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What is Web3, and why should we care about it? Will it be the digital revolution that brings the internet back to its decentralized and democratic roots? This week, internet expert (and Postlight CEO) Gina Trapani joins Rich and Paul to chat about their experiences with different iterations of the web and break down how it ended up so siloed, control-driven, and centralized. Will Web3 save us? Stay tuned.


Paul Ford For the younger listeners, what Gina is telling you, she was really cool. 

Gina Trapani I was really, rery, very cool. 

PF That’s a cool person right there.

GT I won best smile on the computer lab stuff. So hey, I really was cool. [Rich & Paul laugh]

[music ramps up, plays alone, fades out]

PF Hey, Rich. 

RZ Hi Paul. 

PF We are joined by the CEO of Postlight, Gina Trapani.

GT Hey Paul. Hey Rich.

RZ Hello Gina.

GT Thanks for having me on the show

RZ It’s lovely to have you on the show. 

GT I like barging in on the show. 

RZ I am in the presence of internet legend–legends. I want to actually frame this first. This is a two part series. This will be the first of two podcast episodes where we’re going to talk about the history of the web and I happen to be fortunate enough to have in my rolodex, Paul Ford, a blogging pioneer. I’m just gonna say that out loud. Gina Trapani, founder of Life Hacker but even, there’s an aura around Gina beyond Life Hacker, Life Hacker is one of many things Gina did. And you guys watched the web grow up. I watched the web grow up too. But you guys were active participants, you were inside. And I want to talk about Web1, Web2. And then eventually we’re going to get to Web3. Insert dramatic music.

PF Oh, the Semantic Web.

RZ No, not that one.

GT Uh… Not that. I think that’s somewhere in 2.

PF The new Web3?

RZ Now I would start at Gopher, but I’m not going to do that to you or our listeners.

PF That was pre-web, port 70. We’re not doing–people are trying to bring it back. But no, okay, so, Rich, you have an agenda. Why don’t we just just like our meetings, get driving? [Gina laughs]

RZ Okay. I’m going to interview you guys. I want to do it this way. I mean, I read a lot and watched a lot but you guys were in the middle of it. It’s 1994. A friend of mine said get off the BBS dial ups that you’ve been calling into. And check this thing out. You just need an Internet service provider.

PF What was your favorite BBS called? What was that?

RZ I was in there like hacking and cracking and blue box scene and all that stuff. Like I was into all of that I broken laws. But I would have been a minor. Let’s put it that way. It was just fun. I didn’t really want to steal anything. It was just so cool to be able to, to do all that stuff. It was nonsense. It was just us sitting outside the lines that they told us to stay within.

PF Stealing Commodore 64 programs. Yeah. And even like hacker intros. And just those were better than the games in a lot of cases, right. And music that was traded on the C 64 was awesome stuff. The web shows up. What is the vision of the web? Um, this is actually a hard question. I mean, the spec comes out HTTP and HTML. There’s the Mosaic browser, what is the beginning of the web, Paul?

PF I mean, there’s a couple different ways to define beginning but the simplest way to define it is that a nice person named Tim Berners-Lee made a system for organizing information while at CERN, which is the Swiss French high energy physics lab facility. And he’d been playing around with this stuff for quite a while, like since that, since the 80s. And he was there as a computer scientist, and he built this thing called an HTTP server that let you access a computer remotely and using a web browser, that point terminal based later based on sort of the next computer. And it let you get to a web pages. And it kind of did a lot of the stuff that we associate like, there is the idea that it would be the Rolodex for this whole big facility. And you could search for stuff and it would let you publish physics papers online, anyone could set up a server and share their physics papers so that the thing about it is it was purely opt in, you could say I want to publish a webpage. And if you could figure out how to get a server and publish one, then you were on the web.

RZ That doesn’t sound that different than a BBS. So I want to actually say it in words, like what was different here?

PF The BBS is weren’t all networked in the same way. They had to dial each other up and share stuff, and so on. And this was just, these were just pages, it was just publishing. Here you go.

RZ So the currency was pages. And there were images, I remember, it was like a big deal to see better and better images in the 90s. As the browser’s got better and better. Tell me about the user at that point in time. I want to ask about the user in each of these iterations of the web. What is the user? The typical user? genome? 

