The Learning Leader Show With Ryan Hawk - 315: Gabriel Weinberg - Using Mental Models To Make Better Decisions

Episode Date: June 16, 2019

The Learning Leader Show With Ryan Hawk #315: Gabriel Weinberg - Using Mental Models To Make Better Decisions Full show notes can be found at www.LearningLeader.com Gabriel Weinberg is the CEO & Founder of DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs.He co-authored Traction: How Any Startup Can Achieve Explosive Customer Growth and co-wrote, Super Thinking. Gabriel holds a B.S. with honors from MIT in Physics and an M.S. from the MIT Technology and Policy Program. He has been profiled in The Washington Post and Fast Company, and is routinely quoted in leading print publications such as The New York Times and the Wall Street Journal. Weinberg is also a frequent TV commentator, appearing on CNN, CNBC, and CBS This Morning, among others. Notes: Commonalities of leaders who have sustained excellence: A desire and openness to grow as a person People want to follow them -- They set up systems for others to succeed They make sure the team is headed in the right direction The North Star -- Must always orient yourself towards whatever that is for you Your personal mission statement Maximize impact on the world -- Where do you want to go?  Define what that is for you DuckDuckGo is an internet privacy company -- Started in 2008 for private search (a competitor to Google). Gabriel discussed how he was ahead of his time -- The secret is something you know about the world that others don't yet.  Search is the most personal thing on the internet.  Gabriel wanted to create an alternate (private) to Google. Mental Model -- A concept for general decision making.  A few hundred concepts that are useful for better decision making Become a 'chef' with your thinking -- 1st principles thinking.  Your intuition can be wrong.  Best practices can also be wrong.  You need to focus on being wrong less. 1st Principles = Most intentional way of thinking:  Question assumptions. Every project has a scoping template: What is the objective of the project? What is success criteria? What are you trying to solve? Does everyone agree? Discussion with team -- Operationalize 1st principles Why the pro/con list is not as helpful as the cost/benefit list: Write down cost over time -- Rate everything vs that Example: Where should we go on vacation?  Rate on a scale 1-10.  Combine cost and benefits. Do a post mortem after every project -- It forces critical thinking and analysis What went well? What didn't? Given those things, how can we operationalize to do better? Why is it rare to do a "success autopsy?" By default, an after action review will not happen.  It must be built into the process.  Our default setting is to move on to the next project. What was it like writing a book with his wife?  Lauren McCann is Gabriel's wife and co-author on Super Thinking "We would walk together every morning and talk about the book."  It became the primary topic of conversation for a long time Charlie Munger multi-disciplinary approach: At DuckDuckGo, this is their goal --> Grow people internally.  They work hard to help their team make better decisions Structure of DuckDuckGo: 70 team members -- fully distributed all over the world Immense delegation happens daily What does Gabriel look when hiring someone to the team? Self starters -- The team is fully distributed.  They have a lot of autonomy and ownership.  People are empowered and must be willing to work without a boss watching them. Question assumptions Great communicator -- There is a lot of written communication when the team is all over the world.  Must be able to write well. Experimental mindset Validate direction -- Run experiments if you have a hunch and then analyze your findings Build trust -- Very key.  There is heavy transparency at DuckDuckGo.  Must be trustworthy. How to find candidates who possess these qualities? Do paid projects as part of the hiring process... Get a feel for them actually doing the job before you hire them full time. Culture: "We have a 'thank you' culture" "Most respectful interpretation" of every interaction.  Give people the benefit of the doubt. Thoughtful and intentional Gabriel's upbringing: His dad was a doctor.  His mom was an artist. How to flex your market power?  Combine two particular sets of skills, go deep learning them (eg. be a great finance person  and public speaker.  Look for gaps in the market or within your company, and use your unique skills (like Liam Neeson in Taken) and attack the problem.  Most people just do what they're told.  Don't settle for that. Why shouldn't we trust our gut? Availability bias - May not remember all the options Confirmation bias - the tendency to interpret new evidence as confirmation of one's existing beliefs or theories. Use it as a hypothesis generator, then question it.  Don't fully commit until the necessary work is done. "Thinking gray." --> Delay decisions until they absolutely must be made. Jeff Bezos opens a door, but may come back through it.  "We'll do this now, but we may walk it back." How to build trust? Vulnerability speeds up the process of building a trusting environment. "Relationships move at the speed of vulnerability." Anders Ericsson -- Deliberate practice. Work at the edge of your comfort zone.  Receive coaching in real time. Hire an executive coach Create a board of advisors Day to day -- check your thinking and explain it (write, give speeches) Writing is the best form of thinking critically --> "It's the best way to clarify my thinking" Overall life advice:  What is your north star?  What areas do you want to pursue?  What are you current skills? Find your highest leverage point, study those areas More Resources: Read: Super Thinking  Follow Gabriel on Twitter: @yegg Be part of "Mindful Monday" -- Text LEARNERS to 44222 Connect with me on LinkedIn Join our Facebook Group: The Learning Leader Community To Follow Me on Twitter: @RyanHawk12

We have three core values that we really align everything on. Question assumptions, validate direction, and build trust. And what it really comes down to is being able to communicate well and have an experimental mindset and really make good decisions on the fly. This episode is brought to you by Roan. Roan is the maker of the most comfortable dress shirt ever made. The luxury performance alternative to the classic dress shirt, Roan's commuter shirt utilizes your body heat to release wrinkles naturally so you can ditch the dry cleaners.

It's got four-way stretch material which leads to immense comfort. The commuter shirt fabric is soft, lightweight, and breathable so you can stay cool despite long hours at the office. It's moisture wicking, the incredible Italian fabric wicks away your sweat to keep you dry and corner office comfortable regardless of the conditions. Some of my favorite Roan gear is found at Roan.com slash hawk. That's R-H-O-N-E dot com slash hawk. Welcome to the Learning Leader Show. I am Ryan Hawk. Thank you so much for being here.

Texts learners to 44222. In order to join tens of thousands of learning leaders from all over the world, receive mindful Monday updates what I'm reading, watching, thinking about, and writing. give you the opportunity to be a part of my book launch team. Text learners to 4422. Now on to tonight's featured leader, the CEO of Duck, Duck Go, it's Gabriel Weinberg. Duck, Duck Go is the internet privacy company that empowers you to seamlessly take control of your personal information online without any tradeoffs.

