Episode 164
Henry Blodget on the media business in 2025
Henry Blodget built Business Insider into one of the few breakout successes of the traffic era. Now, with his new project Regenerator, he’s taking a different path—one that reflects the broader shifts in digital media. We talk about the collapse of platform-driven distribution, why subscriptions are a more durable model, how venture capital never quite fit the media business, and what it takes to build in the current environment of fragmented attention and AI disruption.
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Transcript
Welcome to the Rebooting Show.
Brian:I am Brian Morrissey.
Brian:This is the busy season at the Rebooting.
Brian:I'm preparing for, my annual pilgrimage to Cannes Lions.
Brian:I think I've been there about 20 times at this point, and complaining about going to Cannes is, is very, gosh, it is never a hardship.
Brian:Assignment if the location is the south of France, particularly in early summer, I'm gonna be hosting a series of conversations there during the week, with our partners at Hearst, the Washington Post, and Dot Dash Meredith.
Brian:We're also gonna be holding our now third annual Cannes Media Leaders dinner.
Brian:we're doing that with our partners at, exco.
Brian:This, this one is gonna be different 'cause it's gonna be at a club store on.
Brian:I am really curious to see how that goes.
Brian:And I suspect, knowing Europe that the intensity of the DJ will slowly rise throughout the meal.
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Brian:we'll also have an apply to attend for these.
Brian:These little gatherings.
Brian:they're small scale affairs.
Brian:I, I prefer those.
Brian:I know that a lot of the incentives are to actually have big, events, but, I don't really love big events, I gotta be honest with you.
Brian:anyway, you'll get the first shot at these if you are gonna can, if you are a TRB Pro, or insider member.
Brian:So consider joining TRB Pro, which is, the rebooting membership program.
Brian:It's, $200 a year or 20 bucks a month.
Brian:you can.
Brian:Find out more information about that on the rebooting.com.
Brian:couple other notes.
Brian:We've recently published research with our partners at Blueconic about the use of ai, at publishers for audience development.
Brian:Our findings back up the qualitative research we did.
Brian:alongside the survey, publishers are still in experimental phase and possibly at risk of getting caught in between as they, in the words of one exec invest just enough to stay behind.
Brian:I will leave a link to the research in the show notes, but it's also available on the reboots website.
Brian:And finally, we are holding an online forum tomorrow.
Brian:this is our version of a webinar.
Brian:It's not a webinar 'cause it's much better.
Brian:so if you do not like webinars, I'm with you.
Brian:And that's why I make these online forums because they are webinars for people who are not necessarily into webinars.
Brian:And even if, and this is the thing, even if you're into webinars.
Brian:You'll still like it, so I'm trying to have, my cake and eat it too.
Brian:Anyway, it is tomorrow, Wednesday, May 21st.
Brian:we're doing this in collaboration, with our partners at WordPress VIP, and we are gonna dig into a case study of how recurrent pulled off a substantial replatforming without slowing down.
Brian:Recurrence, head of, product and engineering.
Brian:Aaron Siegel is going to walk us through, this case study.
Brian:if you run product, or tech at a publisher, this is going to be an in-depth look at the strategic, and tactical trade-offs that come with a CMS migration.
Brian:This happens from one to 2:00 PM if you cannot make this live.
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Brian:I, I always think, you know, you have to, provide, you know, content in different formats for people.
Brian:I don't know why it needs to be one way and it's not that hard to, to reconfigure content.
Brian:So we're trying, this is the first time we've tried it and I have a feeling that it should give people who don't want to necessarily attend.
Brian:You know what's, what's basically a video zoom with a lot of great graphics, but instead just want the takeaways.
Brian:So anyway, you'll get that, link to the, replay and the cheat sheet, after the session.
Brian:but you gotta register for it.
Brian:So I will add a link to that in the show notes.
Brian:It's also, If you get the newsletter, you know, I've been promoting it there.
Brian:So, onto this week's episode, in the last year of digital media, that was the scale era.
Brian:Few pulled it off quite like Henry Blodgett.
Brian:I think he's one of the few winners really of that era.
Brian:If you think about it.
Brian:Business Insider was one of the few success stories.
Brian:when I. Comes to the big digital, media companies that were being built mostly with venture capital funding.
Brian:and it was built for those conditions.
Brian:It was venture backed, traffic hungry, and it was tightly aligned with the platform distribution of that era.
Brian:but BI did some things that I think were a little bit different.
Brian:It operated in my view with a little bit more.
Brian:Or operational discipline than most.
Brian:It, it was able to blend aggregation with original content, you know, to, to drive growth.
Brian:And it had a, most importantly, it had a high metabolism that really outpaced traditional publishers.
Brian:At the same time avoided the bloat, the sank, many digital upstarts.
Brian:You know, it, it really ran in my, in my conversation though, I always thought that they ran like a, a unit economics business there.
Brian:and, and you know, that, that has trade-offs of course, too, but I think it, it instilled a discipline That basically got it to the point
Brian:where in 2015, you know, Henry, and the team there sold bi to Axel Springer for what was a legendary six x forward revenue multiple.
Brian:It was, I always like to joke, the bi comp was in every single digital media, m and a pitch deck, from the next day thereafter.
Brian:it prob people probably don't do it now because there's just.
Brian:There's zero chance that you're gonna get that multiple.
Brian:Anyway, congrats to, congrats to Henry and the team there for, for that, nearly, nearly a decade later, you know, most of bis contemporaries are, are in retreat.
Brian:I don't need to tell you that they're consolidating, they're pivoting.
Brian:you know, some like, like vice just, you know, went bankrupt.
Brian:but like, you know, Henry has left, Axel Springer and bi and you know, I always wonder what people will do then, and a lot of people.
Brian:You know, they had, he had a home run, right?
Brian:And they, they go and they do a little investing and he, they sit on boards and, and things like that, but.
Brian:I really like when people like Henry get right back in the fray, you know, and he's building again.
Brian:And he's not only building again, but he's doing it from the ground up.
Brian:and he started, this substack called Regenerator.
Brian:It's just Henry.
Brian:He's got a few AI coworkers, don't we all?
Brian:but it's really to me, like I really have been enjoying it because it's, it's his analysis of, of tech and, and business.
Brian:And to me It's kind of going back to, to Henry's roots as a financial analyst.
Brian:I mean, I got my start in this business as a reporter at this publication called Silicon Valley Reporter right at the end of the.com days.
Brian:And like Henry's like a celebrity analyst.
Brian:I remember like emailing him a couple times just being nervous.
Brian:I I was like amazed when he like, when he responded like a couple times to like, my emails just like desperate for a quote.
Brian:With Regenerator, he's starting, from scratch.
Brian:And I think we're seeing this like a lot, and I think it's telling, and we, we discuss, a lot of this about why he's, doing it on Substack.
Brian:but he also talks about why, you know, he really no longer sees much of a future in the old model, which is basically putting display ads on web pages.
Brian:I know this is like very basic and I come back to it a lot, but I think it's very fundamental.
Brian:I think he said it's hard to see a long-term workable model that puts at the center, the act of attracting visitors to webpages to expose them to advertising.
Brian:I couldn't have said it better myself, and I agree with it.
Brian:and so, we talk about that.
Brian:We talk about his experiments with ai, his view of the Substack business model and also.
Brian:A fun one.
Brian:What advice he'd give?
Brian:Jeff Bezos, who invested in bi, by the way.
Brian:on what, Bezos should do with the Washington Post.
Brian:I know they called him Jeff is if I know him, I don't actually know Jeff Bezos.
