An entrepreneur teaching Japan how to take more risks

That's seen as very risky, albeit he had a huge safety net when he decided to do so given he already had enough money to retire.

It's not so much about taking risks as being in a position to take risks.

Nothing about this article says the Japanese are incapable of taking risks (obviously the subject of the article is a prime example), if it said no Japanese people ever take risks, that would be racist. However, it is well known and documented by themselves that their culture has values that avoid risk and those that take risks are looked upon as foolish and shunned for failure. That's more a collective decision made by their society and one that can be changed over time or individuals can choose to deviate from. Their economy has seen stagnant growth because there just isn't the start-up culture you see in other countries. Just look at the web design of a typical Japanese web site if you want to see how adverse the culture is with experimenting with anything new once they find something and establish it as standard.

Disclaimer: Also, there are no real judgments being made on a culture being risk adverse either. Obviously, that carries its own advantages that has probably greatly benefited their country over time. However, anything can be detrimental if taken too far to an extreme. Obviously, if no one ever takes risks or deviates from accepted norms of how you do things, you are less likely to find a new way of doing something or as quickly adapt to changes in the economy. If you want to encourage entrepreneurial businesses, its a cultural value that will need to be dealt with, where as it probably has great advantages in an normal office culture or an island nation where there are few natural resources and everyone lives in tightly packed spaces.

There are some pretty prevalent cultural attitudes in Japan with regards to toeing the line or knowing your place. Not to mention aversion to failure, saving face, and all that.

edit:typo