One on One with Jonathan Oakes of Trivial Warfare for May 29, 2026

In this episode, Glenn sits down with one of his longest podcasting friends, Jonathan Oakes of Trivial Warfare. It is a fun and engaging conversation that dives deep into the world of podcasting, the importance of building a strong community, and the enduring power of friendship. Plus, they explore the fascinating world of trivia, making for an episode that is as informative as it is entertaining.

HORSES IN THE MORNING Episode 3961 – Show Notes and Links:

Timestamps:

  • 02:24 – Meet trivia host Jonathan
  • 02:56 – Childhood Trivial Pursuit roots
  • 04:31 – School quiz bowls & pub trivia
  • 05:55 – What makes a good trivia player
  • 08:27 – Creating Trivial Warfare podcast
  • 14:21 – Building community & loneliness
  • 19:06 – Podcast intimacy & parasocial fan feel
  • 21:18 – Writing good trivia questions
  • 25:24 – Reciting U.S. presidents in order
  • 29:14 – Evolving trivia canon & diversity
  • 31:32 – Trivia Hall of Fame induction
  • 35:37 – Monetizing podcasts & time cost
  • 42:09 – Co-host chemistry, roles & sign-off tease

Listen Now

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