Gabriel Weinberg: Practical Steps to Safeguard Your Data and Identity Online | The Knowledge Project

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.

It's short and sweet.

Contains recommendations for articles we've found online, books we're reading, quotes we find interesting and worth thinking about, and so much more.

It's all signal, no noise, and it's one of the most popular things we've ever done, and it's free.

You can learn more at fs .blog slash newsletter.

That's fs .blog slash newsletter.

Most of the guests on the show are subscribers to the weekly email as well, so check it out.

On the show today is Gabriel Weinberg, the founder and CEO of Duck Duck Go and author of Super Thinking, 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 Metalab.

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 that 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.

Metalab wants to bring the 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 metalab .co.

That's metalab .co. When you get in touch, tell them Shane sent you.

Keril, 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?

I grew up in Atlanta, which the closest thing I had to the engineering world was Georgia Tech.

I went to an engineering summer camp there.

I thought an early age I wanted to be a computer engineer, but I honestly had no knowledge of the different schools.

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 mind set for some reason I'm going to MIT.

That was the only school you applied to?

I applied early to MIT and got in early.

Then I was going to apply to a bunch of other schools, but I just stopped applying because I figured I'd just go.

You did a double degree.

What was your degrees in?

I was an undergrad in physics and I met my wife there.

She was undergrad in math.

Then I started a company right out of school.

Actually, I graduated early.

It's a different story.

I 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. My wife stayed there for nine years.

She got a PhD in operations research.

I was already hanging out at MIT.

Even after I graduated, I was running my company based out of the library and I would go audit classes.

Her department was in the interdisciplinary area.

Operations research is like statistics and logistics.

There happened to be this other cool interdisciplinary program in her building.

I was like, I'm going to apply here.

I actually ran my second company while I was doing this degree and just still work in the library, that kind of thing.

What was the company that you're?

That company, the first company I started was a 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, electronically.

That's what we were trying to do with this whole portal and system for lesson plans and things like that.

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 the privacy practices.

We had a paid business model.

We didn't collect much information.

It was mainly about getting in touch 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 DuckDuckGo.

Let's dive into that.

Let's start with the privacy issues online in terms of not just DuckDuckGo, but in terms of Facebook and what should people understand about this that they don't understand about online privacy and 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 increasing over the last two years, but it's all over the map in terms of what people really care about.

In 2013, when our company started to take off, that was a Snowden revelations.

That was DuckDuckGo.

Do you want to explain that just for a second?

Yes, sure. DuckDuckGo is a search engine that doesn't track you.

It's an alternative to Google.

Then in the last couple of 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 Google and Facebook trackers across the web, and encryption, which helps stop your ISP from snipping on you.

In any case, even though privacy was a main thing for our search engine, it wasn't the main attractor to it until 2013, when the Snowden revelations happened.

Then that was all about government surveillance, so it's like, is the government spying on you?

Which is now 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.

They're linked. But corporate surveillance, namely like corporations tracking you all over the web and building big profiles about you, has additional harms.

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? A 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 run 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 XYZ Purpose, but then they're aggregating all that information into big profiles that they can go sell.

And ultimately, this comes in large profiles about you that are being bought and sold in the end.

So something as 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.

A 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 something happens on Facebook newsfeed 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 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 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 that people are 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?

Yeah, I think by default.

Because with DuckDuckGo, that's what you use.

Yeah. So on DuckDuckGo, 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, but everybody wants more Canadian.

Exactly. Or do they?

You should opt into something like that.

And so there are some notions like that.

But I don't think it should be personalized in the way it is 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 US.

And it's relatively correlated with all of this 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.

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.

If you don't have any, you're definitely not going to engage with the other side.

And so aside from the annoying ads that we see that follow us around, is that the Facebook tracking pixel sort of?

Yeah. So on all these sites that are lurking behind web pages, if you go and look and analyze which companies are there, Google's on about 80 % of the top million sites.

And a lot of that's Google Analytics, but also the Google ads and stuff like that.

Facebook's on 25%. And that's this Facebook pixel where it could be the Facebook login, or just sites run Facebook ads, or they want to have the biggest trackers.

I remember last year, we took the Facebook tracking pixel off.

Tired of people targeting our audience.

Yeah. And it 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, but it can be used for everybody.

