Transcript

#528: Jimmy Wales, Founder of Wikipedia, on Homeschooling, Atheism, Understanding Financial Markets, Ayn Rand, Favorite Books, and More

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Hello, boys and girls, ladies and gents. This is Tim Ferris and welcome to another episode of the Tim Ferris Show My guest today is internet and technology entrepreneur Jimmy Wales. You can find him on Twitter at Jimmy underscore 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. Will serves on the board of trustees of the Wikimedia Foundation, the nonprofit charitable organization he established to operate Wikipedia. In twenty nineteen, Jimmy launched WT Social, a news focused social network. In 2006, Jimmy was named to Time Magazine's list of the one hundred most influential people in the world for his role in creating Wikipedia. Jimmy, welcome to the show.

Oh, thanks for having me. It's good to be here. I've been looking forward to this. It's been many years before we hit record. Seems like a hundred years ninety nine of which you mentioned are the last twelve months since we last saw each other. Yeah, it's done. 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 um some uh some uh you know eastern German intelligence officer. In some 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. 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 Two 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 five rockets that sometimes the windows would rattle in the house. Ha. 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 and particularly 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 unfold. What did your parents spend their time doing. If you could paint a picture.

So my dad's uh Was a grocery store manager? For many years to manage the local Group 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 one room schoolhouse. So I I grew up like Abraham Lincoln. There were four kids in my class. 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 have compared it to Montessori, but it was not technically speaking a Montessori school in that

Unfortunately got reported wrong, so on a lot of Montessori websites they list He is one of the 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 just if we just could 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 the encyclopedia. And so it was a I think a very conducive kind of education

To being an entrepreneur Slash it also probably ruined me from having any kind of a normal job. Um 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. How's 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. Yeah. My oldest daughter, Kira, who's now in college. She's uh University of Miami. She was home schooled her whole sort of time growing up, but that was really quite

particular to her. It wasn't really an ideological thing or you know, I never really in advanced 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 It's like she was getting ready to go into kindergarten and I asked her, you know, 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, so we were like, Yeah. And then You know, we went to another school a year later and uh I said, Well what did you think? She said, Boring

So So she didn't she didn't 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 my two younger kids here in London, they have much more straightforward, you know, they go to the local school down the street where we live in in London. So it's much more of um traditional normal education. How did you

And I think this will be of of great interest. Two. 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. We went to

Various home school groups. I mean it it was kind of weird actually because A lot of the home schooling 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 I mean 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. I would say there was a similarity to my childhood. It was this idea of like Actually what really works well if a kid is interested and motivated

Is just Follow whatever you're interested in. I mean, you know, if 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, uh right for every kid. That's very much a

Personal thing, but In general There's a lot of ways to end up at eighteen. with a quality education, and one of them is to go through a traditional school process.

Another one is to not Through traditional school process and And pursue it in different ways. 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 wanna fact check something I've 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? No, I do. What is interesting is I At one point in my Wikipedia entry, which I try not to

pay too much attention to because uh you know I recommend that for everybody. It can drive you a bit crazy'cause it's your uh I mean it 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.

Right. I mean there will be an obituary published somewhere, but it's not gonna be as important as your Wikipedia entry. So that means that you can probably pull heavily from your Wikipedia page. But at one point in time they had put me into a category of American atheists 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 Madeline Murray O'Hare 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 like 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, you know, it's like okay, yes, true. However, not really sure that it's an encyclopedic fact, so It's not the defining characteristic that you would. Put on your business card. If that if that were still the thing. Yeah. Exactly. Did you come to

Atheism. Of your own accord? Was that something Absorbed through the household. How did you come to that point? 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 mild church compared to some of the very intense churches you can get in the deep south. You know, I mean 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 I remember this very vividly. So I would have been uh I'm born in August, so it was getting close to Christmas, so you know, four plus um. And I Didn't you know, the whole Santa Claus thing was I don't know, I found that quite

Perplexing and not Not particularly believable. And I came up with a very brilliant experiment that ultimately had a deep, deep flaw in it, but 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 sixty six, 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 G. I Joe for my G. I Joe to play with.

And I didn't tell mom and dad, uh 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 that. So this proved to me that this whole Santa thing was 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.

It's 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 I didn't get a uh a G. I Joe van. So there's that story, which was really I mean, the r the relevance to your question is just It was me having a a doubting mind and a testing, you know, I wanted to experiment, I wanted to find out the evidence.

Or something. And then later on, you know, as as I grew older, I I really I came to a position because there there is a a struggle with, you know, am I going to go to hell? The stories that people tell kids about religion are quite Terrifying.

And I just finally thought, you know what, 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 Gob will go, You know what? You can't buy it honestly.

