I never liked his use of the term 'entitlement' - these things a lot of the time aren't privileges, they are needs. Mom used to call this moxy - picking up the phone when you get a rejection letter or something similar and asking questions. Just to find out more, to do better next time, sometimes these conversations turn rejection letters into wait-list letters, and so-on. Sometimes politely inquiring why you didn't get a job is the ticket to doing better in the next interview, or the reason the HR person saved your resume for 'next time' rather than file it for 'never'.
I do this for my kids now, but I show them and explain what I am doing so they learn (hopefully).