The problem with the challenge is that in the eyes of many people with real self esteem, cars like Rolls Royce, Bentley, Ferrari etc. are strictly for wankers.
The richest man I know, who is not a billionaire but could certainly afford a couple of expensive cars without having to check with his bank manager has a 52 year old Mini Cooper, the kind that was used in the original version of The Italian Job,) and his second vehicle in a Husqvana motor bike.
That's true self esteem, knowing who you are and liking yourself.
So I guess the poor response to the challenge shows that most people who live in the real world know a lot more about self esteem than Dan Peña.