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.