The Tim Ferriss Show Transcripts: Jimmy Wales, Founder of Wikipedia, on Wikipedia’s Real Genesis Story, Best Business Decisions, Understanding Financial Markets, Developing a Questioning Mind, and the Value of Optimism (#528)

Please enjoy this transcript of my interview with Jimmy Wales (@jimmy_wales), founder of the online nonprofit encyclopedia Wikipedia and cofounder of the privately owned Wikia, Inc., including its entertainment media brand Fandom, powered by Wikia. Jimmy serves on the board of trustees of the Wikimedia Foundation, the nonprofit charitable organization he established to operate Wikipedia.

Transcripts may contain a few typos. With some episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

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#528: Jimmy Wales, Founder of Wikipedia, on Wikipedia’s Real Genesis Story, Best Business Decisions, Understanding Financial Markets, Developing a Questioning Mind, and the Value of Optimism


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Tim Ferriss:
Hello, boys and girls, ladies and germs. This is Tim Ferriss and welcome to another episode of The Tim Ferriss Show. My guest today is Internet and technology entrepreneur Jimmy Wales. You can find them on Twitter @jimmy_wales.

He is founder of the online nonprofit encyclopedia Wikipedia and co-founder of the privately owned Wikia, Inc., including its entertainment media brand Fandom, powered by Wikia. Wales serves on the Board of Trustees of Wikimedia Foundation, the nonprofit charitable organization established to operate Wikipedia. In 2019, Jimmy launched WT.Social, a news-focused social network. In 2006, Jimmy was named to Time magazine’s list of the 100 most influential people in the world for his role in creating Wikipedia.

Jimmy, welcome to the show.

Jimmy Wales: Thanks for having me. It’s good to be here.

Tim Ferriss: I’ve been looking forward to this. It’s been many years, before we hit record, seems like a hundred years, 99 of which you mentioned, or the last 12 months since we last saw each other. 

Jimmy Wales: Yeah, it’s been a long time.

Tim Ferriss: And it’s fun to reconnect. And it also gave me an excuse to do what would seem very strange with anyone I know on some level, which is putting together a dossier of information like I’m some Eastern German intelligence officer in some type of film. But I learned a lot, and I also have a whole slew of questions to ask, and I thought we would begin with the beginning and would love it if you could just take a little bit of time to describe where you grew up and what your family and education looked like in the early days, if you wouldn’t mind starting there.

Jimmy Wales: I grew up, I was born and grew up in the Deep South in Alabama, but I was in Huntsville, Alabama, which is a little bit different from what your typical stereotype of Alabama is in that after World War II, they brought all the German rocket scientists over, put them in Huntsville to work on the space program. And they built the space program; all of the real science aspects of it were built there in Huntsville.

So it was, it was a high-tech town. There was a point in time I remember they used to brag about locally when Huntsville had the highest per capita number of PhDs in the country. So they brought all these amazing people in to work on the space program and what that meant for me as a kid growing up, we lived close enough to where they tested the Saturn V rockets that sometimes the windows would rattle in the house when they were testing the rocket. So that was kind of exciting. And it was a big deal. And basically what it meant was that, the space program in particular, the scientists were like our hometown sports team. All the kids were very much into it and so forth. And therefore, it made it natural for me to be into computers and technology later on as that began to unfold.

Tim Ferriss: And what did your parents spend their time doing, if you could paint a picture? 

Jimmy Wales: So my dad was a grocery store manager for many years, managed the local grocery stores, and my mother was a school teacher. And in fact, I attended a school that my mother and my grandmother set up, which was a very unusual sort of a one-room schoolhouse. So I grew up like Abraham Lincoln, there were four kids in my class. And then so therefore, because it was so small, there were four kids in my class, but there were four grades together at a time. So we had first through fourth grade and then fifth through eighth grade in two rooms. But what that meant was it was a very flexible and unstructured kind of education. It wasn’t everybody line up and sit in rows in the same kind of way. I’ve compared it to Montessori, but it was not, technically speaking, a Montessori school, and that unfortunately got reported wrong.

So on a lot of Montessori websites, they list me as one of the graduates of Montessori, but that’s not technically true. What was cool about it is that we were allowed to go ahead if we wanted to. So we would have our math workbooks and then we would, if we could just crash through our math workbook in the first four months of school, then we were allowed to go and do other things with our time. And so I spent a lot of time reading, I spent a lot of time reading encyclopedias because I really enjoyed the encyclopedia. And so it was a very conducive kind of education to being an entrepreneur / it also probably ruined me from having any kind of a normal job, because I’m used to sort of getting up and saying, “Oh, what’s interesting to do today?” And I’ll just do the interesting thing that I can find to do.

Tim Ferriss: How has that informed how you think about education for your own kids and how have you thought about that? I don’t have kids, but I suppose I’m on the cusp feeling the biological imperative to reason myself into having kids.

Jimmy Wales: Well, so my oldest daughter, Kira, who’s now in college, she’s at University of Miami. She was homeschooled her whole sort of time growing up, but that was really quite particular to her. It wasn’t really an ideological thing or, I never really in advance thought of that, but it just suited her. I remember we took her to tour a local school, thinking about what school she should go to. And then she was getting ready to go into kindergarten, and I asked her, “Well, what did you think of that school?” And she said, “Oh, that lady was really funny. She said they would teach me how to read.” And she was on her third Harry Potter book at the time. And then we went to another school a year later and I said, “Well, what’d you think?” she said, “Boring.”

So it didn’t make sense for her to go to school later on. She did go to kind of a gifted program one day a week and that sort of thing, but it just suited her. She was better off just kind of studying what she wanted to when she wanted to. And then my two younger kids here in London, they have it much more straightforward. They go to the local school down the street where we live in London. So it’s much more of a traditional, normal education.

Tim Ferriss: How did you, and I think this will be of great interest to an incredible number of parents, particularly after quarantine and COVID, how did you think about or decide on how to approach homeschooling in terms of teaching yourself, vetting teachers, and so on?

Jimmy Wales: We went to various homeschool groups. It was kind of weird actually, because a lot of the homeschooling community is extremely religious, which I am not. And so that whole world was a bit not to my taste, but there’s a lot of great resources out there, but really, the truth is her mother did it far more than I did. And that’s just because of my work causing me to travel and so on and so forth. But in terms of, I would say there was a similarity which was to my childhood, it was this idea of actually what really works well if a kid is interested and motivated is just following whatever you’re interested in.

She got interested in penguins, she would read five books about penguins, and that was that. Just incredibly powerful in terms of mindset to just be free to pursue whatever you’re interested in. I’m not suggesting it’s right for every family, right for every kid. That’s very much a personal thing. But in general, there’s a lot of ways to end up at 18 with a quality education. And one of them is to go through a traditional school process. Another one is to not go through a traditional school process and pursue it in different ways.

Tim Ferriss: So you mentioned that you’re not particularly religious. You also mentioned that you’ve been incorrectly cited as a graduate of Montessori. So I want to fact-check something I’ve read. I don’t know if you self-describe as a non-believer or atheist, do you self-describe that way or would you put it differently?

Jimmy Wales: No, I do. So what is interesting is I, at one point in my Wikipedia entry, which I try not to pay too much attention to because I recommend that for everybody, it can drive you a bit crazy because it’s really is a hilarious sort of thing. It’s like more than anything else, it’s your obituary, but it’s written while you’re alive. There will be an obituary published somewhere, but it’s not going to be as important as your Wikipedia entry. So that means that you can — 

Tim Ferriss: — probably pull heavily from your Wikipedia page.

Jimmy Wales: You can feel pretty strongly about it. But at one point in time, they had put me into a category of American atheist, and I said, “Technically speaking, that is true, but putting me into that category is a very odd thing to do in the sense that that is not what centrally defines me.” There are people like, historically, Madalyn Murray O’Hair, who was a massive atheist activist, and yes, she’s clearly an American atheist like that. That is exactly a good description of who she was. But for me, it’s just, I don’t know, it’s a weird category to put me in. You know, it’s like putting me in a category of people who eat ice cream. It’s like, okay. Yes, that’s true. However, I’m not really sure that it’s an encyclopedic fact.

Tim Ferriss: It’s not the defining characteristic that you would put on your business card. If that were still a thing. Did you come to atheism of your own accord? Was that something absorbed through the household? How did you come to that point?

Jimmy Wales: My parents are religious, but not, I mean, even though we’re from the Deep South, I wouldn’t say they are incredibly involved in it, but they tick the box and we went to a Methodist church, which is quite a mild church compared to some of the very intense churches you can get in the Deep South. And I would say there were a couple of fun stories that are relevant here. So one fun story is when I was four and I remember this very vividly, so I would have been — I was born in August, so it was getting close to Christmas. So four plus some. And the whole Santa Claus thing was, I don’t know. I found that quite perplexing and not particularly believable. 

And I came up with a very brilliant experiment that ultimately had a deep, deep flaw in it, which was when I went to the shopping mall with my parents and I went and I sat on Santa’s lap, my mom was too far away to hear everything. So Santa asked me what I wanted for Christmas, and I told him a bit of this and that. And then I mentioned in particular, I wanted a G.I. Joe ranger van. So this was actually a time period. I was born in ’66. So at this time period, I would say G.I. Joe had become a little bit less military and he was more of a park ranger because everybody was not that happy about the military due to Vietnam and all that. And I wanted this park ranger van for my G.I. Joe to play with. And I didn’t tell Mom and Dad, I told them about a few other things. So Christmas morning came and I got everything I asked for that I told my parents about, but I did not get the G.I. Joe van.

So this proved to me that this whole Santa thing was a hoax. But then I realized literally on Christmas morning, the flaw in my plan, which was, this was the gift I wanted the most. I was like, why didn’t I ask for something stupid that I didn’t even want to test the theory? So then I’m like, oh, great. I’ve ripped myself off. I didn’t get a G.I. Joe van. So there’s that story, which was really, the relevance to your question is just, it was me having a doubting mind and a testing. You know, I wanted to experiment, I wanted to find out the evidence for something. And then later on, as I grew older, I came to a position because there is a struggle with, “Am I going to go to Hell?”

