create an audience for myself.” 

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Beyond the shallowness of the journalism, what was it about that moment, again, the pre-Substack, the pre-easy-to-charge moment, that caused you to do it?

[00:04:58] Jessica Lessin: 

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Well, something had to change, Michael. And, you know, I had covered startups for so long that I kind of understood you don't just build great things by thinking you've built lightning in a bottle, or you kind of can through doing things incrementally better, build a great different company. And I think that was an insight I had that was different. Like, the outside world thought you became a startup cause you woke up one morning and you dreamt up, you name it.

But I had seen all these companies, you know, Instagram was a little bit better at photo sharing, right? Dropbox was a little bit better at file sharing, and so on. And so, my calculus was like, I can do more of these stories that take people behind the scenes that are about important issues. You know, my last beat at the journal was Apple, and I saw that if I wrote about some dynamic inside Tim Cook's new management team, post Steve Jobs, the readership for that was vast. People around the world across industries were trying to understand that.

So I knew there would be this huge market if we just did things a little bit better. And at the time, I also remember going to an iPhone launch for the journal, and my boss wanting me to live blog what color Phil Schiller's shirt was, because that was the traffic-grabbing approach of media at the time.

And I'm just going like, “I got to go talk to Phil Schiller and build my relationship with him. I don't need to be live blogging the color of his shirt.” And so I did feel like it was an urgent moment that if we, as a news industry, facing this onslaught of disruption from technology, we're going down the same road of trying to play the traffic game, we'd be in deep trouble.

And, at the same time, I'd see these same technologies and tools that could be so empowering for media companies that we could use to segment and personalize for our audiences, and embrace that. And I just thought it was more urgent than, I think–a couple of years later, the industry also sort of began to believe it was urgent.

I mean, when we launched with a premium subscription, many people who are close friends of mine, you know, would–I remember Business Insider publishing, “Oh, we'll just summarize every Information article, so you don't have to pay a dime.” You know, they have copied our subscription–

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Michael Eisenberg: 

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And now they’re charging. 

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[00:07:30] Jessica Lessin: 

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The Verge has done the same. And, you know, at the time we were one of a number of tech sites, you might remember AllThingsD, Pando Daily, there was a whole cohort and–those brands don't exist anymore. And so, and they had different models, but there's also been a sea change in the business, which I think has been very healthy overall, but it was kind of isolating back then. Kind of isolating.

[00:07:54] Michael Eisenberg: 

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You actually led me to the question I wanted to ask after this first question, which is–what causes an august institution like the Wall Street Journal, known for its quality journalism, to become a click baiter over time, and to kind of get in this traffic run rather than delivering a quality product?

[00:08:10] Jessica Lessin: 

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I've been thinking a lot about this now, because I'm worried we're doing it again around AI a little bit. Because your question really gets to the heart, I think, of what is the time frame of building out your organization? And what are your real aims, and objectives, and that real alignment? And I think in media, it's been a challenged industry.

A lot of publications had one eye on the door, as many startups do, and have been trying to kind of ride the tide to an exit of some sort. And if you think that the tide is X or the tide is Y, you chase those games. And, I think it honestly comes down to a short-sightedness or a more long-term point of view. And obviously, if public companies versus private companies probably have that dynamic as well a little bit.

But, ultimately what I spend a lot of time thinking about is, how do I make the right choices for The Information for the next 10 years or 20 years? And in media that's very different than the right choices over the next 5 months or 12 months.

[00:09:31] Michael Eisenberg: 

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But, like, the Journal's been around for, like, forever, okay?

Like, what caused them to do this? Now, I was at an event once with somebody very senior from CNN right after Trump was elected. And a young woman who was a graduate student at Columbia University got up and asked this executive at CNN and said, “What are you doing to give Trump more air time than–” at the time, “Hillary Clinton?”

And he said, “Sold ads, we got a lot more viewers, and we need Trump.” She was furious at the time, and without getting into the politics of it, the question one could ask themself is, is it that people put business model ahead of good journalism? Is it that they got caught up in the zeitgeist?

It wasn't an answer like, this is what the news was. It was “Hey, you know, sold ads.” 

[00:10:25] Jessica Lessin: 

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Yeah. I think even the largest legacy institutions have been facing tremendous business pressure. I mean, look at the Washington Post right now, right, losing millions and millions of dollars a year.

And so that business pressure has been real across the industry. And so, yes, even the most legacy of companies are making, I think, wrong short-term business decisions. And I think you can look at some of the deals they're striking with the large language models and say the same thing is happening.

But also, our model is really difficult, doing journalism, or in other models that, that are aligned with this are–they're very difficult. And that isn't to pat ourselves on the backs of being geniuses, but I think you've got a lot of entrepreneur listeners to this–you know, sometimes doing the right, aligned thing over the long term is just really difficult.

And it doesn't grow exponentially. We've grown 20 to 30 percent a year for 11 years, and that's an awesome business, but it doesn't look like a business you would invest in. It doesn't look like a venture-backed kind of business. But it's an awesome and profitable business.

And so I think also that alignment–and I see this a lot with startup site investment and advice around news–you have to be really clear about what success looks like and not get caught up in the zeitgeist of what's happening over at Open.AI or whatever's in the headline, because that's not what success looks like in our industry.

And I think people really got caught up in that as it related to the tech startup ethos.

[00:12:17] Michael Eisenberg: 

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This is an important point for entrepreneurs listening: not every business is a venture-backed business, nor should it be.

[00:12:23] Jessica Lessin: 

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Absolutely. I haven't raised any investment, and a lot of people look at that and say, “Why not?

Like, “Why did you grow so slowly? Why didn't you put more gas on the fire?” But this was what's right for us. We always had the resources to back the ideas we had conviction in, and we also had to hold ourselves to the bar that over the course of a year or two, those ideas would bear fruit.

