DiscoverHospitable HostsFrom 2 to 220: The Checkmate Rentals Expansion Story with Hospitable Hosts
From 2 to 220: The Checkmate Rentals Expansion Story with Hospitable Hosts

From 2 to 220: The Checkmate Rentals Expansion Story with Hospitable Hosts

Update: 2025-11-05
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In this episode of the Hospitable Host Podcast, we interview Chad Phyllis, the founder of Checkmate Rentals, a short-term rental property management company. 

Chad shares his journey from managing two properties to overseeing 220, emphasizing the importance of a hospitality-first mindset, effective communication, and the role of design and amenities in enhancing guest experiences. 

He discusses strategies for optimizing property listings, the significance of direct bookings, and the challenges of managing a large portfolio while maintaining quality service. Chad also highlights the importance of security measures and risk management in the property rental business, and shares his vision for the future of Checkmate Rentals.

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From 2 to 220: The Checkmate Rentals Expansion Story with Hospitable Hosts

From 2 to 220: The Checkmate Rentals Expansion Story with Hospitable Hosts

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