The stories that people tell kids about religion are quite terrifying. And I just finally thought, if there is a good and kind and loving God, he wants me to be honest. And I can’t honestly say I believe this. So if I go through my life and I don’t believe it, and then I die, I think God will go, “You know, what? You came by it honestly. So come on in, you know, it’s fine. I’m not asking for stupid, blind obedience, because what meaning is there to that?” So that kind of helped me get my comfort with it. And then later I studied philosophy and the various arguments for and against and so on and so forth. But I think for me that emotional point where I could say, “Okay, look, it’s kind of the opposite of Pascal’s Wager,” if you’re aware of that? 

Tim Ferriss: I am, yeah.

Jimmy Wales: “I’m going to be fine.”

Tim Ferriss: What did you think you were possibly going to be, or what did you aspire to do when you grew up when you were in, say, high school?

Jimmy Wales: High school was when I actually, I got interested in the stock market. I got interested in finance in a way kind of accidentally. And actually we could go back and look at the timeline. So if you go back and see, when did Winnebago stock go from three to 18, let’s just say, some kind of numbers like that, within a year’s time. Basically what happened was I had this sort of moment of insight that gas prices had been incredibly high. There was this whole inflationary crisis and the recession and everything. And obviously Winnebago sales were quite down because who can afford to buy a big thing to drive around in a recession? And then also, gas prices were high. And then gas prices came tumbling down.

And I said, “You know what? I think Winnebago is going to have a great year.” So I just started watching their stock price and it went from three until 18 and I was like, “Oh, this is easy. Like anybody can make money on the stock market.” So I had one good idea, which also reminds me, people say, “If you could go back and tell yourself something when you were 20, what would you say?” And I would say, “Buy Apple stock. Literally. Don’t buy that car. Just buy Apple stock. Thank me later.” So I got interested in finance and the markets and decided that when I went to college, I would study finance. So that’s kind of what I thought I would do.

Tim Ferriss: What appealed to you about finance and markets? You have this childhood of following your interests, whether that be, well, in your daughter’s case, hypothetically penguins, or fill in the blank. What was it that grabbed you or compelled you about finance and markets?

Jimmy Wales: Well, I think in part, this idea that it’s a very intellectual activity. Figuring out the valuation of something. I feel, I don’t know, excited by things that demand of you, rationality, really being objective, if you are trading or gambling on the basis of some emotional feeling with no facts behind it, then on average, you’re not going to do very well. You have to kind of be ruthless with yourself. Am I investing in Tesla because I think Elon Musk is cool, or am I actually overpaying for something that’s extraordinarily highly valued at the moment? And so I think that appealed to me and then as I got further into it, just the mathematics of it, I like math and enjoy thinking about things like arbitrage, where you buy and sell. That’s something that’s different, but similar, but you can actually figure out what the relative valuation between the two should be. And the harder that is to figure out, then the more likely it’s to be mispriced. That’s the sort of thing that I enjoyed about it.

Tim Ferriss: Were there or are there any particular investors who stood out or stand out to you? Who capture your imagination, perhaps?

Jimmy Wales: I would say certainly at this point in my life in particular, I would say the long term value investing type of approach is something I see a lot of wisdom in, so Warren Buffett type of investing where you definitely aren’t trying to time the market from day to day. You aren’t doing the kind of arbitrage that brought me into thinking about it and so forth. It’s not about that. It’s about really thinking about long term trends and patients and sort of putting your money aside. In a way that, part of the reason I think is such a bill to me is something that I never did. So I can joke about buy Apple stock when you’re young. But in fact, I been an entrepreneur my whole life.

So basically I’ve never really built up like a normal retirement portfolio and things like that. I just put everything into the projects I’m working on, which is good and bad. But I think that kind of idea of, and I think this is something that young people have a hard time with, which is a weird kind of shame because it’s the time when it matters, which is compound interest really does matter. If you can earn X percent a year, it’s kind of boring when you’re young, but when you’re old, you look back and go, oh, actually that’s quite a pile of money. Interesting.

Tim Ferriss: The value investing sort of buy and hold, as you mentioned, the Warren Buffett, “You get 10 whole punches for the rest of your life; how will you think about your decisions?” is also a fascinating thought exercise, even if you don’t fully ascribe to it, because there is a measure twice; cut once emphasis on rational decision-making and people would argue, “Well, that’s great, and it worked before 2014 really well before FAANG and so on and so forth contributed so much to the S&P 500” or whatever it might be as a counter argument. But when you read these annual letters of Howard Marks or other investors who would often be put into that class, they talk quite a lot about cognitive biases and different types of malfunctions of reasoning that that is perhaps not emphasized in other places. When and how did Objectivism enter into the picture?

Jimmy Wales: So I, like many people, when I was, I don’t know, maybe 20, I was interested in philosophy and I was interested in economics and got interested and very excited by Ayn Rand and, in particular, The Fountainhead being a real mind-blowing, eye-opening book for me. And so really, as I do tend to pursue whatever interests me, I would say I dove very, very deep into that whole world. And I would say at a point in time, I would consider myself a real expert in a lot of the real details of that body of thought and body of knowledge. And in many ways still today has an impact on how I think about things. And what’s problematic about it is that the general understanding of her work that most people have is so superficial, it’s a cartoon caricature of what her ideas actually were — 

Tim Ferriss: Could you describe for folks who have no familiarity, what is the caricature?

Jimmy Wales: Sure. I think the thing she’s most known for is her advocacy of free market capitalism and her advocacy of self-interest — rational self-interest — and those are both true, by the way. But they’re also nuanced and subtle and complicated in some really interesting and different ways. And for me, I think what I would say impacted me more, and you can still see it in me today, is the idea that ideas matter and that a really important and incredibly valuable thing to do in life as part of being a successful, flourishing human being, is to think and to chew on ideas. And so a lot of people have a very knee-jerk approach to what they think she was about. And even the knee-jerk approach is something that I find irritating — whether you’re for or against some of her ideas. It’s really more like, okay, no, let’s actually slow down. Let’s think about what we know, how do we know it? How can we find out what’s true? What does it mean to gather evidence? What does it mean to reason based on evidence? And all of those things to me are incredibly valuable. I would almost say in and of themselves, but they’re not just in and of themselves, they’re towards the end of being a human being, really.

Tim Ferriss: And one could also argue that even if aspects of it, and I’m just playing Devil’s advocate here, but if aspects of it could be rightly considered cartoonish or exaggerated, it doesn’t mean that there aren’t components that are incredibly — still — incredibly practical and valuable.

Jimmy Wales: For sure. And I think if what you draw from her sort of sense of life and philosophy and ideas is the idea, “I have a fundamental moral responsibility to think really hard about what’s right and what’s wrong,” that’s good. That’s a really good thing. And if what you conclude is, “Yeah, you know what? She’s actually wrong about this aspect of economics,” or “She’s actually wrong about that aspect of interpersonal morality,” that’s okay because what you got from that was that you’re a thinking person. And for me, I always say this, and this is really what I think is the best bits of Wikipedia is, if I bump into someone and we disagree about some ideas and I find myself having to grapple with and think through their perspective and understand it, whether I come out the other end agreeing with them or not, that’s an incredibly valuable thing.

And I will love that person who has sort of grappled with me and, in an equal, kind of intellectual way. That’s hugely fascinating. And for me, this is one of the sad things about Twitter for example, is that there’s just the design of the space is so bad for that. The design of the space is really all about the one-line quip that destroys someone with humor, whether or not you even bothered engaging with what they had to say. For me, it’s just so much more valuable to really kind of understand someone, even if I end up disagreeing with them.

Tim Ferriss: You mentioned design of the space with reference to Twitter. When were you first exposed to design of any space online in a meaningful way?

Jimmy Wales: Well, in a sense, obviously the minute everyone gets online in whatever space you’re in, you’re subjected to the design elements of that space, even though you may not have thought through it. But I remember getting on very early on to Usenet groups. And so for those who aren’t ancient like me, and may not remember or know about Usenet, Usenet was an enormous, sprawling message board system. But unlike say Reddit, which is probably the, in some ways the successor, it was not only kind of uncensored, it was also uncensorable because it was a peer-to-peer system shared across many, many networks. It was basically a protocol for exchanging data where this sprang up and the cabal that was loosely in charge of it did begin to build ways of canceling posts, sort of by sending commands to cancel things that the other servers could or could respect or not respect, and so forth, to try and bring it under control because what happened in that design was a lot of really, really, really bad behavior. A lot of abuse, a lot of flame wars. So people started creating moderated groups, which had a lot of problems.

I was very interested in that space, and as I was using Usenet as a reader, just like anybody would use Reddit or something today, I got very interested in — because I was studying economics and game theory — very interested in thinking through, okay, what are the incentive structures? So everyone who’s participating here, they’re facing, because of the design of the software, because of the social design of the space, they face various incentives and the incentives might be — there was, of course, spammers.

So people would just come and just spam newsgroups with useless advertising and things like that. So okay. That’s one incentive structure people have. And one of the things, and this is something that I would say today is true of Twitter, which is because of the way Twitter works, let’s say you see somebody doing something terrible on Twitter. So abusing another person, abusing you, whatever it might be. Spamming. Well, what are your choices? What are the three things you can do? And they are this. That you can block that other person, which helps you, but doesn’t help anybody else. You can report it. But because their reporting on abuse system doesn’t scale very well because it’s very just top-down, and there’s a very sad job involved if people have to look at the worst things in humanity and make judgment calls at very low cost. So therefore, they’re overworked, underpaid, and they’re doing a great service at great personal expense, I believe. Or you can yell at them, as your third choice, is to yell at a person, which if you’ve ever been on Twitter is very popular. It’s like just yell, yell at them. They’re yelling at you, you just yell back and there you go.

