Pillow Talk Sessions
Pillow Talk Sessions Podcast is the go-to podcast for exploring the future of hospitality and serviced living. Co-hosted by Jessica Gillingham and Kristian Lupinski and brought to you by the team at Abode Worldwide, each episode features insightful conversations with pioneers shaping the built-to-rent, co-living, PBSA, later living, multifamily and hospitality sectors.
Each episode explores the transition from simply providing spaces to creating value, community, and experiences. We discuss everything from operational shifts away from asset-focused approaches toward customer-centric models to changing customer behaviors, convergence of asset classes, global trends, and typology issues. From cutting-edge prop tech innovation to flexible stays and changing demographics, we uncover how hospitality and serviced rental living are reshaping the way we live, work, and play.
On the podcast, we cover three core themes:
- The ‘hotelization’ of real estate: How are the demands for concierge-level service, seamless tech, and elevated design are changing residential rental.
- Proptech as an enabler: How tools are unlocking smarter operations and richer resident experiences.
- The convergence of asset classes: We chart the strategic convergence of hotels, BTR, multifamily, and co-living as boundaries blur between short stays and rental homes.
Whether you're in real estate, hospitality, multifamily, short-term rentals, proptech, PBSA, build-to-rent, retirement living, co-living, or just curious about where these industries are headed, Pillow Talk Sessions offers engaging, thought-provoking conversations that will inspire and inform.
Your Hosts
Jessica Gillingham - Jessica is the CEO of Abode Worldwide, a strategic public relations and communications firm focused on raising the profile of transformative technology solutions across global hospitality, lodging, and serviced living. Jessica is a regular industry speaker, author, adviser, and the founder of Pillow Talk. Jessica is also the author of the book “Tech-Enabled Hospitality - Strategies to Elevate Guest Experience and Operational Efficiency.”
Kristian Lupinski - Kristian is the content and events producer for Abode Worldwide. With extensive media production experience and a hospitality industry background, Kristian has a proven track record of creating engaging content and collaborating with influential figures shaping the sector.
The podcast is brought to you by the team at Abode Worldwide.
Pillow Talk Sessions
Scaling Hospitality Through Automation with Alexander Limpert (RentalReady / GuestReady)
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