[00:12:50] Michael Eisenberg: 

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I want to ask what I think is a question that you led me to about AI. A little bit you're saying, and I won't put words in your mouth, that for a few extra bucks, the news organizations are selling their soul to the AI devil by giving away information, their content, to the AI models. I was told, I think this is true, that in the early days of the AI models, they got a lot of their news from Al Jazeera, and that's where a lot of the results look like they do. Now more are coming in. Why do you think that's selling your soul to the devil?

[00:13:21] Jessica Lessin: 

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I do think that, and you're not putting words in my mouth. And I say it in such strong terms because we've seen this play before.

We've seen what happens when quality news organizations take a quick buck from a tech company, to hit that quarter's revenue without thinking about how it is helping them build a sustainable business that serves their end user. And look, AI is tremendous.

Twice a day I'm using AI, or more than that, for research, for summarizing transcripts, for cutting podcast clips, like, you name it. But the idea that there is a consumer product here that we know benefits news organizations to be a part of, that has a revenue stream you can model, I mean, we are just so far away from that.

It's crazy to me. And we saw this when publishers rushed to give Google free versions of content because Google News was gonna change their business, and every publisher I know has walked back some type of that arrangement and restructured it, and so on. And you add to that this uncertainty–there's just so much uncertainty. And so I have been very concerned to see, you know, major deals.

I mean, I think the only publisher candidly that hasn't struck them of size–we obviously haven’t–but the New York times has taken a very courageous and different approach of challenging Open.AI and Microsoft in court over this ,and letting the courts kind of figure out what makes sense around copyright going forward.

So yeah, I think we saw a bunch of these deals, and I got a lot of angry feedback from people I respect in sharing my opinions, because they were just saying, “It's money, we should take it.” But I also find the point of view that it's not going to require much distraction or doing things differently, that's not how it works.

You always end up bending to your partner who's going to make or break your quarter. And I think tech companies and news companies should have long ago figured out we're in very different businesses, and there are areas for partnership, but we actually don't need each other in that way, and it's important we kind of fulfill our own destiny.

So, we'll see.

[00:15:55] Michael Eisenberg: 

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If I play the model forward, okay, so everybody other than the New York Times kind of capitulates, gives their content to the LMLs, or a couple of niche publications like The Information. So all these news companies collapse, so they all have to be bailed out by billionaire tech entrepreneurs like Jeff Bezos.

[00:16:18] Jessica Lessin: 

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Perhaps, perhaps, but who wants to sell it? So, you know, I think that's an even shorter-term solution. 

[00:16:24] Michael Eisenberg: 

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So you're all going out of business. Like Elon's right. Elon Musk is right–X becomes the primary news source, because that's where individuals create news and all these other people, maybe, except the New York Times, go out of business.

Is that where we're headed?

[00:16:38] Jessica Lessin: 

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No. And Elon Musk is not right. We should just be on the record about that. But I think you do see a lot more news publications go under. I think it's largely in that, it's not the Wall Street Journal and the New York Times, probably not the Washington Post, but I have to put on that asterisk there.

[00:17:02] Michael Eisenberg:

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I'm not gonna lie, given their coverage over the last 12 months, I may not be sad to see them go.

[00:17:07] Jessica Lessin: 

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I think they'll figure it out, but they have a lot of figuring out to do, maybe is how we should phrase it. But, no, the big guys will exist, but we'll continue to see–the collapse across the industry has been seismic.

It's quite interesting. And I live and work in Silicon Valley where you're right, sort of, the animus towards the press is at an all-time high, in large part led by the cult of Elon and others. But what's so amazing to me is that these same people can't stop talking about the news. They can't stop talking about what, in a given day, professional journalists are writing and breaking.

They just riff on it, and opine on it, and attack it, and so forth. But still, the surfacing of original and new facts, is still, I think, a wonderful business with the right models. And I think it's something that is still sort of the bedrock of our information society, and that a lot of the opining, and talking heads, and so forth, is sort of built on top.

So I think for the institutions that can have sustainable models for doing that, they'll be in great shape and actually see very strong growth. Yes, we'll continue to see other information economies like X, and the new ones that will emerge. And I think readers will have to decide for themselves–and this is concerning, because many of them won't–how trustworthy what they read is or isn't.

But I think there will be enough institutions that are injecting good facts into the system. And those institutions are just going to have to work really hard to continue to do that, and to continue to earn people's trust, which I agree with you, they haven't done a great job of in the past few years.

[00:18:54] Michael Eisenberg: 

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Well, I'll speak for myself. I was a religious reader of the New York Times as a kid, and then the Wall Street Journal later. What you call facts, I haven't seen in a lot of parts of the mainstream media. And the other thing I find kind of really interesting is how often TV news in particular, but also written news uses X as a source, and as a prompt for what's news today. And it's almost like the opposite of the way it used to be, right, which is, you don't opine on something that was on TV on X, now it's TV opining on what was on X.

[00:19:25] Jessica Lessin:

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I occasionally see my husband's Tweets splashed across CNBC, and I crack up. And I have a lot of respect for CNBC. But, no, look, there's obviously tremendous challenges inside these newsrooms ,and part of it is–I think in this political climate, it's particularly hard to chart what you feel is an independent course, because everyone you talk to is, I mean, it is just so loaded. And that isn't an excuse, I think. You know, I was being critical of the New York Times for some of their headlines around Trump's victory recently. They were using words like ‘strongman.’ And again, you could have your own opinion and think that's totally justified, but it sets a tone as a news organization that I think is really problematic.

I don't know if we can put that genie in the bottle. And I think from my point of view, building new organizations that try to have different values and different independence. I mean, I think we have a strong and growing advertising business that I'm excited about, but our core is also just individual readers around the world thinking we're worth $400 a year.

And to me, that really keeps us honest, in a way that's very different if there were one, or two, or three companies or people who we really had to keep satisfied. And so I think those business models matter a lot too.