And so to some extent, Usenet was like that. You would go into a friendly, little unmoderated newsgroup on some subject you’re interested in and it could go very well for a little while. And then as it got bigger eventually, you would see, oh, this is now dominated by the most annoying person here and the second most annoying person here, and all they’re doing is yelling at each other, and it’s kind of like good people are like, “Yeah, you know what? I’m out of here. This isn’t the interesting place to chew on ideas. This is just people screaming at each other.” And so that kind of thing made me start to think a lot about, okay, what are the principles of designing software, but also designing social rules and norms that can help contribute to building something that’s healthy, that’s meaningful to people, as opposed to just creating yet another sort of cesspit on the internet.

Tim Ferriss: Creating another neighborhood that features people throwing potted plants at your head as you walk down the side street.

Jimmy Wales: Yeah, exactly.

Tim Ferriss: So we’re going to segue to the onset of entrepreneurship, so to speak. Before we get there, because you mentioned The Fountainhead and I may lose track of this question, I want to ask, are there any books in particular that you have gifted often or more often than others to other people? Is there a shortlist of any type or any that come to mind?

Jimmy Wales: Not really gifted, but in the sense of gifted or recommended, let’s just say.

Tim Ferriss: Recommended.

Jimmy Wales: I would say there were two. They’re both quite simple in a way, as recommendations, and quite common, but one would be 7 Habits of Effective People, which is a classic Stephen Covey kind of motivation, self-help kind of thing. I wouldn’t say that I have applied all of it or buy into all of it, but I did find at a certain point in my life where I, being a person who’s prone to following whatever interests me at the moment, it’s like, “Okay, pull myself together. Here’s a system for getting things done.”

I tried looking into Getting Things Done, which is a more contemporary kind of popular thing. And I thought it was quite interesting and good, but I didn’t buy into it. And I felt like you needed to really buy into it to make that work.

So 7 Habits, and then the other one is a book called Your Money or Your Life, which basically sets forth the argument that you don’t need as much money as you think to live. And in fact, a lot of how we live, which is very expensive, traps us into things that we would rather not be trapped into. So you’ve got to commute, you’ve got to wear certain clothes, you’ve got to do this, that, and the other.

Certainly, something that I feel like you would also resonate with, with 4-Hour Workweek, which by the way, also had a huge impact on me. My favorite story about that is I read 4-Hour Workweek, and then I, not that long after that, I was like, “Okay, fuck this. I’m moving to Argentina for a month.” And I did. And I got a Vonage phone with a number that rang as if I were in New York. So I got into my apartment in Buenos Aires and nobody knew I was there. They all thought I was in New York because I was working remote anyway. I realized the flaw in my plan because that month when I was supposed to be there, I needed to do a speech — to be fair on me, these speeches came up after I had already booked the apartment and had plans to go. I had to go and give a speech in Korea and a speech in Milan. And I got to tell you, to get from Buenos Aires to Seoul, South Korea, that’s just, there’s no way. There’s no path to get there. It’s like, you’ve got to fly around the world twice to get to that place. So it was a hopeless month. I’m like, “Okay, well, I still love the idea.”

But anyway, I don’t want to embarrass you by recommending your book on your show, but I assume everybody who’s listening will have read that. But it’s really interesting because what I like about Your Money or Your Life, and what I liked about your book, is kind of that, okay, hold on, you’re doing this whole thing. You’ve got this whole rat-race thing going on. You’re following all the normal things. Why don’t you just step back and go, “Hey, is there a radical, different way of looking at this?” To say, “Is there a way I can make my life super much better and still kind of do the things that I want to do, but without all the things that are blocking me from doing it, because I have to make the money to make the money to do the things?” It’s kind of that cycle you can get into.

Tim Ferriss: Well, thank you for sharing and thank you for the kind words. I love the Argentina story. There’s almost always a wrinkle in the master plan. “I’m in Chiang Mai, but uh-oh, I could not have foreseen the amazing ping-pong-like travel plan that I will now have ahead of me.”

How did you go from, or maybe this was the intention all along, I don’t know, but how did you go from finance and markets to founding companies?

Jimmy Wales: Internet, yeah.

Tim Ferriss: Exactly.

Jimmy Wales: I was working as a futures and options trader in Chicago, worked for a small firm of local traders, so local traders are traders who are on the floor. So I wasn’t working at a big bank. We owned our seats on the floor and we traded with the firm’s money, and I was doing arbitrage between the Chicago Mercantile Exchange and the Chicago Board of Trade for fed funds and LIBOR, if anybody really wants to geek out on what all that is. And as a result, I actually had — the markets opened quite early there, 7:20, and finished at 2:00. I could be out of the office by 3:00.

I was just super interested in technology, super interested in the internet. I had been using the internet when I was in grad school quite a lot, and I could see this thing brewing that was really something very interesting. And I was interested. One of the things I was doing, because I was a geek. Also, I had just moved to Chicago. I didn’t know anybody. I didn’t really have a life, so I would get off work and I would go home and I would do programming and I was writing a web browser, just from scratch, or using various components I could find online, open-source stuff, writing my own web browser. When I was in the middle of doing that, and it was barely functional, to be fair, that was when Netscape went public and Netscape on the first day of trading was worth something like $4.3 billion. And I saw that number, 4.3 billion. And I was like, “You know what? Netscape 1.0 is better than my web browser that I’m writing at home, but it’s not $4.3 billion better. It’s kind of not that brilliant a piece of software.” And it wasn’t. It was really early days.

And so I was like, “This is really interesting. And I’ve been excited about the internet for a few years, but this is for the first time, the market validating, like this is going to be a big thing. This is quite interesting.” And so had a friend, Tim Shell, and he and I started tinkering around on the internet. And we did a bunch of different stuff.

We started a little web directory search engine called Bomis, which was basically about building web directories. So you could go in and — well, web rings, we called it. So you could go in and create a list of websites on any topic and just link them all together to each other so that other people could come. What was interesting about that is we — and the foreshadowing bit for the future is we decided that we would just let people come in and build these web rings. So you could sign up for an account and create a list of anything you wanted. And the idea was really an early, it was like Yahoo Links, so Yahoo used to have, I mean, maybe they still have, I don’t know, but they had a web directory rather than a Google-style search engine, and they would categorize things and they hired staff to do it. And so there was a big giant list of links with categories and subcategories, and we’re like, “Oh, maybe anybody could help us build that. Why would you need to hire staff to do that?” So that’s kind of the early, user-generated content concept.

Then we tried a lot of different things over a few years time, we had a, I would say early blogging. Slashdot was a big tech news site that was massively popular at the time. And they open-sourced their code, slash code, they called it. So we grabbed that and started opening a bunch of different blogs, trying to sort of leverage the traffic we had built. And it went well for a while. So it was growing and it was doing well and it was the dotcom boom.

And then we got approached by, this is actually a really funny, great story. We got approached by NBC TV network. NBC, NBCI, or NBC Interactive because at that time, I mean, it sounds like a joke today. It sounded kind of like a joke back then, but they were very dead serious. They thought, okay, the big TV networks should move into, like, “Why should these upstarts like Yahoo and Google, we’re going to create a web portal and a search engine. And we’re going to have all these different web properties and it’s going to be just like a TV network.” And so they started building things. So they paid us a lot of money. They bought out our full inventory for far more than we’ve been able to sell it forever. And in exchange, we moved the whole site to So we became a subdomain of theirs so that they could count our traffic for their media metrics numbers. And we were about 10 percent of their traffic, which was kind of interesting, because they didn’t pay us nearly 10 percent of what they were blowing on everything.

So there for a short period of time, that was really our dotcom boom era. It was amazing. We were making good money, and then, lo and behold, they realized, somebody higher up realized they were spending about a hundred million a quarter, losing a hundred million a quarter. And they were like, “You know what? We better stop doing this.” Like, “This is definitely not working. This is a really bad idea.” So then we had a bit of a contract dispute at the end because they were just like, “Okay, fuck you. We’re not paying you anymore.” And I was like, “Fuck you. You’ve got a contract.” And whatever. A tiny company versus a giant company. Yeah. You just take what they give you because there’s no way of fighting it really.

So then we went back, so then we were sort of off of there. And then that was actually a really complicated time. And I can’t tell you whether — I would have to really go back and study, was that before or after the founding of Nupedia, which was the first encyclopedia. It was probably around the same time, because I think that that wealth made us feel like, “Hey, we can launch some new things. Let’s take this money that’s coming in and let’s see what else we can create.” And that was when we sort of started thinking about the encyclopedia project, I would say.

Tim Ferriss: Couple of questions related to the stories you just shared. The first is at what point did you leave your finance job? So what experiments were with the safety net of this background of appointments and when did you make the jump?

Jimmy Wales: Yeah, so basically, yeah, exactly. So my boss — as I say, it was a small firm, we had, I think there were probably 20 staff total and my boss was a trader himself and he sort of knew that I was going home at night and working on stuff on the weekend. And that Tim and I were sort of thinking about website ideas. I mean, really, actually, I kind of glossed over, we had a couple of, I would say, brilliant ideas that we weren’t able to pull off. So one was like So basically, I was like, “People could post ads for the cars they want to sell and get in touch.” And so we went to car dealers, they weren’t interested.

I had this idea for ordering food online, which of course now is a huge business. At the time, again, restaurant owners looked at me like I was from Mars when I would go in and go, “I want to put your restaurant online.” And they’re like, “We’ve got a fax machine. We don’t know what you’re talking about.” But we were doing this and that.

Then the web ring concept started to take off and we could show traffic is increasing, increasing, and Michael was a trader, my boss, and had seen the markets go wild. And I was like, “Hey, you know what? I think I can build something here.” And he became an angel investor. So he invested some money, not a huge amount, but enough that I was able to kind of carry on paying myself a little bit of a salary and Tim a salary and we hired a couple more programmers and so on. Also moved to San Diego because I was fed up with the Chicago weather. Yeah, so we started that way.