Yeah, that's the real problem.

If it was, if these companies are 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 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 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 US at least after, so what happened is Europe, China 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 made in 1995.

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.

So then California, in the US, 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 was happening right now over the next 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 the government needs to play a role here because I mean, my general proposition I've seen 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.

Data breach is a good example.

All these companies are collecting information about you.

The general 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 externality for everybody.

And so the government definitely has a role to clear 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.

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 data becomes a public good, like a public utility, or does it mean?

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 US Senate on this notion about general privacy legislation, but my message was exactly what you're saying is that in the world, there's duopoly in digital advertising.

And it's Google and Facebook owns basically all 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.

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 has a inherent network effect in it, because 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.

What I suggested to the Senate was a few things.

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, they run DoubleClick, they run a bunch of other things.

The government and Germany is starting to do this already, can prohibit them from sharing data across their business units.

That's kind of like a lot of financial firms.

Exactly, kind of a Chinese wall situation.

That's kind of a weaker argument, which I think would work, of the get a 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 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, bringing up the data monopoly over the monopoly writ large in terms of the size of a 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.

We've had some trouble competing in search just because of search issues that are specific to search and nothing to do with the data monopoly.

And Europe has come out and find, say, Google a bunch of times related to those practices.

So I view them as independent and generally they've 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 like one of the reasons that they get so big is because of the data.

Yeah, no, they're related.

Okay. Yeah, I just think that there are, you can address them separately, sort of.

Also, if you clean up one, it won't necessarily clean up the other, because say you regulated privacy, 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 Apple's 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 people say they care about privacy, but they don't really care, they won't do anything.

We've been running our own kind of research data on this for years now, really trying to dig into 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.

We've seen about a third of people take some actual significant action to reduce their digital footprint online in some shape or form.

A third of all people?

A third of a subset of people?

A third of all people.

Our polls are in America, but we think it's related similarly to other major development countries.

Like across socioeconomic, across gender, across - Yeah, that's a whole other interesting thing.

Another people think, it's like, and we didn't find that to be the case either.

It's like across all demographics, a decently similar percentage have 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 the general survey stuff 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 - Exactly.

Apple recognizes this and I think they also view it on principle kind of like we do, that privacy is a fundamental right and people deserve it, therefore.

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.

If you have two options and both of them are bad, you still have to pick one, people want a smartphone.

But now that Apple's offering a smartphone that has privacy, those group of people can now choose Apple's smartphone or they can choose to have to go as a search engine.

I think that people need actual tools that work.

So if our search engine was terrible, they're not willing to have too much sacrifice, but let's suppose it's equal.

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 Apple, for example, and their integration and their solutions, you tend to pay a higher price for that?

Do you think we - Like DuckDuckGo, 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 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, 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 that kind of recounting their stories for doing so.

And one of the things that happened is he started spending 50 % less.

Oh, that's interesting.

Yeah. Because he wasn't being exposed to the ads.

Exactly. And 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 A -B 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 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, of things that'll 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 it 50%, that was money directly out of his pocket.

And so he did pay for that.

He was paying for that, just he didn't sign his credit card up to them, 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, 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.

This competing interest almost like wide influence versus running a profitable business in a way.

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's 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, this is a good thing to say, is not bad.

We make this distinction, this is what I'll say to the Senate, between contextual advertising and behavioral advertising.

So contextual advertising is just advertising based on the context of the page.

So like, you search for something on DuckDuckGo, 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, right?

Or an ad based on the video you're watching, the content of the video, nothing to do with you.

And 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 over the last 10 years, but no one's been doing that for contextual advertising.

If we have been doing it for textual 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 the New York Times decided to ditch all the behavioral advertising and put up contextual advertising only, and they increase revenue.

This is 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 DuckDuckGo 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 a bit on keywords.

They're just using your search history in addition to target ads 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?

That strikes me as surprising.

I think it went up probably because I don't know the whole story, but my guess is they're first party ads now they're selling it themselves.

Instead of using them broke.

They're cutting out a whole middle man at that point.

So if you even get near the same advertising rate, then you're just cutting out the 15 to 20 % you're paying to a broker.

Yeah. Sometimes the rate, the splits could be worse for different advertisers depending on the network.