[00:21:11] Michael Eisenberg: 

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Well, speaking of that, and I think this is a really important point–the claim that has been made is the following. Once you move away from advertising to subscription, you need to get a harder core readership that is willing to pay whatever it is, two, three, $400 a year. The claim is that, for example, if you're the New York Times, you actually want to call Trump a strongman because that panders to someone who'll give you a few subscription dollars.

And in fact, it's subscriptions, particularly at the higher rates they're at now, that cause these news outlets to be more ideological, let's just call it that, and therefore panders. I'm curious what you think about business models that create better journalism versus worse journalism.

[00:21:53] Jessica Lessin: 

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And that's real. So we talk a lot at The Information about the right kind of subscriber. And by that I mean, we just mean someone who gets value from our journalism, not someone who subscribes because they happen to agree with an opinion piece or happen to disagree.

And I actually think if you look at what happened to the Washington Post, it demonstrates this. Losing almost 300,000 subscribers over a decision to not endorse a presidential candidate, to me, really said–those subscribers came in, because they felt they had an ideological alignment that then they all of a sudden felt they didn't have.

And The Post had an explicit campaign when Trump was first elected, “Democracy dies in darkness,” and they courted people based on their political beliefs, not based on how important it was to know what had just happened inside the Oval Office based on an anecdote they reported, or something like that.

And so I think that's very important. And you can make the strategy–and many publications do– and so they get these sort of ‘Trump bumps’ or these Trump troughs, I guess, you know, based on that sort of, “Hey, I agree,” or “That validates me” kind of journalism, and I think that that is a very dangerous game to play. We're playing the game of, how many people need to know what AWS is going to announce next for their AI strategy, or how many people need to get inside the TSMC NVIDIA relationship, and what it means for the future of semiconductors. It's not to say politics doesn't play a role, but it's very different. And so I think it's the business model, but it's also the type of customer and what their value proposition is that's really, really important.

And so I do think that kind of broadly distributed subscription base is the healthiest way to build a quality news company.

[00:23:56] Michael Eisenberg: 

‍

I'm actually going to come back to that. I have one more question before we transition to what I want to hit on also, which is your subscription base. But I think it's interesting, before you get there, like another person I think of similar to you is like Bari Weiss, right?

So you looked around the Wall Street Journal and said, “This is becoming clickbaity. I'm going to do some serious journalism.” And Bari Weiss, you know, took a look at the New York Times and said, “This has become an ideological cesspool,” and left to start her own subscription news business, an opinion business and column business.

Compare and contrast what you went through leaving the journal and what you think Bari went through leaving the Times.

I think you're both successful. 

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[00:24:37] Jessica Lessin: 

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I remember taking a walk with Bari, probably, I don't know if it was a few months after or a few weeks, around San Francisco.

And I actually, for people who know her, was just struck by how hard working–like even on that walk, she was like doing business and texting people. And I'm like, “I'm taking a walk with you! I'm giving you my advice.” What she and Nellie are building at The Free Press is so impressive, and I think they identified an opportunity.

You know, I think The Free Press has a lot more really insightful columns, and opinions and analysis, whereas we focus a lot more on breaking news, and obviously business journalism. But I think at the core, Bari has built a great community–and that's an overused word in some ways, but it's also the right word to use. And to build a news brand in this decade, you have to also build a community–and perhaps this is true of other brands, but I know news–of people who really value your product and the experience that they get out of it. 

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And I think brands like The Free Press with their events, and debates, things we've also had great success with, are really capturing that. There are so many others too. I'm an investor in Semaphore, a great publication that is heavy on events and community, and many others as well.

I think there is great opportunity in this moment–I'm perhaps a bit contrarian–if you have a quality and differentiated news or media product, if you get the alignment right, and you got the investing sec right, and you work your ass off, I think you can build not just a great business, but something that's really important in this moment. And there are good examples of that, and we should probably talk more about them in the context of the troubled landscape.

[00:26:35] Michael Eisenberg: 

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This is exactly what I wanted to get to. So I've been around this industry long enough to remember Red Herring–

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Jessica Lessin: 

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Oh, my goodness, yes. 

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Michael Eisenberg: 

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Fast Company, PandoDaily, as you said, Sarah, right, AllThingsD, which was kind of a conference first and then a media site later, you know, rode Walt Mossberg's and Kara Swisher's brand for a while. They had great conferences, I used to go every year. 

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Jessica Lessin: 

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Yeah, me too. 

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Michael Eisenberg: 

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And now like, all of those people are more or less gone. Gone. Didn't make it. And here's Jessica, and The Information, 10 years running, which continues to grow, started with the kind of subscription business just for news, which was bold by the way, right? How do people get exposed to a product that they got to pay for? This trial that was bold. Now you've moved into conferences, and community, and there goes Bari Weiss, who I think follows the playbook roughly, which is, “You're going to pay for my content, and I'm going to do conferences and community.” 

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And it strikes me that maybe there's a new model here, which is the old kind of WSJ, New York Times, whatever it was, which was, “Hey, I'm going to send you a newspaper. I'm going to just sell you news.” Just give it away to the model you described, which is, community, content, conversation. And I'm just trying to put my finger on what's different about this moment. Because there was seeds of it in AllThingsD, and seeds of it in the Red Herring too, they used to have conferences too. 

[00:28:13] Jessica Lessin: Yeah.

[00:28:14] Michael Eisenberg: 

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But you made it, and they stopped making it. I mean, I think All Things D did great for a long period of time. 

[00:28:20] Jessica Lessin: 

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Yeah, a fantastic franchise and obviously, has morphed in a lot of ways. So I think one of the big differences between that era–well, actually, I don't know. Maybe I'll play this out a little bit. But I think a lot of people today talk about vertical media, and the idea that the newspaper has been unbundled.

