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

EPISODE · Apr 29, 2026 · 30 MIN

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

from The Modern Hotelier · host David Millili & Steve Carran

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/271Follow on LinkedIn: https://www.linkedin.com/company/the-..Join the conversation on today's episode on The Modern Hotelier LinkedIn pageConnect 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/271Follow on LinkedIn: https://www.linkedin.com/company/the-..Join the conversation on today's episode on The Modern Hotelier LinkedIn pageConnect with Steve and David:Steve: https://www.linkedin.com/in/%F0%9F%8E...David: https://www.linkedin.com/in/david-mil.

NOW PLAYING

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

0:00 30:12

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

Frequently Asked Questions

How long is this episode of The Modern Hotelier?

This episode is 30 minutes long.

When was this The Modern Hotelier episode published?

This episode was published on April 29, 2026.

What is this episode about?

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...

Is there a transcript available for this episode?

Yes, a full transcript is available for this episode. You can read the complete transcript on the episode page.

Can I download this The Modern Hotelier episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!