Brian:Anyway, let's get into my conversation with, Henry Blodget.
Brian:Henry, thank you so much for joining me.
Brian:It's been a little while.
Henry:it has been, but great to see you again and thank you.
Brian:so I like when I, I love journalism tropes and, and one of them is like, so, so and so resurfaced recently.
Brian:It's like, but like you just started regenerator.
Brian:obviously you've been out of BI now.
Brian:I mean, you left.
Brian:The board, I think about six months or so ago.
Brian:and he left the CEO position like a year before that.
Brian:So you, you've been gone for a little bit.
Brian:and I think of BI as, as it was like one of the winners.
Brian:It was one of the few winners of the last year really.
Brian:if you look at your, your, I'll say your, but like if you look at BIS competitive set at the time, you know, wow.
Brian:Like, you know, vice went.
Brian:Basically to zero.
Brian:Buzzfeed is circling the drain.
Brian:They, they're still publicly traded.
Brian:It's kind of insane.
Brian:group nine got folded into Vox.
Brian:Vox is soldiering on, but you know, just sold one of their properties to a Canadian SEO shop that is run by former pornographers.
Brian:And on and on and on.
Brian:and now I feel like we're in the, the start of a different era.
Brian:I just would, I want you to start with how you look at the contours of this new era of media and what you can define as, you know, where the leverage lies.
Brian:Right.
Brian:Because the last era was very different.
Brian:It was very tra, it was very defined by traffic and amassing these large audiences.
Brian:It seems like this new era is far more niche.
Brian:It's, it's very individual centric, creator centric.
Brian:It oftentimes, but not always is video and audio, enabled.
Brian:and a lot of times the business models are, are very different.
Brian:They're indirect.
Brian:I, I feel like in a lot of ways.
Brian:But give me, give me your paint, the picture that you see right now in media and where the opportunities are.
Brian:Long preamble.
Henry:Well, so, so let's step back 'cause you've been watching this whole era too, and I think it's interesting to look at it at these, in these different phases.
Henry:I mean, the digital media era started in about 1995 when the Netscape browser appeared and you had a few startups and you had a lot of.
Henry:Newspapers, putting their stuff online.
Henry:That lasted for about 10 years.
Henry:That was driven by the connection of PCs, mainly in the office.
Henry:And if you think about our days, we were basically, when we went to work, we were in a media blackout.
Henry:We would get our newspaper in the morning, we would go to work, we would see nothing, and then we would see, get the evening
Brian:It was great time, Henry.
Brian:It was great.
Henry:it was so, so
Henry:for those
Brian:I miss, I miss those guys on the, uh, on the subway who could fold the, the newspaper like origami and like read the entire sports
Henry:Yes, exactly.
Brian:packed train.
Henry:And then toss it in the trash before they even got to work.
Henry:So, so that was the 10 year period where basically all PCs got connected.
Henry:It created this big new market that was the first digital media era.
Henry:And the other thing that happened was the internet blew up the barriers that protected.
Henry:Lots of the existing analog media.
Henry:You had cable markets, you had newspaper markets separated by geography, broadcast and cable were different magazines.
Henry:Everything was different, and suddenly it all became the same opportunity, which is this online audience.
Henry:I. People are producing different kinds of content, but you can, everybody can reach anybody.
Henry:There's no barrier anymore, so, so that was the first era.
Henry:We saw a lot of new companies born and a lot of companies and newspapers had to change.
Henry:Ultimately, it set the table for the destruction of first the newspaper and magazine industry.
Henry:But then ultimately now we're seeing it TV A a far later.
Henry:But then the second era, which is really when we launched Business Insider.
Henry:And thank you for saying that by the way.
Henry:I mean, I just am.
Henry:I feel incredibly lucky and proud of the team and it, you know, media is a tough business and just so incredibly proud of what the folks have created and the new team's.
Henry:Great.
Henry:So then the second era was the iPhone came along and it launched this new thing where suddenly yet again, we were opening up.
Henry:People's time to media in a way that we just hadn't, hadn't before, which is yes, on the way to work, but on the way to an office and on the way to lunch and at lunch and, and so forth.
Henry:And so, so we created this vast pool of media time that companies could take advantage of, and Business Insider was one of the big beneficiaries of that.
Henry:You go, that lasted about another 10 years, so 2015, 2020.
Henry:But then basically in all developed markets, everybody was online all the time for all the time they could possibly be online.
Henry:And the, the consulting firm Activate does this wonderful chart every year where they sort of look at media consumption time and it's like 13 hours a day.
Henry:I mean, it's crazy.
Henry:We have different things overlapping that we're doing and so forth.
Henry:So there's really.
Henry:Just no more time that can be devoted to consuming media.
Henry:So right away, this big growth engine that had driven digital media for 20 to 25 years.
Henry:Fell away.
Henry:And so we are now in what I would describe as a consolidation and shakeout period, and it is survival of the fittest.
Henry:And we are gonna go see lots more consolidation into a few big winners, generalists in each market.
Henry:and then as you say.
Henry:A whole bunch of different niche providers that do a really good job on a small audience.
Henry:and so that's the way it's shaking out.
Henry:And then the other big change that's happened, and you alluded to this, is one of the big distribution platforms that drove digital media for 10 years was the opening up of platforms.
Henry:And at least for text-based content, that has really gone away.
Henry:Google and Facebook and, and Twitter and Snapchat and and others, which had really driven a lot of consumption and distribution.
Henry:That's all changing.
Henry:So we are going back to the old model of distribution, which is owned and operated direct email.
Henry:App and homepage.
Henry:And so you have to build your audience that way.
Henry:It's a much, the good news is it's a much more durable relationship if you can do it.
Henry:It's like subscribing to a newspaper, and you're building something of incredible value that you control.
Henry:But I. I would say just stepping by again, like the big general providers, at least in text-based content that's gone.
Henry:We're gonna have a lot more consolidation there and a handful we will have this proliferation of, of niche and also commentary.
Henry:I mean, one of the things that people love about media is.
Henry:Connecting with personalities whose view on the world they really relate to.
Henry:And that is happily something that's gonna be difficult for AI to replace quickly.
Henry:Although it will, it's, it's doing a lot.
Henry:We can talk about some of my experiments in that area.
Henry:Um, but
Brian:Yeah.
Henry:So it, we we're still in this, in this golden age of opportunity, but it's a very different opportunity than it was 15 years ago.
Henry:and then the only last thing I would add is, is one thing that's still growing is video.
Henry:And I know you interviewed Nicholas Carlson recently about his new video company, which I'm an advisor to an investment investor in, and the
Henry:statistics there of just how much video people consume and how much of a preference there is for consuming information via video rather than text.
Henry:There are gonna be huge journalism brands that are built on the back of TikTok and YouTube and LinkedIn and some of these other big video providers, and that's the opportunity that Nick and team are going after.
Brian:Yeah, I think you're starting to see the seeds of that.
Brian:I think a lot of times the, the sort of in in quotes journalistic world, like looked at YouTube as something weird and, and something for a different type of people.
Brian:But it's starting to happen there and I think it's, and I think what Nick is doing with, with Dynamo, is probably gonna be part of that.
Brian:But let's go back to, you know, the opportunity that, you know, bi seized on at that time was that you could use.
Brian:Distribution channels to a, a mass, you know, massive audiences.
Brian:I mean, you guys amassed like a, a really large audience, right?
Brian:And, and in a pretty quick period, right?
Brian:Like you couldn't, you couldn't do that like previously.