He's also the author of a couple books. Most recently, he wrote with his wife. It's called Super Thinking, the big book of mental models. A few of the topics we got into, flexing your personal market power, meaning how you can create a sustainable, competitive advantage in the marketplace. Some great ideas, tips, action steps you could put into play right now. Then the unique qualities Gabriel looks for in the hiring process and how this impacts. you and your desire to build a dream team, then why you should not trust your gut instinct and what to do instead? Ladies and gentlemen, I promise this one will make you think it's so good

with Gabriel Weinberg. All right, Gabriel, so good to have you here on the Learning Leader Show. Welcome, man. Thank you. My pleasure. I'm curious to get us going. You have spent a great deal of time studying and surrounding yourself with some leaders who sustain excellence. And from your perspective, what have you found to be the commonalities among those leaders who sustain excellence? Yeah, I mean, I think there are, it's plural, right? I think there are a few different things. One is really just the desire just to grow as a person. I mean, as a leader, it's not like just one skill or quality that's necessary. There's a whole host of things. There's a whole host of things depend on the situation. And you need to be open to really growing and learning to whatever

is coming before you. And then the second thing is any great leader by definition is having people following or working with them. And you need to set up all the systems and processes to help those people around you succeed in the best way possible. And so there's a whole set of kind of ways to do that. And then the third piece of that kind of three-legged stool, I think, is to make sure you're headed in the right direction, right? So you can arrange people the best way and have them work on things, but if they're the wrong things, then you're kind of just wasting everybody's time. And so you need to have some kind of process to figure out if you're working on the right things as well. What is your, so you're the CEO of Duck, Duck, Doe, so you're running a company. We'll talk

about what Duck, dot Go is here in a second, but I'm curious, what are some of the ways that you make sure you're headed in the right direction as the leader of a company? Yeah, I mean, the most central one is this model or concept called the North Star. And so the basic idea, the North Star in reality and like the physical world is this star Polaris that's pointed pretty much direct or oriented directly north with regards to the Earth. And so it hardly never moves in the sky. And you can orient yourself and navigate towards north or another direction by following that star. And as a metaphor, the North Star is like your personal or the company's mission statement. And effectively, if you have the North Star, then you can point in that direction.

If you don't have it, then you're kind of a drift. So the North Star for DECO go is to raise the standard of trust online. And kind of my personal North Star, at least in a professional context, is to maximize my unique impact on the world. And knowing that, then you can make all sorts of decisions and kind of at the very top high level gut check, whether they're moving towards that NarF Star or away from it. And if you're generally moving toward it, you're at least moving in the right direction. Let's say there's somebody listening who has a really good job, Gabriel, they're a mid-level manager type. And they have kind of risen the ranks for this portion of their career.

However, they've never truly defined what their North Star is. And they hear you say this. It's piquing their curiosity. And they're saying, interesting, how or what should I do for myself? What advice do you give to that person who perhaps hasn't defined that yet in their career? Yet they have been successful. They're doing well, but they want to do better. They want to make sure they're aligned properly.

What's the right process to define that for a person themselves and their career? I think you really need to think about where you want to go. And it doesn't have to be forever, like on your deathbed where to go. it could be the next five years, 10 years, but it's kind of like, are you trying to maximize, people can have all sorts of different North Star, so I'm not criticizing, but it could be that you really want to make the most money for the next 10 years, so you could become financially independent. It could be that you really care or are passionate about a particular field just because you're really happy working on that field and you want to become a leading expert in that

field, so it just gives you more opportunities to do something in that field, whether you stay your organization or not. It might be that you're motivated by the mission of your organization, and your whole goal is to do whatever it takes to advance that mission, and you don't really care what you're working on. But those three North Stars, which are all fine, would have you do very different things as kind of the next stage of your career, projects you pick, jobs you might take. And so really internalizing which of those, and there could be many other ones that you choose, is really the goal that you have for yourself will really help you make better, just ultimate career decisions.

We brought up the fact that you're the CEO of DuckDuckGo. Can you explain what Duck, DuckGo is and why you started it and how it's going? Sure. So Duck. Dock Go is an internet privacy company, and as people have been much more aware in the past two years, there's a lot of bad privacy practices on the internet. And Duck, Duck, Go is really designed to help you avoid those kind of privacy, sinkholes, pitfalls, traps, etc.

and it's a simplified product where you can just download that. Go and get all the privacy essentials you need in one download to give you a little piece of mind online and reduce your digital footprint. And in particular, those essentials include tracker blocking. So block kind of Google and Facebook trackers across the web. It includes encryption to make you go to encrypted websites so your ISP can't be tracking your browsing history.

And where we started, it also includes private search. So we've been running a non-tracking alternative to Google, search for the past 10 years, kind of our roots of the company are in that. And then we expanded into this broader privacy offering. And so, yeah, I started it back in 2008, so it was a while ago. And we started out as this search engine alternative. And honestly, it was a third depending on an eye account, kind of third company I worked on. And this whole North Star concept was at the center of it. I really wanted to, I wasn't necessarily aligned as much with the work I had done before in the way that it wasn't my ultimate goals. And so I did take a step back

and try to find something that I was particularly motivated to do. And that ended up being ducted I go. I, yeah, I was on using the search engine. And it's really interesting to see, I didn't even know this existed prior to starting reading a lot of your work about mental models. And that led me to your company. So it's interesting how people get to where you are. You seem to be. You seem to be ahead of your time. 2008, when this got started, I'm trying to recall back to my mindset at that point, but I wasn't thinking nearly as much about, I guess, privacy or how we're tracked. And now that seems to be a new story on a daily basis.

A lot of it from Facebook, but others as well. It felt like you almost could see the future here. What made you think of this, you know, more than 11 years ago before? felt like that this was as big of a deal as it is now. Yeah, it's a bit of a happenstance, but it hits upon some kind of mental models that help people think about how to make interesting bets on the future. And one of those mental models is the concept of a secret, and it's really, the colloquial term, a secret, just something you know that other people don't know.

