Unscaled 1: What Went Wrong with the World Wide Web?

Welcome to the Unscaled Series, eight new episodes from the All Turtles Podcast featuring Phil Libin in conversation with General Catalyst’s Ronda Scott and Hemant Taneja. Hemant’s book Unscaled provides a framework for the series’ discussions on what it means for a company to scale today. Episode 1 examines the internet’s role as an equalizer—both for businesses and for bad actors—and asks how entrepreneurs can address the most pressing problems online today.


Show notes

Hemant Taneja’s book Unscaled: How AI and a New Generation of Upstarts are Creating the Economy of the Future (referral fees will be donated to charity)

Venture capital firm General Catalyst


Hemant Taneja bio

Ronda Scott bio

What went wrong with the world wide web (2:01)

The problems with moving fast and breaking things (2:21)
The original goals for the Internet (3:08)

Hemant’s first internet job (4:05)
Ronda’s first internet job (4:45)

The difference between being right and being statistically right (6:30)


The biggest problems online today (7:55)

Governance doesn’t exist (8:13)

Current environment won’t support new businesses trying to do good (9:44)

Ronda’s 1972 GMC, “Kitten” (10:55)

This is a photo of Ronda's 1972 GMC truck.

Siloing has created deep divisions and polarization (11:30)
Do San Francisco’s problems reflect those of the tech industry? (12:20)


Is education better or worse today? (13:45)

Khan Academy (15:50)


Three classes of problems online (17:15)

Unintended consequences (17:25)

Intended, legal consequences (17:31)

Intended, illegal consequences (17:41)

Scale makes consequences more damaging (19:25)

Problems are the same as the 1990s, but the audience is orders of magnitude larger (20:41)


It’s time to rethink the concept of scale (22:03)


We want to hear from you

Please send us your comments, suggested topics, and questions for future episodes. Season 2 is coming soon!

Email: hello@all-turtles.com

Twitter: @allturtlesco with hashtag #askAT

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Phil Libin: Hi, this is Phil Libin. cofounder and CEO of All Turtles. A few months ago, my friend and former business partner Hemant Taneja at General Catalyst wrote a book called Unscaled, which traces the evolution of the concept of scale and how it applies to the tech industry. This was a really fascinating book, changed my thinking a lot, and so we decided to do this 8 part series called the Unscaled Series of the All Turtles Podcast, with Hemant and Ronda Scott, a marketing partner at General Catalyst.

Phil Libin: This first episode called “What Went Wrong with the World Wide Web”, or WWWwtWWW, we’ll talk about what it says in the ten. How come we started out wanting to change the world for the good, and didn’t quite get there? So welcome Hemant and Ronda. Really glad to have you on.

Ronda: Thanks, good to be here.

Hemant: Thanks Phil.

Phil Libin: You just wrote Unscaled, which is a book that’s been really influential on me. We were talking about some of these concepts for the past couple years before the book came out, and it really influenced a lot of how we’re thinking about things at All Turtles, and I’m glad to have this opportunity to take an in-depth dive with some of the themes in your book, and also happy to have Ronda here to add some common sense perspective.

Ronda: I’ll try.

Phil Libin: Try is all we can ever do. I think the main thrust of your book, or the main hypothesis is actually now is kind of the best time in the history of the universe to actually make something. To actually start a company. It’s the fastest way to actually get impact. They’ve got all of these things set up in the world to let people get to [inaudible 00:01:37] as quickly as possible, and I want to get to all of that, but I kinda don’t want to start there. I want to start with all the crappy. I want to start with why does it actually feel like the world is more broken now than it’s ever been before? And why does it feel like that, at the same time, where allegedly this is actually a great time to be alive and to be making stuff, and to be starting stuff? So what went wrong with the world, or maybe more specifically, what went wrong with the internet?

Hemant: Well, we did build this generation of companies with the mantra that we should move fast and break things. So it’s not surprising that we moved fast, we organized community and commerce online, and we’ve broken a bunch of stuff.

Phil Libin: We broke a lot of things.

Hemant: We broke a lot of things. And if you think about it, these new societal representation hasn’t really had deep regard for here’s the core values in society, and here’s the things we did in the offline world to manage bad actors, and discrimination, and bias. We focused much more on how do we get there fast? And I think we’re seeing the effects of that, and hopefully this was a learning moment, or learning decade for us, that we’ll do great things, but in the future and be much more responsible.