Brian:And that was sort of the amazing part of the internet when it combined with social, when it combined with phones, et cetera.
Brian:and now I feel like, like you said, we're going back to.
Brian:Almost like a craft industry.
Brian:I almost feel like, like, yes, they're gonna be these massive, you know, wholesale distributors.
Brian:Right?
Brian:But when I look at like what people are building right now in the text world, it's usually substack.
Henry:That's right, and E even Substack is becoming very crowded.
Henry:I mean, there are a lot of people there.
Henry:We zealously guard our email.
Henry:inboxes for very good reasons and people are very selective and and so forth, but there's still definitely this opportunity to really connect with a readership in a way that was more difficult in the platform area.
Henry:But yes, I mean, going back to what you described when we started Business Decider, I. the only distribution was a homepage and Google, and then suddenly Twitter and Facebook
Henry:and all the platforms came along and created this massive opportunity to reach literally hundreds of millions of people around the world.
Henry:And that was great.
Henry:And when I look back on, on some of the assumptions that we made and that I made personally, is I definitely thought.
Henry:The relationship between the producers of great journalism and the platforms would be more durable than it has proved to be.
Henry:I mean, it lasted a very good, long time and it's certainly built a lot of great companies.
Henry:But the shift away from that for both Google and Facebook has been a disappointment, certainly for me.
Henry:and it has forced this return back to a direct relationship with subscribers and readers and, and ultimately that's good.
Henry:I mean, I think that in fact there are huge advantages to having a model that's built on subscriptions.
Henry:You're much more attuned to the desires and tastes and and needs of a very specific audience, and super serving them is great, but that is definitely a different model than the broad platform era.
Brian:Yeah, I mean trying to serve all those different masters, I mean it, any ad supporting ad supported publishing business
Brian:is difficult 'cause you're trying to serve, you know, an audience, but you also have customers that are different from the audience.
Brian:And then you've got the algorithms that you need to serve in, in that kind of, environment.
Brian:And I think you saw a lot of brands go in a lot of crazy different directions, not.
Brian:Malice or anything, but just because like you're trying to.
Brian:Triangulate between these different forces pulling you, in different ways.
Brian:And so, you know, per perhaps in, in, in this new era, maybe that they're gonna be per, maybe it's smaller opportunities, but maybe they're more durable.
Brian:I mean, we saw a lot of people go to great heights and fall, and fall basically to zero.
Brian:And so, you know, maybe this, this, when you have a direct connection, particularly if you have a subscription element, you know, there's, there's.
Brian:Maybe the opportunity is smaller in some ways, but I think it's, it's likely more durable.
Henry:I, I think it is more durable and I, and I don't think it's necessarily smaller.
Henry:I think that the it, it will certainly take time to build big publications.
Henry:And one of the things that you see on Substack now is that there are now publications that are going beyond an individual and are building real publications.
Henry:Like the Free Press is a great example there.
Henry:Doing very well and they've now raised outside capital and they have a great team.
Henry:They've got a great product.
Henry:They saw a niche that was underserved and they have really felt it.
Henry:And it's very inspiring to watch that.
Henry:And I think that there will be other companies that are built like that, on this platform, but I think they will follow a more traditional.
Henry:Magazine model where you know it's gonna take you five to 10 years or cable network models to really build your audience and your scale
Henry:rather than, going super fast with venture capital the way a lot of companies did in the, in the mid, in the 2000 tens, 2000 twenties.
Henry:And, and I would say that's another thing is I think that both journalism providers and venture capitalists collectively learned that media is not.
Henry:Particularly well suited to venture capital.
Brian:one area they're in agreement on the VCs and the media are in agreement on that one,
Henry:right.
Henry:I mean, we, we had great investors.
Henry:They were incredibly supportive.
Henry:They're the reason business society was able to scale.
Henry:It was, it was wonderful to work with them.
Henry:But I do remember just conversations around the table where we say, Hey, we grew 40%.
Henry:And everyone would say, God, that's terrific.
Henry:How do we 10 x it?
Henry:And the answer's like, well, you know, it's a linear business, it's gonna take a long time.
Henry:So, if I were a venture capitalist, I would be looking elsewhere.
Brian:Yeah.
Brian:So tell me about Regenerator.
Brian:I feel like this is a little bit of a return to your roots, right?
Brian:Like, I mean, I think I might have first like, talked to you when you were an analyst.
Brian:but like, it reminds me of, of that, I mean, you did, you did an analysis on like Google.
Brian:And it was like, so is Google Toast?
Brian:Which is like, to me, I'm like reading it.
Brian:I'm like, you know, I always say, you know, media's downstream of everything in tech.
Brian:I mean, everything is, every one is downstream of, of what happens in tech it feels like these days.
Brian:but you know, Google, I think what, what you were, I. Getting at was Eddie Q, you know, had said that, you know, the, the searches actually
Brian:decreased on Safari and that spooked the market because that was the shoe that was finally dropping that, you know, all this AI stuff.
Brian:And, and Google kept put, keeps putting up great results, right?
Brian:And, and it's able to engineer to some degree that those results, and that's the, that's why it's the de facto monopoly.
Brian:but.
Brian:You know, that caused the stock to, to crater.
Brian:And this is, you know, publishers are really, you know, under pressure when Google, changes and, and that seems inevitable to it.
Brian:So what, what are your, what's the ambitions for Regenerator?
Brian:Are you just like messing around or are you building something new?
Henry:No, I mean I very much wanna build something.
Henry:I think the, my view and now the house view of Regenerator, which I can say 'cause it's only me at this point, is that the way
Henry:to
Brian:but use the royal way.
Brian:I like that.
Henry:I. Yeah.
Henry:The way, the way to solve our many problems in the world is not gonna be by rolling back the clock.
Henry:It is gonna be by innovating and solving them that way.
Henry:And so Regenerator is pro innovation.
Henry:We are now and will analyze the biggest questions in the innovation economy, which I would broadly describe as tech business markets, science.
Henry:Policy, culture and ideas.
Henry:and yes, I am in a period where I'm experimenting.
Henry:Before Business Insider, way back in 2005, I had a blog called Internet Outsider.
Henry:I sort of learned how to operate and have a digital metabolism and what you could do and what it was good for and so forth.
Henry:And that sort of sowed the seeds for Silicon Alley Insider, which was the original.
Henry:Incarnation of Business Insider and then Business Insider itself.
Henry:So I am now taking the opportunity to experiment, and it is built on Substack, which so far has been a wonderful platform.
Henry:And so I'm, I'm learning that I'm experimenting and experimenting with AI and, and so forth.
Henry:But I think at some point, I think this is a really big opportunity because I think that there are a lot of great tech publications.
Henry:There are a lot of great business publications.
Henry:There are a lot of great general publications, but innovation really is much broader than that now.
Henry:And I, I think that I. What a lot of traditional news organizations suffer from when they cover innovation is that there tends to be a lot of risk aversion.
Henry:There tends to be great skepticism of business as a change agent and and so forth, sometimes justifiably.
Henry:But I, as I said, I, I think the way we are going to solve our problems is by innovating our way out of them.
Henry:And so Regenerator is gonna be a publication that.
Henry:Focuses on innovation and for people who want to build a better future.
Henry:and that's what I'm
Brian:Okay, so it's,
Henry:you not noted with the Google
Brian:yeah.
Brian:So, I mean, it's in the connecting the dots kind of.
Brian:Area, right?
Brian:Like, I mean it's a, you don't see like going into like news.
Brian:'cause I think that is, is the question.