You don't need to read it cover to cover to get your news. You can get that in real time over the internet. And so, I think that one of the things that's where I think we're going, is I think we are going in publications that are deep, deep authorities in specific areas and then build communities around that.

Because I think readers want to go deep, and have the best and the most insightful information from the people who are in the know. When the election rolls around and political cycle's big, I go to Politico, I go to Punchbowl News, which is focused on Congress, even, within the world of Washington.

And I think the mistake a lot of people make is they see those businesses as narrow. And take Politico. Politico had a billion dollar exit. Politico is the most successful media startup since Bloomberg Media. Maybe that's true, I don't know. Sounds right. I'm going with it. But certainly a huge success story, a wonderful business, a real authority, global, so on and so forth.

Back in the day when Jim and Mike founded it, it was seen as very narrow. But it turns out that that sometimes these focus areas are actually massive. And so that's where I think we're going. And I think that's one difference. Because 10, 20 years ago, there might not have been as big an audience for some of these verticals, or you couldn't find all those people globally who were in your demo.

But now, if we have a big story–what's going on inside Google as it's trying to fight OpenAI with Gemini, that's just a global story with a global audience. So I think we are moving to more of that fragmented model, but everything's a pendulum and you bundle and you unbundle, right?

Look at what we're seeing in streaming now. It turns out I've just re-aggregated all my one-off, unbundled subscriptions, and Amazon, and YouTube TV, right, of my Comcast world or whatever it is. So, I think there will be room for consolidation. It's companies like us that might do some of the consolidating too, and I think that will look very different.

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[00:31:09] Michael Eisenberg: 

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I'm paying much more for news than I ever did before right now. I'm subscribed to so many things. It's a little bit ridiculous. 

[00:31:15] Jessica Lessin: 

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Yeah, and you'll winnow that out, and people will be forced to compete for that. But yeah, it is a very different time, but I think, and maybe it's too hard for the consumer in some ways.

So that should present an opportunity, I think.

[00:31:33] Michael Eisenberg: 

‍

Well, I think you put your finger on something important, which is tech has become mainstream. And like I said before, I've heard from a lot of people that they subscribe to The Information who surprised me, like in Red Herring days. There was no outside of this clique of Silicon Valley that subscribed to the Red Herring, a couple of guys in Israel.

You know, when Jason Kalkanis, before he was famous for the All In pod, was at Silicon Alley Insider, the August publication way back, there were a hundred people in New York. I'm not trying to be–

[00:32:05] Jessica Lessin: 

‍

No, it was very different, yeah.

[00:32:05] Michael Eisenberg: 

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It was a very, very, very niche thing and nobody, you know, cared that much.

But today tech is totally mainstream. We witnessed the All In pod, and witnessed The Information. And I'm curious, have you had to kind of talk about tech differently, report tech differently, or is it just everyone's interested because this is what is shaping the global economy now?

[00:32:25] Jessica Lessin: 

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So I've been struck by how, and again, we have a broad business readership.

So I mean, our readership actually largely maps to a Wall Street Journal or a Financial Times. I mean, about half work in technology, about a third work in finance, and then the rest is sort of broadly distributed around other industries. So we do see readers who are product managers that, you know, name the company.

And I think, so in some ways, our point of view is, I guess we've ultimately still stayed pretty focused on that core that wants to go deep, and we're not necessarily going just for that tech-savvy consumer, per se. But I think those areas are bleeding into each other pretty quickly. And I'm constantly surprised that people who I'll run into and they'll be like, “Oh, your story on like Inference and what's going to happen with the chip market, because we're moving fromTraining to Inference.”

It’s crazy. I'm like, why is that relevant to you? But people are deeply interested in things that would have seemed a year or two ago as too niche or narrow. I mean, talk about data center, architecture and energy, the number of businesses that have a real stake in that transformation from retail and real estate, it is massive.

And so that's sort of where we play. We do have a three-year-old weekend section that's really fun, talks a lot about tech and culture and lifestyle, and gadgets, and things that may be interested, appeal more broadly to people interested in how tech's shaping culture. So yeah, we, I think, explicitly tried to stay focused on what we're uniquely good at and have been very pleased how that segment is growing pretty quickly too.

[00:34:27] Michael Eisenberg: 

‍

Do you have to hire–let me back up with the question. Like I can find on Twitter an expert on data center energy consumption and someone who is crazy about the topic and goes really deep. My experience with traditional journalists was they never went that deep as you could find on Twitter.

My experience with The Information is, people go that deep. Have you had to hire a different kind of person, you know, than maybe traditional journalism did, to work for The Information? And how do you think that kind of projects onto the future of where journalism goes?

[00:34:57] Jessica Lessin: 

‍

So yes, but not necessarily that they have to be total subject matter experts, but they have to be really, really deeply curious, and intelligent, and kind of interested in understanding the weeds.

And so, journalists are never going to get to the level of the person building the data center, and you maybe don't want them to. Because you want them to be able to synthesize multiple points of view, but they have to get in their head wonky enough that they love learning from those people and kind of being the student.

When our team talks about our travel budget, like, I mean, we probably go to CES or–but we go to the wonkiest conferences. I'm like, why is so and so in Hawaii? And it turns out, you know, there's this kind of, it's actually a lot of data center conferences lately–but there's very, very wonky.

So, yeah, you don't have to know it all, but you have to really, really want to learn and understand. And it's hard. I think a lot of people get into journalism for a different reason, but to have a big impact, you have to really get in the weeds to earn the trust and expertise to build those sourcing relationships.

So that's what we look for. We did just hire a new venture capital reporter who has been a venture capitalist though. She worked at Emerson Collective, and it's been really fun already to see her story ideas. She's not as afraid to go after some of the wonkier concepts, you know, SPV structure, you know, stuff like that.

And I think having that confidence and knowledge will just allow her to go deeper. And then we'll have to explain that to readers who aren't immersed in it, but it's been fun to watch her get started.

