The Knowledge Project with Shane Parrish - Gabriel Weinberg: Practical Steps to Safeguard Your Data and Identity Online

Episode Date: May 14, 2019

I am joined by Gabriel Weinberg, founder of privacy-focused search engine DuckDuckGo and author of Super Thinking: The Big Book of Mental Models. Our conversation will help you upgrade your thinking, prepare your kids for the future, and protect your privacy online. Gabriel shares powerful mental models like ‘thinking gray’ and ‘foreseen function’ that you can use today to make better decisions, avoid mental biases, and get to the core of any issue. He also reveals his secrets for raising curious, creative kids who love learning – including the surprising technique of discussing adult-level podcasts and debates with his children. Finally, Gabriel reveals the hidden ways companies track your data online and shares simple, practical steps you can take right now to protect your digital privacy without sacrificing convenience. Whether you’re an executive looking to sharpen your thinking skills, a parent trying to set your kids up for success, or just someone who wants more control over your digital footprint, this episode will give you the tools and strategies you need. Don’t miss this masterclass on upgrading your thinking, parenting, and privacy from one of the sharpest minds in tech. -- Go Premium: Members get early access, ad-free episodes, hand-edited transcripts, searchable transcripts, member-only episodes, and more. Sign up at: https://fs.blog/membership/   Newsletter - I share timeless insights and ideas you can use at work and home. Join over 600k others every Sunday and subscribe to Brain Food. Try it: https://fs.blog/newsletter/ Follow me: https://beacons.ai/shaneparrish   Learn more about your ad choices. Visit megaphone.fm/adchoices

You don't need to track people to make money because it's all based on the contextual advertising. So the better user experience would be like not track anybody at all. Hello and welcome. I'm Shane Parrish and this is the Knowledge Project, a podcast exploring the ideas, methods, and mental models that will help you learn from the best of what other people have already figured out. You can learn more and stay up to date at fs.blog slash podcast. We also have a newsletter. It's called Brain Food. It comes out every Sunday.

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On the show today is Gabriel Weinberg, the founder and CEO of DuckDuck Go, an author of Superthinking, a giant book of mental models. We're going to explore data privacy, touch on a bit of cybersecurity, go deep on mental models, and explore how you can help your kids think better. You don't want to miss this. It's time to listen and learn. Before we get started, here's a quick word from our sponsor. Barnum Street is sponsored by Meta Lab.

For a decade, MetaLab has helped some of the world's top companies and entrepreneurs build products that millions of people use every day. You probably didn't realize it at the time, but odds are you've used an app that they've helped design or build. Apps like Slack, Coinbase, Facebook Messenger, Oculus, Lonely Planet and so many more. Meta Lab wants to bring their unique design philosophy to your project. Let them take your brainstorm and turn it into the next billion dollar app

from ideas sketched on the back of a napkin to a final ship product. Check them out at Metallab.com. That's Metallab.com. And when you get in touch, tell them Shane St. Gabriel, man. I'm so happy to be sitting here with you. I'm happy to be here. When did you know that you wanted to go to MIT?

So I grew up in Atlanta, which the closest thing I had to kind of the engineering world was Georgia Tech. I went to like an engineering summer camp there. And I thought in an early age I wanted to be like a computer engineer. But I honestly had no knowledge of the different schools. So I think I had an irrational want to go to MIT that didn't really understand the landscape of the schools. But around like in maybe freshman year of high school, I had my mindset for some reason. to MIT. And that was the only school you applied to you? So I applied early to MIT and got in early and then I was going to apply to a bunch of other schools, but I just stopped applying because I figured

I'd just go. And you did a double degree. What was your degrees in? So I was an undergrad in physics and I met my wife there. She was in undergrad in math. And then I started a company right out of school. Actually graduated early. It's a different story. And did this company for a few years, and then went back to graduate school at MIT and technology and public policy, which is like this interdisciplinary economics law, public policy degree. You couldn't get enough. Yeah, exactly.

Well, my wife stayed there for nine years. She got a PhD in operations research. So I was already, like, hanging out at MIT. So even after I graduated, I was running my company, like basically out of the library, and I would go audit classes. And her department was in the interdisciplinary area, operations research. which is like statistics and logistics. And so there happened to be this other cool

interdiscality program in her building. So I was like, I'm going to apply here. And I actually ran my second company while I was doing this degree and just still working in the library, that kind of thing. What was the company that you were? So that company, the first company I started was a social, I mean, an educational software company

right out of school. The idea was to help use the internet to increase student achievement by increasing parental involvement. Good in theory, 15 years too early. that stuff's still just happening now I know you have kids and it's still hard to get what they're getting in school

chronically oh totally so that's what we were trying to do we put this whole like portal and system for lesson plans and things like that so that ultimately didn't go anywhere second company was a really early effectively social networking company that we eventually sold to classmates.com

it was kind of the almost antithesis of Facebook and their privacy practices Like we had a paid business model. We didn't collect much information. It was mainly about getting in touch, you know, with old friends. But we also just got destroyed by Facebook. And so eventually sold it and then moved on to the current company, which is duck.

And so let's dive into that. I mean, let's start with the privacy issues online in terms of not just duct. Go, but in terms of Facebook and what should people understand about this, that they don't understand about online privacy and like just something as innocuous as a search and what happens behind the scenes? Yeah. I mean, there's so many aspects of privacy and harms. And I think it's interesting.

Awareness has really started to increase over the last two years. But it's all over the map to terms of what people really care about. So in 2013, when our company started to take off, that was a Snowden Revelations. That was Duck, Duck, Go. Do you want to explain that just for a second? Yeah, sure. So Duck, Do you go is a search engine that doesn't track you. So it's an alternative to Google.

And then in the last couple years, we've expanded. And now we offer a suite of privacy tools. It's one download. It's called Privacy Essentials or Privacy Browser. And it includes private search tracker blocking. So it blocks like Google and Facebook trackers across the web. and encryption, which helps stop your ISP from snooping on you. But in any case, it wasn't, even though privacy, like, was the main thing for our search engine,

it wasn't the main attractor to it until 2013 when the Snowden Revolutions happened. Right. And then that was all about kind of government surveillance, right? So it's like, is the government spying on you, which is not becoming more an increasing thing. China's doing some crazy things. But in the intervening years, corporate surveillance has really spiked, and they're actually related because government surveillance actually uses the data you give to corporations. That's where they're getting most of the data from anyway.

And so they're linked. But corporate surveillance, namely like corporations tracking you all over the web and building big profiles about you, has additional harms. So we're talking about corporations tracking you as you go along the web, not corporations tracking employees. That's right. Effectively, as you browse the web, there are hidden trackers on all the pages that you visit. What's a tracker? Tracker is, so you go to say a random site, say the New York Times or something. You expect to interact with the New York Times. But in reality, there are about like 30 other companies sitting on that page that the New York Times embedded into it. Now, some of them

are for like analytics, like who's looking at this page. Some of them are for advertising, like they're on Google ads on their page. Some of them are to help them run their site, but the privacy policy of these companies are generally, they can use your data for whatever they want. And so they may help the New York Times and X, Y, or Z purpose,

but then they're aggregating all that information into big profiles that they can go sell. And ultimately, it comes in large profiles about you that are being bought and sold kind of in the... So something is, like, simple as Google Analytics can then be used to affect your search engine ranking because Google would know that the page

on the site is popular, and therefore it could bump it up. Yeah, and so there's a few kind of negative effects to that. One is all the creepy ads that follow you around is one that people notice. Second one, the one that you're just mentioning is called the filter bubble. So when you're on search results, say on Google or the same thing happens on Facebook news feed or even things like Netflix and whatnot, they're using your search history or your profile information or your browsing history to show you certain things they think you're going to

click on. But by doing that, they have to hide things that they have to hide things that they're don't think you're going to click on. And that can end up being opposing viewpoints. And we've done several studies on political terms. And people in different areas are seeing completely different results when you search for things like gun control or a political candidate name or something like that. And effectively, especially in search engines, your expectation is you're seeing the results, but you're not getting the results. And it effectively biases you when you're doing research. That's one harm. The other harms of people are

or I'm justifiably really upset about are things like data breaches, which relate to identity theft. And so people would just like to reduce their digital footprint online, kind of block all this extraneous information that's getting out there about them. And that's kind of what we allow them to do. Do you think that everybody should have the same search results? So, yeah, I think by default. Because with Duck.comgo, that's what you use. Yeah. So on Duck. On Dock, we don't have a filter bubble. And so if you search for the same topic at somebody else at the same time, you'll get the same results. I think that things can be made opt-in. So, like, we have a region setting where you can say, I want more Canadian results, if you want. Everybody wants

