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How Guesty Helped This Short-Term Rental Business Expand Across The Country

Jay | Happy Tokyo
Tokyo, Japan • Member since November 2011

Airbnb Listings (Shibuya, Japan | Setagaya, Japan | Tokyo, Japan)




For Jay, it all started about a little over 3 years ago.

He and his wife decided to list their Shimokitazawa apartment on Airbnb, which was newly gaining traction in Tokyo at the time. The expectations for success were relatively low: the couple figured that maybe somebody would rent out the property every once in a while – at which time Jay and his wife would just migrate to their family’s home, only a couple of hours away in the mountains.

As it turned out, the two ended up living in the mountains…full-time.

Of course, they didn’t mind the extra cash, but Jay and his wife wanted to have the option to go home or to live in central Tokyo at the very least. So, apartment number two was purchased with the idea that it would be listed on Airbnb from time to time as well. Not surprisingly, the popularity of the second property followed suit, and Jay and his wife ended up living back in the mountains, away from central Tokyo yet again.

That’s when they resolved to begin an Airbnb business which took off as a more sophisticated short-term rental system and soon became Happy Tokyo. The company continued to expand and fine-tune its process and system, and luckily, Happy Tokyo has successfully grown exponentially while maintaining its high quality.


Maintaining quality and personal aspects of a business is a key struggle for fast growing hospitality companies. For Happy Tokyo in particular, communication etiquette was held to the highest standard, both before and throughout guests’ short-term rental experiences. But developing a sophisticated systematic messaging system while maintaining high standards proved very difficult as volume increased; Happy Tokyo was scaling, and messaging efficiency was becoming more of a concern.

They knew they needed something more structured. To keep the experience personal, they hired a professional messenger. Yet even one individual was not enough! That’s when it became clear that building an entire messaging team was the only option. While forming a team of fellow hosts seemed appropriate (as hosts have a firsthand understanding of both the Airbnb experience and expectations), Happy Tokyo soon found that most hosts had already developed their own styles of guest communication, making it difficult to train them with a synchronized company tone.

On top of that, experienced hosts typically cannot afford to offer full-time dedication, let alone 24- hour availability. But 24-hour availability was Happy Tokyo’s goal, as quick response times are vital to the company’s reputation.



For Happy Tokyo, quality communication over Airbnb requires a knowledge and a focus of the platform itself, as well as a certain level of flexibility that would allow for their preferred style of messaging. That’s what made Guesty a perfect fit.

“Guesty was already at a place where we wanted our messengers to be, in terms of technology and knowledge of the industry and of how Airbnb works. Guesty’s messaging is great – they know us super well and they’re just awesome.”

 Building a 24-Hour Team

Guesty is a solution that extends beyond a quick-fix, and instead offers long-term and around the clock collaboration. The team partners with companies and helps every step of the way, thus creating both a safe and comfortable environment from which business can grow and expand.

There are many advantages of using Guesty, including the fast response times and 24-hour service. Using Guesty is less of an outsourcing relationship and more of a partnership.”

Business Expansion and Advancement

Guesty’s team already manages thousands of listings, allow companies like Happy Tokyo to manage infinitely more. In this structure, Guesty and its clients grow together, breeding a certain confidence that helps drive success.

Happy Tokyo is currently doing a major push in Kyoto, with 10 properties in the works already. In addition to expansion opportunities, this confidence has allowed Happy Tokyo to focus on other aspects of their business, such as room setup and design of their properties and improving the service standards for their guests.

“By working closely with Guesty, we’ve been able to maintain our quality standards while incorporating a system that allows us to grow. We’ve finally found a way where we don’t need to reinvent the wheel once we reach a certain threshold. We would not be expanding so aggressively and into new cities if we didn’t feel confident that Guesty would onboard quickly and handle the new listings for us without breaking down.”

Guesty offers a team that is available at all times of the day, which helps maintain high communication scores and online Airbnb reputation.

The time saved and shifts in focus have afforded Happy Tokyo some major advancement in business. Next, Happy Tokyo will be putting up their first website listing all their short-term rental properties. Their business has taken on some other new directions, as well. For one, they’ve added the role of property manager to their repertoire for the first time. Though this new management role is simply experimental at this time, it nonetheless marks an exciting time for the company as they explore new and different opportunities.

“We’ve saved time using Guesty – we don’t have to do a lot of direct messaging and that takes a lot of time; it also takes a lot of focus. There has [even] been improvement with response times, and that’s huge.”