I know we get less money on Fernam 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 Google AdWords based on page views, we'd probably get more money, but then you tie into this whole 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, there's a good, Darren Fireball and John Gruber, he sells his own ads directly.

I think if you have a niche audience like you do, you might actually make more money if you start selling them.

I got to talk to him.

Yeah. I want to come back to the privacy and hardware and I want to take the role and expand it.

So thus 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.

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?

Walk me through. Yeah.

So there's a lot of nuances in here, but I'm of the view that privacy is kind of two fundamental principles.

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 have that, should have that fundamental right.

So just to be clear, that's not like a US right.

You believe that's a fundamental worldwide.

Yeah. 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 emails.

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 crossing some line.

But at least in the US, the idea has always been like you have a private thought space.

You 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.

Chilling effect is a big one, which is 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 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've been investigated if they search.

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 same time analysis and found that health related terms also went down on Google.

So people stop searching as much for their own 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 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 and 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 able to be able to communicate with people completely privately.

And so I do think that end -to -end encryption, which is what you're talking about, built into iMessage now.

That was the Apple FBI case.

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 value online than ever before.

So what does that mean?

There is all 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 sending out location information, which isn't necessarily encrypted.

Even on the text that we send each other, there's a record that it went through the internet at least.

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 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?

Oh, 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 think the reality is of the current tools that is discoverable.

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 if individuals could communicate completely privately, governments could communicate completely privately.

Well, this is the 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, US, China is 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 for example, I don't know how familiar you are 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 is 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, 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 can basically go into - Can you explain Tor?

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.

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 using Flash, 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 the world?

And walk me through your thinking, I don't want to use specific countries, but should one country be able to e -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 prohibit 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, and they would 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 I need to talk about the mental models book.

I'm interested in everything and have this degree in general public policy and technology policy.

I started this company and kind of backed in the 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, what's your policy on search privacy and such?

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 tracking anybody at all.

And so just made that unilateral decision.

It was just me at the company.

It was a one person company.

And that's basically how I fell into it.

Funniest side, do you remember when Gmail used to display ads based on what was in your email?

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 tags so people would get ads that have nothing to do with the email, but we could control what ads they were seeing based on the keywords we're putting there.

How does search work?

I'm really curious on the backend.

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 DuckDuckGo builds a search database, how it determines relevance for a search term at a site.

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.

I just want to make sure that everybody understands the terms again.

Yeah, right. I crawl in the whole internet basically.

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 realized it was somewhat unnecessary because there were a few different web indexes at the time that existed, and they had reached diminishing returns in 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 -indexes at the time.

AskGeez was still crawling.

There were 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...

You just start typing.

Web results. Well, not the autocomplete stuff.

You get weather, or product instant answers, or sports scores, or local restaurant listing, or whatever it is.

Those are not full web indexes.

Those are Wikipedia information.

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 ended thing I ended up doing...

This was way back in 2007.

There was a lot of spam in web search back then.

There was 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.

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.

Yelp is the best in class for restaurants.

And you have maps. There's only a couple of 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 deliver you the set of results.

And in any given search, it might be two or three different providers to get the web.

So does Google give you access to their...

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.

We work with Yelp and Trip Advisor.

And there's literally 400 different partners because it goes into all the different long tail stuff.

Some of the stuff we still have to build ourselves.

So we still build use Wikipedia and build it ourselves.

Stack Exchange, Stack Overflow, that kind of stuff.

We build our index of that.

So we have a bunch of these we actually have to do ourselves, 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?

What kind of search is this?

And then give you results back.

And then we have to make decisions of how newsy is this search.

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 indexing Wikipedia, and then you mentioned Knowledge Graph.

What does that mean?

So Wikipedia... 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?

Structured would be, here is the person's name and their age and everything like that.

Wikipedia is 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 figure out all the different edge cases for all the different markup and somehow extract your name and age and all that stuff.

How do you do that?

There's a lot of code.

Do you literally just write for one -off exceptions?

There's a lot of edge case exceptions.

They tried to standardize it, but it's not very standardized as well as it should be.

It's a large code base.

But you're effectively standardizing it for them in a weird way or am I misunderstanding?

Yeah, we're kind of reverse engineering it, if you will, turning it into a standardized format for our own purposes.

