We’re excited to share that our CEO, Chai Kanda, recently sat down with the team at Unpacking Japan for an in-depth conversation about Japan’s short-term rental market, the art of machiya restoration, and the evolving landscape of tourism in Kyoto and beyond.
The full episode is now live on YouTube (video below) and available on all major podcast platforms including Apple Podcasts and Spotify.
What This Episode Covers
From Sydney to Kyoto: Chai’s Journey into Japanese Real Estate
Chai traces his path from growing up between Japan and Sydney to ultimately choosing Kyoto as his long-term home. He shares what drew him back to Japan, his early career experiences in Kansai, and the moment he discovered real estate as a path worth pursuing.
Investing in Machiya: The Pros, the Challenges & the Charm
Machiya , traditional Kyoto townhouses , sit at the heart of Shiki Properties’ business. Chai breaks down what makes these century-old properties compelling as vacation rentals, the realities of renovation budgets, and how he approaches funding and partnerships to make projects viable. He also discusses what today’s guests are looking for when they book a machiya stay.
Navigating Japan’s Airbnb & Short-Term Rental Regulations
Operating in Japan’s short-term rental space means staying on top of a constantly shifting regulatory environment. Chai offers a frank look at how Japan’s tourism boom has prompted new rules, including Kyoto-specific restrictions, and how operators can adapt to remain sustainable and compliant.
Expanding Beyond Kyoto: New Markets & Japan’s “Little Venice”
Shiki Properties isn’t standing still. Chai talks through the process of entering new markets, what he looks for when evaluating a new area, and why Japan’s so-called “Little Venice” (Amanohashidate / Ine area) caught his attention as an expansion opportunity.
Sustainable Tourism & the Overtourism Debate
Few topics in Japan travel are more pressing right now than over tourism. Chai shares a nuanced perspective , from crowded Kyoto bus lines to the challenges of transit expansion , and how he thinks about building a business that benefits both visitors and local communities over the long term.
From Real Estate to Hot Sauce: Chai’s Entrepreneurial Side
In a lighter turn, Chai opens up about his venture into the Japanese food market , specifically, launching a hot sauce brand – Habanebros, and what the experience taught him about the realities of bringing consumer products to market in Japan.
Key Lessons from Two Decades in Business in Japan
After 20+ years navigating business in Japan, Chai reflects on the fear of failure that shapes Japanese business culture, how to come prepared, and what he wishes he’d known earlier.
About Shiki Properties
Shiki Properties specialises in the restoration and management of machiya townhouses as luxury vacation rentals in Kyoto and select destinations across Japan. We believe that thoughtful tourism, rooted in authentic local experiences, is better for guests, better for communities, and better for Japan’s architectural heritage.
Explore our properties to stay at→ https://shikiproperties.com/
Explore properties to buy→https://shikirealestate.com/