And in terms of that feeling of that moment, when do you jump ship, it felt okay because it was quite clear that Michael and I got along well, he liked my work as a trader. He felt this sounded cool and interesting too. I did feel like, okay, if this whole thing doesn’t work, I can just go back to Chicago and start trading again. It didn’t feel like cutting ship and I’m never going to get to come back to my old career, which not everybody has that.

There are certain careers, I think some of the worst are places that I consider to be virtually like cults when people join them. The big consulting and accounting firms where they’ve got a really rigid kind of up-or-out culture, where if you think you’re about to make partner in two years’ time, which is a fat salary, you’d be kind of crazy to quit, even though you’re unhappy because you might get fired anyway, or you might make partner. So it’s like a weird, sick kind of life. I wasn’t in that kind of situation. It was a very entrepreneurial company I was working for. So therefore it felt like, “Okay, look, this is a side thing I want to do.” To him, it was just like another trade. It’s like, “Okay, we’ll put some money on this and see how it works out.” It’s like, “Here, Jimmy, here’s some money to trade with. Let’s see how it works out.”

Tim Ferriss: Right. And if doesn’t work out, there are other options, there are follow-up opportunities.

Jimmy Wales: Yeah. And I talk about this, none of this was in Silicon Valley, but I also, I talk about this, particularly in places — I travel all over the world, well, I used to. This year, I’m just in my attic. But I think one of the great things about Silicon Valley is precisely this concept, which people get in a very deep way, which is if you try a start-up and it doesn’t work out, that’s not the end of your career. You’re not forever a failure at all. Then you get a job at Google. And if you’re interviewing for jobs in Silicon Valley, having been at a start-up that didn’t work out isn’t a black mark. In fact, it can be quite interesting. If people can look at it and go, “Oh. That’s interesting. You were working on food delivery two years before it became a big thing.” That’s actually not a good example. Because that’s been a big thing for a long time now, but it’s like, “Oh, wow, that’s interesting. Because you were too early or you missed it because of this, that and the other. But actually, that was a great idea.” And it’s like your talent is so great. Not a problem.

I think in a lot of societies around the world — I mean, I have talked to Japanese entrepreneurs, Korean entrepreneurs, and they really struggle with this, that this idea that if I go and work at a startup and it fails, my whole career is doomed. I’ve missed the boat. I should have gone to work for a big company. And I think that’s unfortunate because it sort of fails to generate the culture that can generate innovation.

Tim Ferriss: It highlights a number of things for me as we’re talking, or rather, as I’m listening. Number one, the cultural consequences, both internationally, but even domestically are different depending on location. The financial consequences and the optionality that you have or don’t have, are also affected by your choices in this case of, say, employment, right? What type of game are you signing up for? What are the incentives? Your boss viewed it as another trade. He’s like, “Sure. I’ll stake this guy.” It’s like, you’re at a blackjack table and you have possibly a system for beating the odds. “Yeah, great. Let’s try it. I have to make sure that he has enough money that he can survive a short string of bad luck, but let’s see what happens,” versus as you put it, maybe in a Big Five accounting firm or somewhere else where it’s up or out and the game is kind of zero-sum. And then you have to completely switch lanes.

I want to come back to actually one question that if I don’t ask is going to bother me, how did the television network find the web ring? Was it dominant enough that it was on everyone’s radar? Or was there something else that happened? Because that seemed to provide the fuel for some of what happened later. How did that actually come together?

Jimmy Wales: I would say, no, we were by no means dominant. We only ever had a little bit of press coverage. It wasn’t a famous thing. We were on certain lists. So back then, there were a few — sort of like today you can look on Alexa and get the Alexa ranking of something. And it isn’t very accurate necessarily, but it’s the thing that’s out there. And so I think you could look us up and see, “Oh, this has a lot of traffic or a fair amount of traffic,” but I actually think, I literally have no idea.

I mean, I got a call out of the blue and they’re like, “Well, we don’t want to buy you, but we’d be interested in this type of partnership.” I think they did that type of deal with a lot of different sites. I think they were just looking to build out. And in a way, if you think about a TV network, that’s kind of their mindset. This is like paying for a production company to create a show so we’re going to go out and we’re going to find a production company and a writer, and we’re going to back them to build this thing. And they’re not necessarily actually making the TV shows, they’re working with other companies to do it. I think that was kind of their view. It’s like, “Let’s put some money in and let’s sponsor and let’s bring onto our network 50 of these things to generate a bigger property.” But I literally have no idea how they found me. That’s a good question.

Tim Ferriss: I would imagine there’s some behind-the-scenes, although predictable, conversation on their part, which is some type of arbitrage, right? They’re saying, “Hey, look, we can pay these guys X, and then we can charge two X for the CPM of the advertising,” even though they ended up losing a hundred million per quarter, which isn’t ideal, but it makes sense they would just try to roll up a bunch of this traffic and then sell it for a multiple of some type.

Jimmy Wales: Yeah, no, I think it was slightly different from that, because that is a perfectly valid strategy. Today, it’s not uncommon that a successful smaller website gets bought by a bigger company for the simple reason that the bigger company has traction in the ad sales market and can get more. So it’s a win-win, they can pay you more for your small website than you would make on your own and they can arbitrage and make money on it. That’s great.

But in this case, I believe because it was the dotcom frenzy, I think it was really more like, “If we can get big enough that we can go to the market and say, ‘We’re as big as Google,’ and that’s worth this amount of billions, we can spin it out for those billions.” That’s kind of what I think.

Tim Ferriss: I see.

Jimmy Wales: Whether they could actually make money or not as a real business, because this was in the dotcom mania, which by the way, has mostly left us. But I would say there’s a lot of this stuff going on now, where people are more interested in, “Can we blow up big enough to sell to the market before it kind of becomes obvious that this isn’t actually a great business?”

Tim Ferriss: The new new economy, as it was back then.

Jimmy Wales: Exactly, exactly.

Tim Ferriss: Now, you mentioned a few different kind of shots that you took. You mentioned food, you mentioned this Autotrader-like concept. You were trying different things, presumably to see what would stick, what might gain some traction, but you don’t have infinite time, right? You have this finite resource of time, so you can’t try everything. How did you choose these particular shots?

Jimmy Wales: So really seat of the pants, gut. I would say certainly not through a long process, like you might engage in if you were a Big Five accounting firm or a consulting firm coming into advise, where you would create lists of 25 opportunities and then tick through the pros and cons of each one. It’s much more — 

Tim Ferriss: You didn’t write a hundred-page white paper for yourself.

Jimmy Wales: Yeah, no, exactly. And in fact, later on, when I realized that it would be a good time to start thinking about raising venture capital, one of the things that was really impossible for me is to write a business plan in the traditional sort of MBA school kind of way, because I’m like, “Most of the numbers you’re going to write down are complete fiction because it’s like write a three-year revenue estimate.” I’m like, “Oh, wow. I don’t know.” Literally, I — 

Tim Ferriss: Why don’t you pick the numbers?

Jimmy Wales: You pick the numbers. I don’t really, that’s kind of not possible. And so it was actually good. Good VCs know that, and don’t waste your time with a lot of nonsense. So that’s kind of how that worked, but no, I would say, it would have to do with, did I find it personally interesting? Did I find a way? Did I think we could leverage where we were to get somewhere?

So just as one example, we knew, because of the web rings, people were coming in and building things, and we knew what was most popular on our site, which was basically female actresses and porn stars. That was massively popular in our search, that was so much of our traffic. And so we’re like, “Okay, that’s weird. What are people who are into Pamela Anderson” — who was huge, she was our number one sort of thing for a long time — “What are people who are into Pamela Anderson also into?” And we’re like, “Well, they’re into TV, they’re into sports. They’re basically men. So let’s figure out that.” So we started a baseball blog and just stuff like that. And it didn’t really work, but that was kind of the thinking on some of the projects is to go, “We’ve got this big audience, what else could we do with them? And what might be a good thing to do?”

Other ones, like the food one and the used car one, those were all before any success. So that was sort of just random ideas of like, “Let’s build a website; what could it be?”

Tim Ferriss: And then you’ve started looking at these adjacent opportunities once you had identified the type of people who were providing traction.

Jimmy Wales: Yeah, exactly. Although, to be clear though, the Nupedia project was not something I thought that was adjacent traffic to. It was kind of like actually this idea of a free encyclopedia for everyone, that’s just awesome, meaningful. And so that was really much more — there was no clear business idea, no business plan, no nothing. That was like, “Okay, I think I know how to build this. I’m just going to build it and we’ll figure the rest out later,” which was also kind of a dotcom-era thing. It’s like, don’t really know a business model, but I just know this sounds like a cool thing. And if it’s a cool thing, we’ll find a way to fund it eventually.

Tim Ferriss: The Field of Dreams approach.

Jimmy Wales: Yeah.

Tim Ferriss: Build it and they will come. And in this case, just so I understand the transition. So you have this web ring, you partner with this network, you begin to amass enough capital that you have fuel for whatever purpose you may decide. And then this deal falls through. Big company, huge-company-versus-small-company contract dispute, forget about it. Right. Just bloodletting exercise. Did you have to make the decision to abandon the audience and what you had built to then jump to Nupedia with no real plan for business or revenue? Or was it an easier decision than I’m making it out to be?

Jimmy Wales: It was. I would say the immediate thing that happened and a great lesson for entrepreneurs, immediately after we lost the big sweet deal, we basically started looking for another deal, looking for partners. And we basically carried on. And over the course of a year, we basically spent all the money that we had made during the term of the deal. And what I should have done is recognize that we were in a dotcom crash long before I could admit it to myself, and that there was going to be no more sweetheart deal like that, that that was just ridiculous and they were overpaying and we weren’t going to find any way of making that much money. And I could have cut the staff sooner. What we did though, I think I would say, we were about 18 to 20 people when the deal blew up.

