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Jimmy Wales is the founder of Wikipedia, the free encyclopedia that anyone can edit. After his daughter Kira's birth faced medical challenges and he couldn't find reliable information online, Jimmy launched Wikipedia in January 2001. In this conversation, Jimmy shares why extending trust before it's earned creates better outcomes, how to deal with bad actors, and the seven rules for building things that last.

Notes:

Key Learnings (in Jimmy's words)

Wikipedia launched 20 days after my daughter was born. When Kira was born, I realized that when you go on the internet, and you've got a question like, "what is this condition my daughter has?" It just wasn't there. There were either random blogs or academic journal articles that were way above my head. Kira was born on December 26th, and I opened Wikipedia on January 15th.

Nupedia failed because of the seven-stage review process. Before Wikipedia, we worked on Nupedia. We recruited academics to write articles. You had to send in your CV showing you were qualified before you could write anything. We had very slow progress. I was on the verge of giving up. This top-down approach with a seven-stage review process before you publish anything that's no fun, and nobody's doing it.

We let anyone edit and figured we'd add structure later. We thought we'd have to figure out who the editor-in-chief of the chemistry section is. You're gonna have to have some kind of authority and hierarchy. But I thought, let's just not have too much structure for as long as possible.

"It's fun. You could be the first person to create a page."

There was a point in time when you could write, "Paris is the capital of France". That's amazing. It's not much of an encyclopedia article, but it was fun. It's like, oh, we can just start documenting whatever we know. People started just doing all kinds of stuff.

The magic is when you come back and see others improving your work. You could just write a few facts down and hit save, and it's not very good yet. But you'd go back a few days later and see somebody dug in, and they added more information. That element has always been really important. Is it fun? Do you enjoy the activity? Do you meet interesting people? You spend one afternoon, you add a few facts, and then you think, you know what? The world's just ever so slightly better.

Trust is conditional, not naive. Out of every thousand people, probably a small handful are gonna be really annoying. But it's really rare to have somebody who's actually malicious. The idea of assuming good faith, as we call it in Wikipedia, is extending trust first before it's been earned. It's conditional. You extend that friendly hand of trust. And if the person proves themselves to be super problematic, then you have to deal with it.

To get trust, give trust. Most people are decent. It also creates an environment where trustworthy behavior is rewarded. As a boss, wouldn't it be fantastic if you said, I'm going to go off and do this other thing, but I just trust my people are so good, they're gonna crack on with the work? Sometimes they'll make a call I would've made differently. That's okay. They're smart. Sometimes they're going to get it better than I did.

"You haven't earned my trust." When somebody looks you dead in the eye and says, "You haven't earned my trust," that's destruction. It's the opposite of building a culture where people can thrive.

Extending trust works in parenting, too. When teenagers say, "Well, it doesn't matter what I do, they're going to think the worst anyway, so I might as well do the bad thing." That's really unfortunate. As opposed to saying to your teenager, "Yeah, you want to go out and stay a little later than before. I want you to do that. I trust you, but you gotta do it the right way." You give that trust and believe me, they come home right on time because this is my chance to actually nail this. Give your children an opportunity to live up to building trust.

When trust is broken, you can rebuild it faster than you think. Frances Fry is a Harvard professor who had a huge job at Uber when they had an enormous crisis of trust. People say once you've broken trust, that's it, you can never get it back. But is it really true? No, it's actually not true. She thinks companies can rebuild trust faster than you think. A teenager who's broken a rule can rebuild trust pretty quickly. And our job is to let them rebuild that trust.

The eighth rule is walk the walk. The rules of trust aren't just a lot of good words. You actually have to walk the walk. If you say "I screwed up" and you own that, but then you go back to being the same as you were before, you're not going to rebuild trust. But if you walk the walk, people will see that.

Airbnb rebuilt trust by walking the walk. Really early in Airbnb's history, someone rented out their apartment and came home and it was absolutely trashed. Airbnb handled it very badly. They were stonewalling. In this era, that's often the wrong advice. Not saying anything just means it goes viral. So they ripped off the band-aid. They said, Look, we screwed this up. They started requiring ID's for people renting apartments out, ID's from customers, and substantial insurance for owners. They walked the walk.

Transparency doesn't mean sharing everything; it means sharing the process. If people can see your workings, they can see what you're doing and how it works, it gives them assurance in the process. It's about judgment calls. What would be helpful for us to share so people can trust the whole process?

If you think people are fundamentally rotten, you can't work with them. It's very easy when we look at the state of the world to be downtrodden, cynical, and don't trust anybody. If you think people on the other side of you politically or people at your workplace are fundamentally just rotten people, then you're going to have a hard time listening to them. You're going to have a hard time understanding where they're coming from. You're not going to do the right things that make sense to people. Which hurts all of society.

When you've been beaten up by life, change the channel. If you work somewhere where your boss doesn't trust you and your coworkers are all backstabbing freaks, it's time to change the channel. Every night, you should be trying to find a better position. Your number one criteria in looking for that next position is finding somebody who you think is a proper person to be your manager. Think of it as you're interviewing the company just as much as they're interviewing you.

When you give trust, you attract trustworthy people. When you become known as a person who gives trust before it's earned, you magically attract trustworthy people. It's kind of cool how it works. Will you get burned every once in a while? Maybe. But you attract the type of people that you wanna be around.

Curiosity is the ultimate love language. Get out there in the world and be curious. Asking people questions and being genuinely curious about their stories and learning about them and asking follow-up questions is a great way to show love and to connect with people. When you find yourself in a curiosity conversation where everyone's asking and learning, and they're head nodding and into it, there's nothing better. That's human nature connecting.

We are born to connect and collaborate with others. It's quite easy and natural for people to fit into whatever culture is around them. We naturally like to work together to build something good. We're social, and we like to be social. We collaborate to build experiences together. A party with only yourself is not a party.

Do what you love, even if it takes time to get there. One of the things that I think is really important is do what you love, do something that you really care about. Oftentimes for young people, there's this struggle between here's the thing that I really want to be doing, and here's the thing that's going to make me some money. Work really hard to find a way to put those together.

Reflection Questions

Jimmy says extending trust before it's earned creates better outcomes, but it requires not being naive when someone proves untrustworthy. Think of a situation where you're withholding trust. Is it because of actual evidence that this person is untrustworthy, or are you bringing baggage from past experiences with different people? What would it look like to extend conditional trust in this situation?
If you're in a leadership position, honestly assess: are there team members who feel you don't trust? What specific actions could you take this week to demonstrate trust before they've "earned" it in the traditional sense?

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Audio Pod Timestamps

02:07 Jimmy Wales' Early Fascination with Encyclopedias

04:28 The Birth of Wikipedia

07:35 The Trust Factor in Wikipedia

12:04 Managing Bad Actors on Wikipedia

15:28 Personal Reflections on Trust

27:05 Setting Reasonable Boundaries for Teens

28:18 Rebuilding Trust After It's Broken

32:37 The Importance of Transparency in Leadership

36:50 The Power of Positive Purpose

39:06 Practical Advice for the Trust-Broken

43:01 Connecting and Collaborating with Others

45:17 Career Advice for Young Professionals

49:41 EOPC

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