So come on in, you know, it's fine. I 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 if you're aware of that. It's kind of like I'm gonna be fine. 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. High school Was when I actually

I got interested in the stock market. Not 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 and see When did Winnebago stock go from

three to eighteen, 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 have 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 gonna have a great year. So I just started watching their stock price. And it went from three until eighteen, and I was like, Oh, this is easy. Like anybody can make music. So I have one good idea, you know.

Which it also reminds me, people say w if if you could go back and And tell yourself something when you were twenty, what would you say? And I would say, Buy Apple stock. Like literally. Don't buy that car. Just buy Apple stock. Take 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 it would do. What appealed to you? About finance and markets. Whether that be Well, in your daughter's case, hypothetically penguins or fill in the blank. What what what was it that grabbed you?

Or compelled you. About finance and markets. Well, I mean I think In part it's just This idea that

It's a very intellectual activity. You know, figuring out The valuation of something I feel I don't know, excited by things that

demand of you Rationality. really being objective. Like if you are trading or gambling on the basis of some emotional feeling with no facts behind it, then on average you're not gonna do very well.

you have to kind of be ruthless with yourself of like 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

something that's different but similar. You can actually figure out what the relative valuation between the two should be. And it's 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. Were there or are there any Particular investors.

Who stood out or stand out to you? Who capture your imagination, perhaps? 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 patience and putting your money aside.

In a way that I Part of the reason I think I have such a building is that it's something that I never did. Yeah. You know, so I can joke about, you know, buy apple stock when you're young. But in fact

I've been an entrepreneur my whole life, so basically I've never really built up 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 mean I think that 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 you go, Oh, actually that's quite a pile of money. Interesting.

Yeah. The value investing. Sort of buy and hold. As you mentioned, the Warren Buffett, you get ten hole punches for the rest of your life, how well 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 Fang and so on and so forth contributed so much to the S P five hundred 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 is perhaps not emphasized at other places.

When and how did Objectivism. Enter. Into the picture. So I like many people when I was

I don't know, maybe twenty, got interested in 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

The the general understanding of her work that most people have is so superficial. It's a cartoon caricature. of what her ideas actually were. Could you describe for folks

For folks who have no familiarity, what is the caricature and then Sure. Yeah, 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 which I 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 whether you're for or against some of our 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? Uh and all of those things to me are incredibly valuable, I would almost say in and of themselves, but they're they're not just in of themselves. They're Towards the end of being A human being, really.

And I suppose it's 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. For sure. And and you know, it's like 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. You know, like 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,'cause what you got from that was that you're a thinking person and for me I always say this. And and this is really what I think is the best bits of of Wikipedia. Is

If I bump into someone and we disagree about some ideas And I find myself having to grapple and think through their perspective and understand it.

Whether I come out of the other end agreeing with them or not. That's an incredibly valuable thing. And I I will love that person who sort of grappled with me in in an equal kind of

intellectual way. That's hugely fascinating and and for me this is one of the 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 quit. that destroys someone with a humor, whether or not you even bothered engaging with what they had to say.

For me it's just so much more valuable to to really kind of understand someone, even if I end up disagreeing with them. 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. Well, I mean in in a sense, obviously the minute i everyone gets on online in in whatever space you're in, you're subjected to the design elements of that space, even though you may not I've thought through it.

But I mean I remember getting on very early on to Usenet groups. So for those who aren't ancient like me and may not remember or know about UseNet, Usenet was An enormous sprawling kind of 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. And the cabal that was loosely in charge of it did begin to build ways of

Cancelling posts. by sending commands to cancel things that the other servers could or Could respect or not respect and so on 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. So I I was very interested in that space and as I was using Usenet as a reader or you know, just like anybody would use Reddit or something today. I got very interested in

Because I was studying Economics and game theory. I'm 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 You know, might be uh there were s of course spammers. So people would just come and just spam newsgroup with useless advertising and things like that. So okay, that's that's one incentive structure people have. And you know, like 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 could block that other person, which helps you, but doesn't help anybody else. You can report it, but because their their reporting on abuse system doesn't scale very well'cause it's very just top down and there's A very sad job involved of people have to look at the worst things in humanity and make judgment calls uh 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. That's your third choice is to yell at the person, which if you've ever been on Twitter is very popular, you know, it's like just yell yell at them. They're yelling at you, you just yell back, and there you go. And so to to some extent Usenet was like that. You would go into a little Friendly little

unmoderated news group. on some subject you're interested in, and it could go very well for a little while and then as it got bigger and 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, you know? And it's kind of like good people are like, Yeah, you know what?

I'm outta here. Like 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 sespit on the internet. Creating another neighborhood that features people throwing potted plants at your head as you walk down the spice street. Yeah, exactly.

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So we're gonna 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 you.

Are there any Books in particular that you have gift. Often or more often than others, to other people. Is there a short list of any type or any that come to mind? Not really gifted, but but in the sense of gift or recommended, let's just say.

