#335 Rebuilding Trust in the Digital Age with Jimmy Wales, Founder at Wikipedia

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Dec 8, 2025

In this engaging conversation, Jimmy Wales, the founder of Wikipedia and co-founder of Fandom, delves into rebuilding trust in the digital age. He shares insights on Wikipedia’s rise through neutrality and community governance. Wales discusses the critical role of empathy and transparency in fostering meaningful digital spaces. He also contrasts Wikipedia’s constructive environment with toxic social media dynamics. Additionally, he highlights the necessity of combining human oversight with emerging AI tools to enhance information reliability.

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ANECDOTE

High‑Profile Error Prompted Policy Change

Jimmy Wales recounts a damaging false claim about John Seigenthaler Sr. that forced a rapid fix and policy change.
That incident led to a Biography of Living Persons rule prioritizing removal of unsourced negative claims about living people.

INSIGHT

Clear Purpose Scaled Participation

Wikipedia succeeded by meeting an unmet need for straightforward factual information online.
Core principles like neutral point of view and clear purpose fueled broad participation and trust.

ADVICE

Use The Trust Triangle

Use the triangle of empathy, authenticity, and logic to diagnose and rebuild trust.
Check which pillar failed when trust breaks and apply the appropriate repair strategy.

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The internet has transformed how we access information, but it's also created unprecedented challenges around trust and reliability. How do we build digital spaces where collaboration thrives and quality information prevails? What separates toxic online environments from productive ones? The principles of neutrality, transparency, and assuming good faith have proven essential in creating sustainable knowledge communities. But these same principles extend far beyond the digital realm—they're fundamental to effective leadership, successful business relationships, and even political discourse. When trust breaks down, everything becomes more difficult. So what practical steps can we take to foster trust in our organizations and communities?

Jimmy Wales is an American-British internet entrepreneur best known as the founder of Wikipedia and co-founder of Fandom. Trained in finance at Auburn University and the University of Alabama, he began his career in quantitative finance before moving into early web ventures, including Bomis and the free encyclopedia project Nupedia. In 2001, he launched Wikipedia, which quickly became one of the most visited websites in the world. To support its growth, he established the Wikimedia Foundation in 2003, where he continues to serve on the Board of Trustees and act as a public spokesperson. He later co-founded Fandom in 2004, expanding the wiki model to entertainment, gaming, and niche communities. Wales has also pursued experiments in collaborative journalism, including WikiTribune and its successor WT Social. His work in open knowledge has earned recognition from organizations such as the World Economic Forum, Time magazine, UNESCO, and the Electronic Frontier Foundation. He has held fellowships and board roles at institutions including Harvard’s Berkman Center and Creative Commons.

In the episode, Richie and Jimmy explore the early challenges of Wikipedia, the importance of trust and neutrality, the role of AI in content creation, and much more.

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