Leap Academy with Ilana Golan - Wikipedia Co-Founder: How Jimmy Wales Changed the Internet Forever | E133

Episode Date: November 11, 2025

He could have built a billion-dollar company, but instead, Jimmy Wales built a movement. When the dotcom crash hit and funding vanished, he didn’t sell out or add ads. He doubled down on values, creating Wikipedia, a global temple for the mind that made knowledge free to billions. In this episode, Jimmy joins Ilana to share the story behind that decision, the failures that shaped him, and the community that built the impossible. He breaks down why the best ideas come from doing something interesting, not chasing money. Jimmy Wales is the co-founder of Wikipedia and the founder of the Wikimedia Foundation, the nonprofit that supports Wikipedia and its sister projects. He also co-founded Fandom (formerly Wikia), one of the web’s largest community platforms. In this episode, Ilana and Jimmy discuss: (00:00) Introduction (02:31) How Childhood Curiosity Sparked Wikipedia’s Vision (05:59) Turning Crisis Into Innovation During the Dotcom Crash (08:08) The Creation of Wikipedia (14:19) The Power of Community When Capital Runs Out (20:14) Why Jimmy Refused to Monetize Wikipedia (29:54) Early Fundraising Efforts for Wikipedia (34:21) What Makes Someone Truly Notable on Wikipedia (39:11) AI’s Role in Wikipedia's Future (46:15) Inside The Seven Rules of Trust (57:17) Jimmy’s Ultimate Advice to Just Start Jimmy Wales is the co-founder of Wikipedia, the world’s largest free encyclopedia, and Wikimedia Foundation, the nonprofit that supports it. An advocate for open, collaborative knowledge sharing, he has empowered millions to contribute to a global resource of information. Recognized by TIME as one of the 100 Most Influential People in the World, Jimmy is also the author of The Seven Rules of Trust, where he shares the principles that guided his journey and offers insights on building lasting endeavors. Connect with Jimmy: Jimmy’s Twitter: x.com/jimmy_wales Jimmy’s LinkedIn: linkedin.com/in/jimmy-wales-919a8b Resources Mentioned: Wikipedia: https://www.wikipedia.org/ Jimmy’s book, The Seven Rules of Trust: A Blueprint for Building Things That Last: https://www.amazon.com/dp/0593727460 Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence: https://www.amazon.com/dp/0143115766  LEAP E122 with Nathan Blecharczyk: https://podcasts.apple.com/us/podcast/nathan-blecharczyk-the-raw-truth-of-scaling-airbnb/id1701718200?i=1000723574008  Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out our free training today at https://bit.ly/leap--free-training

Wow, this show is going to be incredible. So buckle up, and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream rules, jump to entrepreneurship, or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success. So subscribe and download.

ever miss it. Plus, it really, really helps me continue to bring amazing guests. Okay, so let's dive in. People who want to be entrepreneurs, one of the most important things that you can do is get your personal values to a point where you don't really need a lot of money, which is ironic because that's probably a way you're going to make a lot of money. Jimmy Wells, co-founder of Wikipedia, the world largest collaborative encyclopedia making information free, accessible, two billions. And he just recently written a book, The Seven Rules of Trust. As we were growing, we had no money, we had no ability to hire staff. It was the dot-com crash. There was no chance of raising money. Therefore, we, as a community, had to innovate.

In many ways, Wikipedia is a child of the dot-com crash. There is no money coming in, and you're still deciding not to monetize, which is a really weird choice. For me, it should be like a temple for the mind. Like, it's a place you go to think, to learn, to reflect. This whole of going to a community and raising capital is something that wasn't really there. The goal was to get $20,000 in one month. Within about two weeks, we had raised $30,000. Do you think that Wikipedia will change now in the era of AI? I mean, I think broadly the answer is...

We speak to many incredible leaders on the show, but not many have changed the world like my guest today. So I'm so excited about this show and this episode. And the weird thing is that most of you will actually not recognize his name, but you'll certainly recognize the company you founded and the impact he created. Jimmy Wales, co-founder of Wikipedia, the world largest collaborative Encyclopedia. making information free, accessible to billions. And Wikipedia is around 20 billion page views a month. I mean, it's extraordinary. And it obviously completely changed how we access knowledge altogether.

And he just recently written a book, The Seven Rules of Trust, that we'll talk a little bit about. But I really, I can't wait to dive and understand how somebody just decides to start an encyclopedia. And many decisions that Jimmy made in order to make it as impactful and neutral versus revenue generating, Jimmy, thank you for being on the show. Oh, well, thanks for having me. It's fun to be here. I have to take you back in time a little bit because I think everybody in listening to this

probably had these book Encyclopedias back home. But except for having an encyclopedia in the house, did you have any special relationship with that? Like, what got you so excited about this thing? I think there were a lot of different things. So, yeah, as a child, we did have the World Book Encyclopedia, which is an encyclopedia for kids, really. And then later we had Encyclopedia Americana and Encyclopedia Britannica. And I did always love the encyclopedia, but, you know, I was very excited in the early days of the internet. And one of the experiences that I had that I, you know, really remember this day is like, you could email almost anybody, a professor anywhere. And if you asked a thoughtful and intelligent question, they would answer. And by the way, that's still true today. Like, a lot of people are just very, very helpful. And I had a friend online who was a philosophy professor at Brown University. And he and I sort of emailed each other back and forth for years and years.

