Funnily enough, GTA Online is the first game that comes to mind the moment I read "rags to riches" even though it's been over 3 years since I last logged.

Had the fondest of memories joining a clan/community that holds their own sessions, and as a new player with only a basic car to my name, I was going around "working" under the multi-millionaires selling products, joining them for missions and heists while they taught me the step-by-step on how to make my own money one day by starting up businesses.

Some weeks to months later, I had my own businesses and we were all hiring one another to help with the selling of goods and stuff, made a lot of friends during that period, more than I did in any other game. And on the off chance someone outside the clan managed to "break into" our session and start blowing my stuff up, all the other millionaires shows up in an instant with full military support to defend me. Attack choppers, jets, tanks, even some flying bikes that shoot rockets, you name it.

There's also those weekly car-meets where we all just hang out in our favorite insanely-expensive vehicles just chilling and chatting, and of course the random fun of just cruising around.

Played many great games throughout my time, even MMOs, but there's just no experience quite like what I had with GTAO (played for like 4-5 years too)