#271: Creating a Better Hotel Booking Experience | with Richard Aday

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.