Phil Libin: So what do you think were some of the original hopes of the first internet pioneers … Or maybe not the first, but at least our generation, the people who made the last couple of generations of companies. What were we trying to do?

Hemant: Well, internet was supposed to be this amazing enabler of a level playing field, and uplift conveniences that weren’t easily available to everybody, and the quality of life that wasn’t easily available to everybody. But if you think about it, what we’ve created is a pretty significant digital divide, and society’s only become more polarized. If you think about it, we’re actually, with the internet, we’re eviscerating the middle class and creating a bigger divide in the affluent and the rest of the population. If you look back at the wealth creation that this has led to, for example, it’s very concentrated on a few people. And that was not the purpose of what we started out to create by bringing everything online.

Phil Libin: What was your first internet job, and what were you trying to do?

Hemant: My first internet job was to actually teach how to build websites in 1993 at MIT when I was an undergraduate. Kind of had no idea where that was gonna be leading to, but I found it fascinating.

Phil Libin: ’93?

Hemant: ’93, it was just Mosaic and Links, and it was very early days.

Phil Libin: Whether you remember, what were some of the most ambitious ideas that people thought they would do on the web?

Hemant: Making a page for yourself.

Phil Libin: Yeah. You think right from the beginning it was that shallow?

Hemant: I was at MIT, and these were the shallow things that people were building in the very first instances, yeah.

Phil Libin: What was your first intro job, Ronda?

Ronda: Full on internet job? I was making my pages in the mid 90’s as well. I was only four years old, so I was quite precocious. Yeah, no, I created … I built out the art section of Boston.com in 1996, 1997.

Phil Libin: Wow.

Ronda: So yeah.

Hemant: That’s much more productive than what I was doing.

Ronda: But I would say what people were doing in the early ’90’s was more … They were looking for the next Tetris, right. Everyone had wasted hours and hours of their lives everyday on Tetris, and then suddenly MUDs became a thing.

Phil Libin: Yeah, multi-user dungeons.

Ronda: Yeah. Yeah. I think that was sort of … There’s a certain discovery there, and a giddiness of … You could find other weirdos like yourself. Weirdos in a positive sense online, all over the world, and that’s kind of how I got into the internet. Not MUDing though. I knew people who MUDed. I just watched them. Disclaimer.

Phil Libin: Yeah. I remember … We all had such high hopes, and more than high hopes. I think lots of people have high hopes. I definitely had a lot of certainty in my own self righteousness and correctness, right. My first few internet companies, I was very confident that what we were doing was good, was changing the world. All of these people that were there before had done things slowly and stupidly, and there was this certainly that we were correct. It was quite strong, and didn’t really start doubting that until much more … Until actually fairly recently. I think this is a common thing in Silicon Valley. I think a lot of us are just pretty sure that we’re right, and it’s getting harder and harder to reconcile that with what we actually see in the world, and in the streets every day.

Hemant: Yeah. I think we’re … The problem is we’re statistically right, but we’re not comprehensively right. Meaning-

Phil Libin: That’s interesting. So talk about the difference between those two things.

Hemant: Well, so … If you take the last decade and you create Facebook, well 99.99% of the people use it for the great use cases that Zuckerberg and the team there envisioned.

Phil Libin: Great, or at least maybe mostly benign. Like mostly harmless.

Hemant: Harmless, but I would say great in the sense it has brought a lot of joy and happiness connecting you to others. You know, I grew up in India. I’m so much closer to my friends, where the first 15 years of being here, I just didn’t know what was going on in their lives. So there’s a lot of joy to having that kind of extended community that you feel part of. But they didn’t know how … Well those same tools were gonna get weaponized, with what just happened in the elections, or the hate mails that you get, or messages that you get from all these communities, or how you can quickly navigate your way into these dark spots on the web that have been created as well. That was not the goal.

Hemant: So statistically, it’s actually all positive. It’s just … Where there’s good there’s bad. There are bad actors that are gonna use these technologies that are on the way, and we just haven’t put frameworks in place to protect against that.

Phil Libin: So what do you guys think are a handful of the sharpest problems on the internet right now?

Hemant: Yeah, so I would say a few things. One, is that the ability to replicate our governance that exists in offline, in a software defined way online, hasn’t been done. That is at the intersection of technology and policy, that’s at the intersection of how businesses and governments engage, and that framework just does not exist. And some of it is because the ideological principles of the Silicon Valley founders have been, “Hey, no government. This needs to be all open and free.” And some of it is because the existing government just fundamentally does not understand what’s going on.

