The Learning Leader Show with Ryan Hawk

Episode 671: Jimmy Wales (Founder of Wikipedia) - To Get Trust, Give Trust
Release Date: January 19, 2026

Overview:

In this enlightening episode, Ryan Hawk sits down with Jimmy Wales, the founder of Wikipedia, to discuss the philosophy and practice of building trust in organizations, communities, and everyday life. Drawing from his latest book, The Seven Rules of Trust, Wales shares lessons from Wikipedia’s groundbreaking journey and offers actionable insights for leaders seeking to cultivate high-trust cultures. They also explore personal anecdotes, the failure of Nupedia, parenting, transparency, trust recovery, and the power of curiosity.

Key Discussion Points & Insights

1. The Roots of Wikipedia & the Joy of Knowledge

• Jimmy’s Early Fascination: Jimmy recounts his childhood love for the World Book Encyclopedia and how annual updates and “sticker” corrections sparked his passion for revising and expanding knowledge.
  • (02:34 Jimmy Wales): "I always joke that was my first update of the encyclopedia."
• Importance of Diverse Curiosity: The ability to look up anything (“tigers!”) fueled an appreciation for random, diverse knowledge—an early sign of the future vision behind Wikipedia.

2. From Nupedia’s Failure to Wikipedia’s Breakthrough

• Nupedia: Too Slow, Too Hierarchical: Nupedia’s academic, peer-reviewed model stalled progress and failed to inspire contributors.
  • (05:07 Jimmy Wales): "We had very, very slow progress... I was really on the verge of giving up."
• Wikipedia’s Launch: Motivated by a personal crisis (the birth and medical challenges of his daughter Kira and the subsequent frustration with the lack of accessible information), Jimmy embraced the wiki model’s openness and speed.
  • (07:23 Jimmy Wales): "Kira was born on December 26th and I opened Wikipedia on January 15th."
• Why Did Wikipedia Work?
  • Emphasis on fun, low barriers to contribution, and a positive community vibe.
  • Speed over perfection and openness to improvement led to rapid growth.

3. Trust as the Foundation: “To Get Trust, Give Trust”

• Trust from the Outset: Wales’s leadership style is to start every relationship with trust, not making people “earn it” through tedious hoops.
  • (17:59 Jimmy Wales): "To get trust, give trust. And actually, one of the things about giving trust... creates a willingness to trust back and to live up to that trust."
• Assume Good Faith: Wikipedia’s core principle. Most people act in good faith; expect good until proven otherwise.
  • (12:57 Jimmy Wales): "The idea of assume good faith... you extend that friendly hand of trust and if the person proves themselves to be super problematic, then you've got to not be naive."
  • Notable story: Kaylana, who turned from a young vandal to a respected Wikipedia contributor after being met with kindness.

4. Dealing with Bad Actors

• Stepwise Response: First, gentle correction; continued issues lead to restriction.
• Blocking & Second Chances: Block only when necessary, but always allow a path back for those willing to contribute positively.

5. Trust in Leadership and Teams

• Micromanagement vs. Trust: Trusting your team and giving them autonomy leads to higher satisfaction and better outcomes.
  • (17:59 Jimmy Wales): "You're going to have autonomy. You're going to be treated as a proper human being, and I trust you're going to do a great job for me."
  • (21:00 Ryan Hawk): Share of a destructive leadership example: "You haven't earned my trust" moment led him to leave a job.

6. Transparency: Walking the Walk

• Transparency vs. Oversharing: Strategic openness builds legitimacy and clarity; not every detail needs to be public, but enough should be shared to foster trust.
  • (33:48 Jimmy Wales): "If people can see your workings... it just gives them an assurance in the process."
  • Open source software as an analogy: even if very few review the code, the possibility fosters trust.
• Leaders in Sports & Business: The best coaches and leaders are transparent, overcommunicate, and communicate the “why.”

7. Rebuilding Trust After It’s Broken

• It’s Possible—If You Own It: Sincere ownership and visible change enable the rebuilding of trust, both at organizational and personal levels.
  • (26:43 Jimmy Wales): "You actually have to walk the walk. If it's just a bullshit press announcement... you're not going to rebuild trust."
  • Reference: Airbnb’s early mishap, handled poorly at first, but trust was rebuilt when the company acted transparently and corrected policies.

