Charlie Osmond on the Battle Against Booking.com and Expedia

In this engaging podcast episode, we dive into the heart of hotel technology with Charlie, the dynamic founder of Triptease, a company that revolutionizes how hotels drive direct bookings and enhance guest experiences. Charlie shares his entrepreneurial journey, starting from his frustration with booking family holidays to identifying a massive opportunity within the online travel market. He underscores the importance of targeting big markets and the decade-long vision required for startup success.

The discussion also illuminates the unique and playful essence of the Triptease brand, emphasizing its role in making a technical product fun and engaging. Charlie recounts the rollercoaster of the initial 18 months, marked by extreme highs and lows, and the transformative pivot when faced with legal challenges from booking.com, turning potential threats into opportunities.

Furthermore, the conversation explores the strategic maneuvers of OTAs expanding into direct booking services, highlighting the implications for hoteliers and the broader market dynamics. Charlie discusses the critical importance of assembling a senior management team and the evolution of his leadership role, focusing on unique contributions as the company scales.

Highlighting company culture, Charlie emphasizes transparency and the educational journey of growing a fast-moving business, aiming to inspire employees towards entrepreneurship. The dialogue also covers strategies for identifying early adopters among hoteliers and the pivotal role of inside sales in scaling the business.

Charlie reflects on the invaluable lessons learned from ignoring conventional advice, underscoring the importance of following one's conviction in product development.