Hemont: So there’s this growing divide between the two stakeholders as well. So I think that’s one.

Phil Libin: How are people experiencing that? What is the actual … What is the experience of peoples’ lives that is negatively affected by how we’ve built things? Are people angrier? It feels to me like people are angrier.

Hemant: People are more polarized. People are not … We’re losing a shared sense of reality. One of the things I’ve started doing when I read the news now is I go to CNN and I go to Fox News right after it, because it just … And I’m … I want to make sure I’m not just seeing one side of the view, because there is no balanced way to understand what’s happening in the world. Everybody’s got their echo chambers because the key metric is engagement. That’s what fuels the business models on the internet, right.

Hemant: And so as a result, your biases are exploited as opposed to accounted for in making sure you have a balanced view of what’s happening in the world. That’s a major problem. I think going back to your question about what else is broken, I think the other thing is there are entrepreneurs trying to figure out how to do right, and have learned from this past generation of innovation, and build companies that can address these issues.

Hemant: The whole crypto movement, or cult that exists, is along those lines. There’s a bunch of folks leaving these large tech companies that want to start new companies, to rethink media and other areas. But the other issue is, I don’t think we’re in an environment where new businesses can survive and thrive alongside these platforms, so the monopolistic existence of these platforms is another problem that I think is slowing down innovation in my opinion, versus not.

Phil Libin: What do you think are the everyday life effects of whatever’s gone wrong?

Ronda: So I’m not as negative about what the internet is doing. I do the same thing as Hemant. I will listen to NPR in the morning, but then I quickly turn over to AM Talk Radio. I listen to a lot of AM Talk Radio, because I want to understand how people are formulating the opinions that they’re coming to.

Phil Libin: Well, plus you own a really cool pickup truck, and you probably only have an AM radio in it, right?

Ronda: The truck is not currently running, but-

Phil Libin: Okay, we’ll put a picture of the truck in the show notes. Ronda’s got the best truck of anyone I know.

Ronda: The truck does have FM, but that’s it. AM/FM. In any event, I do think like what’s going on with the internet … I’m a naturally very negative person, but I’m actually not that negative about what’s going on on the internet. I do think the polarization and … There are benefits to being able to silo, there’s benefits to be able to find your tribe on the internet, and that’s been true since dial up, BBS’s, all the way through ’til now. I think that’s brought a lot of people a lot of comfort.

Ronda: It’s allowed them to connect with communities that they wouldn’t have otherwise. But this is the siloing. The only seeing news to … Only seeing the news that you actually already agree with, is causing division in our society, and I’m not sure the United States can withstand it. I mean, I don’t want to put a tin foil hat on, but I think that that is the biggest issue. Otherwise I think, mostly people are trying to solve hard problems. They’re not making judgment calls on whether this is a good thing or a bad thing, people in Silicon Valley and similar areas, are looking for meaty problems to sink their teeth into, and they’re trying to do what’s right. They’re ultimately problem solvers, not necessarily money makers, and definitely not trying to do things that are nefarious right out of the box. That does leave it open for exploitation, though.

Phil Libin: What about the kind of real world places where the internet may have caused some deterioration? For example, we’re sitting here in the middle of San Francisco, and to me at least, San Francisco feels markedly worse now in terms of crime, homelessness, dirt, than it was ten years ago. And I gotta believe that at least part of this is responsible to the way that we build the industry and society. But, maybe not.

Ronda: I don’t really know. I mean, I was here in the late ’90’s and early 2000’s. It was similar to what it is now. I mean, my car got broken into just as much in 1999, 2000 as it does today.

Phil Libin: But like, did the Muni, did the public transportation system get hollowed up by Uber, or was it always unusable in San Francisco? Like I barely remember.

Ronda: So, I would say the bus system was always terrible. The bus system, if you lived in Potrero, the rest of the city was completely inaccessible, and Uber has changed that. If you lived in the outer reaches of the city, the outer Richmond, the outer Sunset, suddenly the whole city is opened back up to you. You’re not sitting around waiting for Muni all day. And that was a universal problem 20 years ago. I don’t know that it’s necessarily gotten worse. I would say that, as one of the dot comer’s we blamed investment bankers and lawyers last time around, and now it’s definitely the techy’s that are taking it on the chin. We are a bunch of entitled people, and we’re probably … Some of us are massive jerks, but overall I don’t think you can blame the state of San Francisco on the tech industry.