I would say There are two. They're both quite simple in a way. as recommendations and quite common, but one one would be Seven habits of effective people.

Which Is a classic Stephen Covey. m 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 Being a person who's prone to following whatever interests me at the moment. It's like, okay pull myself together and here's a system for like Getting things done.

I tried looking into getting things done, which is a more contemporary kind of popular thing and 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 Seven Habits and then the other one is a book called Your money or your life. Which

It 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 know, 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 four hour work week. Which by the way also had a huge impact on me. My favorite story about that is I read four hour work week 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 uh a Vaughn Age 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. 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.

I gotta tell you, to get from Buenos Aires to Seoul, South Korea, that's just there's no way. Like it's there's no path to get there. It's like you've gotta 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 I don't wanna embarrass you by recommending your book on your show, but I assume everybody who's listening will have read that, but

You know, it's like really interesting because what I like about your money or your life and what I liked about your book. Is Kind of that like, 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 like 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, you know, it's kind of that that cycle you can get into. Well thank you for Thank you for sharing and thank you for the kind words. I I love the Argentina story. There's always there's almost always a wrinkle in the master plan. I'm in Shang Mai, but uh oh I forgot I could not have foreseen the amazing ping pong like travel plan that I will now have ahead of me.

You go from or maybe this was the intention all along, I don't know, but how did you go from finance and markets? Two Founding. Companies. Exactly.

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, you know, on the floor. I wasn't working at a big bank where we owned our seats on the floor and and we 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 Logboard. If anybody's really want to geek out on what all that is. And As a result, I actually had The market's open quite early there, seven twenty and and finish at two. I could be out of the office by three.

And 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 interesting. So I

One of the things I was doing,'cause I was a geek, also I just moved to Chicago, didn't know anybody, 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. So just from scratch, uh using various components I could find online.

Open source stuff. Writing my own web browser And When I was in the middle of doing that, and it was, you know, barely functional, to be fair. That was when Netscape went public.

And Netscape on the first day of trading was worth something like four point three billion dollars. And I saw that number four point three billion and I was like, You know what? Netscape one point oh is better than my web browser that I'm writing at home, but it's not four point three billion dollars better. Like it's kind of not that brilliant a piece of software. And it wasn't. You know, it was like 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, this is gonna be a big thing. This is quite interesting. I had a a friend Tem Shell and he and I started tinkering around on the internet and we we did a bunch of different stuff. We started a a little web directory search engine called Bomas, 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 and What was interesting about that is we

And and the 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 No, it was like Yahoo Links, you know, 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 why would you need to hire staff to do that? So that's kind of the early user generated content concept. And then we tried a lot of different things over a few years' time. We had I would say early blogging. Slash dot was a big tech.

news site that was massively popular at the time. And they open source their code, slash code, they called it? So we grabbed that and started opening uh a bunch of different blogs trying to leverage the traffic we had built. And you know, it it went well for a while. So so it was growing and it was doing well and

It was the dot com boom. And then we got approached by This is actually a really funny We got approached by N B C

T V network, you know, NBC, NBC I N B C interactive. 'Cause 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 T V network should move into like why should these upstarts like Yahoo and Google. We're gonna create a a web portal and a search engine.

And we're gonna have all these different web properties and it's gonna be just like a T V network. So they started building things and so they paid us a lot of money. They bought out our full av inventory for far more than we had been able to sell it for ever. And in exchange we moved the whole site to bombers.nbc.com, so we became a subdomain of theirs. So that they could count our traffic

For their medium metrics and numbers. And We were about ten percent of their traffic, which was kind of interesting because they didn't pay us nearly ten percent of what they were blowing on everything. And so there for a short period of time, that was like really our dot com boom era. Like it was amazing. We were making good money.

And then Lo and behold, They realized somebody higher up Realize 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 got a contract and you know, whatever. A tiny company versus a giant company, yeah, you just take what they give you'cause there's no way of fighting it really. So 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 New Pedia, which was the first encyclopedia project? 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 started thinking about The encyclopedia project, I would say. The the first is

At what point Did you leave your Finance job. Ah. Yeah. What experiments were with the safety net of this background of employment? And when did you make the jump?

Out. So my My boss, as I say, it was a small firm. We had I think there were probably twenty Staff total.

And my boss was a trader himself and He And sort of knew that I was going home at night and working at 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

We weren't able to pull off. So one was Auto trader dot com. So basically I was like people could Post ads for the cars they want to sell and get in touch and and so we went to car dealers. They they weren't interested. So I had a This idea for ordering food online, which of course now is a huge business and

At the time, again, restaurant owners looked at me like I was from Mars when I would go in and go, I wanna put your restaurant online and they're like W we've got a fax machine, we don't know what you're talking about. But we were doing this and that and then the the Webring concept started to take off. And we could

show like, you know, traffic is increasing, increasing and Michael was a trader, uh, my boss, and had seen sort of 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. 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 and Tim a salary and we hired a couple more programmers and so on.

