In this episode, host David Millili brings listeners inside Indie Cultivate Boston, hosted in partnership with ILC.

David sits down with leading vendors and innovators including Airbnb, Watermelon Ghost, Direct Booker, Stash Rewards, Cloudbeds, Directful, and Canary Technologies. Across these conversations, a clear theme emerges: the independent hotel space is at a turning point driven by AI, evolving guest expectations, and the ongoing battle for direct bookings versus OTAs.

Guests discuss how AI is reshaping discoverability, guest engagement, and operations, while also raising critical questions about visibility in AI-driven search. From loyalty programs and retention platforms to booking infrastructure and guest experience tools, each guest shares how they’re helping independent hotels compete, differentiate, and thrive.

You’ll hear perspectives on:

• How AI is changing hotel discovery and booking behavior
• The future of direct bookings and OTA dependency
• Experiential stays and evolving guest expectations
• Why independent hotels have a unique opportunity in the AI era

Watch the FULL EPISODE on YouTube: https://youtu.be/wZUi1eIuS5A

LinkedIn Links:
Audrey Yates - VP of Hotel Partnerships, Stash Rewards
Adam Harris - CEO, Cloudbeds
Tim Kinsella - Global Sales - Strategy, Canary Technologies
Ron Sandel - Director of Hotels, Airbnb
Georgie Downie - Co-Founder & CEO, Watermelon Ghost
Lindsay Wenger - VP of Sales, Directful

Sanjay Vakil - Co-Founder & CEO, Direct Booker
Meg Gutowski - ILC

For full show notes head to: https://themodernhotelier.com/episode/272

Follow on LinkedIn: https://www.linkedin.com/company/the-..

Join the conversation on today's episode on The Modern Hotelier LinkedIn page

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

In this episode, host David Millili sits down with Richard Aday, CEO and Co-founder of ThinkReservations, for an insightful conversation on entrepreneurship, technology, and the evolving hospitality landscape.

Richard shares his journey from building websites as a child in a tech-savvy family, to studying electrical and computer engineering, working at Amazon, and ultimately founding ThinkReservations after a chance encounter with a boutique hotel in Puerto Rico sparked a bold idea. He also reflects on growing up in a Cuban-American family in South Florida, the influence of a strong work ethic, and how his passion for travel and guest experience shaped his career in hospitality tech.

The conversation explores how ThinkReservations is redefining property management systems by prioritizing guest experience, simplicity, and customer support. Richard discusses the company’s evolution from a bootstrapped startup to a full hospitality platform, now including booking engines, channel management, marketing websites, payments, and accounting solutions.

In this episode, you'll learn about:

• How independent hoteliers can compete with OTAs and increase direct bookings
• The role of AI and automation in guest engagement
• What defines high-performing modern hoteliers today
• The biggest friction points in the guest journey and how technology is removing them

This is a must-listen episode for hoteliers, hospitality tech leaders, and anyone interested in how innovation is reshaping the guest experience and the future of independent hospitality.

Watch the FULL EPISODE on YouTube: https://youtu.be/qTgezcv7DbU

Links:
Richard on LinkedIn: https://www.linkedin.com/in/richard-aday-59182452/
ThinkReservations: https://www.thinkreservations.com/

For full show notes head to: https://themodernhotelier.com/episode/271

Follow on LinkedIn: https://www.linkedin.com/company/the-..

Join the conversation on today's episode on The Modern Hotelier LinkedIn page

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

In this special episode, host David Millili takes listeners inside Indie Cultivate Boston in partnership with ILC, capturing candid conversations with some of the most forward-thinking leaders in hospitality.

Across the discussions, a common theme emerges while AI and automation are transforming back-of-house operations, the future of hospitality remains deeply human—rooted in creativity, storytelling, and meaningful guest connection. Leaders also reflect on the importance of independence in hotel development, the value of intimate industry gatherings like ILC, and how new models are reshaping ownership, management, and guest experience.

In this episode, you’ll learn:

• How leading hotel operators are thinking about AI—not as a replacement for people, but as a tool to automate and augment hospitality operations while keeping guest experience human-first
• Why independent hotels continue to thrive through creativity, storytelling, and strong emotional connection with guests
• How technology platforms like integrated PMS systems and “hospitality operating systems” are helping smaller hotel brands scale more efficiently
• What “Powered by Kasa” and similar models mean for hoteliers looking to build brands faster without losing creative control
• The emerging balance between technology-driven efficiency and analog, human-centered hospitality experiences

Watch the FULL EPISODE on YouTube: https://youtu.be/A6U4jtjfbpg

LinkedIn Links:
Roman Pedan: https://www.linkedin.com/in/roman-pedan-594897325/
Steven Rubin: https://www.linkedin.com/in/stevenmrubin/
Jen Parks: https://www.linkedin.com/in/jenniferfigariparks/
Jason August: https://www.linkedin.com/in/jaugust/
Brian Meyer: https://www.linkedin.com/in/brian-meyer-b004832b6/
John Flannigan: https://www.linkedin.com/in/john-flannigan-73550a1/
Jen Barnwell: https://www.linkedin.com/in/jennifer-barnwell-a8689ba/
Matt Schwartz: https://www.linkedin.com/in/matthewaschwartz/
Andrew Benioff: https://www.linkedin.com/in/llenrockgroupbenioff/

For full show notes head to: https://themodernhotelier.com/episode/270

Follow on LinkedIn: https://www.linkedin.com/company/the-..

Join the conversation on today's episode on The Modern Hotelier LinkedIn page

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