Paul: Kaido Chiwata is a co-founder of BillPay, a Tokyo-based billing solution for foreign companies entering the Japanese market.
Kaido and I spoke about how he went from bullied returnee to professional kickboxer, how his career in financial services led to his own entrepreneurial journey, the difficulties faced by foreign businesses coming to Japan, and much more.
Hi Kaido. To get started, please tell us a little bit about yourself.
Kaido: I was born in Ogikubo, Tokyo, but spent most of my early childhood on the East Coast of the U.S., growing up in New Jersey and Connecticut from the ages of 1 to 9. Throughout my life, I’ve always been passionate about combat sports. As a third-culture kid, I often found myself struggling to fully understand and define my cultural identity.
Settling into a new life in Japan at age 9 must have been quite a culture shock!
Unfortunately, I didn’t have U.S. citizenship, so when we moved back to Japan, my parents raised me as a typical Japanese child. They were quite strict about it—rather than allowing me to attend an international school, they placed me in a regular Japanese public school, armed only with a Japanese dictionary for support.
How well did you speak Japanese at that time?
My Japan speaking was ok but I had a hard time fitting in because I didn’t understand the kind of rough language boys typically use with each other. In general, I think Japanese kids have pretty high standards when it comes to Japanese language skills.
Kids can be cruel, especially to someone perceived as different, and bullying is a big problem in Japanese schools. What was your experience as a returnee?
If I had looked completely foreign, I think people would have treated me as a foreigner. But since I looked Japanese yet spoke poor Japanese, I was discriminated against as a gaijin. My way of coping back then was to prove myself through sports and academics
You studied business and economics at Keio, choosing the school for its rugby team. You also got into kickboxing, turning pro in 2021 and fighting in RISE. That’s quite an action-packed student life. Tell us about this period.
What saved me – someone who struggled to fit into the Japanese school system as a returnee – was rugby. Up until junior high school, my rugby journey was going smoothly. I was selected for the Tokyo representative team and achieved strong results at the national level.
Unfortunately, in high school, I suffered two major injuries and was unable to perform as I had hoped. I also continued playing rugby until the fall of my senior year, which left me little time to prepare for university entrance exams. As a result, I had to take a gap year.
After a year of studying, I was able to join Keio University’s rugby team. However, due to the gap in training during high school and the bullying I experienced from senior teammates, I lacked the confidence that I could become a regular starter in my four years there.
What ultimately led me to quit rugby was my parents’ divorce. Around the same time, our family home was put up for sale, and I had to help clean and pack things up, which kept me away from practice. I also had a dispute with my father over club fees. That was when I made up my mind to walk away from the sport.
But I didn’t want to end my university years without taking on one last challenge—something that wouldn’t be constrained by financial concerns. That’s when I discovered kickboxing. Thanks to the physical conditioning I’d built through rugby and my natural fighting instincts, I took to it like a fish to water. Within a year, I reached the semi-finals of the national amateur championship and made my professional debut.
As a professional kickboxer, I later became runner-up in the rookie tournament and climbed the ranks, eventually reaching #6 in the national rankings.
Instead of pursuing kickboxing as a career, you joined Sumitomo Mitsui Banking Corporation (SMBC) in 2014. Why did you choose a career in financial services?
During my student years, I devoted myself entirely to kickboxing—to be honest, I was performing at a level where I could have made a living from it alone. Because of that, I didn’t have a strong desire to work in any particular industry.
However, in the final year of university, while still active as a fighter, I interned at the Japan launch of Glory, one of the largest international kickboxing organizations at the time. Through that internship, I became disillusioned with how underdeveloped the kickboxing industry was from a business standpoint. That experience made me realize I wanted to pursue a career in business instead.
When considering which path to take, I decided to join SMBC. I believed that working there would allow me to engage deeply with a wide range of industries and executive teams, regardless of company size or profitability.
How did your career progress from SMBC? Walk us through it.
At SMBC, I spent two years in corporate sales at a local branch, followed by nearly two more years at headquarters in a product management role. After that, I briefly worked at HSBC, but I quickly became disillusioned with how large institutions often struggle to respond flexibly to individual client needs. That led me to step away from the traditional finance industry.
It was around that time that I came across Stripe. While Stripe is now recognized as a global megatech company, the Japan office back then was a true startup – just a small one-room space where everyone worked shoulder to shoulder. Getting into Stripe was a turning point for me. I was inspired by incredibly talented colleagues from around the world and started to develop a vague but growing aspiration to one day become a country manager or even start my own company.