And, you know, I realized, gosh, we've basically written probably a couple of books together just in our email correspondence discussing and debating ideas. And so that was great fun. it's really interesting, you know, that people are actually really eager to share knowledge and really eager to help with all kinds of things. And so that was part of the impetus behind Wikipedia. And then I was watching the growth of open source software and free software and seeing programmers coming together to collaborate in new ways and share their work freely online. And I realized that that kind of, you know, online collaboration in a spirit of community could extend. beyond just software into all kinds of cultural works. If I take you back kind of through your career a little bit, you actually studied finance,

so not something directly related, if you will. And I think you also enrolled to a PhD in finance, and at some point you change your mind. Talk to us a little bit about the moments because I think, you know, especially on this Leap Academy show, like I'm trying to give like a little bit of blueprints of decisions that kind of build you to that. So take me back to that time in college, if you well. In college, you know, and sort of in graduate school, I was really interested in the markets. As a very young child, I had this idea just as the 1974 oil crisis was coming to an end. And I had read a news story. I was eight years old. I'd read something about Winnebago. And Winnebago was in really.

deep trouble because during the oil crisis, gasoline prices had gone through the roof. There was quite a recession on. It's obviously a huge discretionary purchase, and people couldn't afford to drive a big RV around. So their sales were terrible. And then I just remember that. It stuck in my head. And then when the oil prices and gasoline prices came down, I thought, oh, I bet Winnebago is going to do really good now. And I looked in the newspaper and I found their stock price. And I just watched it for a while. And, yeah, It went way up. And I was like, oh, look at me. I'm a trading genius. You know, I wasn't really, but it got me really interested. I'm like, oh, that's actually very, very interesting. And so

so much later, I was, you know, to go to the beginning of Wikipedia, I was working in Chicago as a futures and options trader. Really enjoyed that, really liked that. But I was also keeping one eye on the growth of the internet and started sort of dabbling. I mean, the great thing about the job I had in Chicago, I was very mathematical. It was really mathematical trading, so I wasn't doing deals or anything like that. I mean, we were truly a trading firm, and I was on a trading desk. And basically, the markets closed at 2 o'clock, because they close on New York time in Chicago, be done with my paperwork out by three. And then I had the whole afternoon. I had no life whatsoever. So I just would go home and sort of do stuff on the

internet. And one of the things that I was doing, because I was really interested in this new worldwide web thing, I started writing my own web browser at home. And, you know, just using free software components I could find. And I was just learning, really. And when Netscape went public, and on the first day of trading, it was worth over $4 billion as I remember. And I thought, you know, my browser that I'm writing at home isn't nearly as good as Netscape. And I'm, scape 1.0, but it's not $4 billion worse, right? The market is really telling us something. This internet thing is there's a lot of opportunity. There's a lot that's going to happen. So I just started doing different stuff. So a friend and I, we started a project called Loop Lunch.

So downtown Chicago, they call it the loop because the elevated train, the L goes kind of around the core downtown area. And I thought, oh, like people should order food online. Like, why you know, people were faxing in orders. It was all very old-fashioned, of course. So we started loop lunch and tried to sign up restaurants, and going into restaurants to try to get them to come on board, they had no idea what I was thinking about. I might as well have been from Mars.

They're like, we don't know what you're talking about. What are you talking about? Internet. I have no idea. Sorry, not interested. You know, so it didn't really work. But I got really excited about the Internet and sort of moved into that area. But I want to go there for a second, Jimmy,

because that was roughly 9095 when Netscape went public. And, you know, the rise of the internet, what's interesting is that you were spot on. You were just early, right? They didn't catch up to what you were already seeing, which is kind of tying really beautifully to Wikipedia later on. But for me, it's beautiful to just see that you're kind of always seeing the possibilities that are upcoming, but in that case, you were just a little early. So I, yeah, go on, Jimmy.

I think it's important to this thing. No, it is funny. You know, I sort of can say, it's like Uber Eats. I'm like, yeah, I had that idea, but way, way, way too early. The world wasn't ready for it yet. But so anyway, first started a project called Newpedia, which didn't work. So basically Newpedia, same vision, free encyclopedia online, written by volunteers, open licensing, free license.

But we didn't know, I didn't know anything about organizing an online community, didn't really know we had a seven-stage review process to get anything published because, you know, we felt like we had to be even more academic than a traditional encyclopedia or no one would take it seriously. I knew it wouldn't work when I tried to write an article myself. And because I had been sort of working on a PhD in finance, and I was an options trader in Chicago, I thought, oh, I could write about Robert Merton, who had won the Nobel Prize in economics for his work on option pricing theory. And so I sort of said,

okay, I'm going to write this article. And it was super intimidating. It wasn't fun at all because I've been away from academia for a few years. And I just was trying to write a short biography, but they were going to send it to the most prestigious finance professors they could find. And it just wasn't fun. And I realized, like, nobody's going to do this. And it sort of explained to me why,

even though we had a lot of people who were signed up on the mailing list and talking about it, not much work was actually getting done. And I think it was because it wasn't fun. It wasn't easy to contribute. And so that was when I knew we had to change. And I want to stop you here, Jimmy, because I think this is such an important piece of it. Because sometimes when you start something, if you don't walk the walk or you don't feel it firsthand, you don't realize we're the biggest gaps.

And I think that was a really important distinction. You know, actually in my new book called The Seven Rules of Trust, Rule Number One is be personal. It has a lot of meanings directly related to trust, but this is kind of an example where that personal experience of like, okay, hold on, people aren't finishing articles. They aren't writing, like, even though we all share this dream and people do seem excited about it. So I had to just do it myself and just really kind of experience it and then say, oh, I can now think about these people who are. We're excited to do this, but they are also very likely feeling the way I feel like intimidated.

It isn't easy. So we have to make it easy. We have to find a way. And so the idea for Wikipedia initially had been just have a scratch pad off to the side where people can collaborate on editing first drafts and so forth. And it proved, you know, very quickly to be a dramatic success. You know, from the very beginning, people just started writing. They just started running. It sort of unlocked the talent.

So if I'm going back to like 96, you have, I think, boomists, right? Which is kind of like, you know. That was the company. We did a search engine, web directory, early blogging. You know, we did, we experimented with a lot of stuff. Right. But I think, you know, this helped sponsor the beginning, right? Because you needed some cash coming in.