[00:36:52] Michael Eisenberg: 

‍

Now I'm nervous. Let me ask you a different question. Are you mainstream media, or are you new media or are you–what are you?

[00:37:03] Jessica Lessin: 

‍

You know,I'm not sure. I don't think we're mainstream. New is fine. I was struck, about a year ago, the New York Times did a feature on the new class of news startups. And I saw the headline. I'm like, “So weird they didn't call.” And then I saw that we were the legacy in that. So basically they were talking about the newer, newer class, and we were lumped in with the Politicos and the others that had been the prior wave of whatever.

And I just thought that was so funny, because in my mind we're very much a startup, because our opportunity is just massive, so that's my point of view. But I don't know that the readers think that much about that question. To your point, they think about, do I trust what I'm reading?

So I obey in the trust stream media, or whatever that should be called.

[00:38:01] Michael Eisenberg: 

‍

Sam told me to ask you–I was going to ask you anyway, to be honest–and you kind of alluded to this before in your comment about the cult of Elon–citizen journalism, the kind of “We, the Media,”-- for those who don't know, by the way, Dan Gilmore, another legend of Silicon Valley reporting, he used to write, like no one remembers these things anymore, for the San Jose Mercury News, which is like the only way you can cover Silicon Valley once upon a time.

He wrote a book called We the Media back in like 2000, 25 years ago. And I just want your take on citizen journalism and We the Media.

[00:38:39] Jessica Lessin: 

‍

You know, I am all for citizen publishing, citizen reporting, citizen sharing, citizen publishing, maybe. Citizen journalism to me–journalism as we practice it is very, very different.

You know, we have 80 people who are–not gonna be professionally trained, right, but whose job it is, is very specific, is to learn and verify information and to publish it, and to have that sort of be trusted–and also to really work together as a newsroom to be able to cover really meaningful big things.

[00:39:24] Michael Eisenberg: 

‍

So why does it matter?

[00:39:26] Jessica Lessin: 

‍

Why does it matter? Oh my goodness. Well, it matters because how do we make decisions? How does anyone make any decision in the world? They need trusted facts and information.

[00:39:35] Michael Eisenberg: 

‍

I'll crowdsource it. Get it Community Noted.

[00:39:39] Jessica Lessin: 

‍

Well, for some things that can work actually. So I think for some things, like, did this rocket just go off or, you know, that could work. 

But what about what really went on at OpenAI, with the firing of Sam Altman and what that means for the future development of AI, and every company that interacts with it, and every shareholder that puts a buck in it, right? I think there are just huge swarms of topics and areas that no citizen journalist is going to get at because they don't have the ability to, or the interest to, or the incentive to, and I think that's really important.

And I think this is what's missed in the Elon Community Notes model, or the idea that X replaces newspapers. X could still be very important. It will not tell you the things no one wants you to know. 

‍

And that's what journalism can do. Or, it doesn't have to be scandalous per se, but the things that require the kind of sourcing that isn't publicly available, and I think it's hugely important, because if we go into a world where our source of truth is other people's opinions, and also very powerful people with the biggest megaphones on the planet swarming those channels, that's deeply, deeply problematic. Because again, every citizen needs information to make decisions.

And so I do think professional journalism, the resources that a newsroom can bring are very, very important. Are they flawed? Yes, and to your point, we've seen that in the major news organizations, but there are just simply facts that would not be revealed. And there is just so much that would not be known.

I mean, I think we have a reputation as a publication of being very tough, and some people would maybe say antagonistic in some ways, but what that really boils down to is, we're actually not–they also say that and then they say, “Well, you call us the most times and you give us the most information about what you're writing.”

So we're very cordial, but you can't ignore the fact there are things that people don't want reported because they don't have an incentive to, but there might be a very strong public incentive for those things to be out there. And I think ultimately that is what journalism is at its best, and I don't think community-noting 12 different views or 1200 different views is going to get you to the same answer there.

I think it's actually quite different.

[00:42:27] Michael Eisenberg: 

‍

You alluded before, I just want to point it out, to the Sam Altman, like what happened behind the scenes there. It should be said that the place to go to for what happened there was The Information by 100 miles. 

[00:42:38] Jessica Lessin: 

‍

I had a little bit of PTSD, because we just had the Thanksgiving after last year where we were all reporting in closets when our family were. But I think that, and thank you for saying that, Michael–the team did an amazing job–but I reference that too, because I think it was a moment where, in tech, we have so many really wonderful and knowledgeable Substackers who have great newsletters, who cover so many interesting things that happen, and they analyze a lot of the industry. And I think those kind of went silent when there was a big news event, because it underscored that the places–and there were others, like Bloomberg–that could really peel back the curtain weren't, you know, one or two highly intelligent writers, but really teams that were triangulating and using relationships built over decades across companies and industries that were able to really help readers understand what was going on in a moment. 

‍

And I think it was an incredibly validating time for the importance of a newsroom. It's one I'm close to, but there's so many of those, and I think as an industry, we have to do a better job kind of articulating–I mean, I think readers recognize it, but, yeah, what is it that happens in those moments that wouldn't have happened? And you could have at the same time, right, on X, all sorts of opinions about it, and employees sharing this point of view or that point of view, but none of those people had the full story.

And what a newsroom can do at its best is get everyone closer to the full story. And that's important.

[00:44:23] Michael Eisenberg: 

‍

You said a pile of times since we started that trust has been eroded in a lot of these media organizations. We just talked about the power of a newsroom. A little bit it doesn't matter because, I guess, because of the erosion of trust.

I'll ask you two questions: what does media need to do to earn back trust–and please be very specific–and number two, what happens in a post-trust world of media and newsroom?

[00:44:53] Jessica Lessin: 

‍

I know. 

‍

Michael Eisenberg:

‍

I think we're there. 

