What is it like to join a startup in Japan after 25 years? Interview with Ron Drabkin, Bespoke’s Chief Operating Officer.

Bespoke Inc.
5 min readJun 27, 2022


Position: Chief Operating Officer at Bespoke

Joined: January 1, 2022

Ron Drabkin, a serial entrepreneur, angel investor, advisor to investment firms, and mentor, was appointed Chief Operating Officer at Bespoke Inc. in January 2022. Since then, Ron has moved to Japan from the U.S. to join Bespoke as a full-time employee, the first time he has lived in Japan in 25 years. We asked Ron about what brought him to work with Bespoke and what his job entails.

How did you come to join Bespoke?

Ron Drabkin: Last December, Tsunagawa, the president of the company, asked me to join the company. I met Tsunagawa four years ago when I was working as an advisor for a company called Archetype Ventures.

Archetype Ventures helps Japanese startups expand into the U.S. and was Bespoke’s first investor. We were messaging back and forth frequently, and from out of the blue, I was told about the opportunity. Eventually, I decided to consider the position and joined the company in January.

What was the deciding factor in accepting the offer?

RD: There were many factors, including the fact that Bespoke was growing remarkably, DX (Digital Transformation) was interesting, and the service itself was contributing immensely to society, but first, if Tsunagawa asked me to join, I couldn’t refuse [laughs]. Her sales abilities and skill to involve people are truly amazing. I once sat in on a sales meeting in the US, and she is equally persuasive in both Japanese and English. To this day, I have not met anyone else with this kind of ability.

Were you in Japan at that time?

RD: Actually, I was still in the United States. At that time, I could not come to Japan due to Covid-19, so I had to work according to Japanese time. I had to work from 4:00 p.m. to midnight U.S. time, so it was quite difficult [laughs]. Finally, I was able to come to Japan in April, It’s been about a month, but I’m still getting used to life in Japan. However, compared to Silicon Valley or California, life in Japan is easy. It is very convenient to live in Japan, with small restaurants and convenience stores.

So you’ve studied abroad! Is this your first time working in Japan?

RD: I worked in Japan for a while as a new employee after graduating from university, but since the Internet did not exist 25 years ago, I still have a hard time sending e-mails in Japanese now. I went to a meeting with a customer today, and I learned business manners such as where to stand in the elevator and where to sit. Even if you can speak Japanese, it takes time to get used to customs and correct language usage. So every day I am learning, step by step!

You are the Chief Operating Officer, so what is your role within the company?

RD: In a venture company, there are only a few employees at the beginning, so each one of us does not have an official role. In general, we all work hard together. Change in size and stage of the company creates new challenges, and Bespoke now has about 30 employees, and organizational roles are just beginning to emerge. As the company grows, internal communication becomes more important, so we help facilitate communication and management. Additionally, I also use my experience and knowledge of setting up many of my own companies in the U.S. to build Bespoke’s organization.

Bespoke has people from different countries, how is the communication?

RD: Sometimes, even in a typical company, the salesperson and the developer do not speak the same language. It is often said that there is no common language, but in reality, it is not that, it is just that they do not share the same way of thinking.

However, in the case of Bespoke, it is not an exaggeration to say that there is no common language. The official language is English, and almost no Japanese is spoken. Most of the development team is made up of foreigners from France, India, Russia, etc., and the official language is English. On the other hand, the sales team is primarily Japanese, and since they deal with Japanese customers, English is not really necessary, and many of them are not fluent. The result is that there is no common language, but everyone is nice, and when a meeting starts, we look at the members and say, “Today is English?,” or “Today is Japanese?” and we have a lot of fun!. There are almost no problems, but I think there are still some issues that are different from those in a normal company.

What kind of tools do you use for communication?

RD: We usually use Slack because it is convenient and easy to use, but it’s also difficult to go back and find what information is where. So at Bespoke, we ask people to report their progress every week on a certain day of the week in a certain format. Then, If everyone can see it, they can see each other’s progress. If things are going well, we can reduce the amount on Slack, and therefore be more efficient. We haven’t perfected it yet, but we would like to make progress as much as we can, little by little.

Does it seem as if everyone in the company has an equal relationship with one other?

RD: Aside from Kyoto and Kyushu, we have employees in Pennsylvania, California, and Canada as a result of Corona. That communication is still difficult. Language limitations are not the only problem, as everyone is in different countries at the same time. Of course, sometimes it works, and sometimes it doesn’t. The most important thing is to clearly communicate what you expect from the person. Defining an individual’s role and goals through objective rather than subjective evaluation will facilitate determining when and what they should do.

In a traditional Japanese company, there is a vertical organization like a pyramid. As of right now, Bespoke does not have any vertical relationships, but we are working hard to establish them. However, we want to grow our company without destroying the good working environment we had at the beginning of the company. It’s a difficult balance, but I’m happy if we can get it right.

What are some things you would like to do in the future at Bespoke?

RD: Bespoke has seen a fantastic growth rate over the past year. Sales have tripled and quadrupled from a year ago. It would be my privilege to support the company’s performance and help grow the company even further!

What kind of person would you like to see at Bespoke?

RD: We are an international venture company, so we would like someone with an international mindset. We need someone who is flexible because, in a venture company, your role in the company often changes drastically after two months of employment. When there is something that no one else within the company understands, I want someone who can learn knowledge from the outside and take on challenges on their own.

For more information about employment at Bespoke, please visit https://www.be-spoke.io/careers



Bespoke Inc.

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