Also moved to San Diego'cause I was fed up with the Chicago weather. 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 thought 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. Like it wasn't It didn't feel like cutting ship and I'm never gonna get to come back to my old career, which not everybody has that. You know, there are certain careers

Some of the worst are places that I consider to be virtually like cult when people join them. But like the big consulting and accounting firms. Where they've got a really rigid kind of upper out. Culture.

Where if you think you're about to make partner in two years' time Which is a fat salary. It'd be kinda crazy to quit, even though you you're unhappy. Because You know, you might get fired anyway, or you might make partners. So you know, it's like a weird, sick kind of life.

I was I wasn't in that kind of situation. It was like a very entrepreneurial company I was working for. So therefore it felt like okay, look. This is a side thing, I wanna do it 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. Just like you know, it's like give Jimmy Here some money to trade with. Let's see how it works out.

Right, and if it doesn't work out. There are Other options. There are follow up opportunities. Yeah, and I I talk about this None of this was in Silicon Valley, but

I talk about this particularly in places you know, I travel all over the world well, I used to this year I just did 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 startup 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 f startup 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 came a big thing, that's actually not a good example'cause that's been a big thing for a long time now, but You know, it's like, Oh wow, that's interesting'cause you were too early Or you missed it because of this, that and the other, but actually that was a great idea. And your talent is so great, not not a problem.

And I think in a lot of societies around the world, I mean I Have talked to Japanese entrepreneurs, Korean entrepreneurs, and they 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, like I've missed the boat. I should have gone to work for a big company. And I think that's unfortunate because it fails to generate the culture that can generate innovation. It highlights a number of things for me as we're talking and 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? Like your boss viewed it as another trade. He's like, sure, I'll stake this guy. Like you're at a blackjack table and you have possibly a system for beating the odds. Like yeah, great. Let's let let's try it. I have to make sure that he has enough money that he that he can survive like a short string of bad luck, but let's see what happens versus, as you put it, maybe in you know, big five accounting firm or somewhere else where it's it's up or out. And the game is Kind of zero sum.

And then you have to completely switch lanes. And I wanna come back to Actually one. Mm. question that if I don't ask is gonna 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 That happened. Because that seemed to provide the fuel. for

Some of what happened later. How did that actually come together? I would say no, we weren't we were by no means dominant. We only ever had a little bit of press coverage. It wasn't it wasn't like a famous thing. We were on certain lists so back then there were a few Sort of like today you could look on Alexa and get the Alexa ranking of something. And it isn't very accurate necessarily, but it's it's the thing that's out there.

And so I think you could look us up and say, 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 wanna 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 in in a way if you think about

A T V network That's kind of their mindset. This is like Pay For

A production company to create a show. So we're gonna go out and we're gonna find A production company and a writer and we're gonna back them to build this thing and they're not necessarily actually making the T V 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 let's bring onto our network. fifty of these things to to generate a bigger property. But I I literally have no idea how they found me. That's a good question. And I would imagine there's some behind the scenes although predictable conversation on their part, which is

Some type of arbitrage right there 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. Yeah, no, and I I think it was slightly different from that,'cause 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, you know, like they can pay you more for your small website than you would make on your own and and they can Arbitration to make money on it. That's right.

But in this case I I believe because it was the dot com frenzy I think it was really more 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 smile of billions.

We can spin it out for those billions. That's kinda. Whether they can actually make money or not. as a real business'cause this was In the dot com mania, which by the way is Mostly leftist, but I 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. The new new economy, as it was back. Exactly. Exactly. Now you mentioned a few different

Kind of shot. That you took you mentioned food, you mentioned this auto trader like Concept.

You were trying Presumably to see what would stick, what might gain some traction. But you don't have infinite time, right? You have this finite resource.

So you can't try everything. How did you choose these particular Shot. So really Seat of the pants?

Got You know, I 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 in to advise. Where you would Create. lists of twenty five opportunities and then tick through the pros and cons of each one. You didn't write a hundred page white paper for yourself before starting. Exactly. And in fact l later on when when I was

realized that it would be a good time to start thinking about raising venture capital. Like one of the things that was really impossible for me is Just sort of Write a business plan. in the traditional sort of MBA school kind of way, because I'm like, I just

Most of the numbers you're gonna write down are complete fiction because You know, it's like quite a three year, you know, revenue estimate. I'm like, Oh wow I don't know. Like literally pick the numbers. 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 and don't waste your time with a lot of nonsense. So that's kind of how that works. I would say it would have to do with Did I find it personally interesting?

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 do people who are into

Pamela Anderson, who was huge, like she was our number one 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. Didn't really work. But that was kind of the thinking on some of the projects is to go, like, 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 those were just like random ideas of let's build a website, what could it be?

