My dad died so penniless I had to pay to put his broker-than-broke a$$ in the ground.This was a man who could not get up again as soon as his good opinion of himself as suh-HE-ree-us was more than slightly injured.

Part of the deal here is was to give her the opportunity to find some place to move because she was penniless before the transaction went through.

In the old days, the barriers to entry for securities trading were high (think brokerage commissions) whereas in real estate there was this allure of the no money down "creative" deal that could transform a penniless person living under an overpass into a mogul with a yacht, big house and scores of bikini babes (yes, the marketing was mainly to a male audience back then and still for the most part today though that seems to be changing a bit). 

., one of the world’s largest companies at that time; Leon Frazier, president of the Bank of International Settlements; Richard Whitney, president of the NewYork Stock Exchange; Arthur Cotton and Jesse Livermore, two of the biggest stock speculators; and Albert Fall, a member of President Harding’s cabinet.Twenty-five years later, nine of these titans ended their lives as follows: Schwab died penniless after living for five years on borrowed money.

The borrower is a penniless idiot that doesn't know anything.

What about a nasty divorce leaving one partner penniless when the scoundrel runs off with the savings and checking account money?

After they had my money, it became clear they were close to penniless.

I too have an immigrant father who came to this country penniless with a similar history.  

Don't go in penniless though, things can and often do come up.Also the notion that a property bringing in $18,000 in rent is going to net $15,000 is pie in the sky.Let's assume you purchased a $60,000 property and put $15,000 down.

He overcame ENORMOUS obstacles... leaving him penniless, homeless, taking showers at the community park..Only to as he told me "In a fit of creative consciousness..