And at that point, ad money was a big thing. In the dot-com boom, we did this deal with NBC, the tech. TV network. So NBC had a web portal called NBCI, which they were really touting. It was going to be, they were old media and they thought, well, this is crazy, all these little companies, nobody's heard of like Google are getting a lot of traffic online. NBC can do this better. And so they had a web portal, NBCI, they promoted it heavily on television. And one of the things that they did is they, with us, they, we moved our domain name. They didn't buy the site, but we did a lockup deal. They bought all over.

advertising in Midori at a ridiculously high price, to be honest. And we moved to bommis. Dot NBCI.com. So we were under the NBCI umbrella. For them, that was a good way of thinking. Like, they were like, oh, it's like TV shows. There'll be production companies, and we're the network, and we'll distribute. It kind of made sense in an old-fashioned way. That worked for a while until they were losing $100 million a quarter and decided they better stop doing that. So they canceled the contract with us. For us, that was the beginning. of the dot-com crash. And in fact,

one of the things that was an interesting thing at the time, we had made a good amount of money from them. Like, we were very profitable for those few months. And when we lost that deal,

I was still very much in the dot-com boom mindset. And I was just like, we'll find another deal. We'll find another advertiser. We'll have a lower revenue for a while. But then it really became the dot-com crash.

And it took some time before it was like, wow, you know, revenue is not going to come back. And the mistake I made as an entrepreneur is it took a long time for me to realize I had to downsize. So basically, it was to the point where it's like, oof, we've got another month, and I'm going to not make payroll. So I had to let a lot of people go just to stay alive. Meanwhile, kind of independent to all that, the side project, which was Wikipedia, was doing really, really well and was just growing and growing. And I thought,

But we definitely need to keep doing this. It didn't take long for it to pass the traffic that we had of any other website had ever done. But I didn't want to put ads on Wikipedia. And it didn't make sense. And a lot of the volunteers really wanted it to be in the nonprofit structure. And I thought that's actually a really good idea. Before we talk about the structure of Wikipedia, like at that point, I wanted to take you back to that moment of realizing, like, this is really hard. I don't know if I can make payroll.

What makes you, Jimmy, continue? or do you think of just closing down and shifting? Or you're just seeing such winds of proof that this is working. Like, what gives you the motivation to continue? I saw a path forward to, you know, we had grown quite quickly. And I'm like, well, we can go back to being four people. And the website's doing fine. And, you know, eventually there won't be a dot-com crash forever.

You know, so I thought, we'll just keep going. And, of course, back then I didn't have a clue about how to really. his money. You know, I never really saw it venture capital. I didn't angel investors. I mean, I had my boss who I had previously worked for when I was a trader. He was an investor, but that was, I guess that's angel investing. It's not like I went out and saw it. I just talked to Michael and he was like, yeah, it sounds good. Let's do this. Great. You know, one of the things that I say to young entrepreneurs is sometimes you just have to say, look, this isn't working. I have to pivot. I have to completely change everything. This idea seemed great, but it's clearly not going to

work. So you have to change directions. And sometimes you have to just persist through. You just have to keep going. There's a bump in the road. It seems quite a lot, but just keep plugging away. And the problem is this advice is completely useless because it's two contradictory things. And the hard part is which situation am I in? Right. Is this the time to double down on my horrible idea this is never going to work? Or is this the place to give up on what could be amazing? I don't know. And that's really hard. But I think just having those two pieces of advice to say, well, look, you do have choices. You can pivot, right? Or you can buckle down. And what you really need to do is figure out which one you should do, right? And every context is going to be different.

And you don't have to decide once and for all in many cases. You can have a side project. You can pivot to a degree and not everything. And there's always something interesting. that you might try. And then the other thing, you know, it's just like broadly, I just tell people, look, the next five years are going to go by no matter what. No matter what you do, five years are going to go by. And you might as well be doing something interesting. And in fact, I mean, one of the great things about the Silicon Valley culture is if you do something interesting and it doesn't work out, that doesn't destroy your career forever. I mean, I've had meetings. I've talked to young entrepreneurs in places like Korea or Japan. And there, they do really feel a sense of like

it's going to be shameful and horrible if I don't succeed, which also often stops them from even trying. And I think broadly in our culture, in every culture, human culture, we should say to people who want to try something new, oh, that sounds interesting, go for it. And if it doesn't work out. Hey, good on you for trying. Because we need innovation. We need new ideas. We need people to try things. We need that dream of a better life and a better, you know, way of doing things. So, you know, you just have to, yeah, get on with it. And again, a lot of it is around experimentation. And I think what you showed, and I love that you gave these two decisions, because in Newpedia, that exactly kind of what happened, right? Like, you kind of saw that in a whole year,

you guys had, what, 21 articles, it was really hard to do. There was a lot of approval process, and you're like, I don't know if this is going to be the right one, but then Wikipedia started, right? One of the things that is very interesting is, in many ways, Wikipedia is a child of the dot-com crash, because in the dot-com boom or in an era where funding is easy to come by, What you might have done, you might have said, okay, look, you see some problem on the site and you think, okay, we just need to hire more moderators. We need to hire staff. And they're going to be the ones who decide all these things. And that's, by the way, the system that social media uses, YouTube uses, all of these things. They just hire moderators. They hire staff to be community managers and so on and so forth. Well, you know, I was like, well, we have no money. As we were growing, we had no money. We had no ability to hire staff. It was the dot-com crash. There was no chance of raising money. And therefore, we, as a community, had to innovate. We had to say, okay, like, how are we going to do this? So we have, you know, administrators. But, okay, how do you

make sure the administrators are doing their job in the right way? Okay, well, they need to be selected by the community, and they need to have ways you can lose your adminship, and we need this and we need that. And what are the tools that the community needs to be able to police the site? You know, it's like, there's nobody on staff who can go through wherever you at it. So how do you do that? And how do you sort of of make it, you know, some people have watch list and they can click. Most active editors, anything they edit, it automatically goes on their watch list so they can just go and quickly look at all the things that they've done before and all the new updates and just

see, oh, how's it going? Is there anything? Is anybody causing a problem or is there some new information, that sort of thing? So that innovation came out of the fact that we didn't really have any money. Because with money and when business is comfortable, it's easy to just do things the normal way you do them, and it's harder to actually innovate because you just go, okay, well, right, here's the standard answer, and it will kind of work. So let's just do that. Whereas you're like, well, I can't do that. I have no money. So therefore, we have to really get creative. Right. If you're feeling stuck, underpaid or unappreciated, or you're simply ready to take your career in life to the next level, I have the perfect solution for you.