GT Yeah, I mean, at this time, when we’re talking about 1994, I mean, I have a visceral memory of I was in the computer lab, the basement computer lab in 1994, Poughkeepsie, New York, and I worked in the computer lab of mostly mainframes at that point. And my colleague said, There’s something I have to show you and it’s on the OSD machine downstairs, come on, let’s go. And I was like, okay, I go down there and he brings me up to a screen that’s got, I later learned has got, Mosaic up and it’s it’s a guy’s resume, know his name. And it’s in the you know, the name is like a big headline font and it’s a white screen. It’s got his, you know, employment history and I said, what am I looking at? And he said, that’s his resume. He lives in France. And we’re looking at his resume here on this computer. And I said, I don’t understand is this like a Word document? And I start clicking on it cuz I want to try to like, edit it, I think it’s, you know? And he says, no, no, we got this from this server in France, this guy published his resume. And now we’re looking at it here. I didn’t understand. I still, like just didn’t get it. But that’s, that’s where you’re talking about, or we’re talking about a page loaded in our browser with formatting, you know, a document, the document based web.

PF And then, dun-dun-dun. Some of the words on the page have underlines, and were blue.

GT Yes, the hyperlink. 

RZ I mean, that is the the connective tissue, right, that made the web.

PF Well now it’s a web. Now the pages are linked together. And I can keep reading and keep reading. So now I’m there for hours. 

RZ You’re there for hours. 

GT And then, you know, you look at the address and you say, most of them were .edu for me at that point, I was in college. What server is this? What do you mean, I went from this computer and this server in the in here, and I’m travelling around the world, I’m hitting servers around the world. That was the difference.

PF I remember that moment. That moment when you realized you were like, just looking at some random computer in the UK or in Asia. And you were like, wow, I can literally kind of touch the world from my little college, just because that’s so trivial now, but it was a surreal moment.

GT Blew my mind. Absolutely blew my mind. 

PF Because a long distance phone call to the same country was like $14.

GT This is the reason why I worked in the computer lab to begin with, by the way, I had to pay my long distance bill. 

PF Yep.

GT It was a very different time.

PF That is an unthinkable reason today.

GT Yes, yes.

RZ Okay, so, the hyperlink is really that connective tissue, the currency is the webpage or the document. And the words are like, there are publishers, but most of us were consumers. The web didn’t know who you were Gina, or who you were, Paul–yet. And there was–and I remember this, I remember how utterly democratic it all felt. There’s just nobody was very important yet, on the web. Everybody was out there. It had an academic bend.

PF There was a scene, there was Wired Magazine, and there were like these sort of nascent celebrities of the internet, and they would make you all if you were in this world, it can make you really jealous, but by comparison to like, they were 1/100 of one half of an influencer in modern metrics.

GT Next logical question, when you saw that, you know, the random person’s website or resume was how do I get one of those, right, like, and so then you’re like, I want to learn if this this college student in Paris did, or I want to be able to do it, how do I do it? And then that was what was so compelling. And then, you know, the point at which I realized, okay, this is how you edit the webpage. And I can edit my own web page and get it myself. Like that was the key moment.

RZ I mean, the history if we come out of the sort of the typical iterations of the web, of Web1 to Web2, and we’re going to eventually talk about Web3–asterisk. But if you really look at the history of the web, the history of the web, is shortening and eliminating the steps to publish. That is the entire history of the web.

PF Sure. The first phase for Gina, she had to look at the source code and figure out how to add her own HTML tags to the document. And then maybe, there weren’t content management systems, you would write little scripts that would put all of your words together into different files and upload it to your server. 

RZ And I mean, it wasn’t for the world.

GT It wasn’t. But if you made that connection, like I can edit my own HTML, and then I remember the first time I saw the like, last updated timestamp, or the current date, a piece of server side logic had executed when I downloaded that page and looked at it over the counter of how many visitors came to the site, I was like, oh, there’s a little bit more than a document. You know?

PF There’s a critical thing here too, that I think will be important to come back to, which is that the initial time to publish and learn the basics of this whole thing was like an hour, like you would be able to get a key job following one tutorial, and it would say, I’m Gina Trapani, I’m real cool. I have the best smile on the computer lab. And then that would kind of like that was enough, right? Like, you’d be like, oh, crap, and you’d load it in your browser. And it worked. And everything was incremental after that.

RZ I want to counter what you’re saying, though, because it was this extreme minority. I’m talking pre-blogging, pre-Microsoft front page. 

PF No disagreement. 

RZ .0001% is getting a webpage.

PF No disagreement. But even for us, there were learning curves for all kinds of things. And the learning curve was I could teach this to anybody, even if they just knew a little bit of computing. And I could get them up there pretty quickly. And then everything else was incremental. So people would make those first pages and then of that 0.0001%, that like probably 20% of them would go back and update the page later, right. And then again and again and again until the kind of the web grew out of that. 