‍

Jessica Lessin: 

‍

I know. We're there. We're there. I have to embrace that. A good friend of mine, like, recently was like, “Get your head out of the sand. We're there.” So, media organizations have to not screw up. You, you just have to earn it. You have to earn it with every article. You have to earn it with every headline. You have to– 

‍

[00:45:18] Michael Eisenberg:

‍

We're not doing it. So, like, it's like, there's an institutional problem here, so what do they need to do?

[00:45:23] Jessica Lessin: 

‍

Well, I think you need to make sure you have the right talent, and you have to make sure you have total alignment on the journalists and editors you're hiring; do they fit your mission, and a real sense of what that mission is. 

[00:45:38] Michael Eisenberg: 

‍

And where did they get hiring wrong and you got it right?

[00:45:41] Jessica Lessin: 

‍

I actually think the New York Times has been upfront about some of the mistakes they made in hiring around COVID.

And I have to remember, I think Joe Kahn may have mentioned this in a Semaphore interview, but I read it somewhere, and I think he said, “We got caught up in hiring a lot of people who were here for like ideological reasons.” 

[00:46:04] Michael Eisenberg: 

‍

Yeah, I've been on record saying I think he's there for ideological reasons too, just to be clear.

[00:46:10] Jessica Lessin: 

‍

Got it. Yeah. I mean, COVID was hella disrupting, and weird, and disorienting in so many ways. And we all made decisions. But there is that, which is wonderful, it must be harnessed–that, like, crusading aspect of being a journalist. Like, I think that is so core and awesome for the profession, but when channeled towards a particular ideological position versus, you know, holding power to account or something, I think that can be problematic.

So I think the industry, which again, has been financially troubled, so not exactly the most attractive for a lot of talent, I think they swung too far there. So I think you have to hire the right people. You have to have the right incentives. I mean, we are highly analytical, and obviously very subscription focused, but we do not comp our reporters based on the number of subscriptions they drive, and others do.

And I don't do that because it's distortionary in a lot of ways. And it also doesn't necessarily always reflect the quality of their work or effort. But you have to make–

[00:47:24] Michael Eisenberg: 

‍

I had no idea that people get comped for the subscriptions that they drive. That's pretty stunning.

[00:47:29] Jessica Lessin: 

‍

Yeah, they do. And so it's, you know, it's all of those things, right?

I mean, how do you, your question is sort of, how do you build a trusted institution? And so, I think it's more like a million little things than putting a banner out inside and saying, “Trust us!” I also think we have to make sure we're trusted from a distribution point of view, like reaching a lot of people, right, so we have to stay aggressive, and how we disseminate our news, and grow our audiences and just, you know, be there.

And then there's a movement inside of news to say, we have to talk about what we do more, more of the craft, and help people understand that. I don't know how much people care to be honest, but I have made a concerted effort, when people push back against our stories, to actually publicly explain why we're standing by the story and maybe even reveal more information about the reporting process so that people understand, really, what went into it.

You know, we've had some stories that have gone inside, NVIDIA's rise, but also real troubles that they've had scaling some of the most recent technology that they've pushed back on. And I've gone public talking about the four different people we talked to, and, you know, just really helping people understand that.

Does that move the needle, big picture? I don't know. But it's important and we'll keep doing it.

[00:49:08] Michael Eisenberg: 

‍

And you might be wrong even from four people. It's impossible to know. 

[00:49:14] Jessica Lessin:

‍

No, we totally could. Of course, but I think people just understanding, right?

And also they never, these companies never say it's wrong. It's their corporate speak, or whatever. And so I think I'm hacking that as well. And then, of course,when next quarter on the earnings call they confirm your story, which happened twice, I think it's important to also point that out.

[00:49:36] Michael Eisenberg: 

‍

To remind them on X, of course, or any information–

[00:49:39] Jessica Lessin: 

‍

Yes, everywhere, actually, broadly, broadly.

[00:49:42] Michael Eisenberg:

‍

Is there any event that's happened that has eroded your trust in media? 

[00:49:46] Jessica Lessin: 

‍

Yeah. I mean, I see what everyone else sees, and I'm also perturbed. I think that the coverage from around Trump, you know, I mean, you could pick apart it, it's so many aspects of it, and obviously, the war in the Middle East too, which you've been much closer to. But I mean, I see a lot of headlines that give me a pit in my stomach or that seem off, or make me wonder sort of what's going on. I think it's a constant process. The thing about news, and not to be defensive for the industry, but the big organizations publish thousands and thousands of pieces a week, I mean, I don't know, but a shit ton of journalism.

And I think, do they get it wrong a lot of the time? Yes, but they also get a lot right. That isn't excusing what's wrong, but I'm kind of a believer in, you're gonna get some stuff wrong, fix it right away, and then do better next time–as opposed to thinking that the bar is getting at 100 percent every time.

But what worries me the most is when I see journalists who I think are more crusaders than reporters. That’s what nags at me, in part because I know that if they focused on being great journalists, they could also have a tremendous impact on the things they care about.

And so I think they're almost shooting themselves in the foot by leading with the crusader. And that does worry me, because that's a big part of the eroding trust. 

[00:51:34] Michael Eisenberg: 

‍

I'll say, I think more people are going to journalism to be crusaders now than to be reporters or investigative reporters.

I see a lot of that. Let me ask you a different question. I want to switch channels for a second. I'd like you to tell us about the accelerator at The Information. 

[00:51:51] Jessica Lessin: 

‍

Yeah, sure. So a couple of years ago, we started an accelerator to help new news companies that want to get off the ground.

And it was simply, we had a new model, and people would be interested in learning more. And I thought it was really painful to learn some of the lessons we learned that were very simple. Like make sure you capture that email address so you can remarket to the person down the line. Like the blocking and tackling of the business.

And so, we brought in a couple classes of entrepreneurs who have gone on to build really interesting news businesses, among them on the Anklor, which is a news publication out in Hollywood under Richard Rushfield, Impact Alpha is another that covers the clean energy economy. and many others.