We have a program that helps you fast track and leap your reputation and career. Become the best version of yourself, get the dream role you'll deserve, move up to leadership, jump to entrepreneurship, or even build a portfolio career. This program helps hundreds a year, and it will help you gain the income, influence, and impact that will transform the second part of your life. Watch our free training today at leapacademy.com slash free hyphen training. The link is in the show notes. Now back to the show. Even though you have a hard time having any money, 2000, one, basically, Wikipedia is starting. You're seeing that this is starting to look really good. Like, you guys have, like, a lot of people that want to contribute and be part of this, but you're seeing

that it's hard for you to make money and you still decide that you're not going to put ads in Wikipedia. And I want to go there for a second. That's a huge decision that completely changed how Wikipedia is basically accessible to all and the knowledge is free. And so, So can we talk about that for a second? Because it was not a simple decision. I want the listeners to understand the whole bubble is bursting. There is no money coming in. And you're still deciding not to monetize Wikipedia, which is a really weird choice, but so smart.

Jimmy, so take us there for a second. Yeah. I mean, I used to joke in interviews. It was either the dumbest thing or the smartest thing I ever did. And then unfortunately, like, the headline would be Jimmy regret. He says this is the dumbest thing you ever did. I'm like, that's not what I said, right? I said, or the smartest thing. It's a joke. It's like, you know, it didn't appeal to me aesthetically, artistically. Like, it just would be weird for Wikipedia to have ads. And, you know, when we think

about the question of trust, what are the things that would build trust in Wikipedia? And if you went to the, let's just, I mean, I don't want to pick on any one company, but it's just the example that's easy. If you went to the page on the Exxon Valdez oil spill. And if you saw the ad at the top of the page was an ad touting Exxon's latest green environmental initiative, you might think, gee, that's weird. And by the way, this doesn't seem like it might be neutral. This might be sponsored content. It might not be fair. And so advertising could bring in those kinds of questions. And then the other thing that I, you know, I think about this, I'm like, I have done.

nothing against advertising broadly. It's a perfectly fine business, and that's great. And my for-profit site, Fandom has ads, and that's all fine. I give this example, which makes more sense. I live in the UK now. I live in London, and you just don't see this here. But in the U.S., it's quite common. You go into the grocery store.

There's some new product, and the company that makes the product has put a representative in the store and said, oh, would you like to try our new frozen chicken product or whatever it might be? You go, oh, I'll have a sample, sure, you know? And I'm like, that's great, because I'm there. I'm shopping. I would like to try this. Or, I mean, I remember once I tried some new diet soda and I'm like, oh, that's disgusting. Like, I thank you for the test. I'm not going to buy it. But like now imagine that, you know, it's Sunday afternoon and you've got your family over for dinner and somebody knocks

in the door and says, oh, would you like to try our new product? You're like, what are you doing? It's Sunday afternoon. I'm with my mom and the kids are around. Like, it's just crazy. So I do feel like there's environments where advertising makes sense and where it doesn't. And to me, Wikipedia, for me it should be like a temple for the mind. Like it's a place you go to think, to learn, to reflect, to chew on ideas, to, you know, visit those talk pages and see what are the debates? You know, how did the article get to be the way it is and all of those kinds of things? And not really for advertising. It doesn't really make much sense to me. And I think the other element is also the topic. Like if you're going to start being more like a Google, right? You're going to

start ranking topics and knowledge based on popular demand versus the real knowledge, right? For sure. For sure. And yeah, exactly. And, you know, we see a lot of algorithmically driven content recommendations, which have a strong commercialized component to it, where things are shown to you in the sidebar based on how likely you are to stay longer on the site and to click and so on, which is why on certain news sites, like the mail online, there's always like celebrity gossip over on the right-hand side because people like to click it. And they, you know, it's like, oh, look, what are the Kardashians up to? And we don't have any of that, you know, it's like the sea alsos are chosen by the community because it's relevant and interesting

and it has to do with the subject of your hand. It's, you know, we don't have clickbait headlines or listicles, as they call it. Fifteen generals who, won the war and number three will make you cry. None of that. We just don't do anything like that. And, you know, the titles of articles aren't optimized for SEO based on A-B testing. They're just called like Donald Trump. The name of the article about Donald Trump is Donald Trump. That's it. You know, it's very simple. No hooks. But it works. Because if you think long term, you know what you're going to get, you know, when you click on a Wikipedia entry, you know what you're going to read. It's on that subject. It's going to have references, all of that. So you're deciding not to

monetize, do you freak out? Like, how on earth do I actually pay the bills? The reason I'm going to, Jimmy, is the listener is listening to this. A lot of them, I want to do more in my life. I know there's bigger things that I can achieve, but I'm scared. Like, I don't know how I'm going to monetize. How do I raise a family? Like, how can I actually make this work, Jimmy? So there's a couple things. So one, I just have to sort of put out there, which is that I always say, and I mean it, that I'm a pathological optimist. So I just, by my nature, I think everything's going to be fine. So I don't panic and I don't worry about stuff. And I'm like, I don't know, but like everybody's excited. So surely we'll find a way. But then a little more sort of realistically,

because that's not advice anybody can take, right? I can say just trust, but probably you shouldn't Josh Trust, and I just do, and that's just me. But I do think one of the books that had a huge impact on me that is still on sale. It's a bit outdated. I reread it again just a few years ago. It's a bit old-fashioned in certain ways. But it's called Your Money or Your Life. And it's a book about, ostensibly about personal finance, but it really is just basically saying, you can live on a lot less money than you think, particularly if you set aside a lot of the consumerism and a lot of the things that people think you need, keeping up with the neighbors and things like that. And frankly, the best things in life are free and the things you think you need

to do to be happy, most of them don't actually make you happy. And so that, if you can train yourself and like if you read, you know, nowadays, there's a lot of great Reddit groups on personal finance and retiring early and all those kinds of things. And one of the expressions they talk about is lifestyle inflation. So for young people who are working in a corporate job, they live perfectly happy. Most people, they kind of remember those college years when they were eating ramen noodles and just hanging out as some of the happiest years of life. But suddenly, oh, well, now you've got a job and you got a promotion. And every time you do, you still feel like you're just barely breaking even and barely making it. You spend every penny you make. And if you really examine it,

