Well there has been quite a few tv programs about Trump dodgy finances and various bankrupcies. It shows that sometime he tried and failed. It shows that sometimes is a cruel and shrewd businessman and he came from a wealthy family. As they all are if they made so much money.
What about the Clinton family? Before Bill presidency they were well off, bit normal
After that they started as professional speakers racketing serious money.
An independent Organization, Judicial Watch, made successful bid to disclose their trust account details. They received at least $48 million from donation and speaking fees from Saudi Arabia, Lybia, Congo, Algeria, Iran, China. And also from the US State Department.
Be careful what you wish for.