(Bonus) The Fate (And Legacy) Of Yahoo, With Harry McCracken
6 Apr 2026 · 19 min
In this weekend‑bonus episode of Tech Meme Ride Home, host Brian McCullough interviews veteran tech journalist Harry McCracken to explore Yahoo’s rise, its self‑perception as a media rather than a tech company, its pioneering but ultimately unsustainable business models, and the reasons behind its long‑term decline. The conversation begins with personal recollections of early Yahoo use in the mid‑1990s and moves into how Yahoo positioned itself as a human‑curated portal, hiring Hollywood executive Terry Semel and later Carol Bartz to steer a media‑focused strategy. They discuss Yahoo’s early leadership in web advertising and personalization, its massive market cap during the dot‑com boom, and its invention of the internet portal model that later influenced Google. A large portion of the dialogue examines Yahoo’s aggressive acquisition strategy—Broadcast.com, GeoCities, Flickr, Delicious, and others—highlighting a pattern of spotting promising ideas but failing to integrate or scale them. The hosts contrast Yahoo Groups, a pre‑viral, BBS‑like community platform, with today’s algorithm‑driven social media, noting the lack of amplification and stronger moderation in the former. They reflect on generational nostalgia, comparing the Yahoo era to later platforms like Facebook, Snapchat, and TikTok, and consider whether each generation will look back nostalgically at its own dominant services. Finally, they assess Yahoo’s current state—selling Tumblr and Flickr, shutting down Groups, and existing mainly as a brand—while pondering its legacy alongside Netscape and the emergence of Google, concluding that Yahoo was the first truly great internet company that repeatedly failed to realize its potential.
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Welcome to another weekend bonus episode of the Tech Meme Ride Home. I'm Brian McCullough. The news that Yahoo was gonna shut down Yahoo Groups, as I said, was another gut punch when you realize how much of the web's history is so ephemeral. That also got me thinking that Yahoo as a company or a brand or whatever, might be about to go down the memory hole. And that got me thinking about Yahoo's legacy as perhaps the first great internet company. And that got me talking to one of the deans of tech journalism, Harry McCracken. What is Yahoo's legacy? Why has it ended up the way it has? And also, why do we feel nostalgic for the sort of web that Yahoo Groups represents? What has changed on the internet from the glory days of Yahoo Groups until today? So Harry, as I just said, I kind of want to use this as an excuse to talk about Yahoo, its legacy, what might have been. This is prompted by the news that Yahoo Groups is the latest thing that's going to be euthanized, I guess, to a degree. In, in your piece talking about it, you, you mentioned that Yahoo was the first website you think you ever visited.
I'm quite positive of that. I have very vivid memories of, I believe it was at the end of 1994, uh, logging on and, uh, being shown Yahoo by a colleague who was on the web slightly before I was. And I even remember the first search I did on Yahoo and It got me hooked and I'm sure that almost everybody else who used Yahoo! in that particular time frame had a similar experience.
Yeah. I mean I know for sure I did. I don't know if I've ever told this story on this show, but like the first website I ever made when I got to college was campus movie reviews and I remember submitting it to inclusion in Yahoo! because it was a directory, which we're going to talk about in a second. But in my memory, I always thought that I literally got an email back from either Jerry or Dave themselves. —when I look at the chronology, like, this would have been early '96, so there's no way they were still personally including sites at that point. But, um, but yeah, let's talk about that. You know, when I did research for my book, when you read all of the articles, especially from the '96 to '97 time period, about Yahoo, like, they literally make a point of constantly telling people that they are not a tech company. That was almost their differentiator. Wow. Because remember, it wasn't a search engine. They were competing with the likes of Excite and AltaVista and that stuff. And so they were almost saying, "What makes us different is we have humans curating this." They literally paid hundreds of people to surf the web and find sites and put them in.
And as appealing as that sounds in principle, I think very quickly it became clear that that could not scale. And, um, I mean, even well before Google came along, they were competing with AltaVista, which, as imperfect as it was, was able to encompass the entire internet in a way that Yahoo! never was able to.
Yeah, and I'm wondering though, by bringing that up, is that maybe something about the whole Yahoo! story is that— I mean, I, on one level, I don't believe them that they didn't think that they were tech people, but at the same time, you know, again, I'm thinking of a specific article when they they talked about what they were looking for is they wanted to be— they wanted their version of Friends. They wanted their version of must-see TV. They were thinking of the web in the way that we naturally think of it now, how it was going to be about communities. It was going to be about media and things like that. So in a sense, maybe there was always sort of a dichotomy there where they weren't tech first. They were always looking to be something else first.
Yeah, they certainly envisioned themselves as a media company, and they hired Terry Semel, who was a Hollywood guy, to run the company for a large chunk of their history. And, um, you know, later on when, uh, Carol Bartz was in charge, like, throughout her entire tenure, almost the only thing she did was try to answer the question, what is Yahoo? Are you a tech company or a media company? and, um, they often skewed towards trying to be a media company, and there really were not all that many instances where that paid off well for them, especially when you compare them to Google and later to Facebook.