And then you've started looking at these adjacent opportunities once you had identified the type of people who were providing traction. Yeah, exactly. Although to be clear though The new Pedia project was not something I thought there was adjacent traffic to. It was kind of like Actually

This idea of a free encyclopedia for everyone, that's just Awesome, meaningful. So that was really much more There was no clear business idea, no business plan, no nothing. It was just I think I know how to build this.

I'm just gonna build it and we'll figure the rest out later, which was also kind of a dot com era thing. Don't really know a business model, but I just know this sounds like a cool thing and if if it's a cool thing, we'll find a way to fund it eventually. The field of dreams approach. Yeah. Uh they build it and they will come. Yeah. 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 that then this deal falls through big company, you know, huge company versus small company contract dispute. Forget about it. Right. Just bloodletting exercise. Yeah. Did you have to make the decision to abandon the audience and what you had built to then jump to new Pedia with no real plan for

business or revenue, or was it an easier decision than I'm making it out to be? It was. I mean, I would say the immediate thing that happened and a 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 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 dot com crash long before I

Can admit it? To myself. And that there was gonna be no more sweetheart deal like that. Like that that was just ridiculous and they were overpaying and we weren't gonna find any way of making that much money. And I could have Cut the stuff.

Sooner? What we did though, we were I think I would say we were about eighteen to twenty people when the deal blew up. Obviously we didn't hire anybody and then people move on in any kind of company. So, you know, a couple 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 like lay people off. That's just not my Strong point of being like

kinda brutal with people and stuff and They're doing good work. We're gonna 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. Like I can't carry on like this. We're literally not gonna make payroll. for another month if we don't dramatically cut. And so we did. We went down from I think On that day. We went from sixteen people to four.

That was a pretty brutal time. But sixteen 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 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 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 we're like, Wow, this is now bigger than anything we ever made before. And that's kind of cool and exciting.

But again it was it was not a 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 r 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 kinda sat there making money. Not a huge amount, of course, but it's like

This is enough to pay ourselves to work on this other thing. I certainly want to dive into New Pedia and then what evolved from there. But before I do, I I have to ask, since you mentioned, you know, I should have Cut headcount 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.

Yeah. Who knows? Maybe you'd still be working at that company for all we know. For sure. I mean one of the so as we get from newpedia into Wikipedia really One of the things so I always say Wikipedia is a child of the dot com crash, really. Now it was started before the crash, you know, it was 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. Wasn't gonna change everything to be able to put a few ads on and get couple of grand a month or whatever it might have 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 gonna do about these problems? And what do 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 have evolved into the same type of model that we see

Uh Twitter You two. Facebook like 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 admin. 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 there's 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 would have never occurred to me to do it that way. It was really necessity is the mother of invention kind of thing. 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. And it's just incredible what you see. 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 the

what was described at the time as dot com depression in two thousand eight, early two thousand nine, 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 new Pedia because there are reasons, I suspect, why people know. widely of Wikipedia, not so much newpedia. So What? Didn't work.

Not New Pedia. And when did you know This is really not gonna work. So New Pedia was the same vision, free encyclopedia, freely licensed.

But I didn't know anything about building communities really. 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 it does foreshadow something. That If you're gonna be an encyclopedia written by volunteers on the internet, then people are gonna make fun of you unless you're more academic.

Than a traditional encyclopedia. You gotta 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 you know, to answer your question of when did I know Well 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 gonna 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. When I was in grad school I had published a paper on option pricing theory and I'd worked in the markets in Chicago, so I knew that area.

quite well. And I thought I'll just write a short biography of Merton. I'd read all of his academic papers and worked through the math of all of his work and you know And so I sat down to write and I had a massive immediate writer squawk Because I knew they were gonna 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 like no fun. Like that's scary. And I was like, I'm gonna write this thing and get it back, it's gonna 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 gonna 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 than just pivoting newpedia is that the we thought that our very, very serious new pediat 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 uh just have one little side note that's really interesting. When we were pursuing the new Pedia model. One of the earliest pieces that we published a great fanfare with our small community were like

Great, it's past the seventh stage. And here it is. Dun da da da. And it took a couple of days only before somebody emailed him and said, Hm 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 at and everything. didn't catch the plagiarism nearly as fast as showing it to two hundred 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 Right, informative, really.

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 I 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, uh, who's is best known as as the inventor of the world wide web, was distraught when Mosaic came out because it was effectively read only. We were talking about Netscape earlier. And he really wanted people to be able to modify web pages. Um Mm-hmm.

