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

About this episode

David Millili interviews Richard Aday about the evolution of hospitality technology and improving the hotel booking experience.

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…

People in this episode

Host: David Millili

Guest: Richard Aday

Topics covered

• hotel booking experience
• hospitality technology
• entrepreneurship
• guest experience
• property management systems
• direct bookings
• AI in hospitality

Keywords

• hospitality
• technology
• guest engagement
• direct bookings
• AI
• automation
• property management
• ThinkReservations

Mentioned in this episode

Organizations: ThinkReservations, Amazon

Places: Puerto Rico, South Florida

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