When, um, to give them credit, uh, and again, I think I said this in the book, like, you know, they were the first to scale advertising on the web as a business model in, in a major way, right? Um, they were the first to You know, this is definitely— you can look at it in a negative light today, but they were the first to use your personal information to sell ads against in the sense that, hey, if you give us— they were the first to be like, if you give us your zip code, we'll give you your local weather and your local sports scores and things like that. But they were the first to do that. And they were huge winners in the dot-com era. Like, you know, there was a time when I think their market cap was $160 billion or something like them and AOL. They were the two like huge winners up until, you know, 2000.
They basically invented the internet portal, and, um, for all the problems they had, they did better than Excite and Lycos and all the other internet portals. And essentially today, I mean, Google is nothing more than a very, very, very ambitious internet portal. So in some ways it is following the model that Yahoo established more than 20 years ago.
You mentioned the Terry Semel era because again, you know, this is sort of forgotten, but like in the, in the aftermath of the bubble bursting, Yahoo was one of the first to turn around because of him. Like basically the two survivors by like 2003 seemingly were eBay and Yahoo. But again, Unless I'm misremembering, Semmel's move very much was, "Oh, we're doubling down on media. We are not doubling down on any sort of tech. We're just doing what media does, but just in this new type of platform." Yeah.
I mean, they went through periods where they would stop doing search technology altogether and outsource it like they did with Google for a while, and then they had to come back later on. Attempt to rebuild their search competence, which was really difficult, especially since at that point Google had become a behemoth. I think Semmel did some intriguing things. Yahoo has always had this long history of doing something interesting or creating something interesting and then being really poor on follow-through. I mean, probably the single most classic example of that is acquiring Flickr. Right. Which was a really smart thing to do. And there was a brief period where it was run by the founders, and even though it was part of Yahoo, it was still kept and interesting and evolving quickly. But there are just all these countless examples of Yahoo starting something or acquiring something and just not figuring out how to continue on with that. During the seminal era, they also were a really early pioneer in internet TV. and they were building widgets for smart TVs before just about anybody. Uh, and again, that long term did not amount to anything, even though in theory if they had played all of their cards perfectly, um, they could have been a presence on TV before anybody else.
You know, the, the amazing thing, like, if you go through the list of acquisitions, um, before we even get to like the Flickr and Delicious era and things like that, um, uh, like, they're the most interesting acquisitive company almost of the entire internet era. The reason Mark Cuban is a billionaire is because Broadcast.com— like, they could have been YouTube maybe if they had done that the right way. But even things like, you know, they were early— Yahoo Stores was created by buying ViaWeb, which was started by a young man by the name of Paul Graham. YoYo Dine was started by a young man by the name of Seth Godin. It's interesting, but the point is when you go down that list, all of them were big bets that would be right bets for other people that then they never did anything with. They shut down Broadcast.com by 2002. They didn't— GeoCities stuck around for longer, but GeoCities, if you buy into them being proto-social networks, they let that wither on the vine. Why do you think that was that they were so acquisitive and so good at spotting new ideas but then just not doing anything with them?
Well, I mean, throughout the history of the tech business, most acquisitions by large companies are disappointing. There's— there just are not all that many examples of any company succeeding. Um, I think part of it is that Yahoo became sort of this enormous Hollywood-like media entity, and those types of companies are particularly bad at figuring out what the next exciting thing is going to be. The next exciting thing, generally speaking, is very dependent on technology, which was only rarely their forte. I mean, even Yahoo Groups at its peak, it had more than 100 million users. I mean, even today that would be pretty exciting, but As far as I know, any attempts they made to leverage that into something more powerful were very small. My guess is they did not make vast amounts of money through monetizing that. When Facebook came along, in a perfect world, Yahoo could have leveraged Yahoo Groups to do something to take on Facebook head-on. But another issue with Yahoo was that oftentimes they didn't have one thing in a category, they had several. They had like 3 or 4 different social networks. They also had something called Yahoo 360, which I think sprouted up in the Friendster era and competed with at least a couple of other Yahoo initiatives in the social networking space, none of which went anywhere.
Well, right. And then this is coming to that, that whole Flickr, Delicious, Web 2.0 era. Like again, if you, if you look at the list of their acquisitions, they go crazy in the 2004, 2005 era. there was like this brief period of time right when Web 2.0 was really kicking off where it kind of felt like maybe Yahoo would be sort of an incubator. Not really an incubator because they're acquiring and then— but like a holding company of all these exciting new ideas. But then again, the moment just passed and nothing really became of it. Yeah.
I mean, there was that period where if you were creating a startup, your long-term goal was essentially to be acquired by Yahoo. For the life of me, I'm not sure if I completely understand why they were pretty good at identifying cool companies to buy and so dismally bad at doing anything with most of them.
Well, do we know— maybe no one knows this, but was there some sort of driving force like some executive there that had these good ideas or you were almost describing it as there were so many fiefdoms, so many committees that really it was just like throwing darts at the wall. There was no real strategy to it.
I mean, that's a good question. An awful lot of really smart people have worked at Yahoo over the years. For sure. Their alumni are everywhere. Again, I don't want to blame everything on Terry Semel, but he ran it like a media company, and making movies is just a very different business from taking online services which need to evolve really quickly and scale up in a way that does not have all that much to do with how movies or TV shows become successful.