RZ But it wasn’t seismic, right. It was still the documents. It was this sort of evolution of media, it was viewed that way as this, like, oh, this is where publishing is going. Like what you saw in the late 90s. And I was I was in the middle of it, because I came out of law school and did a hard left into sort of the .com bubble is that they were faking it, essentially, you had a lot of server side processing that was happening that was pushing what is supposed to be an interactive experience. And that was happening in commerce and in other ways. But it was still publishing, it was just publishing a lot, all the time, right. And bubble bursts, Amazon is alive and kicking. It’s like a toddler at this point, eBay is alive and kicking. And there’s the network effects of that.

PF eBay was the hit. eBay was the big hit. 

RZ Because you know what it is it echoed the democratic dynamics at the time, right, which was this idea of storefronts are dead, we’re just going to sell things to each other in very basic bespoke ways. And it’s going to be how the world is going to be. So now let’s fast forward past bubble in the early 2000s. Let me describe my time and place I took a gig down in Atlanta at the Georgia Tech Research Institute. And it was consulting, I was just doing mercenary consulting, I was gonna go back to the law if it didn’t work out. And then Tim O’Reilly puts out a paper called Web 2.0, essentially. And what he said was, the next evolution of the web is not publishing.

PF We have to pause and explain to some of the people in our audience who Tim O’Reilly is and what that means.

RZ Yeah, I didn’t think much of Tim O’Reilly till I saw that paper. To be perfectly frank, I think he’s brilliant. I didn’t know he was that person when he wrote it. I didn’t view him as this highly abstract technology thinker. But Tim O’Reilly, he’s a publisher. He’s a thinker. He’s a technologist in the world. I mean, O’Reilly publishing is widely regarded.

PF But also he was a glue person who brought a lot of the early internet people together.

GT Yes.

RZ Gina is gonna take Web 2.0. What happens? Why is there a version two of the web? What is it? 

GT You know, I always thought that Web2 was just kind of a, I don’t know, it was a buzzword. I mean, to me, I’ll explain what it meant to me. But you tell me what the actual proper definition is. To me, web 2.0 meant that we had we introduced the concept of API’s and integrating one service with another, right. We went from the idea that websites published flat documents meant for consumption entirely in a browser, to websites that served data that other websites could consume and display. This idea of integrating sites and trying to think of like some of the early examples, you guys remember, like Yahoo pipes, it was actually pretty far along at that point. 

PF We’re still trying to get back to that, right. Like it let people connect different data sources, visually, using a web browser, moving things around.

GT And everyone got really super standards, you know, obsessed. And I mean, I guess we could, you know, we could talk about XML and JSON and semantic web, but the idea that, like, the computers could talk to one another, and we could remix the web, in new and interesting ways. I make new things possible.

PF There was a big website at that moment called it was it was the readwriteweb, right. And so like, the idea was that instead of being read only, you’d be able to put stuff back into the web. And that had always been there, there had been formed. And they’ve been, you know, when you make a transaction and buy something on eBay, that gets logged in the database, but now it was getting faster, and everyone could do it. And they could publish their blogs by instead of having to learn HTML and link Gina and add tags to text. They could go and it’d be a box on a web page. And they could fill that out. Web 2.0 was like a little bit of that. And a lot more velocity in kind of richer media, stuff like Flickr showing up and stuff like YouTube starting to show up. 

GT Tags. RSS feeds. You know, a way to consume information programmatically. Yeah, tags were a big thing. Hashtags.

PF Critically, the idea was that the community, the larger web community would still continue to come together, organize data, have control over the kinds of media it saw, everybody can publish and comment on anything that they wanted. And there were two fundamental assumptions. One is that people wouldn’t really want huge centralization they would kind of push back against, and that’s why we would like things like RSS. The other assumption was that communities were essentially not toxic, that you could bring a million, zillion people together and that they would ultimately behave because this commons was really, really valuable. And everybody kind of knew that there was there would be bad actors, but no one–actually Gina was really early with that. She was always very careful to remind people that it wasn’t all going to be roses, which I think came out of your experience as a woman on the internet, right? But like, no one was able to see like the velocity of toxicity that might follow. So those two things were still kind of out there. And in the meantime, it was all these exciting new Lego blocks, and community building and content building and storytelling, without as much centralization.

