I kinda expected him to say that the investor was his Dad or something.

I am pretty sure that if my company is not moving forward and the ROI is not looking good for investors - then they will not be first and foremost concerned with my happiness. They don't want me to feel miserable, but they certainly don't want to see me playing ping pong and drinking PBR all day if the company is not moving in a positive direction.

I think a better question an investor would ask would be "are you still feeling optimistic" or "are you happy with the direction we're going, our progress, etc" Not just am I personally feeling happiness

For a second I was thinking the opposite, in that the investor wanted to continue the happiness and bring in a second round of funding. Thus giving his first investment a greater chance of success.