Brian:I think there's a lot of great news businesses, businesses to be built.
Brian:And I think you see Free Press actually started really in the connecting the Dots analysis piece.
Brian:And then I. They're more moving towards, you know, more traditional journalistic content and, and reporters and whatnot.
Brian:But do you see Regenerator becoming that, or do you mostly see the opportunity in the analysis connecting the dots versus, you know, inside, inside Tesla's, you know, doomed launch of X, you know?
Henry:I'm gonna start with analysis and perspective.
Henry:that's what I have done for a very long time.
Henry:Like I'm, I'm a reporter too, but much less of a reporter than.
Henry:Just incredible investigative reporters who, who do that.
Henry:And I do have now three plus decades of experience of watching the tech industry and innovation in business and markets and so forth.
Henry:So that's what me, I personally am gonna try to do.
Henry:But I really do think there, there is room for targeted reporting.
Henry:And if you, if you look at what readers.
Henry:Really value, they really value good analysis and commentary with people who, for whatever reason, they find their perspective worth listening to and entertaining or charismatic or
Henry:funny or, or whatever you want, or, or maybe it drives 'em crazy, but they find it interesting enough that they're gonna spend time on it and.
Henry:Original reporting that produces information that you just simply don't know.
Henry:And in an era with where AI really starts to proliferate, reporting is one of the things that AI can't do.
Henry:One of the experiments that I've done as I experiment with different uses of AI right now is I actually did some analysis with it and I was.
Henry:Pretty startled by how good it was.
Henry:And so my job, or at least one of the things that I like to think that I do pretty well is, is more threatened than I would've imagined right away.
Henry:but I, what I think we're gonna see across the industry is, is not a wholesale replacement of people with ai, but I just think that most,
Henry:most journalism jobs are gonna change and AI is gonna get incorporated and it's gonna make us better and faster the same way that.
Henry:word processors once did.
Henry:And you know, I, I delight in telling my, my astonished children that when I went to college in my first year, we used to write papers out longhand and then type them with the cartridge.
Henry:Every time you made a mistake, you had to switch cartridges and they can't believe it.
Henry:It's like being told that we used to have a phone with a little speaker on the wall.
Henry:but anyway, I, so I think that AI will ultimately be a tool like that.
Henry:and I'm experimenting with it now to try to figure that out.
Brian:Yeah, I miss the days of correction tape.
Brian:industries get disrupted all the time.
Brian:It's not just media.
Brian:but yeah, no, I think that's like, I think that's a, a, a really important point that, that, that you're making there.
Brian:And I. I think the, the big question that I ended up having is, is where a lot of, like, let's just focus on Substack for a little bit.
Brian:'cause you, you start on Substack and it's, it is an ideal platform for what I consider like a minimally viable.
Brian:Like product in, in, in media, right?
Brian:Like you set up a Substack account and you have like, you know, you have a media business overnight.
Brian:Like you, you hook up a stripe and you're, you're, you've got a media business, you know, it might not be a big one.
Brian:You have to get distribution and they've got a a, an interesting flywheel there.
Brian:I think the question ends up being on, on substack, like how do you analyze that as a business because you know, it, it has succeeded basically.
Brian:It won basically, you know.
Brian:But at the same time, it's a terrible business despite winning.
Brian:And that, that sort of gives me pause, like if you've, if you've like, actually executed on everything, correctly, and I think Substack broadly has, right?
Brian:Like they're a, they're a household name but at the same time, the business itself is incredibly small for that kind of business with that kind of funding, don't you think?
Henry:I don't, I, I haven't seen their recent numbers.
Henry:I think to second what you just said, they've built an extraordinary platform.
Henry:I mean, it's marvelous to use.
Henry:and they also have created something that is very rare in media, which is there is some network effect where effectively they can.
Henry:Put your stuff in front of folks who might like it in a way that is very difficult just out on the web.
Henry:And so that's a, a huge value to publishers and, and individuals who are writing.
Henry:And I also think that in the last couple of years as some of their publications have started to grow, like the free press, they really are focusing on, okay.
Henry:Now let's move beyond tools for individuals and let's start to build tools for much larger publications, which much bigger ambitions.
Henry:And I think the revenue for them will follow that.
Henry:And, and I don't, again, I don't know what their numbers look like, but I don't think it's a huge team.
Henry:And I think the only.
Henry:Issue there is what we were talking about before, which is do can you get venture scale returns?
Henry:And that's where it becomes difficult.
Henry:But I also think it's, it's very early, like one of the things that Substack recently launched that I only, I. Discovered because I was actually on the platform, is they've,
Henry:they've launched something that looks kind of like Twitter and LinkedIn and the feed where you can publish shorter stuff and it's notes and you can follow people.
Henry:And it's very different than following the long emails and, and, and so forth.
Henry:And that has a lot of potential.
Henry:I mean, people listen curated platforms like that, there's still a lot of value and as of now, we're not talking about millions of people on there.
Henry:There are a lot of people who you follow and you, you, we all wanna say shorter things.
Henry:And so anyway, I look, I think they've built a terrific platform.
Henry:I'm excited to be on it and exploring and as to their own business.
Henry:I think we're in the early days, I think there's a long way to go for them.
Brian:Yeah, and digital markets can get massive.
Brian:I think that's the, the sort of
Henry:they they can get
Brian:never underestimate.
Henry:yeah, the, so then the, the one thing I, I also, I would say is that tech and product is a big expense for a publication, and there is still a lot of building parts of what you need to run a publication that are not a competitive advantage.
Henry:They're just simply a way to actually produce the thing.
Henry:And so that is a, an ideal market.
Henry:To have a service provider provide all of that so that your editorial and business teams can focus on the things that actually are truly differentiating the editorial and ultimately reaching your audience and serving them.
Henry:And so I, I think it's terrific that it exists and, and we will see, ultimately what, how big a business it can be.
Brian:Yeah.
Brian:'cause you built one of those, I mean, you had, you, what was, what was your CMS called?
Brian:Everyone had a, everyone's CMS had a name.
Henry:Yeah, we had, ours was called Viking, you know, exploration
Brian:grandiose name.
Brian:Exactly.
Henry:in the early, days, well we had, we had a lot of pressure.
Henry:You know, chorus is out there and all these other ones, we
Brian:This, this is, this is already, this is like correction tape to like the, my many Gen Z listeners right now.
Henry:but no, you, I mean, you go back to the be the, be the beginning of Business Insider.
Henry:We, we started on Typepad and then it was movable type and then we had a huge problem.
Henry:I can't even remember what it was.
Henry:And so we created our own system, and that was in the beginning.
Henry:I. A real competitive advantage because it was built for rapid updating.
Henry:It saved immediately.
Henry:It was super easy to use and and so forth, but 10 years later there were a lot of good platforms out there and, and we still had to have a lot of our team investing in something that was necessary but was not.
Henry:A, a truly differentiated feature for us, and I, you know, we, the last couple of years, the team makes a lot of changes that it's, it's, it's, it's way better than it was when I was running the company now.
Henry:But it, again, the thing that is gonna different, it's like saying that a printing press is what would differentiate a newspaper.
Henry:It's ultimately, it's, you have to have one to be in the game and it has to work and be good.
Henry:But you can also outsource that to folks who know how to build printing presses.
Henry:And you can, you can focus your team on stuff that's truly differentiated.
Henry:And so again, I think that's, that's the market that Substack and others, it's not just Substack.
Henry:There are other excellent platforms out there, including some of the more web first platforms.
