Maybe he was given the trip to Hawaii for free or got it at an amazing deal, plus he said he's doing deals in Hawaii on vacation so he'll probably have a good portion of the trip paid of from his working vacation. Plus you can't measure the boost in happiness and a new perspective of the world that this trip to Hawaii will have on his business.

He might see ideas and get new perspectives on things while on vacation in a new land that he otherwise would not get while at home in work only mentality.