Obviously, we didn’t hire anybody. And then, people move on in any kind of company, so a couple of people left for their own reasons, somebody moved away, and so on. And we didn’t replace them. So we were slowly starting to cut expenses. But being young and feeling responsible for people who work for me and all that, I found it very hard to just lay people off. That’s just not my strong point of being kind of brutal with people and stuff and like, “They’re doing good work. We’re going to find a way. We just have to find a revenue stream and so on.” And then, a black Friday came when it was just like, “Yeah, this is it. I can’t carry on like this. We’re literally not going to make payroll for another month if we don’t dramatically cut.” And so we did. I think on that day we went from 16 people to four. That was a pretty brutal time. But 16 people down to four, it was okay because we could pay ourselves; that actually matched our revenue to our expenses.

And so, as a part of all that, it was like it was possible to carry on and to sort of carry on at a lesser level. And in fact, we did. Then I moved from California to Florida because it was cheaper. We looked at saving money every way we could. We didn’t have an office. We started all working remote because why waste money on an office if you’re barely paying your own salaries? And it was around that time that Wikipedia then had been started and basically just started to boom. It was just growing and growing. We were having fun working on it and were like, “Wow, this is now bigger than anything we ever made before and that’s kind of cool and exciting.”

But again, it was not a sort of moment of, “We have to give up this one thing and take this huge step to do this other thing.” It was more like, “Okay, this thing, we don’t see any way to make a lot of money out of it. It’s not really working. Although it’s popular, it’s not really the right thing. This other thing, which is our side project, is actually doing well so let’s actually go that way for a while and see how that goes.” Meanwhile, the other thing just kind of sat there making money. Not a huge amount of course, but it’s like, “Okay, well, this is enough to pay ourselves to work on this other thing.”

Tim Ferriss: I certainly want to dive into Nupedia and then what evolved from there. But before I do, I have to ask, since you mentioned, “I should have cut head count earlier to stem the bleeding.” When I begin to fantasize about that “What if?” there’s part of me that thinks, wow, sometimes you need life to save you from what you want, because if you had potentially done that triage, who knows? Maybe you’d still be working at that company, for all we know. 

Jimmy Wales: For sure. So as we get from Nupedia into Wikipedia really, one of the things — so I always say Wikipedia is a child of the dotcom crash really. Now, it was started before the crash, it was kind of going. But what I mean by that is when Wikipedia really started to grow, there was no possibility of getting any investment money. There was no possibility of raising money to do it. It wasn’t big enough that if we put ads on it, it wouldn’t have made a material difference, it wasn’t going to change everything to be able to put a few ads on and get a couple grand a month or whatever it might’ve been. And what that meant was, interestingly — 

Okay, imagine you start a community website. Let’s call it YouTube. And it starts to grow and boom, and you’re really excited. And you see some problems on the site and you think, “Okay, what are we going to do about these problems?” And what you think first is, “Okay, let’s hire moderators. Like let’s hire people to do content moderation and behavior moderation.” And had we had funding to do it, we might’ve evolved into the same type of model that we see at Twitter, YouTube, Facebook, everywhere, basically, which is the users use the site and the moderation, other than just person-to-person blocking, is really done in a very opaque way by the company itself.

And the difference with Wikipedia and what makes it so fundamentally different from everything else on the internet is because I had zero money to hire moderators. We were actually forced to invent ways to deal with things in the community. So we started to think about, okay, what would it mean to have moderators, like admins, from the community, volunteer admins? So it’s like, okay, well, there needs to be checks and balances. So they’re elected by the community. They’ve got certain rules. They could lose their adminship if they do the wrong things. And then you can go on Wikipedia and, to this day, there’s hundreds and hundreds of pages of discussions and debates about all of these kinds of things. But the key is it’s all in the hands of that community. And we had to devise things like the Arbitration Committee, which is like the highest Supreme Court. And there’s a million little things in Wikipedia.

Whereas, if we had had money, probably we wouldn’t have done it that way. Probably it would have never occurred to me to do it that way. It was really a “Necessity is the mother of invention” kind of thing.

Tim Ferriss: I remember reading a quote, which I’m absolutely going to butcher, but it’s from Jack Ma, the founder or, perhaps, co-founder of Alibaba. And it was along the lines of, “When we started, we had several huge advantages. We had no money, no plan, and no experience.”

Jimmy Wales: Yeah.

Tim Ferriss: And it’s just incredible what you’ve seen. And I look back also at my own investing career, if I want to dignify it with such a term, and almost all of the best investments were in what was described at the time as a dotcom depression in 2008, early 2009, after the subprime mortgage crisis because, I think, in part, there’s a survivorship bias, of course. I mean, you have kind of the diehards who remain. But there was incredible resourcefulness by necessity throughout that entire period. And I don’t want to skip over Nupedia because there are reasons, I suspect, why people know widely of Wikipedia, not so much Nupedia. So what didn’t work at Nupedia? And when did you know, “This is really not going to work?”

Jimmy Wales: So Nupedia was the same vision, free encyclopedia, freely licensed. But I didn’t know anything about building communities really, I didn’t know anything about wiki software, which was around at the time, but I didn’t know about it really. And it had a seven-stage review process to get anything published. So the idea was, which seemed correct, given what we knew at the time, but was actually incorrect, although it does foreshadow something, that if you’re going to be an encyclopedia written by volunteers on the internet, then people are going to make fun of you unless you’re more academic than a traditional encyclopedia. You’ve got to be really, really super serious, otherwise, it sounds ridiculous.

And so that actually was plausible and correct and so on and so forth. But what it meant was we built a system that was not any fun. It was very intimidating. And to answer your question of when did I know, well, it was basically, we were, I don’t know, maybe a year in. And a point came when I was frustrated because I’m like, “It’s really slow progress. Nothing’s getting through the system. We’ve hardly published anything. What is wrong? Why can’t we produce content?” And I thought, well, I’m going to just write an article myself. And I decided to write about Robert Merton, who won the Nobel Prize in economics for his work in option pricing theory. And when I was in grad school, I’d published a paper on option pricing theory and I’d worked in the markets in Chicago so I knew that area quite well.

I thought I’ll just write a short biography of Merton. I’d read all of his academic papers and went through the math of all of his work. And so I sat down to write and I had a massive, immediate writer’s block because I knew they were going to take my biography and they were going to send it to the most prestigious finance professors they could find to critique and review it. And it was no fun. That’s scary. And I was like, “I’m going to write this thing and I’m going to get it back. It’s going to be full of how stupid I am, because I haven’t been in academia for four years. I left that world.” And I realized then, I’m like, “This is never going to work. This isn’t fun. This is too hard.” And so that was when we, effectively, pivoted to a wiki model where it’s just like, “Okay, here’s a blank screen, type some stuff, and let’s start writing an encyclopedia.”

And in fact, the reason it was called Wikipedia rather just pivoting Nupedia is that we thought that our very, very serious Nupedia community would be radically against this, that they would be very academic and like, “That’s crazy. You can’t do it that way.” So we’re like, okay, let’s just try it as a side project. And it took off. It took off very, very quickly. I mean, we got more work done in two weeks than we had in two years, nearly two years. And that was very exciting.

And actually, just one little side note that’s really interesting. When we were pursuing the Nupedia model, one of the earliest pieces that we published to great fanfare with our small community — we’re like, “Great. It’s past the seventh stage and here it is. Ta-da-ra-ra.” And it took a couple of days only before somebody emailed and said, “This is actually plagiarized. Here’s where it came from.” And we’re like, “Oh, really?” And we looked into it like, “Oh.” So the whole academic review process, with professors looking and everything, didn’t catch the plagiarism nearly as fast as showing it to 200 people and them just like Googling and checking it. And so that was like a really interesting insight to go, actually open peer review, sort of the open review, much like open-source software, is actually quite powerful and may actually catch things that a small group review, even of experts, won’t catch. And so that was quite informative really.

Tim Ferriss: I’d love to ask you how you came across wiki software. And in the course of doing homework for this conversation, I came across — and again, you can’t believe everything you read — but a description of how Tim Berners-Lee, who I believe is not too far from you across the pond, who is best known as the inventor of the World Wide Web, was distraught when Mosaic came out because it was effectively read-only. We’re talking about Netscape or earlier. And he really wanted people to be able to modify web pages. I’m very liberally paraphrasing my interpretation there. Then this software provides that capability. How are you or your team exposed to that?

Jimmy Wales: The first I was exposed to it — so Jeremy Rosenfeld was one of my employees. He worked for me and did a bit of this and that, writing, and so on. He came in, to me, and showed me a wiki. And it was just before Christmas and said, “Hey, I’ve heard you talking about how we have to make it simpler for people to participate. Have you seen wiki?” And I’m like, “No. What’s wiki?” And he showed it to me. And then not long after, I sort of posted on Ward Cunningham, who’s the inventor of the wiki concept. Basically, wiki just means a website anyone can edit. And I asked, “What do you think about using a wiki to make an encyclopedia?” And he responded quite famously something like, “Yeah, you could use wiki for writing the encyclopedia, but it would still be a wiki,” which was quite funny.

So then my daughter was born, the one who was later homeschooled. And she was very, very sick when she was born. And it was quite an emotional, traumatic time. It’s like, “Wow.” And it’s kind of one of those real — throughout the conversation, I’ve told you, no, there wasn’t really like a breakpoint moment, and there was no moment of just leaping, and it was all transitional from one to the next. But that was a huge moment. So when she got home from the hospital, I was just like, “You know what? Life’s too short. We’ve been thinking about trying this wiki thing. We’re just going to go for it. I’m just going to install this wiki software.” So I downloaded an open-source wiki package that was very, very basic, set it up and typed “Hello, world” and we were off to the races. That was really that moment when it was like, “Okay, let’s just make this happen.”