I'm very liberally paraphrasing my interpretation there. Then this this software provides that capability, how are you or your team exposed to that. But first I was exposed to it, so Jeremy Rosenfeld was one of my

Employees he worked for me. Did a bit of this and that writing. He came to me and showed me a wiki. And it was just before Christmas and Said, Hey, you know, I 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 from 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 home school, 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, that wasn't really like a break point moment and there was no moment of just leaping and

you know, it was all transitional from one to the next, but that was like 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 gonna go for it. I'm just gonna install this wiki software. So I Downloaded a an open source wiki package that was very, very basic. Set up it.

Type Hello World and We're off to the races. That was really that moment. When It was like okay, let's

Let's just make this happen. I'm looking at a Paragraph. From an Esquire article. Esquire UK and I'm just gonna read

Two sentences, one or two sentences here. Wikipedia is a universe unto itself, its ambition unequal, and its scale unprecedented. It's three hundred That number I'm sure has changed over time. Staff and contractors are fond of a single phrase. Quote, thank God our little enterprise works in practice because it could never work in theory. And often to this day I'm

Continually amazed that Wikipedia works and you know the the art 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 that made it catch right in those first few months. Just to be clear and and you the way you said it is correct. Sometimes that quote is attributed to me. I've never said that. So not even sure I agree with that. I think it works in theory. It works in practice because it works in theory, but that's that's a whole complicated question.

Mm. So I I would say key decisions that made a huge, huge difference that were really kind of open questions in the early days. We're Things like Neutrality.

So the idea of There was a proposal early on that maybe instead of having one entry about Let's say Abortion, a controversial topic. Save having one entry about abortion, why don't we just have competing entries?

So different people can write whatever they want and and then you know they can vote on them or just competing entries. And I was like, you know what, I no, I 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 size, but just explains the ideas. And I think that was hugely important because the thing about

Neutrality is Yeah. All kinds of diverse people as long as they're thoughtful and kind. can get behind that. They can go, Okay, yeah, like I I get that. That's okay. And you wouldn't know it from Watching

T V debates or Most people are pretty Reasonable. And we'll say, like, I disagree with this, but It should be presented in a

Fair way that the defenders of it would uh identify. 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 what do we think about that? And I was like, you know what?

Uh 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 Wiki Source. Where people put all kinds of source text, you know, things like that. So it was a lot of those kinds of things. I 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 gonna 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

Slash talk would Create a sub page. Wow. 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 debate 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 would 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 a interesting tool for a Weird wiki type of conversation. Listening to you list off these different decisions and maybe this is being really dramatic, but it 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 that 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 a as kind of like a vestigial tail have 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. I always have a hard time with this type of question and I I always explain what I mean by saying I'm I'm a pathological optimist. So I always think everything's gonna be great. That's not correct, by the way.

Everything is not always gonna 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 of the time, so even Let's say

The first attempt with new Pedia. Clearly didn't work. And so you can imagine in a fantasy kind of way, Oh, we could have just started Wikipedia two years earlier instead of doing this whole new Pedia 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 five foot seven.

And not athletic at all. But had I been, you know, it would have been completely different. Yeah, but I'm not. And I I never was. So You know, had I been genius enough to figure out that the new Pedia project wasn't gonna work two years earlier, then great, but how can I regret that? Like I wasn't that genius and I I can't play basketball. So You know it's kind of like Yeah. So

For me I think this is 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. But 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 narcissistic and and fantasy land that nothing can ever fail it. I mean I really like the fail faster, lean startup kind of thinking. I said let's just try little experiments and 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 ID. 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 twenty years on we would have solved. So If you go on the talk page of any Wikipedia article or you go to Wikipedia, you 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 you know, 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 a deck. That's insane. Like why not have a threaded discussion system? Like just automatically in Deb. I hit reply to your comment and it goes just like in Reddit every And there there are some good reasons for it. It's complicated, right? But it's 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 want 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 At Wikipedia if you leave a comment Like if you we 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 words myself. 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 like 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 and 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 W T Social that we're doing. Is We've got comments. It's like can other people hide your comment? Can they edit your comment? And you know, that's the kind of thing that we're experimenting with and it's It's hard, actually.

It's super hard. And it's it's also 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 decision tree of someone who is trying to do something. It it seems so obvious. obviously useful, but it is not always obviously

Done, if that makes sense. Yeah, and actually one of the things I find that it actually does get done and I think slightly overdone. In Let's put myself in the shoes of A bad actor. So what can a bad person do?

And I feel that if you over design 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 gonna 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 to I call it the stake knives analogy. Which is Imagine you're designing a restaurant and you think Okay, in my restaurant I'm going to serve steak'cause I like steak and I'm gonna give everybody steak knives.

