I think you're thinking too much about the restaurant. A CEO can go have a $1000 meal at the same place the analyst has a $200 meal. The CEO could even have the $200 meal. Even multi-millionaires might not want a seven course prix fix for lunch.

If the analyst lives in NYC and makes $250k they aren't living large. If they went to an Ivy League school and have to pay for it they really aren't living large. Regardless, the story makes the CEO look silly.