Toshiyuki Yamamoto, Representative Director, Japan Angel Investors Association / Representative Director, Power Angels

2026.04.29

The angel investment path taken by an entrepreneur who continued to move forward even when misunderstood – a man 10 years ahead of his time.

■ Profile
Born on March 21, 1979, in Neyagawa City, Osaka Prefecture. In 2000, while studying at Chuo University, he founded EC studio (later renamed Chatwork) in Los Angeles, where he was studying abroad.
I established a US subsidiary in Silicon Valley in 2012, managed it for five years, and then returned to Japan.
One year before going public, he handed over the CEO position at Chatwork to his younger brother, and in 2019, the company was listed on the Tokyo Stock Exchange Growth Section with a market capitalization exceeding 55 billion yen.
Currently, I am focusing on "Power Angels," a community of angel investors.
His published works include "The Angel Investor's Practical Bible."

Toshiyuki Yamamoto is an entrepreneur who has taken on the challenge of launching numerous businesses, persevering through setbacks. He shifted from self-funded management to a startup model, expanding his business. Currently, he supports the next generation of entrepreneurs through angel investing, providing both funding and experience. This article explores his background and the potential of investing in him.

■The desire to earn a living through one's own efforts had been budding since a young age.

About 30 years ago, I saw the potential in the internet, which was still in its infancy, and started my own business while I was still in high school. During my student days, my mind was almost entirely focused on business. However, at the time, my mindset was more about "making money" than "starting a business." I didn't have enough IT knowledge, so I was basically fumbling my way through it all. I would spend an entire night sending sales emails to 10 people, and I would just keep trying different things to increase sales.
I attended a prestigious high school where part-time jobs were prohibited, and hardly anyone around me knew about the internet, yet I was earning around 20 yen a month. My classmates didn't understand me and probably thought I was "weird." However, at a class reunion 10 years later, they told me, "You were different even back then." It took time for what I had been doing to finally be understood. That experience was very memorable.

■ Businesses that anticipate the times 10 years from now

Looking back, there have been many times when I intuitively felt "this is something that should be done," but those around me didn't understand. In the past, I used to worry, "Am I wrong?", but gradually I came to think, "I'm just working on something that's 5 or 10 years ahead. The times will catch up eventually." By accumulating these experiences, I can now follow my intuition without hesitation.
My family runs a long-established music studio in Osaka, and my father wanted me to take over the company. However, I strongly believed in the potential of the internet, so I had no intention of choosing that path. I wanted to start my own internet business. To do that, I felt I needed to produce results that would convince my father before graduating from university, so I set myself a deadline. Then, in 2000, I took a year off from university and studied abroad in Los Angeles, where I began to seriously work on starting my own business.

■ We want to create an environment for angel investing and enrich the Japanese economy.

Even after starting my own business in earnest, it was a continuous process of trial and error. I launched more than 30 businesses, repeatedly failing, and learned a great deal from each experience. Through my experience in Los Angeles, I strongly realized the usefulness of chat tools. In 2011, when email was still dominant in Japan, I released Chatwork with the message, "The age of email is over."
For the past 15 years or so, we had expanded our business by reinvesting sales and profits, but we felt that this approach had its limitations due to insufficient manpower and time. Therefore, in order to create a service that could spread globally, we decided to shift to a so-called startup-type management model, raising funds from external sources.
This experience taught me that even within the realm of "management," there are completely different strategies depending on whether you're raising funds or aiming for an IPO. I also became interested in angel investing, which I hadn't paid much attention to before, and this became the impetus for starting Power Angels.
At Power Angels, we don't just provide funding; we prioritize increasing the chances of startup success by offering practical advice based on our own entrepreneurial experience. Therefore, we limit our member investors to those with management experience who can advise young entrepreneurs.
I myself have experience in both startups and small and medium-sized enterprises, have taken a company public, and have also seen the Silicon Valley scene firsthand. Furthermore, through these diverse experiences, I have cultivated networks not only among business leaders but also with politicians and government officials. I hope to leverage these experiences to become a bridge connecting various fields.

■Message to students

Starting a business is incredibly exciting. Being a student is, in a sense, a "golden time for challenges," a precious period when society and adults offer support. You might have anxieties about starting a business, such as "What if I fail?", and there will be opposition from those around you. However, the experiences and failures you gain will undoubtedly become valuable assets for you. They will definitely make you stronger.
Even if you don't start your own business, it's crucial to take everything personally, to take responsibility for your own actions, and to take accountability for any problems that arise. This entrepreneurial mindset will be useful no matter what field you choose to pursue. Furthermore, I strongly recommend taking a year off from school or studying abroad. It's a valuable opportunity to fully utilize your time and challenge yourself while keeping the option of graduating as a new graduate open. That experience will undoubtedly be a turning point in your life.

Student Newspaper Online, March 18, 2026 Interview with Ayuri Nakatsu, 3st year student at Dokkyo University