Phil Libin: How ’bout education? Hemant, you’re involved in lots of education projects. Some very creative ones. You’ve got kids in school. What do you think … Has the state of education gotten better or worse? And maybe for your kids who have more resources than the average kid in the US, but also what about for everybody else?

Hemant: I think the state of education is probably stagnant, if I was to use a word, and not evolving to be aligned with where the future of work is, how jobs are changing, how society’s changing as a whole. So to me, that’s the biggest issue. I think this whole idea that we put kids through this K-12 factory, where every hour is pre-determined as to what they’re gonna learn, and they’re measured on this normalized curve compared to everybody else who’s the same age and learning the same concept as the same hour, as opposed to pursuing your passion … That’s the place where I think it’s broken.

Hemant: Where work has changed into … You’ve got a bunch of these marketplaces you can go work on top of, and pursue your passions. And so I think there’s this period of misalignment of curriculum, and how we do. Especially K-12 education that we’re working through. There’s a bunch of experimental stuff, lots of different kinds, and new schools being created all over the place, ’cause so many people are interested in this topic. But nothing is really scaled yet, and that’s the problem. I think the thing that hasn’t changed is the last 10 years is probably a lot of investment in the sector of philanthropic, as well as venture capital.

Hemant: Nothing has really gained momentum … Say, here’s something we can call… say here’s the future of education. If you look at the car industry, there is a Tesla, there is a proof point, and the industry’s [inaudible 00:15:31] around that to say we’re all gonna get there. You don’t have that in education industry, so like here’s a twenty-first century education system. There has not really been a moon shot. All right. A Manhattan project for education. That’s right. You know, we’re trying that at the Khan Lab School, which is under Khan Academy, and there’s others doing that all over the country as well, but I would say nothing is at scale yet.

Phil Libin: Khan Academy, I think is a great example of something that started out with super noble intentions, at least mostly fulfilled them. I’m sure not to the scale that you guys wanted, because ambitions are always bigger than reality, but that was probably something that wouldn’t … definitely something that wouldn’t have been possible without some internet advantages, and you’ve been pretty fundamental in that. What do you think about Khan Academy, about education, about how to make this reach far more scale than it has before?

Hemant: Well I think the Khan team have done a great job of demonstrating that you can have this concept of self pace education, and you can have a mastery based model, where there’s an AI based master, that’s helping you do that. So there’s scalability to it, if you go back to the older days of how learning was done. There was a master apprentice model, so AI provides scalability to that to bring it to the internet. So I think that part of it is interesting, they’ve shown it.

Hemant: But then there is still this notion of a classroom, and what do you do there, and how do you learn to thrive in society, and develop social-emotional learning skills, and learn concepts in the context of projects and topics that are interesting to you. And that part of the model, still, it requires offline interactivity and hasn’t quite been figured out to say, “Here’s a module that we are now replicate across 250 thousand schools that are there,” and evolve it.

Phil Libin: I think where we look at the problems on the internet, there’s basically three different classes of things. There’s three different classes of ways things break. There’s stuff that are the unintended consequences through normally virtuous actions. So, we try to do the right thing, we have some unintended consequences. So there’s like … that’s always a class of problems.

Phil Libin: Then there is the intended consequences of people who are acting legally, they’re just kind of assholes about it.

Phil Libin: And then there’s the third category, which up until recently just hasn’t been getting that much attention, which is actually bad actors. Actually criminals trying to break the system, and that may be used to be limited to phishing email scams-

Hemant: Well bad actors were there, but so were fraud and so on, but applying it now to social media and main stream populations, obviously once … We’re all out there online, now it’s starting to happen.

Phil Libin: It feels like the people who are actually getting scammed by the actual bad actors and criminals now, all of us, right. It isn’t just a few people, it’s all of us. What are the … The proportion of those three things … I would have said … Ten years ago if I was answering this question, I would have said the vast majority is unintended consequences. Yeah we should do a better job of dissipating the consequences, but it’s mostly people trying to do the right thing for the right reasons, mostly succeeding but there’s side effects, and so we should deal with the side effects.

Phil Libin: Now I’m not so sure. Now maybe the other two categories, the people are acting legally just out of pure, naked self interest, and not really caring the damage they do, but also the actual criminals. Maybe that’s getting worse. What does that feel to you?