Then could you give that information back to Wikipedia and have them address the page, at least in metadata or something?

There have been some projects like that that haven't gone very well.

Other people have tried.

There's something called Wikidata and such.

But yeah, that's effectively what we do for Wikipedia.

So the graph then is like the author is this, the relevant dates are this.

And then how do you pick out when you read text through the computers?

What is the algorithm considering in terms of trustworthiness of the site?

What is the algorithm considering in terms of how do we find the relevant passage in the text we're reading for the query that you're...

It really depends on the vertical.

Can you walk me through a couple of them?

Yeah, so local search, for example, like restaurants and whatnot, really focuses on, 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.

I'll be too broad. And so for that one, once we hear those local search, we have to figure out the what and the where and pull that out kind of semantically from the query and then do different things with them, 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?

Are you talking about Paris, Indiana?

I know there's a bunch of Parises in the US.

I don't know if it's from Indiana.

And same thing with the what.

Is pizza a 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, Stack Overflow is another example, which is programming instant answers.

That has a lot of special characters that you have to do stuff with.

People type in programming pluses and less than, greater than signs.

And in other contexts, you would ignore those.

Right. But in the programming case.

They're super relevant.

Yeah, they're super relevant.

So 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 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 answer.

Well, one thing about local, which is interesting is you can do that so without tracking people on DuckDuckGo 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...

No matter what browser using Chrome, Internet Explorer.

Well, there's some location built into your IP address.

So when you ever connect to anything, you send your IP address over and so you can get a rough location based on that.

You also have something called the browser location and sites request, can you use your location with this app or this site?

That'll send a more granular location based on GPS on your phone.

And so on DuckDuckGo, if it's a very hyper local query, we'll ask for that, would you allow us to use the location?

But we promise to...

Throw it out. Throw it 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's 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 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 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 wading 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, DuckDuckGo, you get to play gatekeeper.

Like do you get to pick winners?

There's a big gatekeeping role.

And I think that's 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 time is trying to give people choice.

And so like, when we have map results, for example, people can choose which provider they want to do the directions when they go off of DuckDuckGo 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, you can't give, you run to a paradox of choice model, just like or Hicks law, it's like, you give people a billion choices.

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're 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, but even then, like, if we're not here yet, because it's not in 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, you had like a favorite, right, you could choose and then be like, okay, see more of that on when you get those kinds of 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 take most markets.

Because I'm thinking 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 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.

No, I mean, there definitely are equivalent ways to get noticed.

But what you're basically saying is, which I think is generally true is your capitalism in general has scale effects in a number of ways, just kind of is 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 US markets in the past 20 years.

Not even online, just even offline in sorts of industries.

For example, what comes to mind?

Oh man, I just read this book that was the myth of capitalism that had all sorts of examples.

And now they're escaping me, but from eyeglasses was one of them.

I think it was like oil refinery.

Oh, because they're effectively the lenses are controlled by one.

Yeah, it just ends up being scale.

So it's all the same effects.

People get bigger. They buy up other companies.

There's been a lot of acquisitions, you know?

And nothing nefarious necessarily.

But the concentration.

Over time, the concentration becomes more and more and more, and that creates less innovation.

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 wealth inequality.

Yeah, but we don't necessarily 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, 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 couple of 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.

It's 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.

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 that.

Yeah, exactly. And then even that, the subset of the employees who are making lots of money is lower.

And that's very different than say like a Walmart who employs like a million people or something in the US.

And so over time, the rise of online and bigger companies has created some of the wealth inequality, at least that's the 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, Dr. Go is obviously one of them, but what are the other things people can do to reduce their or increase their privacy online?

And let's start there.

Yeah. So Dr. Go wise, that's been our goal is to give the one download you need.

Right. And so on iOS, Android, Chrome, and Firefox, you can download either browser extension or our browser.

And it has all the kind of essentials for search and browse.

Right. In addition, we have 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 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.

And for all these services, there are generally like more private alternatives, sometimes really private, but also just getting off of Google and Facebook brand helps you not put all your eggs on basket.

And so for email, there's fast mail.

It's not just built for privacy, they're just an alternative paid email provider.

And so moving your email off of Gmail on something else.

The company that provides search.

Yeah, you want to separate your kind of data as best you can.

