Pelosi's husband started a venture capital firm that mostly invested in real estate development. It has been going for nearly 60 years now, in one of the most dynamic cities in the world. After her husband had made a fortune, and she had raised her children, Pelosi entered politics.
Paul Pelosi came from a good background, but he was not handed a huge amount of money by his family. He has generated a lot of money through his own hard work, intelligence, and luck. He has made a lot more money for those smart enough to invest in him.
Meanwhile, trump has made a below average performance with the money he got from his father. Worse yet, he lost more of his investors money than he made himself. Basically, he is a big negative.