I know a guy who married Shad Khan's daughter(owner of the Jacksonville Jaguars). Lucky SOB. To make things worse she's hot AF.
I admit, I have insecurities. The chick is totally accepting of me, but can’t get past my own demons.
"A shit ton of money " is a relatively speaking experience.
That could mean 50 million plus to some people, 2 million to others, and just 200,000 to some.
The most important thing in life is to be content with what you have and happy (or proud) with who you are. Doesn't mean you don't work to improve your life, just means you should never be envious or jealous.
No, I don't know anybody that married into a shit ton of money, but I know a few that did OK.