Tim Ferriss: I’m looking at a paragraph from an Esquire article, Esquire, UK, and I’m just going to read one or two sentences here. “Wikipedia is a universe unto itself, its ambition unequaled and its scale unprecedented. Its 300” — that number, I’m sure, has changed over time — “staff and contractors are fond of a single phrase: ‘Thank God our little enterprise works in practice, because it could never work in theory.'” And often, to this day, I’m just continually amazed that Wikipedia works. And the article continues, “In theory, Wikipedia should be a disaster.” Et cetera, et cetera. What were some of the decisions — because of course, Wikipedia has evolved over time and a lot has been learned and added to the ecosystem over time. But what were some of the early decisions that ended up in your mind being deciding factors for that sort of minimally viable product that made it catch in those first few months?

Jimmy Wales: Yeah. Great. So just to be clear — and you, the way you said it is correct. Sometimes that quote is attributed to me, but I’ve never said that. I’m not even sure I agree with that. I think it works in practice because it works in theory. But that’s a whole complicated question.

Tim Ferriss: All right.

Jimmy Wales: So I would say key decisions that made a huge, huge difference that were really kind of open questions in the early days were things like neutrality. There was a proposal early on that maybe instead of having one entry about, let’s say, abortion, a controversial topic, instead of having one entry about abortion, why don’t we just have competing entries, so different people can write whatever they want and then they can vote on them or just competing entries. And I was like, “You know what? No. Actually, I want there to be a neutral entry, which kind of tries to take into account all points of view, describes them fairly, doesn’t take sides, but just explains the ideas.”

And I think that was hugely important because the thing about neutrality is that all kinds of diverse people, as long as they’re thoughtful and kind, can get behind that. They can go, “Okay. Yeah. I get that. That’s okay.” You wouldn’t know it from watching TV debates or going on Twitter, but most people are pretty reasonable and will say, “Look, I disagree with this, but it should be presented in a fair way that the defenders of it would identify.” And so that was a key one.

I think another one was the idea — I mean, this is weird now to think this was a big decision. But it really was at the time. So somebody started to upload into Wikipedia the full text of Hamlet, for example. And that was like, “Okay, what do we think about that?” And I was like, “You know what? Hamlet should be available for free online in a well-supported way, but it’s not an encyclopedia article. And so it doesn’t belong in Wikipedia.” So we created a separate project called Wikisource where people put all kinds of source texts, things like that. So it was a lot of those kinds of things.

Tim Shell, who was my business partner from the earliest days, when we first started, there was no such thing as a separate talk page. And he said, “If this is ever really going to be an encyclopedia, we need to separate the discussions about the articles from the articles themselves, so we need a separate page.” And he proposed using /talk would create a sub page. Well, that was genius, right? Nobody knew it at the time and now it seems so obvious. You’re like, “Yeah. So what?”

But actually, it made a huge difference because it meant that you could say, “Look, whatever discussions and debates you have, put them over there. Talk about how to improve the article, but the article itself, you should always try to keep it in a readable format as an encyclopedia article.” Whereas, before that, what we’d do is if you objected to something in the middle of an entry, you would just go in and put in a parenthetical remark, or you would indent a paragraph and comment on what was just written, which made it very hard to read other than just as an interesting tool for a weird wiki type of conversation.

Tim Ferriss: Listening to you list off these different decisions, and maybe this is being really dramatic, but it seems like any one of those taken in a different direction could have mortally wounded the entire enterprise. I don’t know, maybe that’s overstated. But I mean, it seems to be a set of very critical decisions. Were there any significant mistakes made in the early days that either ended up needing to be fixed or that have just as kind of like a vestigial tail, have remained in the system? Were there any mistakes that particularly come to mind as memorable in the beginning days, which could be the first few months, first few years, whatever time frame?

Jimmy Wales: So I always have a hard time with this type of question. And I always explain what I mean by saying I’m a pathological optimist, so I always think everything’s going to be great. That’s not correct, by the way; everything is not always going to be great. But that’s the way I feel and approach things. So when I look back at the past, what I know is we did the best given our knowledge at the time. So even, let’s say, the first attempt, with Nupedia, clearly didn’t work. And so you can imagine in a fantasy kind of way, “Oh, we could’ve just started Wikipedia two years earlier instead of doing this whole Nupedia detour, which didn’t work.” But then again, I’m like, “You know what? We learned a lot.” That detour was kind of a necessary part of the growth of people in the community, of myself, that I don’t know how we could have skipped that step.

And so it’s kind of like saying, “Yes, I could be the greatest player in the NBA other than the fact that I’m 5’7″ and not athletic at all. But had I been, it would have been completely different, yeah, but I’m not and I never was.” So had I been genius enough to figure out that the Nupedia project wasn’t going to work two years earlier, then great. But how can I regret that? I wasn’t that genius and I can’t play basketball. So it’s kind of like that. So for me, I think this is also when I’m talking to people who are interested in being entrepreneurs, or thinking about their career, things like that, is to say, “Look, you have to sort of get your mind to a point where you really do believe, because it’s true, that doing this thing, that even if it doesn’t work out, you’re better off for having done it.” Because otherwise you could paralyze yourself: “What if I fail? What if I fail? What if I fail?”

That doesn’t mean you completely go kind of narcissistic and fantasyland that nothing can ever fail. It’s just like, you’re like, “Okay, let’s do — ” I mean, I really like the sort of fail faster, lean startup kind of thinking and say, “Let’s just try little experiments and if they work, great, if they don’t work, that’s okay, we learned something and we didn’t sort of stake our entire self-esteem on that one idea.” because I think that’s really important.

So when I look back, I would say, yes, of course, there are things — I mean, there are things about Wikipedia that I find weird today that you would think, sort of 20 years on, we would have solved. So if you go on the talk page of any Wikipedia article or you go to Wikipedia and find me, you go to my user talk page, you leave a comment for me, when I go to respond to the comment, I have to type colon, colon to indent my comment, or colon. And then once we’ve had a dialogue of like five layers deep, I’ve got to actually type colon, colon, colon, colon, colon to indent. That’s insane. Why not have a Reddit discussion system? Just automatically indent. I hit reply to your comment and it goes, just like in Reddit. 

And there are some good reasons for it. It’s complicated, right? But it’s actually like, that’s a vestige of the past, that’s there because it’s always been there. It actually works for us. It’s a weird barrier to entry for new people because people come in and they’re like, “I want to respond in this thread. And I clicked edit and there’s all this weird colon stuff. I don’t really get it.” Whereas, in other places you just would hit “reply” to the comment you’re going to reply to.

The problem is once you try to reform something like that, you suddenly realize there’s a huge amount of history and culture and the way we do things that actually is tied up in that software affordance. What I mean by that is like at Wikipedia, if you leave a comment, like if you and I are in a discussion and you comment something to me and I go to reply, and I notice that you’ve misspelled a word, clearly just a typo, nothing weird, but I’m like, actually, that word’s misspelled, I can correct your typo and hit save just as a part of my edit. And suddenly, our conversation just reads much better because your typo got fixed. And people can see that I did that. So if I change your comment to be the opposite of what you said, people go crazy.

But that kind of little thing, which seems kind of silly, it actually is part of the whole process. Or if somebody comes onto my talk page and they’re like insulting and rude, and somebody else is like, “That’s not helpful at all,” anybody, literally anybody, can just come and delete that comment because it’s just a wiki page. And again, everyone could see that they deleted it. So if they’re called out on it, there’s a history. You can track it and you can go, “Oh, this person deleted a comment. Why did they do that?” And then you look at it and you’re like, “Oh, yeah, actually, thanks for deleting that. That person was just being a racist jerk and that’s not really useful, so we got rid of it.” So all that kind of stuff.

So then you think about, okay, well, let’s build a threaded comment system where anybody can edit anything, it’s actually quite hard. It’s one of the things that at my pilot project of WT.Social that we’re doing is, it’s like, we’ve got comments, it’s like, can other people hide your comment? Can they edit your comment? And that’s the kind of thing that we’re experimenting with and it’s hard actually.

Tim Ferriss: It’s super hard. And it’s such a superpower. Maybe it’s a practiced skill. It’s probably both actually, of really — and this term is used a lot: “user centric design,” but putting yourself in the sort of decision tree of someone who is trying to do something, it seems so obvious, obviously useful, but it is not always obviously done if that makes sense.

Jimmy Wales: Yeah, actually. One of the things I find that it actually does get done and I think slightly overdone. Let’s put myself in the shoes of a bad actor. So what can a bad person do? And I feel that if you overdesign for what a bad person could do, then you fail to think about the design for perfectly nice people. So you could say, “Yeah, actually, a bad person could be really irritating by going around Wikipedia changing people’s comments to say the opposite of what they were going to say.” So then if your natural response is “Okay, let’s just not let people do that,” then you also cut out all the health that is possible if you leave people open to do that.

I have this analogy, I call it the Steak Knives Analogy, which is, imagine you’re designing a restaurant and you think, “Okay, in my restaurant, I’m going to serve steak because I like steak and I’m going to give everybody steak knives. And one thing we know about people with knives is they might stab each other. So therefore, I’m going to build a cage around every table so that no one can stab each other. And yeah, when you hear this, you laugh because you’re like, “Oh, that’s hilarious.”

Yeah, but then what do we do about it? Actually that is true, people could stab each other. And what we do is we recognize that it’s really rare, for one thing, that we actually don’t want to live in a society where we live in cages because some people might be crazy. We have various institutions of society to deal with the problem. So for example, if somebody does start stabbing people in a restaurant, usually some brave soul, hopefully, young and strong, will tackle the person and stop the violence immediately. And we would call that a hero. You think that’s a great thing to do in society is to do what’s necessary to prevent damage and a tragedy. And then we’ve got the ambulance that comes to, hopefully, fix things. And we’ve got the police to take the bad person to jail.