Independent of all of that, there are a bunch of all these like people sites that like you look up your name and you see like Shane Parrish or whatever age, whatever, you can opt out of most of those.

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.

I'm super happy to have Shane Parrish, Google that, there's 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 this, it'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 that we talked about using Tor or something like that.

But in terms of just like, no sacrifice, very seamless.

I would use something like TechDiko, 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 a lot, maybe more, I'd 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.

It's 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 yeah, quitting Facebook has had very positive effects for people.

So not only the the ear 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 substitute with something else, which is probably 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 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 that were very like you get emotionally charged.

Yeah, yeah. And it was just like, it wasn't constructive debates.

It was like ad hominem attacks and things like that.

And that's just a lot of negativity.

And so it's like, you're cutting out negativity.

I think that's always a good idea.

You know, it's kind of like the there's not a mental model like the 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 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.

You ever listen to intelligence squared that podcast.

It's pretty good. You only listen to one, the knowledge.

Fair enough. Oh, it's a they've done maybe 200 of these.

It's a structured debate podcast.

They have a topic. I've had a bunch of social media ones like a social media good for your bad for your kind of thing.

They have four really good experts on and then they play both sides of it.

Conversation, moderate debate.

It's really good. And it's totally civil discourse.

We actually listen to it with our kids.

A decent amount. How old are your kids?

10 and seven. And yeah, so I think something like that would be good.

I've worked on a project with somebody else who's been working for a couple of 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 in 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.

We were kind of envisioning is a part of the problem is kind of a bunch of mental models in here, but people effectively just talk past each other and a lot of these kind of debates.

And so take something like climate change.

There's actually like 10 different debates with climate change, probably more.

And I made a flow chart one time to try to isolate.

Okay, if you're going to argue about the individual argument, which part of the argument are you in?

Okay. Do you believe it's man -made?

Okay. Do you believe it exists?

If you believe it's handmade, do you believe we can do anything about it?

You know, do you believe it's, if there's harm, you believe it's intimate harm, bringing it down into his mental.

And so like in any particular argument, 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 supposedly 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?

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 out 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 all 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 do you believe or not?

And then if you're going to engage in 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 into like 11 different things.

Why couldn't the result be sort of like one left 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, 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 recent 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 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, 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.

And that's kind of the idea.

Whereas some of these topics now it's just, you don't even know where to start.

What do newspapers do that in 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 someone called like pro con when we were kind of researching for this.

Vox does it interesting.

They have these explainers, you know, which is 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, but nothing's really hit upon it yet.

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 super thinking.

I've read it. It's great.

Great. What, what made you create the book?

So, um, 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 awhile.

Um, but it would literally lapse for like five years.

I could get into it if you want.

But then what happened was maybe four years ago, dr.

Go started a more takeoff 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, um, you know, needed to step up and learn more.

And, 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?

Cause that's really what executives do.

Um, and I got to thinking, okay, what I really think it is 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 onto 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, um, then you can skip lower levels of thinking and have this whole, like higher level conversation really quickly.

Right. Whereas if you don't know these mental models, you're like starting from scratch every time and you, you may, you kind of don't know the design 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 list, I initially made a list of like a hundred things and I asked somebody and I was like, how many of these do you know?

You know, and they were like, I know like 30 of them.

Were these a hundred things that you applied or did you make this list?

Like you went to university one -on -one and you're like, what are the big ideas out of my head?

I was like, these are the hundred things that keep coming up again to Canada again.

Okay. Um, uh, 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 and mental models or did you come like, did you, this is the more of 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 specialize. Yeah, he specializes immediately.

But then that totally kind of ruins your education in a way.

And you really want to know all these things across the system.

So I was what if we just made this like interdisciplinary textbook, like a survey course of everything.

And, um, 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 onto Munger at that point before though, and I hadn't come onto him.

And then I was thinking, well, um, another formulation I had of this concept was, you know, I keep coming back to problem solve like 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 does this have to do with power law?

Or 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, um, wouldn't it be cool if there was something like a problem solver's 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 look at any solutions.

So I started on that road and then that I, that 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 ended up with this list of a hundred things.

And I asked the guy and he knew like 30 and I was like, okay, well that to me is, um, what people's core curriculum should be.

