The Stash Cast on Substack

The Stash Cast on Substack

Legacy, Leverage, and the AI Takeover of Property Management

Reflections on a conversation with John Reilly.

Stash Geleszinski's avatar
Stash Geleszinski
Aug 07, 2025
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Recently I had the opportunity to sit and chat with John Reilly—CEO of Padgia and a man who’s lived many lifetimes: acupuncturist, investment banker, philosopher, startup operator. We didn’t just talk about real estate software or AI features. We talked about transformation—personal, generational, and systemic.

This post isn’t about Padgia as a product. …

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