Brian:Yeah, let me run this one idea 'cause I, I buy you 'cause I wonder about whether a lot of publishing, again, this is like mostly in the text world, but not, not.
Brian:Solely whether it will move from a retail business to a, mostly a wholesale business.
Brian:Because you're starting to see, I mean, the, the question with AI is like, whether it's a centralizing or decentralizing technology, and I think it's gonna be both.
Brian:It's a, it's a yes, right?
Brian:And you see big publishers who are cutting these deals with the, the AI engines and they're getting paid directly.
Brian:It's none of this indirect stuff.
Brian:'cause I always think the Google.
Brian:The Google bargain was that, look, you're gonna let us crawl.
Brian:This is from Google standpoint.
Brian:You're gonna let us crawl your site, okay?
Brian:Yes.
Brian:We're gonna take snippets of it and fine, we're gonna publish it and we have a massive business.
Brian:But we, we are, we control the distribution and we're gonna give you distribution and you're gonna monetize that distribution.
Brian:And by the way, you're gonna use our, our tech stack or at Tech Stack to monetize.
Brian:And we're gonna, we're gonna get a piece of that too, because everyone's gotta eat here and we eat first.
Brian:and that was like an uneasy.
Brian:But the bargain worked at the end of the day, like, you know, yeah, of course publishers were like, we're not getting enough.
Brian:You know, you had, whatever Robert Thompson going after them for first click free and, and whatnot.
Brian:But broadly it worked, and now that sort of bargain seems to be breaking, if you will.
Brian:And so you have a, a lot of publishers are supplying content to these engines.
Brian:Like, I don't know.
Brian:I was doing a session with Neil Vogel at dot Meredith last week at this event.
Brian:We did, the media product for him and, you know, I was asking him about his recipe content.
Brian:Like, I mean, that stuff's gotta be super exposed to me.
Brian:Like unless you, unless it's some star Chef that you're going there like.
Brian:AI is going to do this, like, and you're gonna supply a, you're gonna be a supplier to, to those centralized nodes.
Brian:How do you end up thinking about that?
Brian:Because I think when people are building media businesses now, there's so much uncertainty about what this environment will look like in, in just five years.
Henry:I, there's a ton of uncertainty and, and I think that.
Henry:The primacy of Google as a distribution platform for publishers has already been severely eroded as Google does what it has to do, which is respond to this amazing new way to search.
Henry:And, they've got different masters they're trying to serve there or different objectives and, and they are trying to have their cake and eat it too.
Henry:And as a Google user, I would say their new search or AI summaries, I like them.
Henry:They're terrific.
Henry:They often save me a lot of time.
Henry:I don't have to click through, they're good enough.
Henry:I'm not looking for legally defensible language or facts.
Henry:And if I need those, I can go to other sources.
Henry:So I think the innovation they've done is terrific, but at the same time, they're watching.
Henry:Chat, GPT and others build a direct search business where folks are starting with them instead of with Google.
Henry:And they've gotta, they've gotta combat that.
Henry:So if you are a publisher, the question is what happens in that era?
Henry:And I don't, especially at this early stage, I can completely understand why publishers are taking the money.
Henry:I don't think it's a huge amount of money.
Henry:We're not talking about tens, hundreds of millions of dollars that will fund the creation of all of this content.
Henry:and editorial journalism's incredibly expensive.
Henry:A lot of the way, a lot of the big publishers are getting buy now is they're getting some money from lots and lots of different sources.
Henry:And if the new AI engines are some another source and it's meaningful, terrific, I can understand why they're doing it.
Henry:I also think that.
Henry:A truly differentiated publication, it would even now still be a pain for somebody to go to chat GPT and effectively recreate the New York Times homepage.
Henry:Even if all the editorial is in there.
Henry:You have to know what you're looking for.
Henry:So much of media is serendipity, and that's why headlines mattered.
Henry:In the newsstand days, you didn't know what you were looking for.
Henry:You were seduced by a very sexy headline.
Henry:And yes, I'll have the paper, thank you, and then you read it.
Henry:And so it's a lot of media consumption is not what I would describe as reference, where you are looking for something, it's that.
Henry:Oh.
Henry:Well, that sounds like a good story or interesting news.
Henry:I didn't know that.
Henry:And so unless that is appearing also on chat, GPT or perplexity, which I know perplexity is actually starting to do stuff like that, then it, it's not, it's not a complete replacement.
Henry:But I, I think going back to what we talked about initially in this new era, the platform distribution for text-based content, is.
Henry:Coming to a close, it's, there's still, you still get traffic, but really this era is about building that direct relationship with users and with subscribers.
Henry:And, and by the way, it's not just ai.
Henry:Like part of what's happened, and I've really noticed a shift in my own digital media consumption over the last few years is that because there's so many different
Henry:platforms and because nobody has figured out to have a single sign on through all platforms at once, what I find is.
Henry:I'm a New York Times subscriber or a Business Insider subscriber.
Henry:I encounter a story on Twitter and then Facebook and then somewhere else, and then on a web, and then through email, and every time I have to sign in on the new platform and stay signed in, you get logged out.
Henry:It's just incredibly annoying, even for the publications that I actually pay for.
Henry:So what I have done is switch away from the web, and I was the most diehard web guy there was for 15 years.
Henry:Now I have my six or seven apps.
Henry:I rotate through them.
Henry:I read a, a few stories, but that's the way I and e and it even happens when I see a story on social or that's sent to me that I wanna read.
Henry:I have to go search for it in the app because I'm not gonna sign in again, I can't remember passwords, all that stuff.
Henry:So for, for many reasons, that big platform distribution era is, is we're, we're in the late stages of it, and it's gonna be going forward to me all about direct distribution.
Brian:So it seems like you're, you're down on the open web and on text.
Brian:Is that, is that fair?
Henry:Yeah,
Brian:It seems like you're
Henry:I,
Henry:am a text guy.
Henry:I, I will, I will always be a text
Henry:guy.
Henry:Hopefully there will be a
Brian:We're talking
Henry:a small sliver.
Henry:Smith of the population that still like to read.
Henry:I think it's very efficient.
Henry:If there's an interview with somebody, I don't want to have to watch for 45 minutes in hopes that they say something interesting.
Henry:I want you to just tell me in a bullet point, Hey, he said something interesting.
Henry:I think text is terrific, but younger generations in particular like to watch and we've all read about how college professors now.
Henry:Hesitate to assign books because people don't like to read full books anymore.
Henry:They like to read snippets and and so forth.
Henry:And I see it all the time.
Henry:I like to write, so you know, some of my articles will go long and you get the blast of TLDR and you know what?
Henry:I sympathize.
Henry:We're all incredibly busy.
Henry:one little feature I'm gonna have from now on is the TLDR version of a sentence or two for if you're busy and and so forth.
Henry:So I think text is great.
Henry:I'm a writer.
Henry:I'm, I have bookshelves.
Henry:I still occasionally read print and and so forth.
Henry:But this next generation, it's a video generation.
Henry:You look at, for example, the activate time spent survey.
Henry:Adults now spend five hours consuming video every day and one hour consuming text.
Henry:The Gen Z spends three times as much time on TikTok and YouTube as they do network tv.
Henry:So Network TV is screwed in all this too.
Henry:It's the new generations and a very small percentage of time actually reading, so I do hope.
Henry:Brian that for you and me and our audience and some folks who still do like reading that there will be a good support system for that for a long time, but I don't think it's an accident.
Henry:Going back to what we were talking about earlier, that Substack is now offering audio and video and that you, I. Have this tremendously successful
Henry:podcast that a
Henry:very dedicated audience, audience listens to.