They should learn the rest that they don't know.

Um, 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 list them all.

Right. So I'm like, okay, well I'm going to list them all.

And then I more systematically tried 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, uh, mental models that I used repeatedly and ended up being about, uh, 250.

Um, and that did really well.

Like people really took to it.

Um, and for awhile 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.

Yeah, go read about it.

I linked all the Wikipedia articles.

So it's like, here's the starting point, you know?

Um, and then we internally, we use them, you know, consistently when we're faced with different problems.

Um, and then our, my publisher from our, my first book reached out and was like, well, this post is 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, um, my wife had just kind of left her job as a statistician and was interested in doing it.

And so we decided to do it together, um, ended up being extremely long and amount of work.

And I somehow like forgot how much work it was.

Um, and it took two and a half years basically to turn that list into an actual book.

Um, but now it's done.

So I'm happy about that.

I have so many questions here.

Uh, let's start with like, what are the big five sort of mental model?

Like say a hundred carry the most weight.

Well, what are the five out of this hundred that you think, yeah, I'm curious what you think about that too.

Cause you, you have also a big list, right?

And so, um, so we, what we ended up doing is, you know, the list was like, 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, to, 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, we're going to get all connected.

They're all connected.

Exactly. So we ended up trying to group them into like really, how are they connected?

You know? And so we ended up with nine chapters, um, that relate all about 300.

And so there's like, you know, 40 in each chapter, roughly, but they, but they're in a narrative related fashion.

Right. Um, and so those like general, uh, chapters end up being a lot of the general formulations of things you should know.

So like the first chapter is on bias in general and second time was on unintended consequences.

Third chapter is on using your time wisely, that kind of stuff.

Um, so within all of those though, if you're going to like boil it down and some of this is 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 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.

Cause 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?

So opportunity cost comes up, another one that comes up a ton, which is more rare that I don't think people mentioned as much as forcing function to me.

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.

Right. 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, uh, you know, board meetings often serve this function because it's a forcing function to get you to pile all your metrics and stuff.

You know, even if the meeting is not that useful, compiling all that stuff is that useful.

Right. And you can just in all sorts of ways, like schedule and time to go to 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 meta model that we kind of run through that is this one -on -one standing have to have a one -on -one with them every week.

Um, and that's a, on search for meeting, that's the advisee, it's their meeting, but it's a forcing function to get them to think about, um, anything that is going on that week.

What's really on their mind.

Um, another one we use is, um, every project needs to have a summary update at the end of every week.

Um, kind of like what happened, what's next.

Um, and it's a, you know, it's, it's again, it's a forcing function to get people to think critically about kind of what's going on.

We have, uh, kickoff calls and post Mortems for every project.

Um, also kind of, are you doing like agile sprints in the background or like, how did 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.

Um, but we do have these like kickoff, sometimes mid -mortem or pre -mortems where it's like a forcing function to keep people to think critically about what's going on.

So we had opportunity cost forcing function.

What would be next on your like intuitive list that I put you on the spot.

Probably one I, uh, I mentioned earlier, which is thinking gray.

Yep. And so, um, 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.

Um, but I think that comes up a lot.

The idea there is like, you know, you could view this as confirmation bias too, but once you commit to a decision, it's really hard to escape confirmation to us and you're, you're like committed to that decision.

Your psychology wants you to look for things that affirm your decision.

If you force yourself to actually not make a decision or not, not commit to absolutely believing something.

Right. So like I'm leaning this way, but 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.

Um, there's another people sometimes mean something else slightly different with that, which I also agree with, which is this notion of, um, but, but I categorize something else in the book of called black and white thinking, where it's like things are either, you know, zero.

So there's only two options.

Right. Usually that's completely nonsense.

I mean, usually there's lots of options and there's, there's a whole degree of things.

It's usually not nothing's usually black and white, you know, and in the podcast we do with Annie Duke, she had a really interesting sort of, um, way of thinking about this, which was like, just by default, say you're 99 % certain on everything, never a hundred percent.

And the reason I love her stuff, right.

It's like, well, you've signaled to the other person that you are open to change in your mind.

So now the conversation becomes like what would cause you to change?

Yes. 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 Munger.

One is my favorite one is like, you know, I always know the other side person, the argument, you know?