more Canadian. Exactly. Or do they? You should opt into something like that, right? And so there are some notions like that, but I don't think it should be personalized in the way it is by, without you opting into it. Do you think we're moving to a world where the least of our worries is sort of like personalized search, and we're moving into more personalized content where you have almost the same fundamental content, but now you can shift perspectives based on if you're Democrat or Republican, and you can sort of play into that? Or is that too sci-fi? Say that again. I mean, I think that's generally the danger that I see coming is the correlation causation piece is hard here, but polarization has just increased, at least in

the U.S. and it's relatively, you know, correlated with all of this social, right, social media and tracking. And so the thought is, at least they're interrelated in the sense that people are just in their own bubbles, you know, and they're not really seeing these opposing viewpoints. Is exposure to opposing viewpoints enough? Probably not, but it's like a necessary but not sufficient condition. Right. If you don't have any, you're definitely not going to start to engage with the other side. And so aside from the annoying ads that we see that like follow us around is that the Facebook tracking pixel sort of yeah so on the all these sites that are lurking behind web pages right um if you go and look and

like analyze which companies are there um google's on about 80 percent of the top million sites and a lot of that's google analytics but also like the google ads and stuff like that facebook's on 25 and that's this uh facebook pixel where um it could be the facebook login or just just sites run Facebook ads or they want to just track what audience and then serve ads on Facebook. And so Facebook and Google are the biggest trackers. I remember last year we took the Facebook tracking pixel off. Good for you. I was tired of people like targeting our audience. Yeah. And I was like, oh, that's really weird when somebody pointed it out to me. And then I was like, okay, we'll just delete that. That'll be. That's the key thing you're getting at is like,

you put it on for your purposes. Yeah. But it can be used for everybody. Yeah. That's the real problem. If it was, if these companies were just a service provider for you, that would be fine. But it's that the data is leaking beyond the use that you set up for it. Yeah, I remember the first time I went into my parents' Facebook account and tried to create an ad targeting Farnham Street readers. And I was like, what? This is crazy. My mom is not connected to like Farnham Street at all. So it was a little weird. What do you think sort of like, how do you think this plays out over the like this Newton stuff came out, which is more about sort of like what governments were doing to protect themselves. Actually, maybe that's a good discussion. What do you feel

the role of government should be in data privacy? So we're having kind of a moment now in the U.S. at least after, so what happened is Europe kind of took the lead on this and they made something called GDPR, the general data protection regulation, which is actually a restatement of something else. They've been kind of advanced to this for decades. But they're really, putting in some rights and saying privacy is a fundamental right that should extend to online and you should have the right to know what companies are tracking you and know what information they're collecting you and have a right to opt out of them sharing it among other things it's a long regulation yeah so then California in the U.S. there hasn't been a general privacy regulation

ever there's some specific ones like there's HIPAA for medical data and there's stuff for financial data but there's nothing like general like that so California, through a ballot initiative last year, passed the first one, which goes into effect in 2020. And that set a clock for the federal government to either make their own and preempt California or have to deal with California's law. And so that's kicked off this process just happening right now over the next, you know, nine months before that law goes into effect to think about what federal privacy legislation

should look like. And I think, to answer your question, that, yeah, I think that. government needs to play a role here because, I mean, my general proposition I'm saying for years is if the data can be collected and if it can be used to make profits, it's going to be used for that by people unless the government stops it. And it's an externality in general. Like the, it has a lot of data breaches, a good example. All these companies are collecting information about you. They generally have terrible security practices, Equifax, et cetera, et cetera. and eventually they get hacked.

All the data gets out there. Tons of people have identity theft, and they didn't really pay to protect the data and it's an actuality for everybody. Right. And so the government definitely has a role to clean all this up. Do you think that the data collected by these companies,

and maybe I'll add some context to this, is like the way that I'm thinking about this problem is if you're a company like Google or Facebook, or Amazon, you get a lot of data that other companies don't have access to you. That data can be used to extend your competitive advantage. It can be used to provide better recommendations that the guy in their garage can no longer do.

Does the government have a role in equalizing the playing field? And what does that mean and how does it look? Does it mean that like data becomes a public good, like a public utility? Or does it mean it? Like how do you see that? Yeah. So you're asking a separate question.

So independent of data privacy legislation, which gives individuals' rights over their data. There's a whole antitrust competition question going on. I actually recently testified in front of the U.S. Senate on this notion about general privacy legislation, but my message was exactly what you're saying is that in the world, there's a duopoly in digital advertising, and it's Google and Facebook owns basically all the digital advertising on the web,

which relates to all this data profiles. And the more data they have, the better advertising they have, the more targeting they can do. Right. And so they're locking up all the growth in the industry, and that's what's putting out a business, things like media companies as well as small business ad tech players and other advertisers. No one can really compete with it. So yes, I think if that that has a inherent network effect in it because, you know, they're getting all the data and all the eyeballs and it just is a feedback loop that is getting more and more. And so unless the government breaks that feedback loop, I don't see another way out of it.

Um, what I suggested to the Senate was a few things. Um, one is, so they're collecting all this data from different kind of business lines like Facebook bought Instagram. They bought WhatsApp. Google runs Google analytics. You know, they run double click. They run a bunch of other things. Um, the government and Germany is starting to do this already can prohibit them from sharing data across their business units. Right. That's kind of a kind of like a lot of financial firms. Exactly. Kind of a Chinese wall situation. Um, that's kind of a, uh, a, uh, a, uh, a, uh, a weaker argument, which I think would work, of the got to break them up kind of argument and spin off some of these different business units. And then there are other things that you can do too. But like if fundamentally you don't kind of break up these data monopolies in some way, then I don't think there's, I think it has reduced competition. And there's no easy way for other people to compete. Do you think that the solution is making the data,

breaking up the data monopoly over sort of like the monopoly? the monopoly writ large in terms of the size of company and maybe the scope of their influence? It's funny because I think that there are, I think this is where it gets complicated. I think there are actually different issues. So I think you have to do something about data monopoly, but independent of that, some of the companies have had bad practices within their core markets, right? Like we've had some trouble competing in search just because of search issues that are specific to search, nothing to do with the data monopoly. And Europe has come out and, you know,

find, say, Google a bunch of times related to those practices. So I view them as independent. And generally, they've been independent agencies pursuing them in the government. The government has the reality is these companies are huge. They do a lot of different things. And so the government, different government agencies need to be kind of on top of it. I want to push back just a little bit on, like, whether they're independent, because maybe I'm thinking about this wrong and you can correct me, but one of the reasons that they get so big is because of the data. Yeah, no, no, they're related. Okay.

Yeah, I just think that there are. You can address them separately, sort of. Well, also, if you clean up one, it won't necessarily clean up the other. Right. Because, like, say you regulated privacy, the data monopoly piece, they're already so big that they can still use their weight to do other monopolistic practices, which would be bad for competition outside of the data monopoly piece. So you need someone else looking at those.

competitive issues. Do you think that like Apple strategy is to be more privacy focused? Do you think that that is a good business strategy? Yes, I do. I think that in general, so people have had this misnomer that like, you know, people say they care about privacy, but they don't really care or they won't do anything. We've been running our own kind of research data on this for years now, really trying to dig in to what people are actually willing to do and what people do.

And there's kind of two realities in there. One is as awareness has increased, people's willingness and interest in doing something has greatly increased. And we've seen about a third of people take some actual significant action to reduce their digital footprint online in some shape or form. Like a third of all people? Third of a subset of people. No, third of all people.

Like, our polls are in America, but we think it's related similarly to other major developed countries. Across socioeconomic, across sort of gender. That's a whole other interesting thing is like another people think it's like, oh, young people don't care about privacy and old people care or vice versa. And we didn't find that to be the case either. It's like across all demographics, a decently similar percentage that's been taking action. I don't know what exactly threads them. It's not education. It's not income. It's not age. It's not political affiliation. None of the main factors that we get on like the general survey stuff like spiked. But we consistently see this growing percentage.

of people trying to take at least actual action. Some of the actions they take, they don't realize, actually don't help them, but they did try to take an action. But they're trying to. But they're actually trying, exactly. And Apple recognizes this. And I think they also view it on principle that, kind of like we do, that privacy is a fundamental right,

and people deserve it, therefore. And if there's no alternative, then people have no choice. And that's kind of what I was getting at. And so people had wanted to take action. There just was no action for them. to take. Right. If you have two options and both of them are bad, you still have to pick why people want a smartphone, you know? But now that Apple say offering a smartphone that has privacy, those group of people can now choose Apple's smartphone or they can choose stuff to go

as a search engine. I think that people need, like, actual tools that work. So if our search engine was terrible, like they're not willing to have too much sacrifice. Right. But let's suppose it's equal. And at that point, it's somewhat a no-brainer, at least for this group, you get to switch, you get to reduce your digital footprint, and you still get all the tools and good search results. Okay. Do you think people pay for privacy? Like, is this the future where, like, Apple, for example, and their integration and their solutions, you tend to pay a higher price for that? Do you think we, like, Dock, dot, do we end up paying for that in the future, or is that? So there's kind of two ways to look at this. And so in the Apple case, yes, I think people are paying for, um,

you know, additional services that are private. In search, you're already paying for it in Google already because you're paying with your data. It just doesn't come out of your wallet. Yeah. And in effect, it does because there was a really interesting story the other day in the New York Times about one of the reporters quit Facebook for five months, or has quit four or five months, and they're kind of recounting their stories for doing so. And one of the things that happened is he started spending, uh,

50% less. Oh, that's interesting. Yeah. Because he wasn't being exposed to the ads. Exactly. And so I think there's two components there. One, he wasn't being exposed to all the ads. Two, some of the ads are just purely manipulative.