It's like, well, you used to live on a lot less money and you were perfectly happy. And now you're still on that treadmill and you're, you know, you want to get that big promotion. But then when you do, you move to a bigger house or you buy a fancier car or you change your vacation habits and things like that. And so suddenly that lifestyle inflation means you're back where you were. And so that had a lot of meaning to me. And I'm a human being. So I have to say, like I live in a very expensive part of London and I sometimes think, oh, yeah,

I'd be perfectly happy on a dorm sofa, but here I am. But I can afford it, and that's okay. But I do think particularly for people who are entrepreneurs or want to be entrepreneurs, one of the most important things that you can do is get your sort of personal values to a point where you don't really need a lot of money, which is ironic because that's probably a way you're going to make a lot of money. But I think it's sort of tied up with, I think, if you want to be an entrepreneur, if your primary motive is, I want to make as much money as possible, that's probably not going to work out for you because you're not going to be excited about the thing you're doing for itself. You're just going to be thinking about how do I make the most money as quickly as possible to buy a Lamborghini or whatever crazy thing you want to do.

And it's probably better to go, you know what, I want to be resilient. And if I have gotten to a point in life where I think I need, because I've had a great job at a tech company, I think I need $200 grand a year just to live, okay, well, I guarantee you don't need $200 grand to live, right? You do need $200,000 if you're living in San Francisco, a very expensive place, to live in a certain way, fine, and you're perfectly able to spend a million a year in San Francisco. But if you are afraid to go out and to do something on your own, just think how much different that would look if last year you made 200 grand and you only spent 50 because you were very careful about where you lived and the choices you made and all of that. Because suddenly, oh, actually, I can take a huge salary cut and I'll still be fine.

I can also save a lot, so I've got some capital to tide me over. So I do think that's quite important. I don't know. We got off on a long ramp there, which is. I haven't talked about in a long time. But do you think it's really important? It is important. And I think, Jimmy, a lot of what we say is that it's not only about the money we make,

but the life that we're creating with it. And I think that's a big part of, like, are you creating the thing? But I will take you to, I think in 2005, you started raising a little bit of capital from the community. And I want to give some context because right now it sounds normal. But Indiegogo, Kickstarter, all of these started kind of a few years. later. So this whole concept of going to a community and raising capital is something that wasn't really there. How did you even think about it and how did, you know, what was, how did

you make it happen? There were two initial fundraisers. And one was very small. It was really internal to the community. So we had a developer, Brian Vibber, who was a legend within our world. And he was effectively working full time for free. He had a job. He was working part time as a programmer. I'm going to say like 20 hours a week, but he was spending at least 40 hours a week working on programming for Wikipedia. And that was amazing. But Brian needed a new laptop. His laptop was about to die. And so we just put out the call within the community. And it took no time at all that people contributed 100 bucks here and there. And we got Brian a new laptop. And that was great. But then the big moment, I had been just buying the servers. We had three servers that we

were using. And on a Christmas day, 2003, Christmas Day, 2003, so Wikipedia is about two and a half years old. Of the three servers, two of them died, hard drive failure. I mean, it was such bad luck. And nobody was in town. We were down to four people then, the company. Everybody was gone. I was in Chicago visiting relatives and so on. So I had to get online and scramble and get the whole website running on one website, which meant it on one server, which meant it was really slow. Everything was running on the database server instead of separate web servers in front of the database server. And I was like, yeah, we are going to have to raise money. And so I set a goal for that first real fundraiser. The first one with Brian, that wasn't

about, it was just sort of put out the word, like, let's chip in and get Brian a laptop. But we just put banners on the site. And the goal was to get $20,000 in 30 days. because I thought with 20,000, we can get probably five or six. I think our first order was initially eight servers, front-end servers, maybe a second database server. And we hoped to do it in a month. And it was basically within about two weeks we had raised $30,000. So that was the first time that we put notice on the site saying,

we need money, please help us. And people did respond. And up until that point, we were still thinking, yeah, maybe we're going to have to put ads on the site. Like, we have to do what we have to survive. And in fact, I don't think we've ever made a formal, formal, formal statement that we will never have ads on the site because you don't want to make promise something that you might have to go back on.

But, I mean, it's been many, many, many years since anybody's ever even thought about it. You know, like, it's not even on the cards. And I think we can safely say now we're never going to have ads on the site. But at that time, it was like, yeah, I don't know. Like, we're going to see. And, you know, there were other ideas people would bandy about, like, could we do some sort of a freemium model, you know, where you pay extra to get what? I don't know. That was the problem. Like, we give everything away. It's whatever, you know. And so ultimately, that was the first time

that it was pretty clear. It's like, oh, wow, like, actually this could work. Like, we could actually run this nonprofit. Oh, and we were a nonprofit by this time. But the other thing was, like, maybe we can get philanthropic grants or another idea is maybe we could just partner with the university and the university will become part of a university or something like, that. And all of those would have been bad ideas. We would have never been where we are now because, you know, I'm sure a university's bureaucracy would have killed it somehow. And large philanthropic donors, that's a tough life to live for nonprofits because they have a lot of power because they're funding you. And if they get tired of something and they move on,

then you're sort of left without funding and so on. So the idea that maybe the general public, would chip in there 20 bucks each. And the fact that that first fundraiser worked was really like, wow, this is fantastic. Like, this means this could work. And, you know, with traffic growing like it was, we knew that, okay, like, we could raise more next time because if we keep growing like we are, then next time we'll be able to raise twice as much or whatever, you know, because we have twice the traffic. In the era of personal brand, and I know there's a lot of regulations around like what should be

on the site and who should be. especially when it's a someone. I want to take you there for a second. This is kind of an era of a personal brand. Personal brand is your currency, if you will. This is what allows you to leap again again. Most people will have some kind of a portfolio of things, so it's not much one thing for 40 years.

A few questions about that. First of all, in terms of Wikipedia itself, what are the regulations? How do people get on Wikipedia? And I think it will be interesting for people to hear. I think one of the important things is to realize, like, Wikipedia is a pretty bad place to try to do self-promotion because it doesn't go down very well with the community. And the only thing worse than not having a Wikipedia page is having a Wikipedia page has a big notice at the top,

saying conflict of interest. And also, it can be quite painful to have your Wikipedia page deleted if people, you know, make that judgment. So I advise people just leave it alone. But the way it works is what people are looking for is sort of multiple independent sources in third-party press coverage, basically. Not always press. Like, it depends on the field. So academics, you know, obviously you're going to look for published journal articles in major things.