Yeah. Yeah. And, um, and that's what I think the thinking grade 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. 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, um, we have some unique way of running the company because it's all remote.

So we're not, everyone's remote.

Uh, it's a remote first company.

Um, and so as a result, there's a lot, uh, 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 is a chaos.

Um, every project has a standard scoping template.

And so it has like a background objective, uh, impact and complexity assessment.

And, um, and so when we have a project and have a kickoff call or post mortem, it's in that framework of like, what was the objective of this project?

Like, what are the success criteria is another way we define the objective.

And we can talk about like what it should be.

Did we meet it? 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, we're small company.

I mean, all, I think a lot of companies are like this, but we're competing against companies that have infinite resources relative to us.

And so, um, this notion of opportunity costs, there is, we don't have a lot of resources to waste.

Right. And so, um, one of our kind of core values that we have three articulated is question assumptions.

And so what is the other two validate direction and build trust.

Okay. 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, um, 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 way.

That's cheaper or better or faster, you know?

Okay. And so there's no list of like mental models in the office wall that you're like walking through.

Well, it's funny cause I do have a, I, I, I got to be friends with a guy around school of thought.

Okay. Have you, am I right there?

So he's got, he's got some, um, uh, websites once 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 listed mental models, but they aren't the list like from the book or anything.

Do you, do you think awareness or maybe to what extent does awareness of, um, because I think people get this list of cognitive biases and 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, 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 a foresight, avoid those thinking hours.

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 true to this.

I mean, this is why we have the core value of question assumptions.

And so I think what you need often is somebody else to call you on the stuff.

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 were, we talk about all sorts of things, company things, but also just current events and we apply these models and stuff, but she helps, you know, call me on my bullshit dinner table conversations.

Yeah. And vice versa, you know, and she's got a PhD, but she's got a double degree from MIT.

Yeah. Yeah. She's, well, there's a whole chapter in this book about statistics, what you read.

She, she was, she was the main one on that.

Um, and to make, she was worried that she gets them wrong, you know, she'd say something wrong.

Um, cause 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 the system to be accurate.

Yeah. What is, uh, the validate direction?

And what does that, and how does it relate to feedback loops and what sort of feedback loops do you set up?

Yeah. So validate direction is, you know, this gets to your point about like decision and like, is the project going in the right direction?

And so what we basically try to set up is another mental model we use really heavily enough to go.

It could be in the top five is, uh, directly responsible individual, uh, DRI, which we, um, 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, um, they are the directly responsible individual and it avoids, uh, 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.

You know, same thing in a meeting.

If you have action items and no one's assigned the task right off, it doesn't get done.

Cause people are like, well, I thought, I thought he was going to do it.

Exactly. Right. There's the worst meeting.

Yeah. 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, um, 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.

Um, but they could go off and spin the wheels that you offer in the wrong direction.

And they can do all sorts of things.

And so we try to say is there are a lot of other smart people in the company who may be able to do things faster or better or 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 and say, not stop yourself, right?

Just say, look, I'm going to go do this.

Does anyone have any ideas or object to what I'm going to do?

No one objects. I'm just going to, I'm going to keep moving forward.

You know, the default is, this is going to happen, but you can.

Yeah, exactly. Chime in if you want.

Um, and that works really well.

Cause 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 not knowledge.

And if they do, they can chime in and if not, they're not.

And so that's really like the core operationalizing of the validated direction.

Like that. How does this relate to being a parent?

Like, how do you teach your kids, uh, 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 best right in the book was train executives.

But then when I got into it, that's with my wife, all right.

But this 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 way and then even half of them, they literally don't learn, right?

Like half of 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 driving kids to school every morning and these are just like random examples, tactical examples.

Yeah, more examples the better.

We've been, I've been listening.

We realized like, my kids like listening to the adult podcast as much.

So we started, I usually listen on 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 Theresa May and all the situation going on there.

And so we just listened daily on the way to school and talk about it.

What do you talk about?

Like, what does that look like?

It talk is 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 the European 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 or, or we're told in the podcast in an adult way and trying to make sure they understand it and the logical chain and to like, okay, well, how did they get to this?

And then do you sort of like nudge them to multiple perspectives to like, how does the EU feel?

