When he got married, Grant's Best Man was his wife's cousin and a good friend at West Point, James Longstreet, later a Confederate general.
In the years at St. Louis, Grant would even go into the city to sell firewood. He wasn't doing well financially at all.
While living in Missouri, his father-in-law gave him a slave named William Jones. Even though Grant was not an abolitionist, he also was not a slavery man and in 1859, he gave William his manumission (freedom) even though William was worth at least $1,000, money Grant sorely needed.
However, Grant's father did arrange for him to get a job at his father's leather goods business there that was being run by two of Grant's younger brother: Simpson and Orvil. There he was, back in the tanning/leather business. However, this enabled him to get out of debt.
Then, came the Civil War.
--Old Secesh