And there are certain, you know, if you think about a category of musicians, well, if you've won an Emmy, you should have a Wikipedia entry, right? Even if maybe there's not that much news about somebody who won an Emmy, I don't know Emmy started, but in the first few years or something. But, you know, like, there's things like that, like specific details, the variance, but mainly it's about sources. It's about, are there, you know, high-quality, independent sources? That's the main thing. And in fact, one of the reasons for that is we think it's a really an ethical responsibility because if somebody doesn't have, you know, enough information about them, then that, because it's hard to verify the

information, it's very hard to prevent vandalism. It's like, how would you know what's correct or what's not? I remember once somebody started to create an English Wikipedia. They made a page for every single contestant on, it's like American Idol, but it was Philippines Idol. And there's some kid who was in round one, who got voted off the show, round one. They're 17 years old. they probably are going to go on to become a local singer in nightclubs or whatever. You know, like, not everybody's going to become a pop star. And how are we going to maintain that biography over time? Like, if the only thing we really know about you is the entry on the TV show website,

and it's one paragraph and, like, literally there's no news stories except the summary of the show where you got voted off, which isn't a biography, like, we just can't have a biography. Like, you've got to have enough information to really write a biography of the person. And so we just don't generally do that. Like, we do look for there has to be sufficient notability, we call it. I don't actually like the term notability because, I don't know, I think my mother's quite notable to me, but you couldn't really have a Wikipedia entry about her, right? It's more like verifiability. So if somebody does believe that they have enough, is there a way for them to reach out or they need the community to find them?

There's pages on the site, request for new pages. if you email, someone will point you to the right place. And, you know, that often can work. But you kind of have to have a little bit of not too much ego about it because it can be quite brutal. And in fact, you know, one of the things that I think we need to improve is around that type of thing. Because often the people who are patrolling new pages, this is all volunteers, they don't really always have the time to give the answer they would like to give. And so somebody, they write a page and they're like, hey, I've followed the rules. I put it in my own, a subpage of my user page to show you my sample.

And they just give this answer no, you know, or maybe it's got a couple of lines. And it's like, but I don't understand, you know, it's like too promotional. Okay, what does that mean? How do I fix that, you know? And it would be nice if we had enough volunteers and enough time to go, oh, great, you know, fantastic. But the truth is, a lot of times the people who are doing that sort of editing, they don't really want to learn how to be a Wikipedian, right? They just want to get a page about themselves published. And I don't mean that in a negative way necessarily.

It can be valid or whatever, but they're not really there to learn. And so, like, investing time to go, here's how you fix it. It's not that helpful. So I wish we had a better way of helping people who might, you know, want to do that. Do you think, by the way, that Wikipedia will change now in the era of AI, because it is, though it is feeding all the information into AI, but do you think that anything is changing? No, I mean, I think broadly the answer is no. Wikipedia will be Wikipedia. It will be as it is. I do think there are opportunities around the community using AI as support for the work. I could probably talk for two hours about. just that alone. What does that mean? I can tell you what it doesn't mean. It doesn't mean let's let AI write the articles because it's terrible. It's really, really, it's not good enough

at all. I use AI every day. I'm really fascinated by it. I'm sort of going back to what you learned about me earlier. I'm just really into anything new and interesting. So I bought a very expensive laptop for the first time in many, many years so that I could run local models on my machine. Because for years, I'm like, I don't need a fancy laptop. I usually got like two generations old Mac because what am I doing? I'm just doing emails and getting on the web, right? You don't need much. But now I run local large language models on my laptop and I'm always experimenting and I'm doing

all kinds of things like that because I think there's some really interesting opportunities. So one of my favorite examples of why it's not good enough yet is I ask every new model that I test, and I test a lot of them, I say, who is Kate Garvey? So Kate Garvey is my wife, and she's not a famous person, but she's known a bit. So she worked for, in Number 10, Downing Street, she worked for Tony Blair for 10 years. She promotes the global goals, sustainable development goals. So she works with the UN and this and that. So she's in the media a little bit here and there. She's in a lot of books that are written by people from the Blair administration because she was right there in the heart of it all. Great. So you would think the AI

could write an article about her or at least know who she is. And it's hilariously wrong, but always plausible. That's what's dangerous. So it will often say that she set up a nonprofit. That's true. It'll sort of get, so it once said that she set up a nonprofit to promote women's empowerment in the workplace and that she did this with Miriam Gonzalez, who is the wife of Nick Clegg, who was the deputy prime minister from a different party, from the Labor Party. And he went on to work at Meta as their policy officer and things like that. So he's a known person. And we know Nick Clegg. I know him from work. He was at Facebook. And his kids went to the same school as our kids, like London, small town London. And when I showed my wife this, she was like, oh, wow, that's bizarrely plausible.

Like, we do know them. They could have been at a dinner party and got to talking and thought, oh, let's set up this thing. And like, why wouldn't that be possible? So it's eerily plausible. And then the other thing is I always ask, and who did she marry? And that's also always wrong. It's quite hilarious because it's often people we know, politicians, journalists. It once said, you'll know who this is now. Americans will know who this is because it's a recent big story, but Peter Mandelson, who was the UK ambassador to the U.S., who recently had to resign because of his old friendship with Jeffrey Epstein. I mean, Peter Mandelson. And I said to chat GPT, I said, well, isn't Peter Madison quite famously gay because he is? And then it got very woke with me.

And it said, oh, it's not appropriate to speculate about people's personal sex lives. And gay people can get married in the UK. And I'm like, okay, but not really my point. So anyway, you can't use even the cutting edge models to write Wikipedia entry. So that's right out. And I don't see any change in that. The hallucination problem. I just was at a talk. from Gary Marcus, who's an AI researcher, who's gotten quite famous recently, and, you know, he was just going through the details of why the hallucination problem is so bad and isn't going to get better anytime soon. On the other hand, there's a lot of stuff that it can do and quite effectively.