Yeah, that's why I liked the debates in particular, because you get really intelligent people talking on both sides 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 are you just leaving it open?

Open, generally open.

Yeah. And do you follow up?

Not really. What are the other things?

Maybe we should follow up.

I don't know. I don't know, man.

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.

So one thing I'm more encouraged about is the kids school at the moment.

My kids are too very different.

I don't know about your kids.

Same. So there's different strategies for each.

So my 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 the production value or thought put into every minute of a good movie is really, really high.

It's a really well produced thing.

There's a lot going on there that you can talk about 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.

My youngest is seven.

He's gotten he's really into math and really he's gotten into programming a bit and into watching like science podcasts and things like that.

I mean, not science, but science channels like on YouTube.

Are you doing like scratch programming?

Yeah. He took a they're in like this Johns Hopkins correspondence courses.

So he took a scratch one.

Yeah. This last semester and now he's taking a cryptography one.

Oh, cool. And my seven oldest is, yeah, he's going to come out with like a blockchain.

He's definitely more advanced than I was at this age.

I'm super jealous of what the opportunities they have.

Oh yeah, that's great.

And yeah, my oldest is 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 guess what I'm trying to say is I try to engage with them at what they're interested in, right?

So you try to bring it back to them and in terms of like whatever they're interested in, but relate the context to exactly, let's talk about that.

Um, 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, uh, it's never my PBS.

Um, but two brothers, they basically made online animated, but, but them talking, talking heads to like courses on economics and biology and chemistry and film and all these different things on YouTube.

Um, what was that called again?

Crash course. Okay.

It's really well done.

Um, I put them all in DVDs and so we drive to school every morning.

It's like 30 minutes.

And so, you know, not every day we watch podcasts, sometimes I watch crash course, you know, and do 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 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 it and then relate things back to it.

What made you switch schools?

You said you switched school.

What was the criteria for the new school and like, what made you leave?

We were at, we were at public school and it was generally good school.

Um, they both have, uh, I don't know what it's like in Canada, but it's in the U S state by state, but they have gifted programs and, um, and they had something called GIAP, which was like an individualized education plan for their kind of gifted cent and, uh, center.

But, um, it just, things were moving really slow.

They were born a lot.

They, um, our youngest who's really kind of good at math, you know, he skipped kindergarten and then, um, skipped another grade of math and then passed out of that grade and they didn't really know what to do with them.

And, and it was just kind of born, I guess.

And, um, so this new school is, uh, is, is kind of brand new.

It was only four years old.

It is a, it's 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, um, they, 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, um, and then on regular things like science or something, they're, they're doing a project related to that thing.

And they also kind of force the kids to do it and they have, they fail if they fail, right.

And they don't, they don't like huddle them with it.

Right. And, um, and then they had all these other kind of things, random things like, you know, do they do things to like build resilience?

Like, as you're saying 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.

Kids love it. Yeah.

Because they, um, they're both like super creative and love projects.

And so it's like half the day is like doing different products.

Like Eli's in the fourth grade, they're building an escape room in their project class for the, this semester that they had like two, they split the, uh, 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 all.

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 would go to school.

Oh my God. Seriously.

We didn't start programming in school until grade 12 and it was like Pascal.

Yeah, that was, I mean, yeah, I'm 39.

So yeah, we're the same.

Yeah. That was exactly my experience as well.

But it was great because I started much earlier than that.

So like the coding class became like super easy.

Yeah. It's a great way to get my grades up for university.

I'm with you. That was my path as well.

Uh, 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 again.

Hey guys, this is Shane again.

Just a few more things before we wrap up, you can find show notes at fernamstreetblog .com slash podcast.

That's F A R N A M S T R E E T B L O G .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 fernamstreetblog .com slash newsletter.

This is all the good stuff I 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.

[The Future of Digital Privacy and Strategic Thinking with Gabriel Weinberg]-[Gabriel Weinberg: Practical Steps to Safeguard Your Data and Identity Online]

📋 Summary

The Imperative for Digital Privacy and Strategic Thinking

The Privacy Crisis and Corporate Surveillance

Data Monopolies and Government Intervention

The Role of Encryption and Government Access

Mental Models and Strategic Decision Making

Parenting and Resilience

🎯Key Sentences

📝Key Phrases

📖 Transcript