And we went from sort of having discrete classes year after year to now just sort of being in constant conversation with interesting businesses. We just invested in Dynamo, which is a new video company from Nick Carlson, the former editor of Insider, and just try to be as helpful as we can.

So I'm an operator, not an investor. I've learned this. My other two, you don't know where you– I kind of feel it's actually pretty black and white. I'd rather climb the hill than look around the corner, but, I've learned a lot from these businesses, and we're happy to be as helpful as we can be both tactically and sometimes with resources.

So it's fun. I've learned a lot.

[00:53:32] Michael Eisenberg: 

‍

What's next for The Information?

[00:53:34] Jessica Lessin: 

‍

Man, I mean, this tech news cycle does not stop. We now have a presidential best friend of chief, you know, coming from Silicon Valley with Elon Musk. And I think we're at some fascinating moments in AI. So, you know, we think a lot. I'm always trying to expand our coverage in our core. How can we go even deeper? We're about to launch our second AI newsletter with a different bent on AI and going even deeper, even wonkier. Probably, I don't know if I should say that–

[00:54:04] Michael Eisenberg:

‍

Say more Jessica. 

[00:54:05] Jessica Lessin: 

‍

It's very good. It'll be very relevant to businesses. and it's coming in January. I think that's enough. 

‍

Michael Eisenberg:

‍

You should tease it out, come on Jessica. 

‍

Jessica Lessin: 

‍

You're a good reporter. It'll be great. I love the team that's working hard on it. 

[00:54:18] Michael Eisenberg: 

‍

Is it like how AI disrupts like classical businesses? And what do you need to do to AI your business?

[00:54:23] Jessica Lessin: 

‍

Those will be questions answered by reading it. Yes, those will be some.

But it'll be, you know, we have a daily newsletter, AI Agenda already that covers AI broadly. And this will be a little more–

[00:54:34] Michael Eisenberg: 

‍

What's the title of the new newsletter?

[00:54:35] Jessica Lessin: 

‍

So good, so good. Maybe even work in progress, but, so we're going to go deeper–energy, data centers, power. We have a franchise called The Electric, which years ago, if you would ask me, would we have a battery publication and cover, you know, manganese, I would have said, what are you talking about?

I mean, it's one of our biggest growth areas.

[00:54:57] Michael Eisenberg: 

‍

Wow. Batteries!

‍

 [00:54:59] Jessica Lessin: 

‍

Batteries. 

‍

 [00:55:02] Michael Eisenberg:

‍

You know when I got into the venture business, it was said the road to VC hell is paved with batteries.

[00:55:04] Jessica Lessin: 

‍

Yeah. Well, that's true. But a lot of good stories along the way. So, but also, everything's been disrupted by tech.

We've had a ton of interesting coverage around the sort of struggles of fintech companies as related to the traditional banking system, and the challenges of fintechs and finding banks to partner with as the regulators have come a calling. And I think that's–

[00:55:35] Michael Eisenberg:

‍

Well, that'll be interesting with the change of the administration.

‍

Jessica Lessin:

‍

Exactly.

Michael Eisenberg:

‍

Because I argue a huge amount of that came out of the den of Elizabeth Warren.

[00:55:40] Jessica Lessin: 

‍

Exactly, it did, but I don't think it's just going to be smooth sailing because of the changes there. So broadly, in finance ,and continuing to do more there, we've been growing a finance team out of New York and we'll continue to do that.

And Asia is also a big area of focus. You know, I feel a little bit contrarian and that many of my peers have pulled out of China, Hong Kong, obviously, but we're actually growing our team in Hong Kong. They've been doing incredible work, and we're looking to grow our business in Asia. So a lot cooking, a lot cooking.  

‍

[00:56:20] Michael Eisenberg:

‍

Alright, what's the hardest thing you do? The hardest thing you do?

[00:56:23] Jessica Lessin: 

‍

Lead.

[00:56:25] Michael Eisenberg: 

‍

Lead. Okay. Sam didn't say it was being married to him. He didn't say that, but he told me to ask that question. So do you admire Rupert Murdoch?

[00:56:35] Jessica Lessin: 

‍

I wonder if that was a Sam question.

[00:56:38] Michael Eisenberg: 

‍

It is.

[00:56:39] Jessica Lessin:

‍

So yes and no. So yeah, as a media mogul empire builder, yes. I don't share his politics, but I do think we need to be better building the next generation of legacy media institutions. And he's done that. And he clearly loves the news. And I think that's cool to watch. And I hope I love it as much at his age.

[00:57:08] Michael Eisenberg: 

‍

What were you wrong about when you started The Information?

[00:57:11] Jessica Lessin:

‍

Oh my God. So many things. There were little things that probably aren't that interesting to people, but I never wanted to launch an app.

I thought it'd be so stupid. No one's going to download another app. As soon as we did, engagement went through the roof. So, you know, a lot of those tactical things. I also was wrong, I made a lot of early hiring decisions based on pattern mapping to myself. Like, you know, there were people we hired who I was struggling to manage, and I realized it was because like, they like to write in a quiet room and I like to write in a loud room.

So, like, little things that it was a big leap in my management curve, when I kind of recognized that, you know, not everyone was like me. I know that sounds very silly, but I was sort of pattern-matching to myself for a bit. And then when I stopped doing that, we really started to take off on the talent front.

[00:58:14] Michael Eisenberg: 

‍

What do you want to tell Harvard-Crimson-Jessica?

[00:58:17] Jessica Lessin: 

‍

Oh my God. Keep going. Keep going.

[00:58:21] Michael Eisenberg: 

‍

It gets better. 

[00:58:22] Jessica Lessin:

‍

Keep going. Yeah, I mean, it's just such a fun and exciting job, but it's also, I mean, there are always those people who never call you back or that story that you don't get or that moment that the industry looks like it's collapsing.

