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

Illustration via 99designs

“Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge.”

— Jimmy Wales

Internet and technology entrepreneur Jimmy Wales (@jimmy_wales) is founder of the online nonprofit encyclopedia Wikipedia and cofounder of the privately owned Wikia, Inc., including its entertainment media brand Fandom, powered by Wikia. Jimmy serves on the board of trustees of the Wikimedia Foundation, the nonprofit charitable organization he established to operate Wikipedia.

In 2019, Jimmy launched WT Social—a news-focused social network. In 2006, Jimmy was named to Time magazine’s list of the 100 most influential people in the world for his role in creating Wikipedia.

In 2021, inspired by his family quiz nights during COVID-19 lockdown, Jimmy created Quiz Night Beyond—a website where people can create and play quizzes online with family and friends wherever they may be.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with someone who might be as optimistic as Jimmy Wales? Listen in on my conversation with venture capitalist Mike Maples, Jr., the man who taught me to invest. We discussed anti-authoritarian disruption technology, parenting advice, acting simple, investment advice, how cryptocurrency helps separate politics from economics, a 60-second idea for changing the world, lessons for aspiring entrepreneurs, the pointlessness of holding grudges, and much more.


  • Connect with Jimmy Wales:

Website | Twitter | Facebook | WT.social


  • Where did Jimmy grow up, and what did his family life and education look like in the early days? [05:22]
  • How did Jimmy’s free-range schooling inform how he thinks about education for his own children? [09:12]
  • How might a parent prepare to homeschool a curious kid who might be too far ahead of the curve for a traditional education? [10:41]
  • Why Jimmy would label himself more as a non-believer than an atheist, and how he came to a point of religious disbelief after being raised Methodist and carrying out a flawed experiment involving Santa Claus and G.I. Joe. [12:13]
  • What did Jimmy aspire to be when he was growing up? [17:08]
  • What was it that compelled Jimmy to study finance and markets? [18:37]
  • Were there any investors who Jimmy looked up to at this time? What influenced the way he built his portfolio in these early years?
  • What wisdom about building a portfolio does Jimmy wish he understood when he was younger, and what investor could have imparted such wisdom? [20:01]
  • When and how did Jimmy’s interest in Objectivism enter into the picture, what does he see as the most common myths and misconceptions about its creator, Ayn Rand? [22:18]
  • Whether or not you agree with the points Ayn Rand (or anyone) is trying to make, Jimmy considers critically thinking them through — rather than just picking a side based on a knee-jerk impression — to be the important thing. [24:46]
  • How Usenet was hijacked by its own design, why Twitter succumbs to many of the same problems, and how Jimmy hoped Wikipedia could be designed as a vehicle for healthier human discourse. [26:42]
  • Recommended reading. [32:30]
  • How did Jimmy go from finance and markets to founding companies? [36:14]
  • When was Jimmy able to leave his finance job behind and dive fully into entrepreneurial endeavors? What made this possible? [42:04]
  • How was Jimmy’s company discovered by a major television network, and how was their symbiotic deal established? [47:24]
  • With a lot of great ideas but only a limited number of resources, how did Jimmy choose what shots to take when setting out in the world of tech startups during the dotcom boom? [50:35]
  • When the deal fell through, was Jimmy’s company able to use the momentum it had built, or did it have to start from scratch in altering course? What sacrifices had to be made in order to weather the storm, and how did these hardships affect the direction taken by the nascent Wikipedia? [54:06]
  • Why did Wikipedia thrive while Nupedia became an internet footnote? [1:00:30]
  • How did Jimmy first come across the wiki software that would provide the building blocks for Wikipedia? [1:05:22]
  • What were some of the early decisions that made Wikipedia catch in its first few months? [1:07:37]
  • Were there any significant mistakes made in the early days of Wikipedia that either ended up needing to be fixed or that, like a vestigial tail, have remained in the system? [1:11:42]
  • The Steak Knives Analogy: why it’s better to design for the benefit of nice people rather than for the deterrence of bad people. [1:16:57]
  • What motivates great Wikipedia contributors, and how are they kept happy? [1:20:25]
  • What organizational decisions aim to cultivate a positive contributor culture? [1:22:19]
  • Has Jimmy always been a self-described “pathological optimist,” or was it something he had to work at? [1:00:00]
  • Does Jimmy have any practices to help him stay the course of optimism if he loses his way? [1:28:23]
  • Aside from Wikipedia, what other projects occupy Jimmy’s time at present? What’s the inspiration and purpose behind his new Quiz Night Beyond website?[1:30:25]
  • What would Jimmy’s billboard say? [1:40:35]
  • Parting thoughts. [1:42:06]


“Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge.” — Jimmy Wales

“You wouldn’t know it from watching TV debates or going on Twitter, but most people are pretty reasonable and will say, ‘Look, I disagree with this, but it should be presented in a fair way that the defenders of it would identify.’” — Jimmy Wales

“I’m a pathological optimist, so I always think everything’s going to be great. That’s not correct, by the way; everything is not always going to be great. But that’s the way I feel and approach things.” — Jimmy Wales

“If you design for the worst people, then you’re failing design for good people.” — Jimmy Wales

“A great Wikipedian, in my view, is someone who really takes seriously the values and ideas of Wikipedia, like neutrality for example, quality for example, reliable sources. And they take all those things as more important than any particular, say, political opinion they might have.” — Jimmy Wales

“We’ve got a lot of problems on this planet. We need as many smart, educated people to figure them out as we possibly can.” — Jimmy Wales

“Try not to be a troll on the internet.” — Jimmy Wales

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 600 million downloads. It has been selected for “Best of Apple Podcasts” three times, it is often the #1 interview podcast across all of Apple Podcasts, and it’s been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.