But as in terms of like a business context, it's something you know about the world that other people don't know that, you know, is going to basically become true. You have high conviction. It's going to become true. And if you know that, you can kind of build an interesting business or company around that. And so what happened was, is I actually started it as a search engine because I was more interested in search. But I was extremely receptive to feedback and thinking about things. And I have a graduate degree in public policy. And I immediately started getting questions from early adopters around privacy. And it really compelled me.

Like, I think other people might have dismissed that, but it compelled me to do some research on it. And what I realized was search is like the most personal thing on the internet. So people basically typed their most private thoughts into their search engine, financial, medical, personal problems, you know, like the itch you have, etc. And then I also realized that you don't need to track people to make money in web search. Because all the money is basically made. off of keyword advertising.

So you type in car and you get a car ad. And then it occurred to me when I looked into this further, because I'm also an angel investor and was starting to get pitches around advertising online, that more advertising was moving in more and more of direction away from this contextual advertising, which doesn't require any information about you, to this profile-based advertising,

so-called behavioral advertising, where these companies are amassing huge profiles about you and selling, trading them back and forth to do this kind of creepy advertising that's probably around the web. And I could see the path from that was just going to get creepier and creepier and creepier because there's really no regulations against it. And so if companies could do it to make more profit, they're going to do so. And then I realized, you know, we could really be an alternative to that because there was

no counterbalancing force. And that's what, how I became interested and kind of set off down that path. Wow. I love, love that it exists and that it's here. and I only see this, obviously growing, people are going to be attracted to this. So let's jump into some of the ways that you think. You've written a new book called Super Thinking, the big book of mental models. Can you first define what a mental model is?

Yeah, absolutely. I mean, it's effectively a fancy word for concept. And so, you know, there are concepts everywhere, right, in every discipline. So in math, you have addition in political science. you have democracy, in economics you have currency, but those concepts are generally applicable to those disciplines. Then there are a set of concepts, and I'd call those all mental models, but a set of what I call like super models, which is why the book's called super thinking, that are maybe from a certain discipline, but they really apply well beyond just to help you

in general decision making and problem solving. So I was a physics major in undergrad, and an example from physics is critical mass. So you need a critical mass of nuclear material, to start a chain reaction for nuclear energy and nuclear bombs and things like that. But the concept of critical mass, the mental model, is useful well beyond. So products and companies and ideas and even like things like house parties and political parties can all reach critical mass. And if you know that a concept like critical mass applies, you can automatically think at a higher order level. Because you can ask things like, okay, well, how can I reach critical mass faster? Maybe what's exactly going to happen when I do reach critical mass. And what I found was there's about a few

hundred of these concepts that are just generally useful as shortcuts to this higher level strategic thinking. And what I wanted to do in the book, me and my co-author, who's also my wife, incidentally, was really give people a compendium of these concepts. And a lot of them could be a whole books to go deep into them. So we weren't going super deep. But we're giving you effectively a survey of all these concepts that you often don't learn in school, but if you knew altogether, you'd be a much greater decision maker. And many of which I wish I had learned, you know, 20 years ago is kind of the book that I wish someone had handed me when I got out of college. It's definitely a thinking person's book. There's a lot of thought put into a ton of great science combined with stories, which is my favorite

style of reading. I'm going to dig into some of my notes from it if you're cool with it. One that jumped out to me. So I spoke with, uh, Tim Urban over a year ago now. You've probably heard of Tim because he's written about some of the same stuff that you have, particularly what it means to be a chef with your thinking. The example

Tim used in his was with Elon Musk, but you've written about what it means to be a chef and arguing from first principles. Could you describe how let's say a person is listening right now? They haven't read anything from Farnham Street like Shane Parris writes about since he's big into mental models.

They haven't read anything from you yet. So this is their first exposure to this. What does it mean to become a chef with your thinking? Yeah, absolutely. So just to frame it a little bit, you know, there's a lot of these concepts, but they're really interrelated and they're grouped. And so what we tried to do was group them into themes, right? And first principles is all around this effective theme of that your intuition can be wrong. and also people in what they're doing in the world

in the kind of the quote unquote conventional wisdom or best practices, it can also be wrong. And you don't want to be subject to all these different biases and kind of flaws and traps and ways to fall into kind of wrong thinking. And so to be wrong less, you kind of need to do the opposite approach and you have these frameworks and mental models

you can use to be much more intentional and make sure you're getting to the right answer and not falling into these traps or what we call anti-patterns. So first principles and kind of first principle thinking is the most intentional you can possibly be with something. It's basically saying, I think we should do X,

and you're kind of justifying whatever that decision is by literally writing down your basic assumptions and trying to make a clear, logical train to get to that conclusion. And why Elon Musk is a great example is, you know, he started a few different companies in industries that people thought there could not be a new company.

And in effect, he's done the same thing in most of the industries, electric cars and in space and in solar. He's come in and offered something at a much, much cheaper price. And what he's done is really thought from first principles and said, well, why is this thing so expensive?

If I look at the constituent like physics of the situation, like how much rocket should cost if I add up the fuel and the metal, he got to an answer that should be much, much cheaper. And from that, he tried to question the assumptions of the whole industry and said, well, maybe if we do it a different way, I could just do it a lot better and cheaper.

And that's really what First Principles thinking is all about. How does it apply to the regular person? Most people listening don't have the intellectual wattage of somebody like Elon Musk or even somebody like you. So how, if we put this in layman's terms for the day-to-day problems and issues that most people, deal with, whether it's at home with families or at work as that person who's just trying to make a few good hiring decisions so that their team can improve. How would we relate it to that? Yeah, absolutely. So the way we've operationalized this at Duck.