I mean, if you think about AB testing, and it's hard to know where this line is, but they're manipulative in two ways. One, advertisers target, hyper-target. So they find the exact group that is, you know, willing to buy this thing, whatever it is. And two, they test different messages over and over. and over again different images until they find what is the exact emotional trigger all these different influence mental models if you will right of like things that will actually get you to buy so some of those things he maybe didn't buy because he just didn't see the ad some of those

things maybe he didn't buy because he didn't see the right manipulative message and so that manipulation piece which is probably i don't know exactly what order but let's call 50% that was money directly out of his pocket right yeah so he did pay for that he was paying for that just he wasn't didn't sign his credit card up to them. Right. But some decent portion was because of using that free product. So one answer is you're already paying.

The second answer is for something like Google, if we charge for our search engine, I just think a lot less people would use. There would be some people who would pay for it. And maybe we'd make the same amount of money, but we just expose less people to it because it is a big friction to take out your credit card free versus not free. And so. This competing interest almost like wide influence versus like running a problem.

A profitable business in a way. And so, yeah, so I could see some markets, the direct answer to the question is some markets definitely that already have a precedence of paying, pay a little extra for more privacy. That one is fine. And a market that is already free, it's hard to see a mainstream provider go paid on it because there's so much friction going from free to paid. That said, just to be clear, then the question is like, how do we make money?

There are advertising in and of itself, is a good thing to say, is not bad. We make this distinction, this is what I also said the Senate, between contextual advertising and behavioral advertising. So contextual advertising is just advertising based on a context of the page. So like, you search for something on Dr. Go, you search for car, you get a car ad, right? I don't have to have anything about you to serve that ad. That's different than the ads that follow you around based on all of your history. That contextual advertising used to be the way the Internet worked, and it could go back to that. And if you imagine, like, you're on New York Times again, you look at an article.

it's an ad just based on that article or an ad based on the video you're watching, the content of the video, nothing to do with you. So that contextual advertising doesn't have all these privacy problems of manipulation and filter bubble and all these things. And my argument is, basically we've been up this feedback loop

of trying to improve behavioral advertising for the last 10 years, but no one's been doing that for contextual advertising. If we have been doing it for contextual advertising, it might be just as good right now. And in fact, there are some decent experiments of that that have just come out like after GDPR in europe the new york times decided to ditch all the behavioral advertising and put up contextual advertising only and they increased revenue um this is like

one of the first data points out of this and so i think this actually has legs and that you could return to a world of contextual advertising and that's all duct dot go does and if you think about it that's really still what google does most of the time on google search because all the search ads are still bit on keywords right they're just using your search history in addition to target ads at you on YouTube and Gmail and the rest of the internet but they don't really have to for the search ads where they make most of their money

it's still all contextual why do you think revenue went up at the New York Times so I think that strikes me as surprising yeah I think it went up probably because I don't know the whole story but my guess is they their first party ads now they're selling it themselves

right and so instead of using a broker yeah they're cutting out a whole middleman at that right so if you even get near the same advertising rate than you're just cutting out the 15 to 20% you're paying to a broker. Yeah, sometimes the rates, the splits could be worse for, you know, for different advertisers depending on the network. I know, like, we get less money on Farnham Street because, I mean, we charge a sponsorship, which isn't based on page views, and there's no tracking code.

There's nothing embedded in there where companies get information on you. Whereas if we use, like, Google AdWords, based on page views, we probably get more money, but then you tie into this whole, like, tracking contextualization. and it would be kind of creepy to go read an article on like mental models and see this book that you searched for like last week popped up in the sidebar. Exactly. I mean, for you in particular, you know,

there's a good, you know, Darren Fireball and John Gruber. Yeah. He sells his own ads directly. And I think if you have a niche audience like you do, you might actually make more money if you, you know, start selling them high price directly. Yeah, you should. I want to come.

We bought his ad before. Oh, cool. I want to come back to the privacy and hardware, and I want to take the role and expand it. So that's far we've sort of been talking about the individual in the role of the ecosystem and sort of like e-commerce. I want to talk about how that role shifts as you think we move up in the stack. And by up in the stack, I'm talking like you have a local government, you have a state government, you have a country, and then globally. Do you, where do you, where do you stand on privacy? Should the government be able to break into your phone?

Do you think that those companies should make that physically impossible? Or should the government have a key? Like, walk me through. Yeah. So I, there's a lot of nuances in here. But I'm of the view that privacy is kind of two fundamental principles, right? Privacy is a fundamental right. So you have a right to have kind of private communications.

In the past, that was. You could write a letter. You could kind of write things down on paper. Now it's in your phone. I still think you should have that fundamental right. So just to be clear, that's not like a U.S. right? You believe that's a fundamental worldwide. Yeah.

So you should be able to like send an email to somebody anywhere in the world and have that. Yeah, it's not currently the case on email. Right. Yeah. But yeah, I think so. I mean, this gets into, you don't want to tell other countries how to run their government. So maybe it's to, you know, maybe it's crossing some line. But at least in the U.S., the idea has always been like you have a private thought space.

You know, you should have private space. Your home is your home. And without kind of really good cause, no one should invade that privacy. I think if you start invading privacy in that way, it leads to all sorts of bad effects. Such as. A chilling effect is a big, big one. which is, you know, people change their behavior once they feel that they're being watched or they don't have privacy. There's all sorts of good examples of this.

To give you, to really back to search, right after Snowden, there were two studies that were really interesting. One is people stop searching terrorism-related terms because presumably they feel that they might have been investigated if they searched. So the terms like Al-Qaeda and stuff like that went down. Wikipedia also saw lower amounts of their articles. being looked at that's interesting i never knew that additionally someone did another uh same time analysis and found that health related terms also went down on google so people stopped searching as much for their own like health symptoms and things like that and the thought was now that they aware that governments or their data was generally being tracked they're worried

about it leaking either and coming back to haunt them either from maybe insurance companies or other things and so it went down but that is is just immediately harmful for people because they're not searching about their health information. Those are two minor examples, but when you get into things like China and stuff like that, you get into much more major ones that people are afraid to say anything bad

about the government and things like that or have public discourse. So I think that you want a private space and enable to be able to communicate with people completely privately. And so I do think that end-to-end encryption, which is kind of what you're talking about, like built into iMessage now. That was the Apple FBI case.

You should be able, I should be able to send you a text message and no one should be able to read it except the two of us. Now, the counter argument to that is, well, what if they're sending really bad things and stuff like that? I think that is a bit of a distracting argument

for a couple reasons. One is there's actually more data about you online than ever before. What does that mean? Like, there is, you're putting out all sorts of data online, it's much easier to surveil you than it has ever been in the past. Like your phone's setting out location information,

which isn't necessarily encrypted. You're even on the text that we send each other, there's a record that it went through the internet, at least. Right. And so maybe you can't read the message, but you can probably figure out the metadata that we talked. All this information didn't exist in the past. And so if you look at like the overall information

law enforcement and government has to surveil people, even with end-to-end encryption existing, it's way higher than it was 10 years ago and way, way higher than it was 20 years ago before. So you believe the government should be able to use metadata? I think we should restrict a lot more. I'm just saying that the general argument of that

I need every last piece of information is not a good one in their own argument because they have more information and all the tools that they have exist are much better than they were 20 years ago. No, I think the metadata should be restricted too. I really think we should be able to communicate privately without anyone knowing, but the reality is of the current tools, that is discoverable.

Okay. Because when we send a message across each other to the internet, unless we're using even more sophisticated tools, it's figureoutable that we talked. So if the government had the capability, I'm just trying to think through this. So like if individuals could communicate completely privately, governments could communicate completely privately. Well, this is your other point about the key. if you enable a backdoor,

which is what some governments are requesting, it is really naive to think that that backdoor would only be accessed by that government who wants it. And that was one of Apple's major points is that if I build this backdoor for you, U.S., China's going to use it. And not only that, it's probably going to get leaked and all sorts of bad actors are going to have it.

So, like, for example, I don't know how familiar with any of this stuff, but the NSA made all sorts of hacking tools. Those eventually got leaked, and they're all floating around the Internet now. Tools that the NSA made for themselves are now available to all sorts of other people. And so all this stuff has a tendency of coming out and being used and exploited if it exists. And that's Apple's point. It's like the only way to protect against that is to have no backdoor.