Just real quick, because you're going to tee me up to make a point or like ask something that I hope is provocative, but just describe for me your own personal experience with Yahoo Groups and— because I— It's almost like there's nostalgia around it. Like it feels when you read about or if you've used Yahoo Groups, you feel like it was the web as it used to be. Like it's a different era almost.
Yeah. I mean, they really were rather similar in some ways to BBSs except they were really easy to set up and Yahoo hosted them for you. There were thousands and thousands of them and they were like really deeply personal in a way that Facebook, generally speaking, is not. Al— although to me the most interesting and fun part of Facebook these days are Facebook groups, which really are quite similar to what Yahoo Groups once were. But Yahoo Groups were— I mean, they were run by individuals. Each one was a tiny fiefdom and the stuff within the group really did not overflow into the rest of Yahoo Groups. There was no kind of overarching attempt to monetize that or to push content out in front of other people. So I— luckily for me, I have a bunch of my old email and I was able to go back and search and see exactly which groups I belonged to. And a lot of them were really cool, but they did not really interact with each other or add up to a larger scalable thing.
So This is the thing that I wanted to poke at a little bit. Like, again, me looking at it and feeling nostalgic about it and like, that's how the web used to be. Like this week I was trying to think about like what's different, what's different than the way— in the way that the web behaved in Yahoo Groups in 2002, the way the whole internet behaves in 2019. And because the point I'm trying to make is there were There's always been garbage on the internet. There's always been bad actors and bad people and things. So what's the difference between the two eras? Why does it feel different now? And the only thing I can think of is that the way you just described how Yahoo Groups functioned and even how Facebook groups are functioning is the lack of amplification. Do you know what I mean? That's built into everything that social media in capital letters does. And, and, and I don't even know that there's a question there, but is there— is that the only difference, or is there something else? Is it generational? I'm not sure.
Well, basically, virality did not exist, um, as far as I know, on Yahoo Groups in its classic form. Um, there was no way for anything to go viral, um, which means that there was no way for bad stuff to go viral.
And well, not only that, you know, so you're saying a dumb post on a message board gets is just a dumb post and it lives there and it dies there, but it's also— but, you know, because you still had trolls and flame wars and things like that, but maybe there's something to the scale of it that if a flame war erupted in a Yahoo group, it stayed there and it didn't metastasize all around the larger web.
It stayed there and it was much more likely that there was a moderator for that Yahoo group who took keeping takes things civil really seriously and would shut down the flame war or delete messages in a way that Facebook does not particularly encourage, I would say.
In your piece on Yahoo Groups going away, you wrote that I fully expect to live long enough to see Facebook announce that it's pushing the delete button on at least some of its old content, which I 100% believe too. I think, would you agree with the fact that there's like a generational thing going on now where a certain people's formative memories were on GeoCities, for example, certain people's formative memories will have been on Snapchat. Now everyone, all the kids are on TikTok. Isn't it, isn't it interesting how seemingly now You used to be able to define generations by music or hairstyles. Now it's almost by the, the platforms that they came of age on.
Yeah, I mean, right, right now there's a TikTok generation, uh, who will eventually look back on it nostalgically in a way that those of us who are a bit older will not understand, uh, and the way that the TikTok generation doesn't understand people being nostalgic about Yahoo Groups.
Is that— I was going to ask, is that inevitable that it would always roll into another, but neither of us know the answer to that. But OK, finally coming back to the notion that, you know, we'll probably live long enough to see Facebook maybe be like, "You know what? The only thing on Facebook proper is now for olds and we don't need them, so we're shutting this down." We're facing the fact that Yahoo is probably going down the memory hole soon. basically, right? I mean, there's no— there's no— it's either going to be sold for parts. There's nothing— there's no main business that's going to be exciting enough for Verizon to keep it going in any meaningful way, right?
Yeah, I mean, it's already selling, um, Tumblr, and it sold Flickr, and it's shutting down much of Yahoo Groups. So that process is already underway. Um, it seems pretty unlikely at this point that anything new and truly exciting will ever launch under the Yahoo brand. Uh, when Marissa Mayer ran the company, there was this brief period where it felt like that was at least possible, although it did not in fact pan out. Um, but essentially Yahoo already is, uh, nothing much more than a brand people recognize and some services that have a lot of users still because they've been around for so long.
So if you were to leave us with what may be the legacy, what we should remember Yahoo for, maybe being the first truly great internet company?
Yeah, I was trying to think about that in my story, and the other one that came to mind was Netscape, which in some ways has certain parallels with Yahoo in terms of having done some great things but having had difficulty following up, although in the case of Netscape Their big problem was that Microsoft was determined to crush them. And I, as far as I remember, it's not like Yahoo had an arch rival who was determined to crush it. It's much more that Yahoo had trouble living up to its own potential over and over again for 15 to 20 years. And by the time Google came around, the stuff, the problems that Yahoo had, had already been created. So it was not like like Yahoo was flourishing until Google came into the picture.