And one thing we know about people with knives is they might stab each other. So therefore I'm gonna build a cage around every table so that no one can stab each other. Uh and yeah, when you hear this you laugh because you're like, Oh, that's hilarious because like yeah, but then what do we do about it? Actually that is true. People could stab each other and and what we do is we 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 So hopefully Young and strong will tackle the person. Stop the violence immediately and

And we would call that a hero. We think that's a great thing to do in society is to Do what's necessary to prevent damage in 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 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 kinda 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'cause 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 you know, I just think

Too often if you design for the worst people Then you're you're failing design for good people. Makes a lot of sense. Metaphor drives the point home. And um 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? That's a great question. It's 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? on all of those things. So a great Wikipedia in in my view Is someone who really take seriously the values and ideas of Wikipedia, like neutrality, for example, quality, for example.

Reliable sources. And they take all those things 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 My blind rage at this ridiculous person.

would make it really hard for me to be a good Wikipedia 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 thoughtness to say I go into this debate It's gotten a little rough and tumble. But what can I bring to this debate that'll 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. 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. Organizational decisions. So one of the things that we've done recently that I think is a really fantastic thing is we've we've introduced a new universal code of conduct which is really came from the community, a huge consultative process within the community to really get the wording exactly right.

And the idea is to say, look, we have a code of conduct which is really about all these values. It's about being inclusive, being open, being friendly. being a safe space not to use a buzzword, but That's been a fantastic thing and it really is about saying, look We know these values work.

Or Wikipedia. They make Wikipedia better. And we also know that sometimes it's quite hard to enforce them because a variety of factors. So In terms of Bad behavior.

So bad behavior at Wikipedia. If you come to Wikipedia and you just start 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. 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. I think any system would struggle with'cause 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 thirty five great entries about some obscure topic

Does not excuse you insulting people. In the story. It's just not okay. And we will find someone else to write those thirty five things because It's not necessary to be a jerk in the community. No matter what we do, those are very human decisions. They're very

You know, there is no simple formula. One of the things we've never done in Wikipedia and never would do is have Points or likes or that sort of thing. Because it's just inhuman, really. It's like human personalities are so rich and so varied. that really like the best thing is like

the kind of great Wikipedian in my mind is the person who's able to go in I kinda Hold hands with that. contributor who's doing great work but being difficult. And kind of coach them into being nicer as a human being, you know? It's like hey, you don't have to go around with the chip on your shoulder all the time.

I'm gonna help you deal with the problems that you're trying to address, but you should probably stop yelling at people. And and we have great people in the community who are good at that. And that's Really kind of amazing. I'd like to revisit this pathological optimism. Because I mean the term pathological is is funny, right? And I mean if we go to pathos, right? I mean this 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 general hight 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? I would say it's just kind of a deeply ingrained

part of my personality, but I also think I do cultivate it. Because You know, like anybody. I I 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 gonna remember, count my blessings

I'm gonna look for the fun bit of this and the opportunity and and what can I change. And sometimes 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 Hm. 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 in 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 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 Saw yourself on having kids. The greatest thing in the world is Going out with your kids and look at

Here in 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 you roll them you know, you get them to roll and you put them on a twig and that's great stuff. That's what life is, it's absolutely free. And If you remember that sort of thing, as a practice, not just

hopefully, but just actually go, you know what? I'm gonna funk about work. But you know what, there's more important things in life. Let's go do that. Then it turns out If you can turn your 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 to the situation.

Whatever that might mean. What are some of your practices? Maybe they are just consistent in 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 what does it look like? I don't know. It's so ingrained. But it's not like Yeah, I don't I don't. You know, it's just sort of like yeah, I just kinda pull myself together. But I don't wanna be too glib. I mean people do struggle with genuine problems of of depression.

uh 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 gonna 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.

Right. Well you you also I mean speaking as someone who has a history of And this this goes back. hundreds and I'm sure thousands of years in my family line just given the software, but 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. Mm. 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. Yeah. Yeah. No, it is. It is. And and I like I say I don't want to be glib about

These are real issues. They're hard issues for lots of people. And so it's 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. You know, like, come on, asshole. Like, are you kidding me? Like 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, you know, sort of remember the good things, you know, at the dark moments can be can be quite helpful.

What are you working on right now? What is it that you're You're directing your time and energies to. So I spend a lot of time on WT social, sort of design and so on. Got a very small team though, so the software progress is very slow. I deliberately chose not to raise money at at the outset because I I felt if I did

If I'm trying to reinvent social networking, if I raise money early, which I could do because of my position, I would suddenly be on a certain kind of V C 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 in in about some quite hard problems.

So I spent a a fair amount of time working on that, but I also During lockdown So at the beginning of lockdown, I'd say when when we first Last March here is when everything went It's a complete

Shut down. It was an amazing weird time, you know, suddenly From traveling all over the world giving speeches, I'm like here at home and the kids are here and and all that.

And Basically For the first couple of months I was like, Oh, I'll just carry on. I always work from home, I work remote, it's no big deal. And then I'm like, actually this is weird because I I can answer more emails, but as anybody who I mean I'm I'm sure you're this way. In fact I have a feeling, I remember there's something

You wrote about email, but like Literally With email. The problem with email is the more email you answer, the more email you get. You know, like there's no such thing as finishing your email.