Go is every project has what we call a scoping template, and every project has a particular life cycle where we have a kickoff call and a premortem and a postmortem. some mid-mortem. And what we do on the initial call is we first write down what is the objective of the project and the background and what is the success criteria of the project. And that sounds very simple, but it often isn't. And so the first step is whatever you're doing is being extremely intentional about what you're actually trying to solve with whatever project you're doing. And then we get on the phone and have this kickoff call and we say, does everyone agree with that? And pretty much every time the answer is no. And that's where the first principles thing can come in, because you write down the objective and people ask, well, I don't necessarily think that should be the

objective. And then you have this discussion of really what should the objective be and why. And the why is the principles. It's because of X, Y, and Z, I think we should do A. And somebody else will say, no, I don't believe in Z. I think that's wrong. Your facts are wrong. I think because of X, Y, and W, we should do B. And that's that kind of discussion is the operationalized first principles thinking. And it just is a way to force yourself to think critically, even about little decisions. So like personally the same thing. It's like I have two kids and a family, you know, my wife and I wrote this book, but are even little things like vacation decisions or where to send kids to school, which we recently switched to kids schools. You could have the same discussion and say, what is our real

objective here. Why do we think they should switch schools? Let's try to write down and be intentional about what our really reasoning is. That's effectively what you do. So I've read that from you, actually, that there's a better way than the pro and con list. Let's actually make it a little bit more light and fun. Let's say you're trying to, you and your wife are deciding where to go on a family vacation or couples, whatever. You're deciding where to go on a vacation. And like I said, I know there's a better way than a pro and con list. And a lot of people make pro and con list when they're deciding to change jobs. So that could be a more serious one that we could tackle as well. But let's stay fun for now. If we're trying to decide where to go for a family vacation, how do you and your wife go about

making that decision? Yeah. I mean, I like to beat up on the pro con list a little bit because it's just the go-to decision-making framework for everyone, basically. But there are many others, and we literally have a whole chapter on it. And so the most simple one to move away from the pro con list is something called a cost benefit analysis. And in the extreme, like whole governments use this for most government programs and companies use this via spreadsheets. And what you basically end up doing is writing down all the costs over time for something and all the benefits over time for something. And then you can get a numerical answer and really compare that across different options. But for a vacation or a personal list that might be overkill. And so the in-between what you can do in a pro-con list is effectively

rate your pros and cons. You could use a one to ten scale or if you want to get a little more intense with it, you can put dollar values next to it and get into why that's better. But that enables you to do a few things. One, you can combine certain costs and benefits. Some of the pros and cons are are probably interrelated. So you can relate them together and give them one score. And then what you can do is you have the pros and the cons and you have. scores on both the positive and negative plus and minus, you can combine it all into one kind of waiting. And then you can go and say if you have multiple vacations, you can compare those and say, look, for this criteria, this vacation is scoring a lot higher. Now, the first time you do that,

you might be like, well, I want to dig into my methodology and maybe I want to change the weightings a little bit and think about that. But ultimately, you get a more objective measure than kind of the fuzzy pro-con list. Because what happens with a lot of people is they write the pros and cons. and then they're like, eh, I don't really know how to make a decision. There's a bunch of pros and a bunch of cons, right?

Exactly. Yeah. And like I said, most people, I think I've been in conversation with friends and colleagues and they're making this list of, should I change jobs?

Should I leave my company and go there or do that? And they make this huge list of pros and cons. And like you said, they're still kind of stuck. Well, like do the pros outweigh the cons and it's still hard to make

the educated decision. But real quick, Gabriel, one thing you said that I think is important. I am a big fan and believer on doing an autopsy of success. I think in big corporate world, which is where I grew up for 12 plus years before leaving to do this full time, is whenever things went bad, we would have two-day off-sites. We would have these what-if meetings, you know, like, what if we tried that? you know, we would do all these different themed meetings. We'd bring in people and, and we'd spend a great deal of time when,

when a quarter or a year went bad. However, when it went well, we did nothing. We would just go on to the next year. Oh, it's great. You know, smack, high five and we'll be on our way. And it always bothered me. And I'd like to bring it down to at my level or for my team. And I'd want to analyze, why did we have such a good year?

Did we get lucky or what was it, you know, and I really do an awesome. autopsy on that, like you said, a post-mortem no matter what. And I enjoyed reading this about how you work on your company. Why is this so important to make sure that we do an after-action review, regardless of the outcome, whether it was good, bad, or in between? Yeah, I mean, it's a great point. This is upon one of my favorite kind of mental models altogether, which is this concept of forcing function. And it's something that you're going to do by default, like a post-mortem that's going to force you to think critically. And the reason that's so powerful is because if you put it in your calendar and make sure you do it

after every project, it doesn't have to be every year. Like we do it literally after every project. It's a feedback loop that's built in of critical thinking. It'll help your organization compound its good thinking. So after every project we do this, and let's say it's a good project, like you said. Like everyone's having high fives all around, right? And the post-mortem template really asks three questions. what went well, in this case a lot, what didn't go so well, there's always something there.

Even in a great project where it had great success, I can guarantee when you ask that question and have people think about it across all the stakeholders, there's something that didn't go perfectly. And it may be just that people didn't communicate as well, maybe that, hey, the project was successful, but it could have been, we could have saved two weeks if we had done X, Y, or Z. And then you dig in and say, okay, given those things, especially in a moment where everyone happy because they're more willing to talk about it, let's try to operationalize that we can improve for future projects on those things we identified that didn't go well. And that's the

third question is like, what can we do better next time? And just because something went well, doesn't mean it couldn't have gone more well. And so I think of that time when things did go well is the real time when people have time to actually adjust and become better. Because when things are going really poorly, like everyone's stressed out. Everyone's just kind of heads down and like they're not in a really self-improvement mode. They're in kind of a flight-or-flight response. But when you're in a happy time, that's the time where you can actually work on things. This seems so obvious yet it's rare.

Why? I think it's rare because people, it's exactly why the concept of forcing function is so important. It's because by default, it won't happen, right? Because if you're not going to step up and say, let's have an extra meeting. after we just had a party, you know? And so if it's not built into the process, it just doesn't happen. And so I think you have to really build it in. I agree.

I'm curious. I don't know why I thought of this because you wrote the book with your wife. And so this is a little bit of the left-hand turn. But what was that like? Did you have regular review sessions with her to say, ah, this chapter, we're just not, we're not there. Or this chapter is fantastic. Let's analyze why.

Were you having these post-mortems as you're writing the book with the love of your life? I mean, what was that like? Yes. Unfortunately, I don't know if we ever had this chapter is fantastic. It was more on the, we need to improve this. How do we improve it? But it was a very interesting process. I'd never really worked with her that closely in a professional setting.