So do you think that that will be fundamentally impossible? I mean, so I think in the San Bernardino case with the iPhone, And Apple basically said it wasn't possible. Then they admitted it was possible, but they weren't going to do it. Do you think we moved to a world where they actually want to be able to say it's impossible for us to do it? I think that would be ideal. I don't know how possible that world actually is because you have to manufacture the phones and things like that. But it's become harder and harder, like built into hardware and things like that.

On the internet-wise, the closest thing we have to that is Tor. You know, you can basically go into... Can you explain Tor? Yeah. You can basically go into a special browser that kind of works like it did the movies where it bounces off things before it gets to the other person. And so it makes like three hops into random places before it gets to the other side. Right.

And so if both of us are using Tor to communicate, it's extremely difficult. to break that. And as far as we can tell, Tor itself isn't really broken. There have been some exploits in the Tor browser, like using Flash. Right. But things like the news organizations now

to give anonymous tips to them, they use something called Secure Drop, which works over Tor. And it's worked decently well. And so that's what you need to do in the non-hardware world to communicate. You can do that on any device. How do you think about government's role

not with their citizens, but government's role in terms of, like, the world. And, like, walk me through your thinking, should, I don't want to use specific countries, but should one country be able to ee straw on another country that they feel might pose a significant threat to their citizens? I mean, I don't think there's any stopping countries from doing that. They've done that from the beginning of time. And so they're going to have an incentive and desire to have espionage agencies. I don't think there's much possible to pray but that.

But then the tools exist, right? The very tools that you would use against your citizens, you would be using against foreign entities. They're making all the tools they can in that process. What I'm suggesting is people like Apple should be the opposite of that or have to go and enable citizens to do the best they can to avoid that kind of surveillance, either corporate or government. What got you so interested in privacy?

Interesting. I'm interested in general public policy of all kinds. So, you know, to talk about the mental models book, I'm interested in, like, everything and have, you know, this degree in general public policy and technology policy. I started this company and kind of backed into search privacy in particular.

I had sold my other company and was trying to find something that I really wanted to do and I got really interested in search in general and eventually started this search engine that wasn't initially private. I hadn't thought about it. It was more just trying to make better results. And then I got some initial messages after launching about like, well, what's your policy on search privacy and stuff? And so I, myself, out of just interest, took more of a deep dive on it and decided, oh, wow, this is really personal data, arguably the most personal, like what you search, you kind of give your financial problems, personal problems to your search engine. You don't need to track people to make money because it's all based on the contextual

advertising. So the better user experience would be like not track anybody at all. And so just made that unilateral decision. It was just me at the company, who's a one-person company. And that's basically how I fell into it. Funny aside, we used to, do you remember when Gmail used to display ads based on what was in your email? Yeah, yeah. So a couple of friends of mine, we figured this out. And what we would do is we put keywords at the bottom of the email, but put them in white text. So people would get ads that would have nothing to do with the email, but we could control what ads they were seeing based on the keywords we were putting there.

Pretty funny. How does search work? I'm really curious on the back end. Like, how does, like, walk me through? We can geek out on this and go into as much detail as you want. Like walk me through how Duck. Dockgo builds a search database, how it determines relevance for a search term at a particular time, and then how that relevance changes over time.

So I started out originally doing all the build your own index kind of stuff, and then quickly realized it is really expensive. and also building your own index is like going out touching every website keeping a copy of it like somehow sort of creating metadata based on the site yep i just want to make sure that we're like everybody understands the terms again yeah right um i crawl in the whole internet basically um and i realized a few things one is there were a bunch of companies who raised a bunch of money all trying to do that basically compete with google at their core game and realize it's someone it was somewhat unnecessary because there were a few different web indexes at the time that existed and they had

reached diminishing returns and quality. And so you could get good web index results from Google, from Bing, which wasn't Bing at the time. It was MSN. You get it from Yahoo. E. Index was at the time. Asked views was still crawling. There were a bunch of, a bunch of ones. And I realized that it was unnecessary then to focus on that and you could treat it as a commodity and instead try to differentiate on other things, I also realized that we were one of the first people to instant answers. And so what's happened major in the last 10 years in search

has been, when you search, about half the time, you don't click or use the actual web results. Not the auto-complete stuff, like you get weather or product instant answers or sports scores or local restaurant listing or whatever it is. Those are not full web index. Those are Wikipedia information, you know, those are very verticalized indexes. And so no one was doing that when we started.

So what I originally figured out was I'll just try to not spend all my time on the web index and focus on instant answers. And so the first thing that I focused on was indexing Wikipedia and getting really good knowledge graph answers. And over time, so the other end of it. thing I ended up doing. This was way back in 2007. There was a lot of spam in web search back then. There was like all sorts of content forms and things like that. So we did crawl the web and looking for spam results and then remove them from the index. It was like a negative index. In any case, what's basically happened is we're a small organization still. We're

like 65 people. And now it's gotten so much more expensive. To crawl the web and make that deep index is probably hundreds of million dollars a year. just to maintain it. Just to maintain it, arguably maybe a billion. And most of the indexes went away. And so what we've decided to do, also the individual verticals have gotten more expensive. So like Yelp is like the best in class for restaurants and you have maps. There's only a couple maps providers.

So what we've decided to do instead is maintain privacy at all costs, but try to work with the best partners in all these different verticals. And so then our basic technology, therefore, is getting a query, trying to figure out what is the best instant answer provider and who are all the providers we need to work with to get, to deliver you the set of results. And in any given search, it might be two or three different providers, you know, to like, if they get the website. So does Google give you access to their sort of like? We currently don't work with Google at the moment, but there's still Yahoo, Microsoft. We work with Google on YouTube because it's the only place where the videos are. So video search is another big one.

Um, you know, we work with Yelp and TripAdvisor and there's literally like 400 different partners because it goes into all the different long tail stuff. Some of the stuff we still have to build ourselves. So like we still build, use Wikipedia and build it ourselves, uh, you know, like stack exchange, stack overflow that kind of stuff. We, we build our index to that. So we have a bunch of these we actually have to do ourselves. Um, but we also work with all these other partners and then try to on any given search, figure out, is this a local search? Is this a programming search? Is this a, what kind of search is this? And then give you, results back and then we have to make decisions of like how newsy is this search like where

should we display news results should it be at the beginning should it be in the fourth result that kind of thing so you mentioned like indexing Wikipedia and then you mentioned knowledge graph what does that mean so uh Wikipedia like you read this page programmatically on Wikipedia unfortunately Wikipedia is somewhat unstructured it would be better if it was way more structured what's the difference like what uh like uh structured would be is like um you know here is the person's name and their age and everything like that Wikipedia is you know edited by anybody and it's got all these different rules but it's basically just a lot of text with some markup on it and so if you index it you have to like figure out all the different edge cases for all the different markup and somehow extract

you know your name and age and all that stuff right how do you do that a lot of there's a lot of code so do you literally just write like for one-off exceptions or is it there's a lot of wedge case exceptions yeah um they've they try to standardize it but there's it's not very standardized as well as it should be yeah it's a large code base but you're effectively standardizing it for them in a in a weird way or am i misunderstanding like yeah we're kind of reverse engineering it if you will you know like turning it into a standardized format yeah right for our own purposes and then could you give that information back to Wikipedia and like have them address the page at least in like metadata or something

there have been some projects like that that haven't gone very well yeah other people have tried there's like a one thing called wiki data and such but yeah that's effectively what we do for Wikipedia and so the graph then is like the author is this yeah relevant dates or this the and then how do you pick out like when you read text through the computers like what is the what is the algorithm considering in terms of trustworthiness of the site what is the algorithm considering in terms of like how do we find the relevant passage in the text we're reading for the query that you're it it really depends on the vertical and so like can you walk me through

a couple of yeah so like local search for example like restaurants and whatnot really focuses on like, when you do a local search, you usually have a what and a where clause. So it's like, I want pizza in New York or whatever. Right. I mean, too broad, but. Yeah. Yeah.

And so, like, for that one, once we hear those local search, we have to figure out, like, the what and the where and, like, pull that out kind of semantically from the query and then do different things with them, like, figure out what the location is. And even that gets more complicated because if you, like, Paris, something in Paris, Are you talking about Paris, France? You're talking about Paris, like, Indiana. I think there's a bunch of Parises in the U.S. I don't know if it's funny Indiana.

Right. And same thing with the what. Like, is pizza category, or is that a name of a restaurant? And so on these verticals, you have different indexes and different rules. And so for like stack exchange, for example, the stack overflow as another example, which is programming instant answers. Like, that has a lot of special characters that you have to do stuff with. Like, people type in.

programming like pluses and and less than greater than signs and in other context you would ignore those right but in the program's super relevant yeah they're super relevant so it it what ends up happening is you really need to first decide what domain this thing is in and then apply different rules different relevancy rules right and search rules per that domain and kind of do different things with it how should we think about search moving forward. Like what is it like I'm just trying to contextualize a couple of things here. One of which is like an argument that Google would probably make is like if you're standing in New York and you search for pizza, like you probably want local contextualized results without your permission. Like we'll just give it to you because that's giving you a better. Well, one thing about local, which is interesting is you can do that. So without tracking people on duct.com. Because your location is generally sent over by your browser automatically. And we can also do that contextually and throw away the location after that query. So how does that work? Like, your location is sent by your browser.