And none of those things are perfect. People sometimes will get stabbed and it is a tragedy and there is no recovering from it. And that’s terrible. But we still say, “You know what? We don’t want to live in cages. We wouldn’t think, ‘Let’s redesign everything so that we’re in a cage.'” And so I kind of feel this way about, when I think about things like the way social networks are designed. I often think, “Why can’t I go and edit somebody else’s comment?” Well, the reason is because they’re thinking, “Well, bad people will do it, and so now no one can do it.” But actually, maybe, if you have the right kind of systems and processes and transparency in place, it could be a great thing. Maybe not. But I just think, too often, if you design for the worst people, then you’re failing design for good people.

Tim Ferriss: It makes a lot of sense. The steak knife metaphor drives the point home. And I have just a few questions. I want to move, shortly, to current projects and how you think about current projects. But I have a few broader questions first. The first is what motivates great contributors? And how do you keep them happy? Or what are the things that keep them happy?

Jimmy Wales: That’s a great question; it is exactly what we think about a lot, what the Wikimedia Foundation thinks about a lot, which is what we call community health. Are people having fun? Are they doing good work? Are they enjoying doing good work? Do they feel supported? Are they supported? And all of those things. So a great Wikipedian, in my view, is someone who really takes seriously the values and ideas of Wikipedia, like neutrality for example, quality for example, reliable sources. And they take all those things as more important than any particular, say, political opinion they might have. So as I consider myself a good Wikipedian, I would not, for example, edit the entry on Donald Trump because he makes me crazy and I wouldn’t be able to be neutral. I would go in and I would probably, just by my blind rage at this ridiculous person, would make it really hard for me to be a good Wikipedian in that area. So I just don’t go there. And I think a lot of good Wikipedians are like that.

It’s like, okay here’s something I really am passionate about, but I know I can’t really be neutral about it, so I really should just stay away from it. And I think that’s a great quality. And also just this idea of kindness and thoughtfulness to say, “I got into this debate, it’s gotten a little rough and tumble, but what can I bring to this debate that will actually help other people be calm, help this be productive? Maybe I can find a compromise between different people who have different perspectives.” And I think those are really great people to have in Wikipedia.

Tim Ferriss: And are there systematically, are there things that you can do with respect to the fostering of those values or the cultivation of the engagement of the people who have those values? Like what are some of the organizational decisions?

Jimmy Wales: So one of the things that we’ve done recently that I think it is a really fantastic thing is we’ve introduced a new universal code of conduct, which really sort of came from the community, a huge consultative process within the community to really get the wording exactly right. And the idea is to say we have a code of conduct, which is really about all these values. It’s about being inclusive, being open, being friendly, sort of being a safe space, not to use a buzzword, but — and that’s been a fantastic thing and it really is about saying, “Look we know these values work for Wikipedia. They make Wikipedia better. And we also know that sometimes it’s quite hard to enforce them because of a variety of factors.” So in terms of bad behavior. So bad behavior at Wikipedia — if you come to Wikipedia and you just start sort of insulting people and being racist and being a real jerk, that is so easy to deal with, like the community will just boot you out immediately.

Like you’ll get blocked. That’s that. End of story. It’s really not that complicated. There’s no internal community drama about it. It is what it is. The harder ones are — what about a contributor who’s like super productive in writing in some area? And they’re also quite rude and kind of jerky to other people. Maybe they’re just on the borderline of the sort of thing that would get them blocked, but they’re just like basically a negative energy in the space and they’re causing a lot of trouble. That’s the ones that the community really does struggle with. And I think any system would struggle with, because it’s like we appreciate the work that you’re doing, but you’re basically probably driving off more good work than you are able to contribute yourself by being a jerk all the time. And that is the kind of thing that the universal code of conduct is really meant to sort of help us step up and say, “You know what? Actually the fact that you’ve written 35 great entries about some obscure topic does not excuse you insulting people.” End of story.

Like it’s just not okay. And we will find someone else to write those 35 things because it’s not necessary to be a jerk in the community. But no matter what we do, those are very human decisions. They’re very — there is no simple formula. There’s no — one of the things we’ve never done at Wikipedia, never would do, is have sort of points or likes or that sort of thing, because it’s just, it’s inhuman really.

It’s like normally human personalities are so rich and so varied that — really like the best thing is like the kind of great Wikipedian and in my mind is the person who is able to go in and kind of hold hands with that contributor who is doing great work, but being difficult and kind of coach them into being nicer as a human being. It’s like, “Hey, you don’t have to go around with a chip on your shoulder all the time. I’m going to help you kind of deal with the problems that you’re trying to address, but you should probably stop yelling at people.” And we have great people in the community who are good at that. And that’s really kind of amazing.

Tim Ferriss: I’d like to revisit this “pathological optimism” because, I mean, the term “pathological” is funny, right? And I mean, if we go to “pathos,” right, and I mean, this is kind of feeling, or in some cases suffering, but let’s go with the feeling. I would like to feel more optimism and not to say that I’m Eeyore, or anything like that. But if I could turn the dial a few clicks for a general higher state of optimism, I feel like I would be better for it. Is that something that just came hardwired in you out of the box? Is it something that you’ve developed? How would you answer that?

Jimmy Wales: Yeah, I would say it’s just kind of a deeply ingrained part of my personality, but I also think I do cultivate it because like anybody, I think you can work yourself into a funk. It’s not hard to do. And you can, therefore, become more pessimistic than you should. It’s not hard for people to do that. And I think if you have a certain set of practices around saying, “No, actually I’m going to remember to count my blessings, I’m going to look for the fun bit of this and the opportunity, and what can I change?” And sometimes, I think what happens to people — and this is actually where, if we go back to things like Your Money or Your Life, there are a lot of people who are stuck in jobs they don’t like, but they don’t feel that they can leave because they’ve got this mortgage and car payment.

And one of the things that book does is say, “Okay, why do you have that mortgage and car payment? What if you drove a crappy car instead of the expensive car? What does that mean? Why would you do that to yourself if it’s causing you to be stuck in a job that you hate?” Now obviously, that’s easier for some people in some circumstances than others, but it is a common thing that people get themselves into a situation where they’re living a lifestyle that’s too expensive for what they’re earning and therefore they’re unhappy and they don’t see a way out. And one way out is to go, “You know what? You’re valuing the wrong things.” So that’s about sort of reflecting and saying, “You know what? Actually, you know what the greatest thing in the world is? The greatest thing in the world is” — and you said you’re trying to sell yourself on having kids — “the greatest thing in the world is going out with your kids and look at — here in the UK, they call them wood lice, which sounds disgusting. We call them roly polies in the south, which is much nicer. But you go out and you find some roly polies, right? And you look under a rock and you get the roly polies and you roll them, you get them to roll and you put them on a twig. And like, that’s great stuff. Like that’s what life is. It’s absolutely free. And if you remember that sort of thing as a practice, right, not just hopefully, but just like actually go, “You know what? I’m in a funk about work. But you know what? There’s more important things in life. Let’s go do that.” Then it turns out that, if you can turn your head around in that way, then actually when you get back to the work problem, you’re more likely to have a creative solution to the situation, whatever that might mean.

Tim Ferriss: What are some of your practices, if it — maybe they are just consistent, in which case they’re kind of preemptively avoiding funk tendencies, or when you get into a funk, are there particular practices? You said “Count your blessings,” for instance. How does that — it doesn’t have to be this example, but if it were something like that, how might it manifest in your life? What does it look like?

Jimmy Wales: I don’t know. It’s so ingrained. It’s not like —

Tim Ferriss: A morning journaling practice.

Jimmy Wales: Yeah. I don’t. It’s just sort of like, just kind of pull myself together. But I don’t want to be too glib. I mean, people do struggle with genuine problems of depression. People are in genuinely very hard circumstances, so it’s quite easy from where I sit to go, “Yeah, just cheer yourself up and everything’s going to be great.” And I know that’s not right, which is why I call it pathological. But I do think there’s something to, if you can find that positive side, then you do have a better chance of working out whatever the actual problem is.

Tim Ferriss: Right. Well, you also, I mean, speaking as someone who has a history of — this goes back hundreds, and I’m sure thousands of years in my family line, just given the software, but a history of depressive episodes twice a year, probably extended episodes up until maybe seven or eight years ago. It’s difficult to see solutions with that shroud of mist over your perceptive faculties, if that makes sense. Like you see problems, but you don’t see solutions. And that in and of itself is a meta-problem, right?

Jimmy Wales: Yeah. No, it is. It is. And I can say, I don’t want to be glib about real — these are real issues. They’re hard issues for lots of people. And so it’s really — if you’re in the midst of a depressive episode, literally the last thing you need is for me to ring you on the phone and go, “Hey, just look on the bright side, man.” “Come on, asshole, are you kidding me? Everything sucks right now and I didn’t really need this.” You know, that’s not really what I mean. But I do think there are things — sort of remembering the good things at the dark moments can be quite helpful.

Tim Ferriss: Yeah. What are you working on right now? What is it that you’re directing your time and energies to?

Jimmy Wales: So I spend a lot of time on WT.Social, sort of design and so — got a very small team, though, so the software progress is very slow. I deliberately chose not to raise money at the outset because I felt if I did — if I’m trying to reinvent social networking, if I raised money early, which I could do because of my position, I would suddenly be on a certain kind of VC-driven treadmill to get to a certain place and to do this and that and the other. And I just didn’t want to; I wanted to have complete creative freedom to really kind of think and innovate about some quite hard problems. So I spend a fair amount of time working on that, but I also, during lockdown — so the beginning of lockdown, I would say when we first — last March here is when everything went into complete shutdown. It was an amazing, weird time.