8. Practical Advice for Individuals and Leaders

• Interview Your Employer: If you’re stuck in a low-trust environment, seek out places where trust is built in.
  • (40:05 Jimmy Wales): "If you work somewhere where your boss doesn’t trust you and your co-workers are all backstabbing freaks... change the channel."
• Curiosity and Collaboration: Human nature thrives on connection and curiosity; being genuinely interested in others is “the ultimate love language.”
  • (42:32 Ryan Hawk): "When you become known as a person who gives trust before it’s earned, you seem to magically attract trustworthy people."
• Family and Parenting: Trust is foundational in raising children—when broken, parents must enforce consequences, but also offer a path for rebuilding.
  • (26:43 Jimmy Wales): "You've disappointed me. That's actually the most terrifying and powerful word that a dad can say..."

9. Pursuing Passion and Purpose

• Find Work That Matters: Find the overlap between what you love and what can support you financially. Don’t settle for a joyless paycheck.
  • (45:35 Jimmy Wales): "Work really hard to find a way to put those together. Look really hard for a way to have. Do what you love be make some money."
  • (48:27 Ryan Hawk, quoting a friend): "The way he defines passion is choosing extra work."

Notable Quotes & Memorable Moments

• On Trust:
  • (17:59 Jimmy Wales): "To get trust, give trust."
• On Fun in Building Wikipedia:
  • (08:18 Jimmy Wales): "It's also fun... There was a point when you could be the first person to create a page. You would just write, maybe 'Paris is the capital of France.' And you hit save and you're like, ah, look at that, that's amazing."
• On Rebuilding Trust:
  • (26:43 Jimmy Wales): "People will see that... they really screwed that up. But they saw that it was a bad move and they changed a lot in the company... Then everything is fine."
• On Parenting and Trust:
  • (26:43 Jimmy Wales): "You've disappointed me. That's actually the most terrifying and powerful word that a dad can say is, I'm disappointed here. I trusted you and you didn't live up to it."
• On Community:
  • (43:55 Jimmy Wales): "We naturally like to work together to build something good... as humans, we're social and we like to be social."
• On Purpose & Passion:
  • (45:35 Jimmy Wales): "Do what you love, do something that you really care about... really think about that passion piece."

Key Timestamps

• 02:09 – Childhood encyclopedias and early fascination with knowledge
• 05:07 – The failure of Nupedia and the birth of Wikipedia
• 08:18 – Wikipedia’s “fun” factor and early community
• 12:57 – Managing bad actors, “Assume Good Faith”
• 17:38 – The “trust wager” and practical applications at work
• 21:45 – Personal story: Trust denied in the workplace
• 26:43 – Parenting, rebuilding trust, and the power of ownership
• 33:48 – Transparency—what it really means in leadership and teams
• 37:28 – Why are the basics of trust and purpose still so neglected?
• 40:05 – Practical advice for those who have been burned by betrayal
• 42:32 – How giving trust attracts trustworthy people; curiosity as love language
• 45:35 – Career advice: pursuing passion and meaningful work

Summary of Actionable Lessons

• Lead with trust—do not wait for others to earn it; offering trust first usually brings out the best in people.
• Assume good faith, but don’t be naïve; address problems directly and proportionately.
• Foster fun and autonomy in collaborative projects.
• Be transparent where possible, but balance it with appropriate confidentiality.
• Own your mistakes and walk the walk—rebuilding trust is possible and crucial.
• Curiosity and collaboration drive connection—cultivate both for deeper relationships.
• Seek purpose and passion in your career—don’t sacrifice fulfillment long-term for a paycheck.

Podcast’s Tone & Language

Genuine, engaging, direct, and warm. Both host and guest share personal stories, use humor (“Nobody stabs you in the steakhouse!”), and take a practical, optimistic approach while acknowledging life’s difficulties.

Final Takeaway

The core of Jimmy Wales’s philosophy—and Wikipedia’s success—is simple: to build anything worthwhile, you must lead with trust, give autonomy, and create a transparent, purpose-driven culture where people feel safe and empowered to contribute. Whether building an encyclopedia or raising children, these rules are timeless—and, despite seeming obvious, are too often ignored.

Recommended for: Leaders seeking to build vibrant teams, anyone interested in collaborative innovation, and all who want practical advice for fostering trust in work and life.