Yeah, so there's kind of... So no matter what browser you're using Chrome, Internet Explorer. Well, there's some location built into your IP address. So when you ever connect to anything, you're sending your IP address over. And so you can get a rough location based on that. You also have something called the browser location and, like, sites request, you know, can you use your location, you know, with this app or this site? That'll send a more granular location based on GPS on your phone.

And so on Duck. Go, if it's a very hyperlocal query, we'll ask for that. Would you allow us to use the location? But we promise to throw it out right after. Immediately. We don't store it at all. We just use it to bring you back the local restaurants around where you are and then it's gone. So there's no location history or anything like that.

And then where is search going, like, in your mind in the next five years? Like, is it going to voice? Is it going more mobile? Is it going to, like, you search based on images? Are any of these trends that we sort of like hear, about a little bit in the media, but are they what you're witnessing? So what's interesting about the history of search is those trends are real, but they've never supplanted earlier search queries.

So like the rise of mobile search queries has been great in the last 10 years, but desktop search queries actually haven't decreased. And so it's just like people have searched more. So that's one thing. And more of that new share is mobile. Yeah, definitely mobile. voice has been slower than I think people predicted but it's definitely a new thing

like people aren't searching less on mobile and moving to voice it's just like other queries so that's one thing the second thing is it's the rise of instant answers and just like more instant more like not waiting through results has just continued and continued

and I imagine that'll keep continuing does that mean that like Google Facebook Amazon to some extent duck dot go you get to play gatekeeper. Like, do you get to pick winners? There's a big gatekeeping role. And I think that's been a bunch of the competitive complaints.

You know, that's an argument in search right now of like the user experience is arguably better if you give somebody one result, but it's a gatekeeping role. How do you think that that should be handled? So we've been trying to do, but we haven't had the luxury because we don't, make our own ones all the case, all the time, is try to give people choice. And so, like, when we have map results, for example, people can choose which provider they want to do their directions when they go off of duct to go onto a directions provider. And so that's the model, I think, would be good, is giving people more choice.

But even that has its own problem because there are hundreds of providers. and you can't give, you run into the paradox of choice mental model, just like, or Hicks law, it's like you give people a billion choices. Yeah. What if I want to start up a company? Yeah, exactly. Well, then it's like you can't, you give a drop box of 100 things because you'll just confuse people.

And so at some point, you do have to make choices. We've been trying to work with the biggest partners that have the most breadth and best results. And so the way that you think about making that choice is like who's the biggest partner, He's got the better sort of results for people. But even then, like, if we're not here yet because it's not like this case in every country, but you can imagine, like, if you were really into Amazon versus Target or something and we give you a choice, would you rather prefer target results or Amazon results

or Yelp or TripAdvisor results? You had like a favorite. Right. You could choose and then be like, okay, see more of that on when you get those type of consent answers. But then we're still like sort of anti-competitive to new. up and coming. Yeah. I mean,

I think it's inherently a problem with instant answers. So do you think, like, in a weird way that we haven't had before, and I'm just, like,

thinking out loud and throwing this out there, but do you think, like, bigger gets bigger? I mean, I think in general, when you have data, network effects,

you have winner-tickmus markets. Because I'm thinking, like, I used to, like, if I wanted to compete with Walmart, I could open a store, and I can compete with them, and people would see my store,

and they would find it, and they would try to buy it, but online that's not necessarily the case right just because you create a website or you have a better product doesn't mean that you actually get noticed um no i mean there there are there definitely are equivalent ways to get noticed but what you're basically saying is which i think is generally true is our capitalism in general has scale effects a number of ways you know just kind of as a scale network effects etc and that is a feedback loop that makes things bigger unless there's some disruption that happens.

And I think that naturally happens. And there's a good argument to show that that's happened a lot, at least in the U.S. markets, in the past 20 years. So if you put your... Not even online, just even offline in sorts of industries. For example, what comes to mine? So, oh, man, I just read this book that was the myth of capitalism that had all sorts of examples.

And now they're kind of like, Donovan, I'm escaping me, but there was like from eyeglasses was one of them. I think it was like oil refinery. Oh, because they're just controlled. They're effectively like the lenses are controlled by one. Yeah, it just ends up being scale. So like it's all the same effects. Like people get bigger.

They buy up other companies. There's been a lot of acquisitions, you know. Right. And nothing nefarious necessarily. Right. But just. But the concentration becomes. Yeah.

Over time, the concentration. concentration becomes more and more and more and that creates less innovation and and that's kind of the general argument that's interesting because as you're talking about that i'm thinking like one of the big national debates is sort of like this uh wealth inequality yeah but we don't necessarily they directly tie this in that book to the same okay yeah because i was going to say we don't tend to talk a lot about like company inequality where you have this big disparity between the sort of i don't want to call it winners and losers but the bigger companies get bigger uh almost as a necessity of them being bigger.

They can make more acquisitions. They have more preferable terms with people. They can be front and center. They can buy advertising more than other companies. They can generate more data that they can use to make their products better. Yeah. There's a direct tie to inequality there in a cover respects. The biggest one is that a lot of the newer companies, especially online companies, have

a lot less employees than the older line companies. taken less there's just more leverage online because digital has no marginal cost generally right and so it takes less employees to reach the same market cap right and so there's less people benefiting from that right like comparing berkshire hathaway which has like 400,000 employees to google which i don't even know what they have but it's nowhere near to that yeah exactly and then even that the subset of the you know employees who are making lots of money is lower right and and that's very different than say like a Walmart who employs like a million people or something in the US you know and so over time the rise of online and bigger companies has created some of the

wealth inequality at least that's a theory what are before we move on out of this area I want to talk about what are some of the things that people can do to reduce their footprint tangibly if they want to do it without downloading anything or like doctor goes obviously one of them, but what are the other things people can do to like reduce their or increase their privacy online? And let's start there. Yeah. So, um, so, um, so Dr. Go-wise, that's been our goal is to give like the one download you need. Right. And so on iOS, Android, Chrome and Firefox, you can download either browser, browser extension or our browser. And it has all the kind of essentials for search and browse. Right. Um, in addition, we have a, a blog at

spreadprivacy.com that has a device tip section. Okay. And so for any major device you have, could be laptop, desktop, or phone, there's a set of settings that you should probably change, you know, on your iPhone or your laptop that would generally help you. That kind of helps you on the main search browse, use the internet side. Then there's like all the other services that you use that kind of aren't search browse like email um and for all these services there are generally like more private alternatives

sometimes really private but also just getting off of google and facebook right who helps you not put all your eggs in one basket right and so for email there's like proton mail we use something called fast mail protein mail is very private fast mail is not just built for privacy they're they're just an alternative paid email provider right you know and so moving your email off of email on something else. Off the company that provides search. Yeah, you want to separate your kind of data as best you can. Independent of all of that, you know, there are a bunch of all these like people sites,

you know, that like you look up your name and you see like Shane Parrish or whatever, age, whatever, you know, you can opt out of most of those. Okay. There are some services that will do it paid, but there are some lists where you can just go through and just request your removal of all. I'm super happy to have Shane Parrish. If you Google that, this guy in Australia, Dieter Berman or something, it was like a TV star.

And so the number one result for Shane Parrish is like, that's great. That's awesome. Yeah, so, I mean, those are the things. I think if you want to get more extreme, there are other things. Like we talked about using Tor or something like that. But in terms of just like no sacrifice, very seamless, you know, I would, you know, use something like TechGo, like a tracker blocker, private search, more encryption, and then tweak your settings.

Do you have Instagram, Facebook yourself? No, so I quit Facebook. I want to say, like, seven years ago, maybe more. It might have been like 2010. And I don't use Instagram. I don't really use my social media except I use Twitter. Do you think that there's a correlation between unhappiness and the use of social media? So I do.

I will say that I have it, this gets to more mental models, but I really try to go with the Thinking Gray model of like not totally making my mind on anything, but all the research that I've seen and haven't like in-depth read all the studies, you know, show that quitting Facebook has had very positive effects for people. So not only the your wallet effect

which we talked about earlier, but just people feel less isolated. You know, they feel less lonely in a counterintuitive way when they quit Facebook. And so I... What explains that?

Like in your mind, like what are the probabilistic reasons that are the majority of like what would explain? Yeah. I mean, I think it would be interesting. So I'm not the expert.

I've done the research. But my guess is twofold. One is there's just an opportunity cost of your time. So, like, you were just spending a lot of time, wasting time on Facebook. That time is substituted with something else, which is probably a better time spent that makes you happier, whether that's talking to other people or, you know, reading something, something else that's better. At least that was certainly the case with me. The second is the actual content that you are engaging with is sometimes pretty toxic.

