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

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Connect with Steve and David:
Steve: https://www.linkedin.com/in/%F0%9F%8E...
David: https://www.linkedin.com/in/david-mil.

#197: Staypineapple's Growth Strategy & Using Technology to Personalize the Guest Experience | with Michael Hirschler

The Modern Hotelier

#197: Staypineapple's Growth Strategy & Using Technology to Personalize the Guest Experience | with Michael Hirschler