Winston Chu
CEO & Co-Founder of Wayfarer
Meet Winston Chu, CEO & Co-Founder of Wayfarer 💫
Winston Chu is CEO and Co-Founder of Wayfarer, a technology-powered hotel operations platform based in Japan. Wayfarer provides an integrated technology and operations solution enabling hotel owners and operators to achieve significantly higher profitability. The company sits at the intersection of real estate, operations and technology to rethink hotels.
Wayfarer operates 17 limited-service, select-service and apartment hotels across Tokyo, Osaka and Kyoto under its own brands, representing over JPY 40B in gross asset value. All properties are powered by Materia, a proprietary platform delivering AI-driven revenue management, digital guest touchpoints, operational and back-office automation, market intelligence and performance analytics on infrastructure that connects to any modern PMS.
Prior to Wayfarer, Winston managed global institutional investments in technology — software, hardware, semiconductors, internet and media — deploying capital since 2013. He earned a BComm in Finance and International Business from the University of British Columbia.
What are you currently building?
AI-powered software that gives hotel operators real-time visibility into revenue, reservations, scheduling, billing, and operations—alongside new hotel locations openings in Tokyo and Fukuoka.
What excites you about Japan?
Witnessing foundational changes across the country. Values that have been locked up for decades is finally being recognized.
A risk that changed your trajectory?
Moving to Japan and entering hospitality with zero industry experience.
A habit that has had the biggest impact?
Always listening first. Great leaders make people feel heard.
Advice for your 20s?
Commit to experiencing and trying everything as much as you can.
Work hard, build skills, expand your network, and spend time discovering your unique edge before committing to a path.
Favorite cafe in Tokyo?
Streamer Coffee Company in Shibuya.