Lessons learned along the way

"There were definitely decisions that I made that ended up being incorrect, but they were good decisions based on what I knew at the time. As an example, before Wikipedia, we had Nupedia, which had the same vision—a free encyclopaedia. It was very top-down; structured and organised in a different way entirely. It didn't work. We wasted nearly two years on that. But I can't say, ‘Oh, I could have started Wikipedia two years earlier had I not screwed up and made that mistake.’ I had to learn. I had to try it the other way, I had to think it through and I had to gather a community. So in the end, was it really a mistake not to launch Wikipedia two years earlier? I don't know. We'll never know. But you can't have regrets."

The importance of neutrality in an age of disinformation

“Very early on, I set down the principle that neutrality is non-negotiable; that that we weren't going to have a debate about whether Wikipedia should be a progressive encyclopaedia, a conservative encyclopaedia or whatever. We said no, we're here to document the facts.”

See also: Gen.T Stream: Creating Social Impact In A Post-Covid World, Featuring Jimmy Wales And Christopher Wylie

The value of failure

"If you are too afraid of failing then you're not going to try the thing that might be super interesting. We need to get more comfortable with failure. If we see a young person trying something new, a new business, and it doesn't work out, that's not a tragedy. That's actually cool, right? The tragedy is the person who took the boring job in the bank and hates it, and three years later still hates it and is in a grind and doesn't know what to do. As opposed to the person who flamed out but learnt a lot of interesting things.

We need to cherish and value that kind of innovation because we're facing enormous challenges. We've got a long way to go to eliminate extreme poverty around the world. We've got a long way to go to eliminate racism, nationalism. There's a lot of bad ideas out there, a lot of bad things going on and a lot of incredibly amazing good things going on. And we need innovation."

On being dubbed the “anti-Zuckerberg”

“I'm thinking about all kinds of ideas not because I want to be the anti-Zuckerberg, but just because that actually sounds cool to me. I'd like more of that, please.”

On choosing to put Wikipedia in a foundation

"If someone had come to me on the day that I was filling out the paperwork to create the Wikimedia Foundation so I could put Wikipedia into that structure and said, 'Jimmy, actually, hold on a second, here's 3 billion dollars that we’ll transfer into your bank account,' I would be like 'Yes, thank you very much. I'll take the three billion.' It wasn't this sort of super-crazy thing I did. It was like, 'Here’s an interesting thing that’s growing, I don't really have any idea about a business model. The dotcom crash is full-on. I think this is an interesting way forward, and I think that this project should be in a non-profit structure.' So I just went in that direction; it wasn't a crazy anti-money thing."

See also: 5 Malaysian Gen.T Honourees Balancing Profit And Purpose

On the importance of social enterprises

"I think one of the first things that we can do is to step back from a very simplistic notion of for-profit bad, non-profit good.

I think what you can do is say, 'Look, how do you think about your whole life and all of your values?' And it's perfectly fine for one value to be 'I would like to make some money.' But also to align that with values. To say, 'I want to have a positive impact. I want to do things that I think are worth doing and that are meaningful.' And in fact, I think that more often than people realise, those two things are actually in alignment."

Quotes are edited for clarity and brevity.

Listen to the episode and subscribe using your preferred podcast platform on the Crazy Smart Asia hub page.