

D&D Designer Meets the Questing Beast! Ep. 61
Jul 13, 2025
Ben Milton, a prominent game designer and YouTube content creator known for his work in the Old-School Renaissance, teams up with Steve Winter, a legendary D&D designer who helped shape the game's evolution over decades. They dive into the creative journey of RPG design, discussing the importance of random tables and collaboration. The allure of dungeons is explored, along with innovations and personal anecdotes from their gaming experiences. Their conversation highlights the vibrant landscape of independent game design while emphasizing player engagement techniques.
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Episode notes
Sandbox Play Sparks Surprise
- Steve Winter shares that he prefers sandbox games with no predetermined solutions to surprise him and challenge his thinking on the spot.
- He values moments when players' unexpected actions create priceless gaming experiences that are hard to predict.
OSR Blogosphere Revival
- The OSR blogosphere mirrors the early days of RPG design where creators share ideas and build off each other in a vibrant community.
- This collaborative, amateur publishing scene is unique among RPG subcultures and fuels OSR creativity and growth.
Dungeon's Inevitable Evolution
- The dungeon setting evolved because it simplifies role-playing into a node-based, physical exploration easier for GMs to run.
- This format likely would have arisen independently if D&D hadn't introduced it due to its perfect fit for adventure and play.