So one idea I've had, and I've played with a bit, is feed it a short article that has five sources and say, is there anything in these sources that isn't in Wikipedia but could be? or is there anything in the Wikipedia entry that's not supported by the sources? And you know what? It's actually pretty good at that. It isn't always perfect, but it doesn't have to be perfect. If all it's going to do is make a suggestion on the talk page to say things like, hey, I noticed that three of the sources mention this person's place of birth,

but Wikipedia doesn't, people go, oh, right, yeah, that should be in there and they can add that. So there's stuff like that where I think work could be done. It's not just like casually just like write a prompt and start doing that. It's like really some experimentation. Another example, I was just saying if a newcomer suggests an article that definitely isn't good enough, wouldn't it be great if somebody could write them a pretty detailed explanation of what was wrong? Yeah, I can probably do that or do a pretty good job of it. And it could have a disclaimer saying, I'm an AI, so sometimes I'm stupid, but here's the sorts of things.

that you might want to look at. That's true. And that might actually be helpful and more, less sad, I think, for the well-meaning newcomer who just gets a no. I'm like, oh, that's not fun. I tried to help it with Wikipedia, but they said no. Instead, it's like, oh, I tried to help with Wikipedia, and I made some mistakes.

And guess what, the AI helped me, and then I got it published. I'm actually quite happy about that. Great, that's a good outcome. So I think there's a lot of interesting stuff that we might do in the future. that will help the community improve Wikipedia. Another area is, of course, we're always accused of bias,

and that's a very complicated topic, and I'm sure sometimes we are biased, and we need to work on that, and how do we work on that? But normally what we find is that the entries on that are really intensely looked at by a lot of people, like the research shows, those tend to be reasonably neutral, and where bias creeps in is in pages

that nobody's really paying attention. to because maybe somebody comes in with an axe to grind and they sort of write something that's their view on the matter and nobody's really noticed it yet. So could an AI sort of say I scan 10,000 pages and here's, you know, it's like it just could constantly be running. And when it sees something and it goes, wow, this is stuff that's not in the sources that seems really one-sided and just go, hey, humans, you might want to look at this one. I think that could be cool, but it has to be good enough. It doesn't have to be perfect again. It has to be good enough not to waste people's time. So if it's just complaining about stuff and then you go and you look at it

and it's like, well, you're just wrong. Like you don't understand humans well enough to understand this is actually fine. Then it's a waste of time. So anyway, I get excited about what can we do that's new and different and not just be afraid of the technology. So for you, seven rules of trust, your book, what are the seven rules of trust? How do you look at trust overall? And I think it is something that you put a lot of focus in Wikipedia overall, and a lot of the decisions you've been making are around how to create that trust in the information, in the community, and the people, and all of that. So how do you view that, Jimmy? So the book isn't just about Wikipedia. We actually interviewed some really amazing people, big journalists, so Christian

Aminpore, Tom Friedman. We interviewed one of the co-founders of Airbnb, and that's a company that had a real crisis of trust early on. And the idea was to say, look, we know that trust has been fundamental to the success of Wikipedia, both, you know, the effort to be trustworthy, to be a good source, to shoot for quality, to try to be neutral, all of those things that we try to do. But also, Wikipedia is very trusting. You know, like you can go to whatever, 99% of the pages in Wikipedia, click edit and make a change, and you don't even have to log in. It's insane. It's amazing, you know. So how can Wikipedia be so trusting when, as we know, the Internet's full of trolls and doesn't that? It turns out it only seems like the Internet's

full of trolls because most of the social media algorithms tend to promote content from trolls because it's good for engagement. It gets people angry. It gets them responding. It gets a rise out of people. It's a train crash. It's not fun. It's not healthy. I think it's a really bad business that's going to bite them eventually. But the rules of trust, a lot of them, I'm not going to tell you all, because I want people to buy the book and learn them all. But like, for example, some of the really simple things would be like transparency. Like, just be as transparent as possible whenever you can. And this applies as well to, you know, when you've messed something up, to just come clean and explain what happened. I mean, a lot of

companies need to get better at this. And in fact, that's one of the big lessons I drew from the Airbnb experience. So the story there is fairly early. They had a woman rented out her apartment and the guests trashed the place. They absolutely destroyed it. And, you know, the company didn't respond very well. And they got bad advice from PR and legal to like keep their mouth shot. It's going to blow over. You can't respond or you might become more liable. blah, blah, blah, blah. And so for, I don't know, a week or two, they just were frozen, and it just got worse and worse and worse. It was a huge social media storm. It was more and more in the press. And finally, they said, you know, forget all you advisors. You're just wrong.

Like, this is killing us. And they basically published a full mea couple saying, we screwed this up. Here's what we got wrong. Here's an apology. We're going to fix the apartment. But more than that, they actually stopped work. for a while at the company, maybe not all the work, but a lot of work. And like, everybody in the company's focus was, how do we become trustworthy? Because if people believe that if you put your apartment on here, it's going to get destroyed and the company's not going to do anything, nobody's going to put their apartment on. Or if, as a renter, if you think, I'm going to travel all the way, I'm going for the first time of my life, I'm very excited, I'm going to go

to Paris, and I don't speak a word of French, and I show up in the apartment doesn't even exist. I'm so screwed. Like, I'm terrified about that. So people have to trust it. So that's when they started doing a lot of new things. You have to upload your ID and prove you are who you say you are so that if you screw somebody, they can find you and do something about it. They indemnify. Like, if you put your house on Airbnb and somebody trashes it, their insurance will pay for it. Because they're like, people won't do it unless they feel safe. And so I'm telling a whole big story about Airbnb, their story. But one of the pieces of that, was transparently about like, oh, here's what we did wrong. Here's why we did it wrong and

here's how we're going to change. And they were like super public. And obviously, it's gone on, it didn't collapse and people didn't stop using Airbnb. They still use it and they trust it and massive success. So a lot of stories like that in the book. Yeah. And actually in episode 122 in Leap Academy podcast, we actually had Nathan Letcherzik. I think I'm not butchering his name. That's who we interviewed. It was incredible stories. Instead of saying his name, I just say one of the founders of Airbnb, I could say Nathan, but his last name.