Now, we walked together like every single morning and have been talking about these concepts for years. And so in that sense, we had a lot of like previous ground that we could draw on. But in terms of this actual writing process, I had written a previous book, but she hadn't. And it was a lot of just, yeah, back and forth. And I'll be honest, it was a slog for a long time. This book took basically two years of intense writing to get done. Were there some really rough patches between you two as you're throwing ideas back and forth? I mean, I think that would be normal, but I'm curious.

Um, not as much as you might think because like there, there really wasn't a lot of ego in this. Yeah. If at all in terms of like, you know, she was like, this is bad. Um, I'd be like, yeah. If it was yours and she said this is bad or she said, this is mine and it's bad. Like how, how would that go? It was me or the reverse. Like I, for whatever reason, maybe it's because we could already sense that, you know,

there wasn't a lot of defensiveness or eagerness with it. It was more like, yeah, I agree. You got any ideas? Because I don't have any ideas. And then it was more of a brainstorm about how to fix it. Because part of the problem with this book is so many concepts, and we didn't want it to look like an encyclopedia. We wanted to be nicely narrative.

And we also wanted to provide examples that you could apply in your personal professional life. And so a lot of the problem with this book was that if you just let go and started writing whatever you could find, it would be like 5,000 pages. And so we had to compress it down. And so a lot of our time was spent really editing down and on keeping it to the essentials. And so that was a collaborative discussion of like, what can we cut? What is the best example, et cetera?

I think I, you know, correct me if I'm wrong. But Charlie Munger is one of the, I guess the titans when it comes to this, this going through life practicing a multidisciplinary approach, meaning it makes your life more fun, constructive, more helpful to others. Is that what initially turned you onto this, somebody like him and reading his work, or what was it that got you on to mental models and going about life in this manner? Yeah, that's right. He had given a speech in 1995, which I came across, it was like a commencement speech in the early 2000s. And he basically said in that speech, he listed out a bunch of models he uses. And, you know, he's for people who don't know, he's with Warren Buffett. leads Berkshire Hathaway, one of the most, you know, they're the best investors in the world and

one of the biggest companies. And he credits their success with thinking, at least from an investment lens through these mental models. And one of the things he said was there were about 80 to 90 models that carry most of the weight and make you a worldly wise person, but no one, including him, has ever written them down. And so part of the idea of the book was actually systematically try to write down what are all those models. So yeah, I first heard a speech and then I happened upon a book called Predictably Rational by Dan Ariely, a behavioral economist who had written a lot of the biased ones at least altogether in a book and I was just hooked. And then I basically started making lists and that lists eventually became the book. And I believe there was a 37-minute

medium post a couple years ago. You're right two or three years ago, I believe that was that kind of the genesis of this book? Yeah. What happened was is internally at Duck, DuckGo, we have really tried to grow people as much as possible. And as we've grown, we've tried to promote from within. But a lot of the people weren't traditionally trained as executives. And so we weren't hiring a lot from the outside. And I was trying to help coach people. And what I feel I realized a long time ago is you need to learn all these models to be a really good decision maker, which is a lot of what middle tier, you know, at higher tier executives are. They need to be good decision makers. And so what I did was I started making that list internally for us. And eventually I got it in a good enough

forum that I just put it out there. I wasn't expecting it to be as well received as it was. But other people really wanted the list too. And then my publisher, who published the last book, reached out and was like, do you want to do this book? And then I, for some reason, said, yes, not realizing how much work it took. So that post was just a list of all these models. And it was organized by discipline. So here's all the physics ones. Here's all the military ones. Here's all the economics ones. But that's really not the right way we realized to really learn them and write a book. You really need to mix them all from different disciplines and organize them by categories. So we have like all the models about unintended consequences, which cuts across a lot of different things and all the bias ones and all the productivity ones.

And so it really took a long time, yeah, three years basically to get from the list to now. How many people work at Duck.com? We are, I think, 65 to 70 people. I'm losing count, but somewhere around there. And people are located anywhere? Yeah, we're completely distributed. And so I think we're in, I should have these numbers better, but something like 15 countries, you know, just all over the map. Wow. So how involved are you in the hiring process now as the CEO? So what I have generally tried to do is delegate, find ways to grade processes to delegate everything that I'm doing, except things I absolutely have to do. And in that case, I question that and see if I can.

can hire somebody. And that's been my continual job over time. So I was extremely involved in the hiring process for a long time and then setting up the hiring process. But now I'm really not. I am, I do an interview. I'm the last interview with everybody. So I insist on interviewing everybody. And most of the time now, our hiring process is so good that like it's not really an interview. It's more my opportunity to set the values and the vision and kind of connect with people before they come internal. But that's my current role in the process. So outside of the necessary skill for that particular role, and you could think back to maybe

the earlier days or now or both, I'm fascinated by this process of what high functioning, high performing leaders, what they look for, the characteristics and people to join their team, right? So for a moment, set aside, okay, well, they. have to be able to, they have to be an engineer to do this. So let's set that aside. But let's talk about just the person and the qualities and the makeup. What are the ones you really look for in somebody to join your team? Yeah, this is a great line of questioning. So we are kind of unique, like we're a distributed, like we said, which means that you really have to have self-starting

people in the company. So taking a step back, like each company is different, right? And so someone who succeeds at one company may be less successful at another. But, But for our company, you really need to have skills of autonomy and kind of ownership, because we're very distributed, even hierarchy-wise. We don't have a traditional hierarchy. And so people are really empowered to kind of run projects and really kind of do their own work. But on the flip side of that, you have to be comfortable with doing that. And we have three core values that we really align everything on.

Question assumptions, validate direction, and build trust. And what it really comes down to is being able to communicate well. and have an experimental mindset and really make good decisions on the fly. Now, to figure those out, which is your real question, is difficult, right? And one thing I learned early on is that it's extremely hard to do from an interview. And so what we end up doing now is we have paid projects for people that are tuned to each role. And they're designed not really to test, I mean, we try to get out functional expertise a little bit, but to your point, they're more designed for general problem solving thinking.

And so for engineering, our first project actually is don't even do an engineering. Take this engineering problem and write up like a project proposal of how you would think about attacking this problem. And from that, we can see if people can really communicate effectively and organize a message and thinking to their colleagues and write about it clearly.

