[2] After his father's untimely death in 1878, Simon found work at a cash-boy at Stern Brothers, a dry goods store located at 32–36 West 23rd Street.

One of the store's principals, Louis Stern, befriended young Simon, teaching him the "ropes" of dry goods.

[3] It was during one of these business trips that Simon became acquainted with Herman A. Flurscheim, one of Stern Brothers' principal suppliers in France.

[3] At that time, Fifth Avenue was primarily a residential street, and Simon's merchant contemporaries derided his choice of location, speculating that the business would be a total failure.

[3] From that point forward, Franklin Simon & Co. remained one of the preeminent Fifth Avenue fashion outlets until its dissolution in the 1970s.

Perhaps the first person to view Fifth Avenue as a major retail and fashion center, Simon initiated "Buyers Week" and "Market Week", thus revolutionizing how manufacturers and retailers presented and sold new fashions and simultaneously generating millions of dollars in business for the surrounding neighborhood.

Their talent helped change the future of department store display windows, creating futuristic designs that stopped traffic on Fifth Avenue.

To dissuade piracy and trademark infringement, Simon was ferocious in protecting his brand and was not afraid to use the courts to enforce his legal rights.

[10] Later expansions followed in Manhasset, Long Island – on the "Miracle Mile", Palm Beach, Florida, and several other locations.

After the Titanic disaster in 1912, Mr. Simon provided clothes and financial support for two French orphans rescued from a lifeboat.

"[3] The New York Times, in an editorial celebrating Simon's achievements wrote "What need of imposing a 'code' upon a man like him?