GT And stars emerged, right, their characters, their personalities, there were little, little projects, you know, that got super popular and that people loved and you know, there was a sort of golden time when we all followed one another by watching each other’s websites. And there’s this open sharing of ideas, it really did feel like a, you know, this is just a golden amazing time of like discovery and–

PF Blog networks are showing up, like this is the era of Life Hacker. And this is the era of–you know, Life Hacker is telling the story, you’re the first editor, it’s telling the story of all these new big platforms and how you can use them. It’s worth, you know, this is kind of not about you, but you were there, right? Like we’re in partially it is about you. A lot of your focus in that time was about personal productivity, how do I use all of these tools, these new wonderful free and available tools in order to organize and structure my life and get lots of good things done? Like it was a very positive proactive message. And that, to me, sums up Web2 is like, look at a amazing things that I’ve got to build amazing things for myself in my community. Yes, there are people who are trying to kind of own the whole thing. You know, Facebook shows up, but we’ve got FriendFeed, we’ve got all these other ways to do it. And we’ll just keep reading on RSS. And we’ll we’ll stick to our standards. And so I have faith in the community. And that’s what people want. And sure, Yahoo! just bought Flickr, but it’s okay, they’ve bought other stuff before, it’s gonna work out fine.

RZ I mean, I think you described it well, in terms of what it was, I think it was this reimagining of this place, as I think the the first iteration of the web was more prescriptive about publishing and documents. And I think the second part of that was like, you know, blow it all up. The hell with that it’s, that’s not the only currency, we accept all foreign currencies. And that currency may be a video, actually it may be anything, it maybe a little tiny, bite size bit of information. And so startups started to emerge where a key component of the startup was that you could use its capabilities in a programmatic way, so you could build on top of it, right?

PF I mean, you want to hear a really, really wacky idea? Here’s one. Google could someday be as big as Microsoft, right? Like for Google to be a competitor to Microsoft, even by the mid-2000s, that’s when it started to feel feasible. But before that was like, that’s just started just the web, like, yeah, then Maps shows up, then Docs, and you’re like, oh, my, okay. 

RZ But up until that point, I think this is another good point. I mean, the richness of the experiences, the browser was no longer feeling like a thing you use to read documents anymore. It was I mean, when Maps came out, everybody fell out of their chairs, like that was this wild experiment.

GT Huge moment. It was proving ground for applications inside the browser.

PF Simultaneously, and we’ve talked about this, simultaneously, the death of the document web, right, like, yes, it’s not super accessible. It was kind of locked in. And Google actually went as far as to make their own browser. They just were like, alright, we’re gonna need some control here.

RZ We’ve got to own the window Chrome. 

PF Just in case.

GT Another very surprising moment from Google. I mean, the thing about the original Google product, that search product, was it was a layer of software on top of the web already, right, like Google’s purpose was to, you know, get you elsewhere. All the content you see in search is content that lives out in the web. What they did is they built the Superfast robots, and they’re very great results. And that was interesting. But then when with maps, and with Chrome, with Docs, and with Gmail. Gmail was another–what was that? April 1 2004. We thought it was April Fool’s Day. Everyone was like, wait, what? Because you know, storage at that size no one had ever heard of, that’s when it starts to change the game.

PF It’s worth noting too, like they were beloved, right, like Scott McCloud, who did Understanding Comics and is just sort of like one of the early heroes of Web 2.0. Just like a good explainer type talking about visual explanations. They hired him to do a comic book explaining Chrome.

GT Yes. I remember that.

PF Out it goes into the world and everybody is like wow, what an org, they get it. It’s weird that they’re making a new browser, but it’s going to be open source. Everything’s great.

RZ But then…we lost our way. [Gina laughs]

PF No, the economic–

GT Things got weird.

PF Yeah, the economic tendency  to centralize took over as more and more humans showed up, the innate, grisly, toxicity of human interaction and just racist grim stuff started to rear it’s head.

RZ Paul, let’s not paint such a dark picture. I think there are–


RZ [Rich laughs]

GT Get in touch!

PF We’ll help you centralize.

GT Let’s talk about why do you centralize? As a company, why do you do that? And why is users, it’s for control, it’s so that you can create an experience that’s glossy and fast and good and aligned with your brand and does exactly what you want it to do, right? Tthe decentralization was what brought me to the web, right. But as a user, you know, if I’ve got a profit driven company building a product, you really want me to want to make my life easier in particular ways they can charge me money for it, like, I’m gonna get a more usable product. 

RZ I think you’re right.