And that in and of itself is like an amazing correlative factor to how well they're going to succeed. Hmm. Can you repeat those core values again? Question assumptions. What's a validate direction? Validate direction? Yep. What does that mean? So validate direction at its core is like running experiments. So I have a hunch. I'm going to go think about doing this and get a little bit of data to prove that I'm going in the right direction. Gotcha. Okay. And what was the third one? Build trust. Build trust. How does that work? I mean, it is key. if you're a distributed company to work on this every day.

And what it effectively means is, you know, I trust my colleagues are going to do what they say they're going to do, right? And if you have that kind of trust, then you can really exist in this kind of distributed autonomous organization. Now, how that's operationalized is in a few different ways. One is heavy transparency. So all of our projects are organized in one place and they all have the same kind of standard template and everyone can follow any project.

And so if you know that's happening for every project, you inherently trust things are going well. And then there's a set of kind of cultural norms that we developed that really help collaborative trust. And so we have something called the thank you culture where people are calling out each other's good behavioral and things that they're working on that are really gone well. We have something called most respectful interpretation, which is another model that says, you know, basically give people the benefit of the doubt, especially on text because we write a lot of asynchronous stuff because we're in different time zones, you know, people can interpret things in negative ways. And we basically say, hey, don't do that, you know, give people the benefit of the doubt. And then we do other things like we have something called neighbors where every Friday we connect four or five people together, just randomly,

random colleagues across the, it literally is random across the company. And they get together and they just basically hang out. Some of that kind of thing would happen naturally if you were in one, environment, but because we're all distributed, we have to kind of make a process for it. You mean the hangout on Zoom or Google Hangouts for something like that? Zoom. Yep, exactly. Okay. Wow. I just love the intentionality behind it. So one of the, the question I'm asked the most, Gabriel, is what have you found after talking to 3010 plus of these? And the two things that come up the most to me are people who are extremely thoughtful and unbelievably intentional.

And that's, I'm just feeling that you exude this in the way it feels like you approach your business and life. Yeah, I believe in the intentionality. And I agree with that. I think if that, that is probably one thread. And really the premise of the book is you don't want to just go through things happenstance, right? You want to think about, is this really the right approach? Have you always been this way? Yeah, I have to say, I think so.

Yeah. Where does that stem from? Is that something for your upbringing? Like, what were your parents like? What was your upbringing like? I think I have a relatively, you know, normal upbringing. My dad is a doctor. My mom was in kind of art, had started her own clothing business at some point.

And I don't know. I'm sure we should give credit to them. But I don't have a direct line from upbringing to now, you know? Yeah. I got you. So let's get back to the person who's trying to build a fantastic career, regardless of what part they are in the company where they work. One of the things you've written about is how to flex your market power. Basically, how can you build a moat around yourself?

And I get this from if you are the CEO of a company and how you're, I mean, it's much easier said than done, obviously, like most things in life. But for that person who's trying to build a great career for themselves, one of significance. where they can make a positive contribution to the world, to their business, to the people around them. And you write about flexing your market power and building that moat. What advice do you give to that person who is in that particular position in the middle of their career, in the middle of a company to say, how can I do this?

Yeah. We have a lot of illustrations and memes in the book. And one I like, because we try to pick from movies, is the scene from Taken where Liam Mason says I have a very particular set of skills. And it's a really good metaphor for this concept. And the basic idea is if you have a very particular unique set of skills that the market values, you can really flex a lot of market power. In this case, if you're an individual, meaning you can demand interesting jobs,

interesting salary. People are kind of seeking you out because of your unique skills. So the question is, how do you develop those unique skills? And it can be happening in a couple different ways in different contexts. And a more general kind of whole career path, I think the easiest path to doing it is like going really deep in something or combining like two deep things from different disciplines. Like if you were like a few years ago, just as an example in engineering, if you were a developer but also were interested in operations, keeping servers up, there was a whole new field called DevOps, which mixed the two. And if you were at the forefront of that, you were in complete demand.

And there's so many examples of that where you're the person at the company who then becomes indispensable and the go-to person for X, Y, or Z because of your kind of deep and interesting skill set in that. And I think you can really cultivate that pretty easily by looking around and kind of looking for gaps or power vacuums, as we call them, and trying to fill them. And then all of a sudden you'll wake up and people are coming to you. That's a sign that it's working because you're the person that everyone should go to for this thing. That's when you can tell you're developing these unique set of skills.

And most people aren't doing this. No, I don't think so. I mean, I think most people kind of do what they're told. And sometimes it happens naturally. But I think this is, again, kind of more intentional and take some initiative to say, I'm going to step up and become like the company. It could be as simple as I'm going to be the company expert on this part of the company process. And I'm going to even raise my hand and say, hey, anybody, if you want help with this,

I'm willing to help you, right? And that's a really quick path to kind of be in this person and kind of jumping up in your career. I remember early in my career, my dad told me if you learn to develop skill, standing up in front of a group and delivering a compelling talk, regardless of length, it will benefit you in ways, more ways than perhaps any other skill you can develop. So get good at whatever it is that you're doing. But then also being able to stand up in front of a group and tell that story in a compelling way that's impactful and a bit entertaining, it will benefit you in ways you have no idea. And it's so true. I've noticed this with others around me and the fact that the majority of

are really underwhelming in that sense that it can be a huge differentiator to compound whatever your first skill is with that of being an effective communicator in front of a group. It can it can really be a superpower for you. That's great advice. I mean, especially if you want to like kind of move up from individual contributor into manager. Because like as you go further up that chain, it becomes more and more of that skill, right? You're, the farther up you go, the less actual individual contribution you do, the more communication you're doing. And, and so like, it's like the surefire sign because the people up at the top are looking

for those people to promote, right? Because that's what they do all day. And so by being a good presenter and just getting up and presenting, and by the way, you can volunteer to present, right? Showcase that skill. You're automatically, like, when they're thinking of who to promote or who's the next person or who's a go-tors or for that, you're going to stand out. Switching gears a bit.

I talked with Annie Duke and Liv Boree about this, and they're both happen to be, lives an active poker player, Annie used to be one. And I think you've talked to Annie from what I gathered, looking at your book blurbs. And I noticed, but with both of them, I spoke about intuition, gut instinct, and you've written about this. And I'd love to get your take when it comes to why we can't. always trust our gut and combine that question with how do we better develop our intuition to make better decisions?