Hemant: Yeah, I mean I would say all of the above are now at scale. The fundamental premise of the internet is Internet’s an equalizer, and you can do things at scale that were maybe small before. So if there was a small business they can now become a global business. Where there was a small criminal, they can actually run a global operation if they have the sophistication of the internet, right. So I don’t think about is one bigger versus the other. The bigger point to me is that all of them can be done at scale, and therefore, the positives and the negatives can actually be that much more significant, and therefore, each of these categories needs to be taken very seriously.

Phil Libin: Now Ronda, when we first met years ago, you were working in the public relations department at Evernote. That’s how we know each other. You’ve got a history with communications and PR in the tech industry. A lot of that has always been … At least that segment of that has always been crisis handling. It’s always been responding to problems. Have the types of problems that PR people worry about changed?

Ronda: Not at all. So again, going back, ’cause I’m old.

Phil Libin: We are exactly the same age. We actually went to college together-

Ronda: You’re a little bit older than me. Anyhow … Anyway …

Phil Libin: Ronda and I went to Boston University but didn’t know each other. Didn’t meet for like twenty years later, probably ’cause I was sitting in the computer lab, and you were sitting in a slightly different computer lab.

Ronda: Correct.

Phil Libin: None of us were cool enough to actually go to –

Ronda: Talk to other humans. Yeah. Yeah. So no, I would actually say … So my first real job in the internet, aside from when I moved out to Silicon Valley, was working for a company called EXCITE. Which sort of exists still, but not really. In any event, we had the largest community online. We had the largest chat community, we had some of the most engaged groups online.

Ronda: We were looking at the same problems back then. There were scammers. There were people trying to find grandmothers to steal bank account information from, there were people trading really nefarious pictures of things, and we worked hand in hand with the FBI. The FBI was just trying to figure out what this world wide web was, it was trying to figure out what online communities were. The difference was is that we were really excited when we got one hundred thousand simultaneous users, right. We were impacting a hundred thousand people at a time in peak usage during the day.

Ronda: Now, it’s a hundred million people. So I don’t think the criminals or the behavior has changed, I just think the audience to which they can impact … That has grown by a couple orders of magnitude.

Phil Libin: Was there as much vitriol. Were internet comments back then as just nasty and misogynistic as they are now?

Ronda: Yeah. Yeah. I mean especially in the live communities, in the chat rooms. We had a lot of problems with people coming in and just completely disrupting. We had people that … We had stalkers. We had lots of stalking issues. We had all the same things that you see today, just at a smaller scale.

Phil Libin: And that, I think, is the point. And that’s I think a really good way to kick off this whole series. It really is a question of scale, and the opportunity I think is unscale, and that’s why your book is called that. This idea that the whole concept of scale is changing. It’s gotten us this far, it’s brought us lots of good things, it’s brought us lots of problems, but now this whole concept is changing, and the way that people can think about scale is [inaudible 00:22:12] different now than it would’ve been when we were getting started ten, twenty years ago. And we’ll talk about that in the next few episodes of this series, which I’m super happy to have the opportunity to do this deep dive with you guys. Thanks for coming in.

Hemant: Great, thank you.

Ronda: Thanks.

Phil Libin: This podcast is a production of the All Turtles Worldwide Media Empire, and I just gotta say I am psyched to be reading the closing credits for once. I am so jealous that Blaise usually gets to do this on a normal podcast, and the closing credits are kind of my favorite part, so I always try to stick around for the whole episode, just so I can hear the closing credits.

Phil Libin: Anyway, All Turtles Worldwide Media Empire, we recorded this bonus episode in the Marvels Donatello Studios in our San Francisco California office. Why it’s called the Donatello studios is an interesting story for a different day. Thanks to Hemant Taneja and Ronda Scott of General Catalyst for co-hosting the series. If you have any questions, comments, or suggestions for future bonus episodes, send us an email to hello@all-turtles.com. Thanks for everyone behind the scenes of this podcast, including Jim Metzendorf for editing, Maria McCoy-Thompson for production supervision and editorial management, Chris Ploeg for his audio expertise, Matt Ammerman for theme music. Our freshly customized artwork is by Micah Rivera, Gabe Campodonico, and Carlos Rocafort IV. On behalf of the All Turtles team, this is Phil Libin, thanks for listening, and join us soon for episode two of the Unscaled Series called “Scaling the Truth.”