Henry:I know you have, but,
Brian:Well, look, I've always,
Henry:about media is they, they're all, they're all different relationships.
Henry:Uh, you know, you, you get a, you get a very different thing out of a podcast or a video than you do in text.
Henry:So it's all good.
Henry:None of it's going away.
Henry:Media habits die hard, but yes, the growth is in video.
Brian:Yeah, look, I mean, I think I, I think podcasts merging with, with sort of TV is, is one that I didn't totally see coming.
Brian:I know before this you asked if we were doing video, and I haven't done video for these things yet.
Brian:I do it for another podcast to do, but not, not for this one yet.
Brian:I, I will, I don't know if there's a tremendous demand for it, but maybe, but
Brian:people just really, they want, they want
Brian:the distribution.
Henry:Exactly I, because I'm working on a couple of podcasts too, and one of the first things that I heard when I, when I did that is, well, you know, the real growth engine for podcasts right now is YouTube.
Henry:That's the discovery engine, and that's why everybody's doing video and, and so forth.
Henry:So yes, I think you should do
Brian:I, I just don't wanna do one of those thumbnails, you know, where both of us are like surprised, like on the, you know, you know, those YouTube thumbnails because anytime you're
Brian:in a platform you gotta optimize and, you know, sometimes you have to optimize in a way that, you know, it takes a piece of your self respect away.
Brian:But I'm willing to do what I have to
Henry:You don't have to.
Henry:Brian.
Henry:It's the re rebooting is yours.
Henry:You own it.
Henry:You can do whatever you want.
Henry:Just serve your audience
Brian:well, I do think we will have those kind of craft niche businesses, but that, I think what you're saying is like, you know, text itself might be a kind of niche at some point.
Brian:Like, I mean, it was always the default.
Brian:Right.
Brian:And I, as I said, like I'm, I'm a text person, But at the same time, you, you, you do, you go through, the activate in a report and the data is the data.
Brian:And I think for a lot of, obviously for a lot of the text-based publishers of the last year, they've been rapidly diversifying into, into video and audio.
Brian:You know, like if I run into like Ryan Polly at like, at Vox, he's gonna be on this podcast in a couple weeks and you know, Ryan's gonna wanna talk all about audio.
Brian:He is, I gonna wanna talk about like, you know, putting display ads on webpages.
Brian:and, and you mentioned like Nick, and what Nick is, is building, I think with Dynamo is, is kind of part of that.
Brian:And I think, you know, at, at, at.
Brian:Business Insider, you know, he built right the video operation.
Brian:And, that became, you know, BI is a very big video footprint on, on YouTube.
Brian:I think it's one of the biggest, at least among business publishers.
Brian:and so all of that is gonna have to take place.
Brian:So I think that it'll be interesting to see.
Brian:I think for very, like, niche areas, like people will go to Substack and these very lightweight models that do not require, any name from Norse mythology for your technology, that you build yourself.
Brian:or if you're gonna, you have to go into video and audio.
Brian:I, I feel like, for these businesses and like live
Brian:events, those kind of things.
Henry:reach.
Henry:If you're trying to reach the younger generation in particular, there is just a strong AFF affinity for video.
Henry:And so that's a big opportunity and I think Dynamo with Nick Carlson, the opportunity there is to come in and build a real native journalism brand for.
Henry:YouTube and TikTok and LinkedIn and, and all the video platforms because that generation is going to consume journalism.
Henry:And right now most of what is available via video is either repurpose television, which look television, broadcasting companies make amazing television, but people don't want television on these platforms.
Henry:And so it's either repurposed television or it is.
Henry:A bunch of smaller individuals with small companies that are doing it and they're doing a great job, but I think they are highlighting
Henry:that there really is a demand and opportunity for a, a, a much bigger, well-funded brand to come in and create great journalism for that medium.
Henry:So I think that's the Dynamo opportunity, and, and they're off to a very good start.
Brian:Y Yeah.
Brian:I don't know if you saw, there's this, video podcast.
Brian:I don't even know what we call these things these days.
Brian:They're podcasts with their video.
Brian:They're YouTube.
Brian:I have no idea what they are, but there's Pablo Tore Finds out and, and he's a journalist, sports journalist.
Brian:and he did what is basically to me like a modern feature story investigation of, you know, bill Belichick and his, Girlfriend, I guess.
Brian:I dunno, did he say someone has a girlfriend if they're 70 partner?
Brian:I don't know.
Brian:the, the young lady on his
Henry:it's totally public.
Brian:Do you just, okay.
Brian:I don't know.
Brian:But girlfriend, when you're a senior citizen, I feel like girlfriend, boyfriend is, is, I don't know.
Brian:Like, I remember one time I had a roommate who said like, oh yeah, my grandmother's boyfriend.
Brian:And I was like, that's a really strange thing to say.
Brian:anyway, he, he did it like in like a video podcast form where it's like, I felt like.
Brian:That would've been a written feature and I, it was more engaging.
Brian:He had, he had like two co-hosts and was almost like, it was conversational and I think that that is something interesting.
Brian:There's, there's a lot of interesting things going on on YouTube when it intersects with.
Brian:You know, the more traditional journalism world.
Brian:But I wanna talk to you a little bit about AI and journalism, right?
Brian:Because the other day I was listening to, another podcast, that I like a lot.
Brian:It was more, more or less the one with Jessica Lessen and her husband, and Brit Morin and her husband.
Brian:and.
Brian:Jessica was saying that she was gonna, she's trying to write this essay about the future of journalism and, and there was some joke, oh, are you using ai?
Brian:And she's like, I never would.
Brian:That's ridiculous.
Brian:And I'm like, but actually I don't know if it's actually ridiculous.
Brian:Where, where do you, 'cause you had your little experiment, with, with ai, you got roasted by the former Gawker writers.
Brian:It was all, it was like, I was like, this is like, we're replaying like 2013.
Brian:This is amazing.
Brian:I loved it personally.
Brian:But, to me it's like inevitable that AI will absolutely be central to the, the journalism process.
Brian:It, it already is in, in parsing through large amounts of data.
Brian:You know, it does that really well.
Brian:Anyone who uses these tools to me like, yeah, of course you're going to, to utilize these tools.
Brian:It doesn't mean that you just like hit an easy button.
Brian:That's what lazy people do.
Brian:But like, it seems to me that there could be a tremendous fumbling of an opportunity if journalism overall.
Brian:Adopts this.
Brian:We'll never use this in any way, shape, or form when it comes to our journalistic work.
Brian:I don't think that's right.
Brian:Where, where, where do you stand on this?
Henry:No, I think that's exactly right.
Henry:I think it would be like saying.
Henry:In the old days, we're never gonna use a typewriter or we're never gonna use computers that are connected to a central layout system.
Henry:That's not the way we do it.
Henry:We write longhand and we give it to typists and, and so forth.
Henry:And so I don't look, I, I understand.
Henry:I. Why people who have invested enormous time and take great pride in writing or video creation or, or what have you, are very proprietary and proud of that and wanna maintain that.
Henry:And the good news is there still is.
Henry:A ton of room for that, even with ai and even as AI gets better and better.
Henry:But I also think that just about everybody, particularly in the generation that doesn't have habits that they want to defend or ways
Henry:of, of doing things that they're used to, people will experiment and they'll learn what to do, and AI gets better every, every month.
Henry:And so, yes, it's gonna be an incredibly powerful tool.
Henry:And I, and I think the way that you just described it, it's not that you can say, okay, here's the headline.