Actually, it was one of the fun bits when I was recording the audiobook. That was a passage I had to do multiple times. His name is very hard to pronounce. Very hard to pronounce. I told him this on the call. I'm like, wow, your name is hard to. And he's like, I know. So it's good if you had him on, yeah.

For sure. I mean, and what you shared is incredibly important for. businesses, individuals, like, how do we convey that belief and trust, you know, it's true for everything that we do. Again, go, you know, look at the book, go get it. I can't think of somebody that changed the world more than Jimmy and, you know, like, so go and do it. And, but Jimmy, if you need to look back at kind of your path, what would be one thing that you would kind of give yourself advice to your younger self? Definitely buy Apple stock. If I could go back to 1990 and say, you know, just like come up with $500. You'll be, you'll thank me later. That's silly. But, you know, it's actually really hard for me. As part of being a pathological optimist, right, is like, I know decisions we made that didn't work out, but I also know we made them in good faith and we probably learned enough from it that it was worth.

it. You know, there are things like the idea of a wiki existed from 1995, and I didn't start Wikipedia until 2001, a wiki meaning a website anyone can edit. And so for the first two years of Wikipedia of the encyclopedia project called Newpedia at first, I didn't really know about wiki. And if I could go back and say, why don't you, because, you know, a wiki would have worked just as well two years earlier. It existed. The rest of it, you know, Wikipedia is not really a technological story because it's like a web server, a web browser, a database, and the idea of wiki, and there you've got it, you know, the rest of its ideas and social, not technology. What's interesting is, like, actually, we spent two years as a community sort of trying to write

articles, but also talking a lot about what an encyclopedia should be, and how do you define that? and learned a lot and sort of formed relationships. And before we got started, right? There was a group of people who were really instrumental. So, you know, was it really two wasted years or was it two formative years? It's hard to say now. Well, but also, speaking of seven rules of trust, I don't know if you would have trusted a community-only wiki

if you didn't go through the whole path of multiple validations and your own experience with it. One of the funny stories is one day somebody vandalized the front page of Wikipedia and put a giant penis picture. And we were experiencing a lot of traffic at the time, and the servers were under a lot of stress. And, like, from the website, I was trying really hard and a lot of community members to, like, fix the page. But it was, I had to go onto the server and, like, physically delete the image. I mean, it was a disaster. It was embarrassing. But we were just a young, small website. And, you know, back then, even the front page wasn't even locked. Like anybody could edit the front page. Obviously today, when I say 99% of the pages, well, one of them is not the front page, right? Because that pages was viewed by millions of people every day. So we can't really just leave that open because trolls will vandalize it constantly. But back then we didn't. And so, you know, would I say, well, Well, maybe we should have locked the front page a little sooner,

except nothing really all that bad happened. That's the thing. Like, nobody would even remember or know about this, except I love to talk about it. And it was part of, like, what made it possible for us to be innovative is that we didn't have a full brand image to protect already. So, like, if you were Britannica, you wouldn't have even taken the slightest risk that anybody would ever post anything wrong. And in fact, actually, one story,

this is not in the book, so bonus for listening to the podcast. But when Microsoft Incarta, so people used to say to me, friends would say, oh, well, it seems pretty successful so far, but what are you going to do when Microsoft launches their competitor or whatever?

I don't think they will, but okay. So they did. They announced a great fanfare that Encarta was going to become editable by the readers. And I'm like, oh, wow, okay. I'm surprised they would take the risk because somebody might put a giant penis up and, you know, whatever. And so I was like, well, I got to find out about this.

So I went and I sent it for an account and I found an article I knew something about. And I made a small change and I submitted it. And they said, thank you. We will get back to you within four weeks. And I'm like, this is not a competitor. We have nothing to fear here because that's not going to take off. Like, people aren't going to go, great, I'm so excited. I'm excited. Microsoft might accept my thing four weeks and now.

When they can come to Wikipedia and just get started and join some people who are like, yeah, let's fix it. Let's do great stuff. So, and it was because, obviously, if you're Microsoft, you couldn't possibly dare to let people write nonsense, you know, and have that on the site for even one second. Whereas, you know, at Wikipedia, it's part of our image and it's not all great, but people understand it. You know, so like if you go to Wikipedia and, you know, you start reading an entry on whatever, hopefully for the really controversial and really big entries, they tend to be what we call semi-protected. You do have to have had an account for several days to be able to do it. But if you go to some obscure celebrities page and you read something that says, and they like chocolate cookies or and they something terrible, you know, and they killed their mom,

like something, it shouldn't be there. But you're probably going to go, oh, yeah, like, vandalism. Like, that's unfortunate. And hopefully you'll click at it and fix it for us and let somebody know. But broadly, that doesn't happen that much. I mean, there's always vandalism. There's always people getting blocked for vandalism. It's kind of ongoing.

But people know, like, that's how Wikipedia is, and it's kind of part of the process. So, Jimmy, for those listening, they want more. They want to create more impact. They want to create bigger things and be part of bigger things. What would you say for that? Yeah, just get started. I think that's really important. There's an expression in Silicon Valley of the entrepreneur,

and this is the person who's always talking about what they're going to do, or they're always writing out a business plan. They've always got a business plan they're working on. And it's sort of like at some point those activities, which making some kind of a plan, obviously, that's a good thing, but you've got to be really careful that those kinds of activities aren't just your coping mechanism for not actually doing something. And at some point, you have to be willing to go, I'm going to start this, I'm going to do it with not enough money.

I'm not really sure how it's going to work, but I'm just going to get started. I'm going to make a pilot, you know, not even quite a minimum viable product, a minimum unviable product, right? Right. And I'm just going to start working on it and showing it to a few people and just seeing if I can do something. Because what is the, it's a cliched old, you know, the longest journey begins with one step. Okay, yeah, that's true. The shortest journey also begins with one step, but no journeys begin without taking that first step.

So you got to go. Jimmy, thank you for being on the show. Thanks for your time. It's really good. I hope you enjoyed this as much as I did. from your own career, watch this 30-minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with Ilan and Golan Show.