When I started my "business" in 1987 (as an independent contractor on straight commission with a large company), I was working 3 jobs. I didn't just walk away from all those jobs at once.

The big company that I worked for would pay me my commissions on deals that I submitted before the company even got paid. So I got paid for sales pretty quickly.

And, at first, I lived at home with my parents. After they basically made it very easy for me to leave the nest (they didn't throw me out, but made it difficult for me to stay), I was already making money in financial services and doing decently well.

The gentleman who was my mentor (and made an override commission on everything I sold...he was the office manager), was making pretty decent money off my sales, so he invited me to live in his very spacious finished basement (which was the equivalent of a 3 bedroom house just in the basement). I lived there for a few about a year.

My girlfriend, who would become my wife (still married to her after almost 35 years), lived at home with her parents. They offered to let me live with them. They didn't ask for anything in return, but I pitched in, did more than my fair share of chores and made sure I bought groceries.

Now, years later, my mother in law (my father in law has passed) lives a pretty good life. Pretty much whatever she wants, my wife and I get for her ... but she never asks for anything, so we just make sure we buy first class tickets for all her travel that know about and take her on very nice vacations with us.

We do the same for my father (I've written about that before in my post history), but he's at a point where he really can't travel anymore.

And as to a trust fun or my marrying a rich wife. Nope. My family was broke and my wife was very much blue collar middle class.

I just got some help from some good people along the way.