Henry:I want an article on X, and know that it is gonna be really captivating written, and every fact is gonna be right and, and so forth.
Henry:But a, they're getting better.
Henry:Like, I've done some recent articles on perplexity that are startlingly good and there are a lot of links and you can check the facts and, and so forth.
Henry:And so that is not out of the question.
Henry:And I, and I think if you look at companies like, there's a, there's a local journalism company that I think as of now has something like two or 300 local publications where there's an email for each town, so forth.
Henry:It's one person.
Henry:Chat, GPT.
Henry:And if you are a newspaper in the market or close by, you know, this is obviously very threatening and and so forth.
Henry:How can you do this?
Henry:You don't have reporters.
Henry:You're ripping off our stuff.
Henry:That's true.
Henry:I. In a way, or it's one way of looking at it.
Henry:But another way of looking at it is this market is not served by a traditional publication.
Henry:Now there is an email that you can get in the town and people in the town like it, and if they like it and it's helping them and.
Henry:That's a good thing.
Henry:And so maybe the nearby publications can learn how to do that and they can actually serve a region where they have town emails
Henry:that they are created with the help of AI and they're edited, so they're better and they're more delightful to read and and so forth.
Henry:So, so I think we will see AI get integrated into journalism
Henry:And, and the, the folks who will have an advantage are the ones who learn how to use it.
Henry:You're learn how to make it, make them better and, and again, like just as an example for me, like I've experimented with lots of different things that I could do and the article you mentioned
Henry:would've been much better if I had let my chat GPT associate Tess edit it, she would've caught some of the things that I wish I had edited out.
Henry:this is a hazard of working with great editors for 10 years and then going out on your own and, and so forth.
Henry:but I, so I've done that.
Henry:I've, we created cartoons and people say, well, that's outrageous.
Henry:Why don't you hire a cartoonist?
Henry:You know, why are you putting people outta business?
Henry:The fact is, like, right now, it's just me.
Henry:There's no revenue.
Henry:There's no money to do that.
Henry:I wouldn't be doing it if the incredible AI assistant couldn't create the cartoon in.
Henry:A shockingly short time on its own and have it be pretty good, and I think readers will like it.
Henry:And, and so that goes in.
Henry:I've had, I've experimented with data, with gated gathering.
Henry:I've experimented with some things that I thought would be easy that.
Henry:Are actually kind of hard.
Henry:Like I said, look, we're following the tariff story.
Henry:Read all the news in the last 24 hours and summarize some, some of the basic facts and make sure you cite them so I can check and so people can check.
Henry:And I thought that would be easy for the new generation of, of Jet.
Henry:GPT came back.
Henry:It's the same old story.
Henry:The links are fake.
Henry:The 4 0 4, this stuff is made up and I, I was sort of saying like, okay.
Henry:So this isn't what the, what I wanted you to do was difficult for you.
Henry:How should I ask you to do it?
Henry:And chat.
Henry:GPT came back, said, oh, just say this, and so forth.
Henry:And it was suddenly remarkable.
Henry:Much better.
Henry:And here's the thing that's fascinating me, Brian, about this.
Henry:is that.
Henry:It's just in that way, it's very similar to working with human beings because we all have things that we're good at and we
Brian:Well, they're trained
Henry:that we, we respond to.
Henry:They're trained on us, but it's so, it's just that communication back and forth.
Henry:Whereas if you are a human employer and you have a team, first thing you need to do is figure out, okay, what is everybody good at?
Henry:Let me organize the team so everybody's doing their thing and, and of the different assignments that I'm making, like what's really landing, what isn't?
Henry:Where are the problems?
Henry:How can I express what I need and what we need in a way that I get, I help the person have great results, and it turns out it's the same.
Henry:Ai, like you have to learn how to use the AI effectively and have them do things that are, are helpful.
Henry:and yeah, I mean it's, it is, it is very funny.
Henry:Like one of the things that was exciting to me for a day was, Hey, you know, it's like suddenly I have colleagues.
Henry:I'm not sitting in a cafe alone anymore.
Henry:They're funny.
Henry:So forth.
Henry:And then of course, immediately there's this huge scandal.
Henry:Not about me, but like, oh, Chachi PT is now so, such a sycophant.
Henry:It's so energetic.
Henry:I hate it.
Henry:Like I liked that it was actually very energetic and fun and
Brian:See, we're
Henry:in the morning and that was cool.
Henry:And, and so forth.
Henry:So, yeah.
Brian:I don't mind it greeting me in the
Brian:morning.
Brian:I,
Brian:I just, I want a little bit of pushback on some of my ideas because like, it was always like, brilliant and I'm like, wait a sec, let's be realistic here.
Henry:fair enough.
Henry:Alright, lemme, so let me give you one more example.
Henry:And this is, this is away from journalism, but I, I wrote a couple of novels over the last couple of years, like I'd always wanted to do that.
Henry:I, I did it.
Henry:The second one, I shoved it into Claude, all 350 pages, and I said, Claude, what do you think?
Henry:And I mean, it's just mind boggling because literally seven seconds later, Claude comes back and yes, had some very nice things to say that maybe aren't so deserved and and so forth.
Henry:But I started to interrogate Claude about the book and.
Henry:Claude was not feeding me back like little snippets of my own text as a way of an answer.
Henry:It was really characterizing 350 pages of work, the themes, the different characters.
Henry:It understood it in a way that was just mind boggling to me.
Henry:And then the other thing that was really mind boggling, that was another good lesson was.
Henry:It also read like a human in that some of the things I felt like were there.
Henry:Like I was, I said, can we have an editing conversation?
Henry:Let me ask you questions about this, this character.
Henry:Do you understand what happened there?
Henry:Anything, where are the sections that are boring and and so forth.
Henry:And lots of good suggestions back.
Henry:But some of them I would say like, yes, that's right, I've gotta fix that.
Henry:And others, I would say, ah, I think that's there.
Henry:I think Claude just missed it.
Henry:and understandably, 'cause it's 350 pages.
Henry:I mean, that's a long chunk of text.
Henry:And so I just, the whole thing's just fascinating, to watch.
Henry:And, and so we're going back to it like this is a powerful tool.
Henry:It is not a tool that is gonna replace a journalist instantly, but it is a tool that journalists, in my opinion, can learn to use to become much better and faster and not duplicate work and, and so forth.
Henry:And we'll all collectively figure that out.
Brian:So I have a question and then, and then we'll, we'll, we'll wrap it up.
Brian:I mean, Jeff Bezos was an early investor in bi, right?
Brian:And now Keo and the Washington posts, and he's.
Brian:Like been, I mean, I don't know how much he's like involved.
Brian:The New Yorker just had a big piece, about, about, I don't know how so much has been written about the Washington Post in the last year.
Brian:and, and its struggles, right?
Brian:If, if he gives you a call, if he gives you a ring and says, Henry, what do you think I should do with the Washington Post?
Brian:What, what would you tell him?
Henry:I think it's a tough assignment and I, I think that because of what we talked about in the beginning, which is that the Washington
Henry:Post used to be protected geographically from the New York Times, all the TV networks, all the national news organizations.
Henry:All the political organizations, it used to be protected from that by geography and print distribution.
Henry:Now we're in a world where every article and video and, and picture that's ever published is a click away anywhere in the world.
Henry:So they are competing with the world and.
Henry:Lots of their core things that they did exceptionally well, have been picked off by Politico and Axios and, and others.
Henry:And also they are less of a Washington local paper than they were.