And so, like, there's kind of two effects of that that have been talked about a lot. One is, like, you're seeing this kind of Instagram, other people's awesome life effect. You're seeing other people being seemingly happier than you or something like that. But it's often a kind of a ruse because they're posting, like, the fake photos are the best things that are coming out of their life. The other is just like, you know, I remember just seeing endless political debates. um that were very like you get emotionally charged yeah yeah and it was just like it wasn't constructive debates it was like at homenem attacks and things like that um and that's just a lot of negativity and so it's like you're cutting out negativity um i think that's always a good idea you know

it's kind of like the um there's another mental like the uh you know you're the closest of the five friends you hang out with kind of thing you are what you eat in a way And so if you reduce negativity and replace it with positivity, you're just going to be happier. Do you think we can have constructive online debates? And what do they look like? I think so. I think it's possible. Do you ever listen to Intelligence Squared, that podcast?

It's pretty good. I only listen to one, the knowledge. Yeah, yeah. Fair enough. It's a, they've done maybe 200 of these. It's a structured debate, podcast. they have a topic they've had a bunch of social media ones like is social media good for you bad for you kind of thing they have four really good experts on and then they play both sides

of it moderate conversation moderate debate it's really good and it's totally civil discourse we actually listen to with our kids a decent amount how old are your kids 10 and 7 and and yeah so I think something like that would be good um I've worked on a project with somebody else who's been working for a couple years on this very topic and have been going back and forth with different ways you can kind of do that. I don't think he's really hit the nail on the head yet, but I do think it's possible, to your point. Do you think it's possible to have a national conversation about a topic in a constructive way?

I don't know. I don't know exactly what that means because it's just so many people. You know, what we were kind of envisioning is, part of the problem is, and there's kind of a bunch of mental models in here, but like people effectively just talk past each other in a lot of these kind of debates. And so take something like climate change. There's actually like, you know, 10 different debates within climate change, probably more. And I made a flowchart one time to try to isolate, okay, if you're going to argue by climate change.

The individual argument. Yeah, which part of the argument is. argument are you in like okay do you believe it's man-made okay if you do believe it exists you know if you believe it's handmade do you believe we can do anything about it you know do you believe it's there's harm you believe it's intimate harm you know bringing it down into his yeah and so like in any particular argument what what you really want to do is or what I try to do at least is if you're really want to have an engaging debate with somebody you want to start with the premise that there's suppose that you

you think you disagree on something, you want to find, break down the argument into premises and find which one you actually disagree on. With something like climate change, there's like a ton of different underlying premises. And so you have to go down and be like, oh, do we agree on that? Do we agree on that? Do we agree on that? Do we agree on that? That's not generally what happens when you have a public debate. What happens is people throw out their fact and maybe someone else throws their other fact and they're arguing like totally different things. And so that's, you can't have a productive debate unless you're arguing on the same premise. And so that's what I was hoping this kind of software or ultimate debate would do,

would help people zoom in and figure out, what do you really believe on this topic? Which premise is you believe or not? And then if you're going to engage in an argument about it, let's define the scope of what premise we're arguing over. Could a search engine do that? Like if I Google climate change, like why couldn't you take that? You had broken that down and like 11 different things. Why couldn't the result be sort of like one, on the left, you get sort of like one side and in the middle you get the argument. And on the right, you get the other side.

And like that is your result and you can click through to. That would be kind of ideal. That would be like an embedded of this software that this gentleman's building. He was calling a context, you know? Okay. Because to really give you context on the argument. Right. And then once you get into a premise, then it's like, okay, well, what are all,

then you can have more reason discussion because you can be like, okay, what are all the evidence pro and con or different aspects of this premise? And then you can cite where the sources come from. Right. And people can comment individually on those sources and say like, okay, well, the main fact that everyone's behind on this is here. And then people can be like, well, I don't, I disagree with the methodology of that study or whatever it is, you know. But you're having a much more reason debate. And if you approach a topic, you can come in and say, okay, here's all the different parts of this.

I can get up to speed on this topic really easily. Right. And that's kind of the idea. Whereas some of these topics now, it's just, you don't even know where to start. Why don't newspapers do that? And sort of like, instead of publishing, like, publishing sort of like simultaneously both sides of an issue with the middle, like, explaining the issue. There's a few sites online that I've tried. There's one called like ProCon when we're kind of researching for this.

Vox does it interesting. They have these explainers, you know, which is pretty. pretty good, but nothing really captures this the way I think it should be. So to answer your question, I think yes, I think it is possible. Okay. But nothing's really hit upon it yet. All right. If I wasn't doing this, I might work on that problem.

Maybe you should do both. Maybe. Let's talk mental models. You have a book coming out. It's super thinking. I've read it. It's great. What made you create the book?

so in a way it's been ruminating for like 20 years like I had wanted to and started writing different versions of this book for a while but it would literally lapse for like five years I could get into them if you want but then what happened was maybe four years ago dr. go started a more take off and we have not really hired a lot of people from outside the company we've really tried to grow people within the company And so we have this executive team that was, you know, needed to step up and learn more. And I was trying to understand, okay, how do I train our executives? Like, what do they need to do to really actually make good strategic decisions more of the time? Because that's really what executives do. And I got to thinking, okay, what I really think it is, which is really counterintuitive,

is I think they need to know like these 300 different topics these 300 mental models which I think you've come on to the same notion is like if you knew all these things and internalized it and could pattern match relatively effectively like the situation applies to these three mental models

then you can skip lower levels of thinking and have this whole like higher level conversation really quickly whereas if you don't know these mental models you're like starting from scratch every time and you may you kind of don't know the patterns of strategic thinking. And so I started making a list. And I was like, okay, I'm going to make a list. And I initially made a list like 100 things. And I asked somebody and I was

like, how many of these do you know? And they were like, I know like 30 of them. Were these 100 things that you applied? Or did you make this list? Like you went to University 101 and you're like, what are the big ideas? Out of my head. I was like, these are the 100 things that keep coming up again. Mental models that I continually use and so did you always think like that or was this something that evolved like did you come into school going like oh I'm going to think about this in mental models or did you kind like did you this is the more the longer term history so I came out of school my undergrad I took a lot of courses in different disciplines and so the original book I wanted to

write was like this kind of interdisciplinary like guidebook right you know and I was like I think a lot of people would benefit because they only have one major right like especially Yeah, he specializes immediately. But then that totally kind of ruins your education in a way. And you really want to, you know, all these things across system. And so I was like, what if we just made this like interdisciplinary textbook, like a survey course of everything, you know? And I eventually gave up on that. Why? I don't know. It just wasn't coming together. And I started my company and other things. And then maybe like five years after that, I was like thinking about, I had come on to Munger at that point before, though, when I hadn't come up. onto him. And then I was thinking, well, another formulation I had of this concept was, you know, I keep coming back to problem solve, like I have problems in front of me. And when you solve them, you want to like run down a list of mental models like, is this a critical mass problem? Or is this have to do with power law? Is that how you solve them? Like you have a mental checklist that you iterate through? Well, I was doing that at the time. And I was like, wouldn't it be cool if there was something like

a problem solvers handbook. And it was like, you know, when you're faced with a problem, like, here's like a checklist or help jog your memory to see if you can the company solutions. So I started on that road. And then that, I didn't, I couldn't get that to work either. So then five years after that was like more like this problem. And then I end up with this list of 100 things. And I asked the guy, and he knew like 30.

And I was like, okay, well, that to me is what people's core curriculum should be. They should learn the rest that they don't know. So then I went and I tried to more systematically list all of them. So like I went back to Munger and, you know, he has that quote about 80 to 90 models, but no one ever lists them all. Right. So I'm like, okay, well, I'm going to list them all. And then I more systematically try to brainstorm my own. And then I went and started going down the rabbit hole of looking in depth at each one and like what are the related articles and Wikipedia and all these different things.

just jogging my memory of other things most of which I already knew some of which I learned from from scratch and then I put out a blog post mental models that I used repeatedly and ended up being about 250 and that did really well

like people really took to it and for a while I was just using that as like in our reviews internally and saying like you should go anything you don't know on this list you should go read a bit Yeah, go read about it. And I linked to all the Wikipedia articles.

So it's like, here's a starting point, you know. And then internally, we use them, you know, consistently when we're faced with different problems. And then my publisher from my first book reached out and was like, well, this post was really successful. Would you consider writing a book on this? And I was like, I just wrote a book and it was really difficult and took me five years to write. That was the previous book. And so I don't really have time for this. But my wife had just kind of left her job as a statistician.

was interested in doing it. And so we decided to do it together. Ended up being extremely long and amount of work. And I somehow, like, forgot how much work it was. And it took two and a half years, basically, to turn that list into an actual book. But now it's done. So I'm happy about that.

