On today’s episode, David Millili and Steve Carran sit down with Michael Hirschler, Chief Growth Officer at Staypineapple, live from Staypineapple Chicago. Michael shares how the brand is redefining boutique hospitality through a combination of 'friend-style' service, a bold brand identity, and guest-focused innovation.
They dive deep into Staypineapple’s growth strategy—from owner-operator beginnings to expanding through licensing and management—and how their flexible, cost-effective model provides a compelling alternative to legacy hotel brands. Michael also unpacks their cutting-edge tech stack, the role of AI in enhancing (not replacing) hospitality, and why true guest service still starts with emotionally intelligent people.
Topics covered include:
- What makes Staypineapple’s brand and service model unique
- Why personalization and emotional intelligence drive guest experience
- Reducing friction between guests and staff through smarter tech
- How to maintain strong service culture across properties
Watch the FULL EPISODE on YouTube: https://youtu.be/A-WLXWkThTE
Join the conversation on today's episode on The Modern Hotelier LinkedIn page
The Modern Hotelier is produced, edited, and published by Make More Media
Links:
Staypineapple: https://www.staypineapple.com/
Michael on LinkedIn: https://www.linkedin.com/in/michaelhirschler/
For full show notes head to: https://themodernhotelier.com/episode/197
Follow on LinkedIn: https://www.linkedin.com/company/the-...
Connect with Steve and David:
Steve: https://www.linkedin.com/in/%F0%9F%8E...
David: https://www.linkedin.com/in/david-mil.
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