And I think, I remember talking to Marni Barron a couple of years ago, the legendary editor of the Boston Globe and Washington Post, and he said to me, “Jessica, journalism has been in constant disruption since it began,” or, I think he said, since the course of his career. And so I think that's really important.

There are a lot of things to kind of give you pause about. This profession, or this career, it's very difficult to–we don't get to launch a product and then tweak it and scale it. We have to launch our product every hour. We have to keep publishing. The second we stop publishing, we haven't earned that trust.

And so there is a relentlessness to it. So I would say keep going.

[00:59:26] Michael Eisenberg: 

‍

I normally ask this question at the beginning. I wanted to ask it at the end today. What is your core value?

[00:59:32] Jessica Lessin: 

‍

I only get one, huh? I mean if you, I really do think, I'm going to make it two parts. I think hard work and alignment are things I think about a lot.

I think that continuing to try, and go, and move, and stay in the game is something I think about a lot. And I've been fortunate to watch so many young CEOs become great CEOs, and I think they really have that in common. They stick around, and they don't give up, and I think that's really clear. But I also think the alignment, making sure that that's going towards something that's your goal, and that, and there's that consistent alignment that you're rowing hard, but you're always rowing in the right direction, whether that's an objective you have with your family, or an objective you have for your business, or an objective you have with your relationship, I think a lot about those things. Because the world is hard, and life is hard, and you're juggling a lot of things, and just being on the same page and being intentional about that, is really important to me.

[01:00:55] Michael Eisenberg: 

‍

Have your values ever come into conflict with your work as a journalist?

[01:00:59] Jessica Lessin: 

‍

You know, this is going to surprise people–they really haven't. Because, and I get this question all the time, because when you've been in the industry long enough, you know a lot of people and those people often get mad at you with your journalism, right?

Or you can face a situation where you've learned something important and unflattering about someone you like, right? But because to me, they're separate worlds, right? I know what my goal is with The Information. I know the values that I'm also more comfortable communicating to people in those situations about those values and articulating why, despite them screaming my ear off, you know, we're kind of proceeding.

So it's not that you always feel great about it, but it's pretty clear cut. And I think I've really learned that good communication can get you through a lot of potential tensions.

[01:02:01] Michael Eisenberg: 

‍

All right, last two. So, who is someone that you'd like to give a shout out to say something kind about, that you think deserves, or should get more attention than they're getting?

[01:02:13] Jessica Lessin: 

‍

These are great questions. Who deserves more attention?

[01:02:18] Michael Eisenberg: 

‍

If it doesn't work for me in VC, I'll come to you for a job. 

[01:02:21] Jessica Lessin: 

‍

Yeah, I mean, you're crushing it. Well, I want to think about folks in my field, but then you talk about other people and then I got so mad. Who deserves bigger shout outs? You know, because I gave them a shout out, I have to take every opportunity to praise the New York Times for suing OpenAI.

I really do. Because I think in that moment, they made clear that they are in this for the long term, and I think the courage every other news organization taking the half a million dollar check, which, by the way, is half in OpenAI credits, not even cash you can do anything with, I aspire to continue to have those courage and the decisions that I make for our organization.

So I think it's really, really important.

[01:03:21] Michael Eisenberg: 

‍

What is a strongly held opinion that you've changed over the last year? 

[01:03:27] Jessica Lessin: 

‍

I used to think if you left The Information, you could [01:03:30] never return. I know that sounds like, I realize now as a founder how naive that sounds because if you have the opportunity–

Michael Eisenberg: 

‍

You're either on my team or you're not!

‍

Jessica Lessin: 

‍

Yeah, I did. I really did. And the reason I felt it was because I would think, when you're a tiny team and someone key leaves, the burden placed on the rest of the team is signable.

And so to me, it was like, okay, you can move on. But now, you're adding to what everyone else is going to have to work harder, recruit your replacement, blah, blah, blah, blah, blah. And you can make that choice, but I'm going to somehow protect the team by saying “fare you well.” I think we've now, we probably have four or five boomerangs of the information.

‍

Michael Eisenberg: 

Oh wow. 

‍

Jessica Lessin: 

‍

And I couldn't feel more deeply that if you were an awesome figure and an awesome contributor, you know, that the door is open. And if there's a role that makes sense, I feel that very deeply. It's not the most significant example, but it really hits home because of how stridently I believed it, and how far I've come to the other side.

[01:04:46] Michael Eisenberg: 

‍

You know, I can’t not ask you this question, Israel is such a big tech hub–when are you putting someone on the ground here? When are you going to come here? 

[01:04:53] Jessica Lessin:

‍

No, I know. It's a great question. Yeah. I'd love to come back soon. I actually, we may have an exciting family thing that pulls us out there before too long.

It is a great question and we absolutely will. And I think I've made the choice–I have felt that being too broad internationally would spread us thin, and that when I go into a place, I want us to be excellent and really stand out. And so we've tended to trying to go into markets where we can have five or six people and really kind of dominate.

So we should talk more offline about how we might do that over there.

[01:05:29] Michael Eisenberg: We'll do that. Maybe I'll put my hand up for the job. I don't know.

[01:05:31] Jessica Lessin: 

‍

I mean, at least a columnist with these questions.

[01:05:35] Michael Eisenberg: 

‍

Well, thank you, Jessica, for joining me on Invested, and you can learn more about Jessica on X. She's not part of the cult of Elon, but you can still find her on X.

‍

Jessica Lessin: 

You can find me!

‍

Michael Eisenberg: 

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J E S S I C A L E S S I N on X, and I highly encourage everyone to subscribe to The Information. It's a great publication if you're in, or not in, our industry. So thank you so much for taking the time, Jessica.

[01:05:58] Jessica Lessin: 

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Thank you so much, Michael. It's great to chat. 

[01:06:00] Michael Eisenberg: 

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Great to see you.

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