Like y you know, it's just like forget. You're never gonna finish your email because you if you email a hundred people a day They're all gonna freak and email you back tomorrow and then twenty more people. So, you know, it's kind of hopeless. So then I realized like this is not productive, this is not it. And I thought, you know what, I actually what am I gonna s do with myself? I don't know. I'm 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

customized to what they're interested in. And I travel and I do my speech, 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 get a chance to do it. So I basically just started doing Online programming classes. And just like I I wanna get my Re up my skills. start doing things, started really learning a lot of interesting things, got very interested in

Web RTC, 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, my family in America. And basically it's just like, you know, you could get on once a week and 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. You know, 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 in 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

Please nightbeyond.com. And I'm really enjoying it. It's like It's it's one of these things that's like that entrepreneurial itch. Of like Here's something that I wanna do.

Which is do quizzes with my family during lockdown so that we get a chance to to see people. And let me in a second I'm gonna go 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 gonna do it. Is it gonna 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. Jimmy, what does the W T stand for? A wiki tribune. It's basically a pivot Wiki Tribune was Kind of.

Thinking about how to get people involved in news and how to 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 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 New There's like we're kind of dispersed. And so whatever we talk, we we have phone calls from time to time. We've got a the family WhatsApp group. We've got the

Kids only WhatsApp group, where we talk about, you know, w 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've the one sister who

I had kind of grown apart from not not no serious break or anything, but just, you know, 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, you know, like What is social networking? What do we when we think about social uses of computers So much better, so much healthier than, for example, something that's completely innocuous, but like If I click like on a picture of my sister's dog on Instagram Are we kidding ourselves that that's social?

That is the most limited form of human engagement. It's just like I like your picture of your dog. Okay. So what, right? That's not that's not a conversation, right? That's not actually joking around It's not talking about the family. It's not Teasing each other about a quiz question. You know, like real human interaction.

So for me that's that's really interesting. And so that's kind of what I'm focusing on is Like, okay, how do we really reimagine? Like 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 Because of lockdown, like everybody's gotten used to doing Zoom calls, right? It's it's a thing. And obviously we'll 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

Well they live all over the world. Who I mean like, Oh now it wouldn't be that weird to go, Oh, let's get a bunch of people together and go on Zoget. Like why not? It's kinda fun. Well count me in. I Love this idea.

In part because Zoom calls. And video conferencing without some type of context can work, but it can also be Very Challenging. So having an activity A hundred percent.

is key, at least for me. Yeah, or Reet my co founder at Wiki Tribune 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. Right? Even if you really love your family, it's like suddenly you you're popped 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 gonna make the mashed potatoes and and then we go and we sit together and and you know, 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 gonna get your whole family together once a week for a call And you got nothing to do, it it's gonna be weird. Quite often can be very awkward, but yeah, it's like let's do an activity together. It's a it's a conversation starter. It's kind of a Icebreaker. I wanna 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 ten year, twenty 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 uh

Than a lot of what goes on. So I'm excited to see where it goes. Yeah, I I think that's right. And I actually what I think is 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 gonna make the most money, but it's kind of boring to you. Chances are you're not gonna make that much money'cause 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 a clever thing. You're like, Well I it's boring, but I'm gonna only do it for five years. I'm gonna sell out for a ton of money. It's like no, you're probably gonna do it for two years and you're gonna hate every minute of it, and you're not gonna be good at it'cause you hate it. First is 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 it doesn't have to be a consumer product, it could be B to B 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. Jimmy It's so nice to reconnect. And spend time together. And I have one

One last question, one or two last questions, and this one sometimes goes nowhere fast, and I'll 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? Well, I mean I think Yeah.

the the thing that immediately pops to my mind is 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 then. You can learn, you can grow, you can heal, you can cure, you No, it's amazing. to think about what are all the implications of that statement. And so I I just think

The more people who Are thinking that way. Obviously for Wikipedia, but it it's not about Wikipedia's organization, but it's just like Wow, what can we do to make sure that education and knowledge are universally accessible?

'Cause you know, we got a lot of problems on this planet. 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. Here, here. Well, Jimmy, people can find quiz night beyond at quiznightbeyond.com. It's always fun. Two. Connect it's been a little while.

And and I really appreciate you taking the time today from so far away. Although so close. Is there anything else that you would like to add? Any closing comments, uh requests of the audience, anything at all before we Bring this.

To a close. No, no, it's it's good. I mean I I hope people will check out Quiz Night Beyond and uh come and visit me on W T dot social and um you know, say hi on Twitter and try not to be a troll on the internet. And that's all Ha ha 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, 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 tim.blog forward slash podcast. And until next time, thanks for tuning in. Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with

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