Yeah. I mean, the real problem with trusting your gut and your intuition is there's just a bunch of biases that basically everyone has that's hardwired into our brain that we evolved with that causes you to make bad intuitive decisions. Just as a couple of examples, there's something called just availability bias where if you have a decision to make and you have a bunch of options to choose from, you may not remember all the options. You just might remember the one that you thought about recently and not even think, if you're not thinking intentionally, about all the other possibilities. And then there's another

bias, very common called confirmation bias, where if you've already kind of be made a decision in a direction, you're much more likely to make a decision in that continued direction than really checking your instinct, whether it's right in this situation. And so for that, and like there's literally like 20 others of these, it's way better to use your intuition. I'm not saying throughout your intuition. You know, use it as a hypothesis generator, but then really check your thinking. And often you have to do this with other people. One thing, though, I really like about Annie's work. And what she said about this is one way to overcome this is to never really commit fully to a decision. Because if you don't commit, then you don't really have this confirmation bias. And I love this concept. And it's a

mental model that we call, and I also pull from somebody else called Thinking Gray. And when you're thinking gray, you're delaying decisions. You're basically saying, okay, I see that information. But if I don't have to decide about that right now, I'm not going to. And in Annie's words, even if you have to make decision, you can say, I'm 99% certain. That's the right decision, but I'm open to hearing the other point of view. Whereas if you say I'm 100% certain we should do X, you're then much more, less likely to reverse your course later. One of the things, though, when you talk about leadership, is you have to be decisive, or at least that's what's said. What do you think about that? If somebody would counter what you just said of delaying, and I remember Annie, actually, we talked

about that when we recorded about that very thing, but I'm from your perspective, Could that be seen as a negative from a leadership perspective as someone they say, yeah, I don't know, he seems kind of undecisive. I don't like that. What do you think about that? Yeah, I think it's a bit nuanced. So by delaying, I don't mean delay doing something. So I think you should go ahead and do things. And there's this other concept of reversible versus irreversible decisions.

And so most decisions in life and companies are completely reversible decisions. This comes from something Jeff Bezos wrote about in a shareholder letter, and he talks about them as doors, right? You can open this door and then come right back through the door. If you have a reversible decision, which most decisions are, what we suggest employees do, and what I suggest and do at the company is to say, look, we're going to make this decision right now. We're going to be very decisive, but we're not 100% sure this is the right decision. So if it ends up being wrong, we're going to just walk back through that door, you know? So we're constantly moving forward, but we're also acknowledging that we could be wrong. Does that potentially, though, create lack of commitment from your team if they think, well, Jeff said this before and we just walked it back.

So should I fully commit to this? Or how do you make sure that the tribe or the group is committed when they know that you may walk it back? I think that is a challenge. Yeah. And there's a challenge in a lot of organization, I mean, basically every organization in communicating constantly why we're doing this, right? Yeah. And explaining to people and getting people behind that. I think the counter, the answer to that is basically to explain your reasoning in a lot and say, look, for this to be, we're not sure this is the right direction, but we're going to go out of full force and we're going to get data back as quickly as possible.

And if it's great, we're going to double down on it. And that would be awesome because we know we're in the right direction. But if we get back data and it's the wrong direction, we're willing to change course. But you know what? The faster we get that data, the better off we're going to be or else we're going to be wasting time. And if you want to waste the least amount of time, we need to go forward as quickly as possible and kind of get this data. I really respect leaders who are willing to do this. I think it's extremely hard.

I have a high level of respect for the ones who are able to say, I don't know, or are able to say I was wrong. We need to change course. I think that takes a high level of security in oneself, of confidence, of belief. So I'm very attracted to leaders in working with people like that that are willing to say, I'm not sure, because I've certainly worked around those unsecure leaders who would never dare, ever say that they were wrong or that they're not sure. It's the ones who, the ones I worry about the most, the ones who always seem like they think they've got it figured out and their decision is right no matter what. That's the one to be nervous about. Yeah, that's interesting.

I mean, it goes back to this core value we have around build trust. And a lot of the research we've read on that and then have believed because we've seen it for ourselves is the fastest way to build trust is where they call vulnerability-based trust. and people build trust with each other the fastest when they see a vulnerability in you. And it feels counterintuitive because, like you said, you're exposing a weakness, right, a little bit. You're basically saying, I'm not sure. I don't know. I could be wrong. Or even saying, admitting that you were wrong.

But if you do that, if you communicate that well and you're really open and honest about it, you actually just formed an immense bond with the rest of the people you're working with. And that actually, if you form that bond, is a way to really get everyone. one really motivated behind what you're going to do next. 100% agree. I like your circle of competence. This is something I've studied in the past, and I liked reading about, you writing about it. You said one of your skills recognizing when you're operating within your circle and when you're

approaching its perimeter. And my goal has always been to continually expand that circle of confidence, I'm sorry, competence on a regular basis to be pushing, pushing, pushing, get an uncomfortable situations. That's partially why I actually wanted to talk to you because I knew I'd be forced to really get ready for a smart dude like you. But you said this is one of your skills is understanding when you're within that circle of competence and when you're reaching its perimeter. How can others develop this skill? It's a high level of self-awareness combined with understanding the need to push the edges of that zone of competency. What are some of the, some of the

advice you'd give to a person in order to get better in this regard. Yeah, that's exactly right. There's a model of getting better called deliberate practice that was pioneered by Anders Erison, right? Anders Erickson, exactly, who studied, you know, basically has a whole career of studying experts and world-class people and how they got so good at things. And it's a simple process. It basically, though, is very hard to do, but it's simple, and that you work right at the

edge of your comfort zone and you work with somebody who really is more of an expert than you who can then coach you in real time as kind of what you're doing wrong and giving you real feedback. And that's really the quickest way to expand that circle of competence in any kind of situation. Absolutely. How do you do this? Do you employ a coach? Do you have a board of advisors or what's your process to make sure you're expanding that zone? Yeah, both. I mean, so I do work with the executive coach. We have, our board is good and I try to use them for that purpose.