At Stripe, I worked on building the company’s first partnerships with Japanese financial institutions. I then took on a sales role at Moneytree, followed by a position at Remo, where I was promoted from Sales Lead to Country Manager. Most recently, I served as the Japan Country Head for Spenmo, a Singapore-based fintech startup, leading the launch of its Japanese entity.
On to BillPay, the startup you co-founded in March of last year. What problems are you solving, for whom, and how?
At BillPay, we aim to become the go-to billing solution for foreign companies entering the Japanese market. While Japan is known as a large and attractive market, many foreign businesses face significant challenges when trying to establish a presence here. BillPay helps overcome these hurdles by providing virtual bank accounts for local fee collection, multilingual support, and other features tailored to the needs of international companies.
What are some of the common challenges faced by foreign businesses setting up in Japan? I hear a lot of foreign entrepreneurs talking about their difficulties in setting up bank accounts.
Japanese banks are notoriously strict when it comes to opening accounts for foreigners. In most cases, banks will not recognize someone as a resident unless they have been living in Japan for more than six months. Opening a corporate account is even more difficult. For instance, if a company is engaged in consulting or other non-tangible services—as opposed to physical product sales—it may be denied a corporate account even if the owner has been in Japan for over six months.
Additionally, the documentation required for opening bank accounts is often written in complex Japanese, which poses a significant barrier for non-native speakers.
At BillPay, we actively support foreign-owned companies by offering solutions such as collecting revenue on their behalf and remitting funds to the personal accounts of the ultimate beneficial owners.
Did a career as a pro kickboxer prepare you for entrepreneurship? I would imagine after having been punched in the face for a living, you take the daily stresses of running a startup in your stride.
Having competed professionally in kickboxing, I’ve become resistant to nervousness or stage fright. Japan is a society where seniority often dictates hierarchy, but as a business owner, I frequently find myself needing to engage with people who are older or more senior on equal footing. In those moments, I believe my experience in fighting has helped me carry myself with confidence and composure.
What does your typical day look like?
I have two young sons, so my daily routine revolves around balancing childcare and work.
Mornings are hectic between 7:00 and 9:00 AM with getting the kids ready and dropping them off, so I usually start work around 9:30 AM.
I typically wrap up work by around 6:00 PM to pick up my children, and if there’s any remaining work, I get back in front of my computer around 9:00 PM after they’ve gone to bed.
What are some of your goals for the future? Short-term, long-term, personally and/or professionally?
My short-term goal is to make BillPay profitable.
In the long term, I hope to eventually exit BillPay and shift my focus to something I had to give up in the past—professional sports. This time, not as a player, but as an entrepreneur. I’d like to build a business that helps grow and innovate within the sports industry.
Quickfire questions
– If you could go back in time to your arrival in Japan as a 9-year-old, what advice would you give yourself?
Be true to who you are, and don’t be afraid of the bullies. Your bicultural background will become a powerful asset in the future.
– How do you learn new skills?
New business trends in fintech come from on-the-job training and networking. I am personally improving my power lifting skills these days. Almost there to reach the total of SBD to 500kg. lol
– Tell me a few of your favourite or most recently read books, movies, podcasts, and games.
One book I recommend is “Culture Map”, by Erin Meyer. This book offers a theoretical overview of the characteristics of communication across different countries. It serves as a helpful guide for effective communication in multinational environments.
– What’s your favourite place to visit in Japan?
Ishigaki Island, Okinawa.
I love Ishigaki Island for several reasons — the food is amazing, especially the Ishigaki beef and tuna, and the ocean is incredibly beautiful.
My kids also enjoy catching marine creatures while playing by the sea. Unlike the Okinawa main island, Ishigaki has a much more relaxed and laid-back atmosphere, which is another reason I like it so much.
– What’s the best thing you’ve spent 10,000 JPY on in Japan?
Yakiniku.
Are there topics we haven’t discussed that you’d like to add?
The concerns I have about Japan’s future, from the perspective of a parent raising children.
In Japan, I feel that it’s quite difficult to develop not just English proficiency but also international communication skills through the public school system. That said, international schools are very expensive, and sending two children there would be a significant financial burden on the family.
I haven’t reached a conclusion yet, but at some point, we may need to consider the possibility of leaving Japan and relocating abroad.
Finally, do you have any asks for our readers?
If you’re a foreign business or an entrepreneur setting up in Japan, let’s talk about how we can help you accept payments from Japanese customers.
Thanks, Kaido. Best of luck to you and the BillPay team!
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