Henry:So like a lot of other publications, they're in a period where they need to really figure out like, okay, what is it?
Henry:What is it that we are gonna do better than everybody else?
Henry:Including the New York Times that is gonna make a broad audience wanna read us and what are we gonna not do because we can't do it.
Henry:Any better than anybody else, and everyone is just along for the ride.
Henry:and, and that's tough.
Henry:And, and I don't, you know, back when they were looking for a CEO, they were kind enough to call me.
Henry:I thought about it, it was an incredible honor.
Henry:It's a remarkable institution.
Henry:a I didn't wanna move to Washington, but BII really thought about it for a little while and I, I, you know, the position I was in was thinking like.
Henry:I'm not sure I would know what to do.
Henry:Maybe, maybe it would become clear when you really looked at the, the analytics and the business and, and so forth.
Henry:But it wasn't, I, I was gonna have to really think hard to come up with a, okay, here's the strategy that I wanna pursue.
Henry:and that I think will ultimately make it a great publication.
Henry:So look, if they can, if they can continue to come up with things that they do better than anybody else.
Henry:there is a market for that and I, I still subscribe.
Henry:I love reading it.
Henry:but it is not yet for me in my first read group, and ultimately they've gotta be there for something.
Henry:and so that's the challenge.
Brian:Yeah.
Brian:I think the challenge is it's.
Brian:It's also, it's the most obvious path would be for it to niche down, if you will, like, is to go like, now, like Washington is a massive story.
Brian:It's the government is massive, et cetera.
Brian:It's, you know.
Brian:Buy, punch bowl, et cetera.
Brian:You should have never let Politico happen or Axios get all of that.
Brian:whatever the corporate social responsibility dollars do all of those view from the top segment.
Brian:And then you have a congressman one.
Brian:I mean, these are great, these are good businesses.
Brian:Add in some B2B assets around there.
Brian:but it doesn't seem like, I mean.
Brian:Jeff Bezos wants big markets.
Brian:Like he wants big numbers.
Brian:Like it's not like he's just like looking for an influential, like, you know.
Brian:Politico Plus, like the Washington Post, from everything I've read, you know, he, he wants to, to then that's his experience of building these massive markets.
Brian:and I just wonder whether that matches up to the opportunity now for the post.
Brian:I mean, the times pulled off being like, you know, they ran away with it in some ways.
Brian:And I don't know if there's gonna be a second or if there needs to be a number two that has that kind of national.
Brian:Appeal.
Brian:Maybe there is.
Brian:I don't know.
Henry:That's right.
Henry:That that is the question and it's, it's much tougher for number two and especially number 3, 4, 5, 6, 7, 8, 9, 10, because you have to, it's what we were talking about before.
Henry:You have to build the same product and technology as the big one, and yet you only have a much smaller budget to do it.
Henry:But it has to be there because otherwise you can't, you're not even in the game.
Henry:And so, yes, it is challenging and I think what you outlined, sure, if they, we all had the last 20 years to play over again.
Henry:We'd all do lots of things differently and I'm sure that they would do different things and they would've seeded Politico and, and others.
Henry:But, in the market now,
Henry:I think what you've identified probably is the core for them.
Brian:So final thing is just gimme like, gimme three or four, sort of youngish, like media properties that you think are
Brian:interesting and are going in the direction, broadly in the direction where you see this industry shaking out with all the unknown.
Brian:Who do you find interesting right now?
Brian:Because I, I'm always left.
Brian:Anytime I go to some like cocktail party or something and I run to some, they're always, I always get the question.
Brian:It's like, who do you think is like interesting now?
Brian:And in like, in a previous generation, I felt like I would have like so many more, so many more options.
Brian:Right?
Brian:And like the reality is.
Brian:There's a lot of people building, you know, some interesting Substack newsletters and you know, some people are doing some interesting things in audio and video, but it isn't all that apparent to me.
Brian:So I'm interested in your viewpoint.
Brian:Who do you, who do you think is interesting?
Henry:Oh, I think there are a lot of super interesting, companies and again, they, they tend to be smaller, but I, we talked about Dynamo and Nick Carlson and team like that is a big opportunity.
Henry:They've got a great team, so forth.
Henry:So, as I said, I'm investor and advisor, so biased, but cool.
Brian:All right.
Brian:You can only do one out of four.
Brian:You can only do one out of four from your investment portfolio though, Henry, that's my role.
Henry:That was it.
Henry:That's the only one.
Henry:Barry and team I think are doing a great job.
Henry:They identified a, an underserved and frustrated group of people, the politically homeless, and they are nailing it and they've built a nice model.
Henry:I think the economics are good.
Henry:That's terrific.
Henry:Podcasting.
Henry:These guys that acquired who do these.
Henry:Incredibly like three hour dives into a single company or single interview.
Henry:Really smart, super prepared, so forth.
Henry:That's great.
Henry:There are a lot of other podcasts where it really is like a new form of story.
Henry:You know, I came out of the TV world and, and early digital where it's like, Henry, you got three minutes.
Henry:You gotta get, I gotta get the stuff at the top.
Henry:You know, you gotta make 'em say this and, and so forth.
Henry:It's like podcasting.
Henry:I am amazed at how long I will spend listening to a person and a decent interviewer who I think is interesting, and you learn
Henry:all sorts of things about them and what they know and so forth, the way they see the world in a way you just never would.
Henry:So that is a. That's a, a new way of doing things.
Henry:That's good.
Henry:And you mentioned my getting roasted.
Henry:I, I'm, I haven't read it.
Henry:It's tough.
Henry:But I was going to say like, I was very impressed with the guys at Defector that they started this publication, they went to subscription.
Henry:That is difficult to do.
Henry:They have built a business where they're supporting themselves.
Henry:It's interesting to watch from the outside because they do a sort of a wrap up post every year where they talk about what they're thinking about and how it works and how people are paid and so forth.
Henry:It's definitely interesting to watch a group of talented journalists struggle with some of the business things that business people and journalists have always struggled with.
Henry:How do you pay people, you know, is it.
Henry:Fair and, and all that stuff.
Henry:That's very interesting.
Henry:But, so they've built a, a, a nice audience.
Henry:you know, so, oh, and then another one who is just like in a year shown how powerful these things can be is Oliver Darcy, it's status, who, you know, he, he has been a great.
Henry:Media reporter and commentator forever.
Henry:Very passionate, did it to business, decide then went to CNN and so forth.
Henry:Look, from what I've read, he's already, he's got an employee.
Henry:He's already got another, you know, he's, he's breaking news all the time.
Henry:He is become the central thing that you read if you're in media.
Henry:that is difficult to do, but it is a great illustration of what you can accomplish if you do that.
Henry:And so hats off to him.
Brian:Yeah, it's like Freaky Friday.
Brian:Remember that movie, like where they switched places?
Brian:This was a long time ago.
Brian:I think it, Dudley Moore was in it, and Kirk Cameron, they switched places,
Brian:father and son.
Brian:So like, it's good that the like.
Brian:There's a lot of, yeah, there's a lot of journalists who, who, who now like are on the business side and then sometimes we see some, some of the folks in the business side,
Brian:you're, you've always been a hybrid though, who all of a sudden are, are doing, are doing the, the writing and the creation aspect.
Brian:And so I think it's good everyone gets to ex walk a mile in the other shoes.
Brian:Um,
Brian:but this has been fun, Henry.
Brian:thank you for doing it.
Brian:Appreciate it.
Henry:It's been terrific.
Henry:Great to see you.
Henry:Congratulations and, and thank you.