PF It’s not just that. Do you want to teach the 500 people in your organization about, you know, some weird, decentralized thing that will take them weeks and weeks to learn? Or do you want them to just check their Gmail and use Calendar?

RZ I had gotten to know, I forgot how I connected to him, but he was one of the most senior engineers at Twitter. And he left and he was visiting New York, he was in San Francisco. And this was like, one of the people who helped them scale. If anyone knows, like the details of internet history. Twitter was really buckling at one point, like they could barely keep it up. 

GT Fail whale.

RZ Exactly. And this guy, he was one of the stars who helped them scale. And he quit. And the reason he quit, and I do think this was a moment, when Twitter finally made the call, and said, no more fun times on the API. It’s over.

PF Right, because you used to be able to build any Twitter client you wanted. And then one day, Michael Sippey, who’s all of our friend, who was Head of Product announced to the world like, sorry, we’re cutting you off.

RZ We need to control the entire experience. But let’s be, I don’t think Twitter or anyone else needs to apologize about this. This was about money, right? Like this was about a business model being put into action. And the fact that they couldn’t control the end to end experience, Twitter was never going to be about charging a fee, it was always going to be about advertising. They needed to control the whole experience. That was a moment because if there was ever a like, folk song written about the democracy and the empowerment of the masses, it was written by Twitter, like nobody at Twitter knew where Twitter was going. All we knew was this one here was this thing that just seemed to empower everyone because it truly finally boiled down publishing to like, just your thumbs. And everybody was talking to everybody.  And then all of a sudden–

PF What made Twitter was mobile, right, like suddenly mobile. Suddenly mobile showed up at the same time. 

RZ Ironically, Paul, the best mobile clients weren’t from Twitter, it would they were built on that open API.

GT Right. And that was the problem, because they weren’t weren’t showing ads, they were hammering API, they weren’t showing the ads, and they weren’t creating the experience that Twitter wants to create.

PF It’s just how can you build your business when the core experience is running through someone else? And and yeah, people have very strong opinions about this. But like, you know, in retrospect, it’s like, yeah, of course they did that.

RZ I was digging into I forget who the client was, this is my old agency, we were digging into using Google Maps and layering data on top of it. And it was really expensive. And they’re like, what the hell? Everybody’s open. Everybody has API’s. What is this? 100 hits a month nonsense. And then it’s like, Google Maps never had to apologize, because they never did it in the first place. Right? Google understood very early days that there was going to be a business application for this. There is no need to give this out into the world and like people will pay. Twitter and Facebook–

PF You have like Eric Schmidt in there, who was coming from true Silicon Valley, let’s make money.

RZ And in a lot of ways, that is the sunset of Web2, right? Like the rise of Apple, Facebook, Google, I forget–there’s like an acronym for the big five.


RZ What is it? FAANG.

PF Facebook, Apple, Amazon.

GT Netflix.

bRZ You know, I’ll never forget, like there’s always somebody who’s got like an open there’s an open source version of everything. So to sort of prove a point, There’s an open source Slack, there’s an open source Facebook, I forget the Twitter one. They’d raised some money too. I remember that.



RZ There you go. But let’s be real folks. The big criticism today is that your identity and data around you is siloed in these four companies, and they will be siloed there forever because it’s immensely valuable for analytics, for advertising, etc, etc. But now, there is a new sunrise, Paul, Gina. [Paul sighs] Don’t exhale. Is that excitement or is that exhaustion Paul, which is it?

PF Oh, absolutely. Let’s call it excitement. 

RZ Okay. [Gina & Rich laugh] And so this is where I get to say ‘to be continued…’ because the promise of Web3 is to finally shatter this stranglehold on our privacy and our identity. So stay tuned for next week’s podcast. But before you go, Gina, tell us a little bit about Postlight. [Rich and Gina laugh]

GT Wow, Rich, that’s a real cliffhanger. 

RZ What do you think?

GT Amazing!

RZ You see what I did?

GT Postlight is a digital strategy, engineering and design firm based here in New York City. If you need a legacy platform modernized or need to build a new platform or launch a new line of business, you should give us a ring, send us a note And come listen to the next episode, which are apparently going to record shortly. 

RZ It’s gonna be good. Check out, all kinds of great case studies. You’ll see a lot of great work coming out of the team these days.

PF Thank you Gina Trapani.

RZ Thank you, Gina. Gina, you’re coming back for episode two right?

GT Absolutely. This is a lovely walk down memory lane.

PF Now, we’re gonna head head straight into the future. 

GT See you there. 

PF See you next week. [music ramps up, plays alone, ends]