I have so many questions here. Let's start with, like, what are the big five sort of mental model? Like, say, 100 carry the most weight. Well, what are the five out of those 100 that you think? Yeah, I'm curious what you think about that, too, because you have also a big list, right? And so what we ended up doing is, you know, the list was like a, the original list was like a big list and it organized it by discipline. Right. And then when we started on the book, we realized that's actually not the best way to do it because they're, even though they came out of one discipline, they're actually interrelated, often cross discipline.

Right. And so we set out organized. They're all connected. They're all connected, exactly. So we ended up trying to group them into, like, really, how are they connected? Right. And so we ended up with nine chapters that relate about 300. And so there's, like, you know, 40 each chapter, roughly.

But they're in a narrative related fashion. Right. And so those, like, general chapters end up being a lot of the kind of general formulations of things you should know. So, like, the first chapter is on bias in general. you know, second chapter is on unintended consequences, third chapter is on using your time wisely, that kind of stuff. So within all of those, though, if you're going to, like, boil it down,

and some of those are on, like, business and management, and so some of that doesn't apply to everybody all the time. But the ones that really come up a lot to me are opportunity to cost, which is where I started, which is that, you know, I would just tell the executive people, and I still do, is that, like, you shouldn't argue that something's important and therefore we should do it.

It should always be, it's important, and it's more important than all these other things, you know? And that just frame of mind is like, changes almost everything because it's almost every decision you ever make about how to spend your time is like, am I spending it in the most optimal way relative to my other options? Right. So opportunity costs comes up. Another one that comes up a ton, which is more rare that I don't think people mention as much, is forcing function to me. Okay. So like forcing function is the idea that it often operationalized as something in your calendar. where you've preset a time or mechanism

where something's going to happen and it forces you to think critically about something. So like in a company that can be a one-on-one standing meeting that you have every week to talk about something, you know, or it could be, you know, board meetings often serve this function because it's a forcing function to get you to compile all your metrics and stuff, you know?

Even if the meeting's not that useful, compiling all that stuff is that useful, you know? And you can just in all sorts of ways, like schedule and time to go, the gym or whatever it is you know what's an example of a forcing function you use that you find super valuable yeah so the another metal model that we kind of run through that is this one-on-one standing meeting so in our company everybody has a career advisor and there's a they have to have a one-on-one with them every week and that's a on structure meeting that's the the advisee it's their

meeting. But it's a forcing function to get them to think about anything that is going on that week, what's really on their mind. Another one we use is every project needs to have a summary update at the end of every week, kind of like what happened, what's next. And it's a, you know, it's, again, it's a forcing function to give you able to think critically about kind of of what's going on. We have kickoff calls and post-mortems for every project. Also kind of are you doing like agile sprints in the background or like how do the projects get run? No, that's a whole different subject. I mean, we've kind of because objectives and projects can be more exploratory and not or may have external deadlines or not, we try to stay away from deadlines if we can. Yeah. But we do have these like kickoff sometimes midmortem or premortems where it's like a forcing function to get people to think critically about what's going on. So we had opportunity cause forcing function. What would be next on your like? intuitive list that I put you on the spot for probably one I mentioned earlier which is thinking gray yeah and so yeah I know I should have probably brought a list oh no no no but I

actually did but maybe that's more realistic because it's the ones that pop in but I think that comes up a lot the idea there is like you know you could do this as confirmation bias too but once you commit to a decision it's really hard to to escape confirmation dice and you're you're like committed to that decision your psychology wants you to look for things that confirm your decision if you force yourself to actually not make a decision or not not commit to absolutely believe in something right say like i'm leaning this way but right i'm willing to entertain other evidence it doesn't become part of your identity right and then you're you're you're a freer thinker and so um that's this concept of thinking

gray there's another people sometimes mean something else slightly different with that which I also agree with which is this notion of but but I categorize something else in the book of called black and white thinking right where it's like things are either you know zero so one way there's only two options right usually that's completely nonsense I mean right usually there's lots of options and there's there's a whole degree of things usually not nothing's usually black and white you know and in the podcast we did with Annie Duke, she had a really interesting sort of way of thinking about this, which was like, just by default, say you're 99% certain on everything. Never 100%. Yeah. And the reason

that you do that, yeah, right, is like, well, you signal to the other person that you are open to changing your mind. So now the conversation becomes like what would cause you to change your mind. Yes, exactly. So you get a more productive debate out of it, but you're less likely to sort of like ignore things that are contrary to your beliefs. I love that, uh, that quote from younger one is my favorite one is like you know I always know the other side person of the argument yeah you know yeah yeah and um and that's what i think the thing and gray is all about it's like you want to understand all sides perfectly from the argument right and do you use these terms internally yeah yeah yeah you actually use the term and do you have like a um i wouldn't say a checklist

but do you have like um what is your decision making sort of methodology or is there one um it really varies. So what we do is we have a, we have some of a unique way of running the company because it's all remote. So we're not, everyone's remote. It's a remote first company. And so as a result, there's a lot of, and also people are in way different time zones. And so there's a lot of asynchronous communication. And the way we run effectively is to make everything really transparent. So all the projects are all open to anyone to follow. And to make all that work effectively, that isn't chaos, every project has a standard scoping template. And so it has like a background, objective, impact, and complexity assessment. And so when we have a project

and have a kickoff call or postmortem, it's in that framework of like, what was the objective of this project? Like, what are the success criteria as another way we define the objective? And we can talk about like what it should be. Did we meet it? You know, right. There's like a way to frame that. And you do that before you start the project. Yeah, before we start the project. That's rare. Yeah. Well, the other thing is like we're a small company.

I mean, I think a lot of companies are like this, but we're competing against companies that have infinite resources relative to us. And so this notion of opportunity costs, we don't have a lot of resources to waste. Right. And so one of our kind of core values that we have three articulated is question assumptions. Okay. And so what are the other two? validate direction and build trust and so with question assumptions like we're basically looking like are should we be doing this at all like is there a simpler way to do this you know and so

we're asking right from the beginning almost trying to like say maybe we shouldn't do this project you know and so the only way to do that is to write out all the reasoning and then kind of discuss it and then really question well maybe we can do this a different thing. different way that's cheaper or better or faster you know okay and so there's no list of like mental models on the office wall that you're like walking through well it's funny because i do have a i i have to be friends with a guy around school of thought okay have you familiar with that so he's got he's got some um uh websites one's called like logical fallacy is and uh it's like a list of all the biases kind of thing and then he's got another list of logical fallacies. And so I have two

posters of his on my door. Okay. And so those are lists of mental models, but they aren't the lists like from the book or anything. Do you think awareness or maybe to what extent does awareness of, because I think people get this list of cognitive biases and their their inclination or default is to be like, oh, okay, well, I'll have a list of them and I'll go through this checklist. but they're really good at explaining like why we why our thinking leads us astray but they seem less good at being able to in the moment or with foresight avoid those thinking errors they're really good at explaining why we were stupid they're really bad at sort of like preventing stupid and my experience has been a lot of times not always but if you have a list of them

the smarter you are the more you just convince yourself that they don't apply so like you're actually not even open them anymore because you go through this list and the smarter more intelligent sort of that you are the better the story you tell yourself about why you're not overconfident yeah i so i think there's something real truth to this i mean this is why we have the core value of question assumptions right and so i think what you need often is somebody else to call you on your stuff yeah and then be open to and then the organization or you need to be open to you know thinking gray about it and and changing your mind right and so what that's what we've tried that's the culture we've tried to create and so I do think it's actually

pretty hard to do on your own to your point yeah you know I think it's better if you have somebody you know to talk to and so like for example um I am lucky in that I I walk pretty much every morning with my wife for an hour and that's also how this book got started is We talk about all sorts of things, so company things, but also just current events and we apply these models and stuff. But she helps, you know, call me on my bullshit. Your dinner table conversations must be awesome.

Yeah, and vice versa, you know. Because she's got a PhD, but she's got a double degree from MIT too, right? Yeah. She's, well, there's a whole chapter in this book about statistics, which you read. And she was the main one on that. And to make, she was worried

that you should get something wrong, you know, we should say something wrong. Because what's funny about these mental models is you don't need to be the world's expert to apply them, you know, but if you're going to write a book on it, you'd also don't want to get... You have to be accurate. Yeah, yeah, first. What is the validate direction? What is that and how does it relate to feedback loops?

And what sort of feedback loops do you set up to... Yeah, so validate direction is, you know, this gets to your point about, like, decision and, like, is the project going the right direction? And so what we basically try to set up is another mental model we use really heavily at Duck. Go, it could be in the top five, is a directly responsible individual, DRI, which we really took from Apple, which is that, but really expanded it, which is that every task, every project, every objective has one person who owns it. And they are the directly responsible individual, and it avoids this diffusion of responsibility. And the bystander effect, other mental models, which basically, like, if you're on a email with five people and no one responds, it's because no one felt they were, like, it was stressed to them. Right. Same thing in a meeting. If you have action items and no one's assigned the task, right? It often doesn't get done because people are like, well, I thought he was going to do it.

