I do have to agree w/you about this, Rio. Bragging and patting yourself on your back over your success is not an attractive trait and it turns most people off.
It's not unattractive to those who have achieved success. Birds of a feather.
Trump is a successful and brilliant business man and the rest of us know it.
SOME of us know it, but not everyone knows it. This is why politicians repeat themselves ad nauseum while on the campaign trail. You need to repeat yourself with every new crowd you come across to increase your base. An analogy might be when a popular singer shows up to perform a concert. The fans may have already have heard the performer's most popular songs hundreds of times, but when it's performed in person, it's like you've heard it for the first time and you'll remember where you heard it in person. Personalize your message for EVERY new crowd.