You know, suddenly from traveling all over the world giving speeches, I’m here at home and the kids are here and all that. And basically, for the first couple of months, I was like, “Oh, I’ll just carry on. I always worked from home. I work remote. It’s no big deal.” And then I’m like, “Actually, this is weird because I can answer more emails,” but as anybody who, I mean, I’m sure you’re this way. In fact, I have a feeling, I remember there’s something you wrote about email, but literally with email — the problem with email is the more email you answer, the more email you get. There’s no such thing as finishing your email. It’s just like, forget them. You’re never going to finish your email because you — if you email a hundred people a day, they’re all going to freak and email you back tomorrow, and then 20 more people. So you know, it’s kind of hopeless.

So then I realized this is not productive. This is not it. And I thought, you know what? I actually — what am I going to do with myself? I don’t know. I mean, I’m normally spending a huge amount of time preparing for speeches, researching the client who I’m speaking for so I can customize to what they’re interested in. And I travel and I do my speech and I do press interviews and all that. And suddenly that’s all gone, completely gone along with, by the way, my income. So that’s a little bit annoying. And I just thought, you know what? I love programming. I love coding, never got a chance to do it. So I basically just started doing online programming classes and just like, I want to get my — re-up my skills, start doing things, started really learning a lot of interesting things.

Got very interested in WebRTC, so video on web. And then with my friends and family, we started doing a weekly pub quiz here and now I also do it with my mom and dad and my family in America. And basically, it’s just like you can get on once a week and somebody has created a quiz and you do the quiz and everybody jokes around and that’s it. And I thought, well, this is great, but it’s on Zoom. It’s not really that great. Zoom is great. It’s just a business video conferencing tool. So I created a new website, which is called Quiz Night Beyond, where it’s just like a fun website. So it’s all about quizzes. You can go on and create quizzes and you can invite people. You can schedule, just like you schedule a Zoom meeting.

And everybody meets, and in the middle is the quiz and everybody’s doing it together. And there’s the videos. And it’s all about teasing your friends and joking around. And that is going to launch well, I mean, hopefully by the time this podcast is out, it will have launched, but it’s and I’m really enjoying it. It’s one of these things — it’s like that entrepreneurial itch of like, here’s something that I want to do, which is do quizzes with my family during lockdown, so that we get a chance to see people. Let me in a second, I’m going to go on a side rant about social networking. And yet it doesn’t quite work the way I would like it to, and now I see a way to solve that problem and like tick and I’m going to do it. 

Is it going to be a commercial success? I hope so. Is it not? I don’t care because it’s something I want to exist, so I’m making it so that I can use it. And if everybody else likes it, that’s great too. And then my side rant on this front and part of what inspires me, the whole concept of WT.Social is around — the social networking is really broken. It’s not healthy. It’s all the things.

Tim Ferriss: Jimmy, what does WT stand for?

Jimmy Wales: Oh, WikiTRIBUNE. It’s basically a pivot. WikiTRIBUNE was kind of thinking about how to get people involved in news and how to collaborate on news. And as we were doing that, I learned a lot, but I came to realize the real problem with news is not what’s going on in journalism. It’s what’s going on in the wider ecosystem where they live. It’s that the advertising-only social media really rewards clickbait headlines, full stop.

And so clickbait headlines, clickbait content, low-quality stuff goes viral, and it’s not conducive to serious, hard-hitting journalism, which also can go viral, but it’s very expensive. So with WT.Social, I just really am in this process of thinking what’s wrong, what’s wrong with social networking, what’s unhealthy here? And I suddenly realized, as we started doing the weekly quiz, my family is kind of dispersed. My mom and dad live in Alabama. My sister lives in Seattle. Brother’s in North Carolina. We’re kind of dispersed. And so whenever we talk, we have phone calls from time to time, we’ve got a family WhatsApp group, the kids only WhatsApp group where we talk about what’s going on with Mom and Dad and how can we help and that sort of thing. And basically, what I realized is by seeing them all once a week, and we’re just doing a quiz, it’s just a fun thing to do.

And there’s Mom and there’s my sisters. And there’s, you know, I have the one sister who I had kind of grown apart from not — no serious break or anything, but just, we weren’t talking that much, for a long time. Suddenly I see them every week and we’re joking around and we’re laughing. We’re laughing about stuff when we were kids and it’s really human. And I realized, what is social networking? What are we — when we think about social uses of computers, it has so much better, so much healthier than — for example, something that’s completely innocuous but like my — if I click ‘Like’ on a picture of my sister’s dog on Instagram, are we kidding ourselves that that’s social? like that is the most limited form of human engagement. It’s just like, I liked your picture of your dog. Okay. Right. That’s not a conversation, right?

That’s not actually joking around. It’s not talking about the family. It’s not sort of teasing each other about a quiz question, like real human interaction. So for me, that’s really interesting. And so that’s kind of what I’m focusing on is, okay, how do we really reimagine? From the ground up, what does it mean to use computers in a social way?

And I think we’ve got this really interesting opportunity to do that around video simply because of the lockdown, everybody’s got used to doing Zoom calls, right. It’s a thing. And obviously we’ll stop doing as much of that once we can go back and meet in a bar or whatever, but you know, there are certainly old friends who I wouldn’t meet in a bar necessarily around London because they live all over the world who I mean it wouldn’t be that weird to go, oh, let’s get a bunch of people together and go on Zoom together. Like, why not? It’s kind of fun.

Tim Ferriss: Well, count me in. I love this idea in part, because Zoom calls and the video conferencing without some type of context can work, but it can also be very challenging. So having an activity is key, at least for me.

Jimmy Wales: Orit, my co-founder at WikiTRIBUNE put it this way. She’s like, “When you go to your extended family for a holiday dinner, one of the reasons we have that huge dinner is to give everybody something to do. Even if you really love your family, it’s like suddenly you’re propped in front of your Mom, Dad, brothers, sisters, cousins. And you’re sitting in a room staring at each other. It could be quite awkward, but instead we’ve got these rituals, we’ve got something to do. We’ve got — who’s going to make the mashed potatoes? And then we go and we sit together and then, people have their traditions, Christmas traditions and that sort of thing. And this is kind of that. It’s like, okay, yeah. If you’re going to get your whole family together once a week for a call, and you’ve got nothing to do, it’s going to be weird. Quite often it can be very awkward, but it’s like, let’s do an activity together. It’s a conversation starter. It’s kind of an icebreaker.

Tim Ferriss: And I want to also emphasize what I think is perhaps, sometimes missed — not always; it gets discussed — but the genius of scratching your own itch, in the sense that there are many companies that people might assume have these 10-year, 20-year master plans that have been executed to perfection with all of these strategies and tactics and plans for team and flywheels and so on.

But there are certainly, I would say just as many examples, maybe more examples of companies that started as products to scratch the itch of one or two people. And if you design in that way, if you build in that way, you have at least a guaranteed market of one, which is far less speculative than a lot of what goes on. And so I’m excited to see where it goes.

Jimmy Wales: I think that’s right. And I actually what I think is interesting about it really is that when you think about what can be successful — so if you’re an entrepreneur and you want to go into business, I always tell young entrepreneurs, “If you just look around and you do some analysis and you pick the thing you think is going to make the most money, but it’s kind of boring to you, chances are you’re not going to make that much money because it’s boring to you. It’s not something you find is a passion in and of itself. You’re just there to try to tick off some boxes and make some money. You might think that’s a clever thing. And you’re like, “Well, it’s boring, but I’m going to only do it for five years. I’m going to sell out for a ton of money.”

No, you’re probably going to do it for two years and you’re going to hate every minute of it. You’re not going to be good at it because you hate it. Versus if you scratch your own itch, you’re like, oh, here’s the thing. If this existed, I think that would be cool. I think it’d be interesting. By the way, it doesn’t have to be a consumer product. It could be B2B. Just anything that you come up with that you’re like, “Wow, this should exist and I think it would be cool.” Then if you’ve built it, you can be proud that you built it. And if there’s some weird reason why it just didn’t work out as a business, yeah, fine. No big deal.

Tim Ferriss: Jimmy. It’s so nice to reconnect and spend time together. And I have one last question, one or two last questions, and this one sometimes goes nowhere fast and I’ll take full blame for, I’ll take full blame for it, if it — if that ends up being the case. But if you could put anything on a billboard, metaphorically speaking, to get a message, a quote, a question, an image, anything out to billions of people, what would you put on that billboard? Or what might you put on that billboard?

Jimmy Wales: Well, I mean, I think the thing that immediately pops to my mind is my original vision statement for Wikipedia, which is: “Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge.” Because to me that is still like wow, that’s so exciting, right?

Just to think every single person on the planet, completely for free, has access to the sum of all human knowledge. You can do anything. You can learn, you can grow, you can heal, you can cure. You know, it’s amazing to think about what are all the implications of that statement. And so I just think the more people who are thinking that way, obviously for Wikipedia, but it’s not about, we could be this organization, but it’s just like, wow, what can we do to make sure that education and knowledge are universally accessible? Because we’ve got a lot of problems on this planet. I mean, we need as many smart, educated people to figure them out as we possibly can. So let’s make sure everybody has the ability to join in that intellectual project

Tim Ferriss: Hear hear. Well Jimmy, people can find Quiz Night Beyond at It’s always fun to connect. It’s been a little while and — 

Jimmy Wales: Yeah and too long.

Tim Ferriss: And really appreciate you taking the time today from so far away, although so close, via voice. Is there anything else that you would like to add? Any closing comments, requests of the audience, anything at all before we bring this to a close?

Jimmy Wales: No, no, it’s good. I mean, I hope people will check out Quiz Night Beyond and come and visit me on WT.Social and say hi on Twitter and try not to be a troll on the internet. And that’s all.

Tim Ferriss: That is a good — that is a good parting message to leave embedded in the minds of everyone listening. When in doubt, don’t be a troll on the internet. It is not net positive.

Jimmy Wales: Yeah.

Tim Ferriss: Jimmy, thank you so much for the time. Really enjoyed the conversation and to everybody listening, we will put links to all resources, all websites, everything that popped up in the show notes as per usual at And until next time, thanks for tuning in.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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