I'd say though, in general, like more day to day, I use the company processes including, and then outside the company my wife, to try to check my thinking and explain, you know, what they think is going wrong or could be done better in a situation.

It's like we talked about earlier having the post mortims at every project. I have no exception of that. anything that I'm involved in, I'm also involved in those post-mortems. And, you know, the more people that can be around you that are kind of can have the ability to point things out, the better. And that's a really hard culture to build, too, because most people don't want to tell, you know, the CEO that they're doing something wrong. And so you have to kind of instill that that's okay. And that's what I've been trying to do, at least.

And you've also talked about the power of documenting your thoughts, of writing. And I've experienced this. I just finished about a month ago, finished my first book, manuscript turned it in. And it was, congratulations. Thank you. Thank you. As you know, the feeling of that. And I actually just got the notes back from my publisher.

So that was a fun day. It actually was. I love the feedback, although she marked it up quite a bit, which is, I think I love because I know it's going to get better. But that process of being forced to document my thoughts, was perhaps as good of a learning experience as I've ever had. Why should everybody be in the practice of regularly documenting their beliefs, even if they don't publish them?

Yeah, I mean, that might be the single quickest way to think more intentionally and better. And we kind of came to it in a bit of happenstance because at Dukto Go, we're distributed in all different times, as I mentioned. And so the only way we can stay on the same page is by writing everything down. And we standardize that. But then we quickly realized that, man, it is the best way to clarify thinking. Because what happens is when you're in your head, you can kind of, you have all these biases. Like we talked about, you can kind of convince yourself you're right about almost anything really quickly and be like, yeah, I know, I know what's going on here.

And I think this is the right move. But then when you're forced to write it down and communicate, especially communicate it to others, although like you said, even write it down to, yourself is good. You can see the flaws in your argument almost immediately because you try to write down why I'm doing something and you write the first sentence and you write the conclusion. And it's remember it reminds me of South Park. Do you ever watch that? A long time ago where they had the underpants gnomes. I didn't see that one, but go ahead. It's these underpants gnomes and they basically steal everyone's underpants. But then Carman or someone was asking like, why are they stealing them and they point to this sign and it's it has one two three on it and one says

steal underpants and three says profit and two just has question marks in the middle and they have no idea why they're doing it but it's it's supposedly for profit and that's why writing down your thinking is so important because like you could have whole gaps in your logical chain that you immediately exposed by writing it down you've written about a cargo cult and that's what I immediately thought of of people who do things and they don't have any idea why they're doing it and that's where the lack of thought or intentionality happens

and that's well I guess so you want to briefly explain what the cargo cult means yeah that's exactly right it's so it came from this really kind of interesting story on this island that people used to supply things at war war II and because it was used

as kind of a supply route all these planes are landing there and all these kind of supplies were coming and some of the supplies would leak to the basically indigenous people who live there. And after World War II, all the planes went away and sort of the supplies. And the people there wanted the free stuff still. And they thought that if they recreated the runway and what they thought was like the key parts of it, all the planes would come back.

So they built like a control tower and they built what looked kind of were like fake lights along the runway. And they thought they had all the systems in place. And obviously the planes didn't come. but they didn't realize that, you know, it wasn't just the facade of a control tower that would create the plans. They didn't know what they were doing, really. And so Cogger Cult thinking is where you just kind of copy things like that blindly, but you don't really know what you're doing. And so you might miss, like, the key ingredient. And you really don't want to be doing that, basically.

Yeah. One more question, Gabriel, before we take off, man, let's say you're in your office and you're actually meeting with somebody in person. They're looking at you. They're earlier in their career. and they'd say, Gabriel, I want to create a great life where I make a positive contribution to the people around me in the world and general. What advice would you give me to best set me on the course to do that? Yeah, I mean, so I like that the person already identified the North Star, kind of right? And then I would basically say, you know, what, drill down a bit more.

And like what area, like kind of what are your current skills? What area of the world do you really want to contribute in, right? Or is it just that you want to do that? Are you like a computer programmer? You just want to do that skill, but you want to do it, you know, towards good ends? Or are you really motivated by like carrying homelessness or something like that? And it's kind of started to drill down into that. And then I'd say, you know, if you want to make the most impact, you got to find kind of the highest leverage

points, which is like the organizations or people or concepts where, you know, you can put in a little amount of work and get a lot of big results. And so like go study those areas and figure out who is kind of doing that, who's making the most impact and kind of go join them. And if if nothing exists, maybe you want to start it yourself. But the likelihood is that there is something out there and kind of go find your tribe, so to speak, of who matches that area of your mission statement. Love it. Thank you so much for being here, Gabriel. The book's called Super Thinking, the big book of Mental Models, which you wrote with your wife, Lauren McCann. I guess you guys did not, she didn't take your name. So it was a little, but you clear that up right away in

the beginning of the book. Gabriel, where would you send my listeners to learn more about you online? you can find me on Twitter at Yegg Y-E-G-G and you can find more about the book at superthinking.com Perfect. Well, thanks so much again for being here, man. This was great. And I would love to continue our dialogue as we both progress, man. That would be awesome. Thank you very much.

All right, man. Thanks, Gabriel. Okay, wow. My head is still spinning a bit. I have multiple pages of notes. Gabriel is one of those next level thinkers that I love to talk to because it forces me to stretch outside of my competency zone and speak with a really thoughtful, intentional, highly intelligent leader. I hope you found it useful and there are some mental models

you could put into play to make you a more effective leader. If you enjoyed it, I would love it if you would spread the message one person at a time. That's tell a friend, have them tell a friend the best form of marketing is word of mouth. You're referring this to someone to saying, hey, this one with Gabriel Weinberg on the Learning Leader Show, about mental models and a different way of going about our career and our life, could be helpful for you. It continues to give me the opportunity to do what I love on a daily basis when you spread the word.

Thank you so much. I will talk with you next week. Can't wait. This episode is brought. to you buy Roan. Roan is the maker of the most comfortable dress shirt ever made. The luxury performance alternative to the classic dress shirt. Roan's commuter shirt utilizes your body heat to release wrinkles naturally so you can ditch the dry cleaners. It's got four-way stretch material which leads to immense comfort. The commuter shirt fabric is soft, lightweight, and breathable

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