More Fun Talking Retro – Episode 7: A Deep Dive with Jim Leonard

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In episode 7 of More Fun Talking Retro, the show continues its mission of keeping a neighborly, if nosy, eye on the retro gaming and vintage tech community. Host and community enthusiast is joined by none other than Jim Leonard—also known as The Old School PC, Trickster, and MobyGamer. (Spoiler alert: Yes, that’s a lot of aliases. No, he’s not on the run… probably.)

Jim brings decades of passion for retro computing, preservation, and community building to the conversation. From helping run the massive Vintage Computer Festival Midwest to co-founding the legendary MobyGames database, Jim’s fingerprints are all over the efforts to protect vintage computer history. And yes, he’s even been known to push a broom after the festival—because sometimes retro computing is glamorous, and sometimes it’s just… cleaning up a very large, very nerdy party.

The episode covers Jim’s early days growing up around tech, his deep roots in the PC demo scene, and the surprising story of how piracy (the friendly, community-minded kind) led to the creation of MobyGames. Along the way, they discuss favorite games like Deus Ex, Taz Times in Tone Town, No One Lives Forever, and even why Jim has upgraded his PC three times just for Cyberpunk 2077.

The discussion is full of great insights into building communities, learning from history, handling panel moderation at giant events (hint: “Thanks for your question” is a very useful phrase), and why documenting not just the hardware, but the people who love it, is so important.

Jim also shares the behind-the-scenes blood, sweat, and nerd tears that went into making his widely-praised YouTube documentary on the Mindscape Music Board—a video so polished it could make a grown collector weep (and probably has).

In short, it’s a long episode—but every minute feels like sitting in the pub swapping stories with the best kind of fellow retro enthusiast: one who’s brilliant, humble, and willing to lug an XT across the finish line for history’s sake.

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