Exactly, right? You know, the worst meetings. Yeah. Just spend an hour in a room. Everybody walks away going, oh, we decided what, but nobody knows who's doing. Exactly. So to avoid that, we assign a DRI for everything. And projects also have a DRI. So someone will go on and they're tasked and we have the kickoff call and they're like, okay, I know what my objective is. I'm going to go off and do this thing. But they could go off and spin their wheels. They could go off in the wrong direction.

They could do all sorts of things. And so what we try to say is there are a lot of other smart people in the company who may be able to do things faster, better, know the right answer. And so generally you should be coming back and validating your direction. And so the easiest way to do that is to just write what you're doing.

doing, and say, not stop yourself, just say, look, I'm going to go to this. Does anyone have ideas or object to what I'm going to do? If don't want objects, I'm just going to keep moving forward. The default is this is going to happen, but you can. Yeah, exactly. Chime in if you want. And that works really well because it doesn't stop people in their tracks, but anyone can follow anything. And if sometimes people will call out certain people that they know might have information about this, you know, or knowledge. And if they do, they can. can chime in. And if not, they're not. And so that's really like the core operationalizing of the valid direction. I like that. How does this relate to being a parent? Like, how do you teach

your kids about not only mental models, but sort of like preparing for like general knowledge about the world in multiple disciplines? Yeah, that was one after we, so the original bit's writing the book was train executives. But then when I got into it, especially with my wife, our impetus was more, we think that all kids, including our kids, should learn all these things. And they generally don't learn them in school. And so, yeah. I mean, they learn a lot of the concepts in school, but in a domain dependent application way. Yeah, they don't learn how to apply them. And then even half of them, they literally don't learn. Like half these things, I either had to come across randomly or I was really lucky to go to this interdisciplinary graduate program where

I was exposed to a lot of these things. Right. But had I not done that, I would have been stumbling along not, you know, knowing these things for a long period of time. So we've been, with parenting, we've been trying to be like really explaining things to kids and our kids in an adult way. So like I mentioned we were listening to this debate podcast with them. And it's an adult show. It's nothing to do with kids, you know? And really complicated topics.

And we just play it and pause it and ask the kids what they know and what they think about it, you know. This morning, I've been, so I've been driving kids to school every morning. And these are just like random examples, tactical. Yeah. More examples the better. We've been, I've been listening. We first came on a bunch of kid podcasts that we listened to. but then I realized like my kids like listen to the adult podcast as much so we start I usually listen to the daily

because the New York Times daily podcast about things and they they do a really good job of like having kind of deep dives on historical topics this morning's was about Brexit and Teresa May and all the situation going on there and so we just listen to the daily on the way to school and talk about it what do you talk about it like what does that look like it's like do you understand what's going on is the first level You know, then it's like, okay, why are they wanting to leave? Why do you think they want to leave their Airbnb Union? You know, like, what are their options? Why is she resigning? You know, all that kind of stuff. Just trying to like pick apart things that we know more intuitively as adults.

Right. Or we're told in the podcast in an adult way and trying to make sure they understand it. And the logical chain into like, okay, well, how do they get to this decision point? Do you sort of, like, nudge them to multiple perspectives, too? Like, how does the EU feel? Yeah, that's why I like the debates in particular. Right. Because you get really intelligent people talking on both sides.

Right. And you get, like, well, what do you like about their argument versus their argument? And it's like, well, what about what this person said versus that person said? Yeah, agreed. And so are you ever like, are you trying to resolve things? Or you're just leaving it open? Open. Yeah.

Generally open. Yeah. And do you follow up? Not really. Okay. what are what are the other things maybe we should follow up I don't know I don't know what are the other things you do sort of like maybe around the dinner table or with your kids to get them just thinking in different sort of ways so that schools don't teach yeah well I'm really lucky we just switched schools and I really love our kids new school so I feel like happy that our school may actually start to do a lot of things that we want to do now that we're not going to stop but so one thing I'm more encouraged about the kids school the moment but um so i my kids are too very different i don't know about your kids same so there's different strategies for each so my uh oldest is really into movies and so one entry point to him

i also like movies a lot is we've just been watching a lot of movies and then talking about them in the same way movies are great because they're they're the production like value or thought put into every minute of a good movie is really really high you know it's like a really well-produced thing there's a lot going on there that you can like talk about and and they're also very entertaining so we've been watching a lot of movies and then kind of talking about them all different kinds um my youngest um seven right yeah seven he is gotten he's really into math and really he's gotten into programming a bit and into watching like science podcast and things like that and i mean not science science science channels like on on youtube are you doing like scratch programming

yeah he took a um they're in like this johns hopkins um correspondence courses so he took a scratch one yeah this last semester and now he's taking a cryptography one oh cool and my that's seven oldest is yeah he's gonna come out with like a blockchain company he's definitely more advanced than i was at this age i'm super jealous of what's the opportunities they have oh yeah it's and uh yeah my oldest is in in a python one and um but he he's more wants to talk about like the YouTube videos he's watching you know and so I try to I guess what I'm trying to say is I try to engage with them at what they're interested in right at their level so you try to bring it back to them and in terms of like whatever they're interested in but relate the context to yeah exactly let's talk about that the other thing we did relatively recently is I put all the

you watch crash course no it's so it's really good um it's a it's not it's not our way PBS but two brothers they basically made online animated but them talking talking heads to like courses on economics and biology and chemistry and film and all these different things on YouTube what was that called again crash course crash course okay it's really well done I put them all on DVDs and so we drive to school every morning right it's like 30 minutes and so you know not every day we watch the podcast sometimes I watch craft course you know and the same thing. I guess it's all the same kind of general concept is find really good content and then talk about the content with them. Right. In a way that reflects. Yeah. I guess it's all

the same really technique, whether it's a video or a course or a movie or a podcast. You know, it's like find something really engaging you can talk about and then relate things back to it. What made you switch schools? You said do you switch school? What was the criteria for the new school and like what made you leave? We were at public school and it was generally good school. school, they both have, I don't know what it's like in Canada, but it's in the U.S. It's state by state, but they have gifted programs, and they had something called GIAP, which was like an individualized education plan for their kind of gifted cent and center. But it just, things were moving really slow.

They were bored a lot. They are youngest, who's really kind of good at math, you know, he skipped kindergarten and then skipped another grade at math and then passed out of that grade and they didn't really know what to do with them and it's just kind of bored I guess. Yeah, yeah. And so this new school

is kind of brand new. It was only four years old. It is a it's a school for gifted education totally. But it's not like you have to be super smart to get in like they're willing to take a lot of people who I think are willing to just

engage with the idea. And it's more project-based learning. And so they do two things I like. One is they don't waste any time during the day. It's just kind of like, so they do way more. And so they have all the regular stuff, but they also have coding every day. They have a project class every day. Oh, that's so cool.

And then on regular things like science or something, they're doing a project related to that thing. And they also kind of force the kids to do it, and they fail if they fail. Right. And they don't like huddle them with it. Right. And, and then they had all these other type of random things, like, you know. Do they do things to, like, build resilience? Like, as you're seeing that, because a lot of, a lot of gifted kids, like, things come very natural to them.

And then when they're faced with a struggle, like, what do they do to build grit or resilience? They, the main thing they do is let them fail at things and just make them try again until they get it. And I think that goes a long way, seemingly. although we're relatively new, so we'll see what happens. And are the kids liking it better? Kids love it, yeah, because they're both like super creative and love projects. And so it's like half the day is like doing different projects. Like Eli's in the fourth grade, they're building an escape room in their project class for this semester.

That they have like two, they split the fourth and fifth grade actually runs like a middle school. And they split them into two groups and they're like making escape rooms for. each other and they have to like build it and like do it and they test it yeah and so they're just like doing that and he loves that kind of stuff oh that's so cool and so I'm excited for them I wish I wouldn't go to the school oh my god yeah like seriously we didn't start programming in school until grade 12 and it was like Pascal yeah that was yeah I mean yeah I'm 39 so yeah we're the same that yeah that was exactly my experience as well but it was great because I mean I started much earlier than that. So like the coding class became like super easy. It's a great way to get my

grades up for university. I'm with you. That was my path as well. Listen, this has been a phenomenal conversation. I want to thank you for taking the time and maybe we can follow up. Yeah. Love to do it again. Hey guys. This is Shane again. Just a few more things before we wrap up. You can find show notes at Farnhamstreetblog.com slash podcast. That's F-A-R-N-A-M-S-T-R-E-E-T-B-L-O-G dot com slash podcast. You can also find information there on how to get a transcript. And if you'd like to receive a weekly email from me filled with all sorts of brain food, go to Farnhamstreetblog.com slash newsletter. This is all the good stuff I've found on the web that week that I've read and shared with close friends, books I'm reading, and so much more. Thank you for listening.

You know,