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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Content provided by Jessica Gillingham and Kristian Lupinski, Jessica Gillingham, and Kristian Lupinski. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Jessica Gillingham and Kristian Lupinski, Jessica Gillingham, and Kristian Lupinski or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.
In this week’s Pillow Talk Sessions, Jessica Gillingham and Kristian Lupinski speak with Alexander Limpert, the founder behind RentalReady and GuestReady, to unpack how automation, data, and AI are transforming operational efficiency in short-term rentals.
💡 Highlights include:
🤖 How RentalReady became the first PMS to integrate OpenAI, now powering a third-gen AI assistant
💬 Why AI replies to “confident messages” but escalates complex ones to humans
🏗️ Why GuestReady is shifting toward entire building management to strengthen revenue stability
🌍 How geographic diversification helps manage regulatory volatility
🛏️ Why GuestReady blends local authenticity with hotel-like standards for a differentiated stay
📜 The case for reasonable, balanced STR regulation that protects housing and enables innovation
Alex makes the case for a future where smarter tools empower operators, improve guest experience, and support sustainable growth across the sector.
🌐 pillowtalksessions.com
32 episodes
