Fleischmann was last seen at the Buckhead Saloon in uptown Charlotte, North Carolina on November 9, 2007. He had gone there with friends after attending a show, then he became separated from the group and his friends went home. The bar's surveillance cameras show that Fleischmann left alone at 2:20 a.m. and got into a cab at Tryon Street. He kept making cellular phone calls after he left the bar and phone records indicate he was still in the uptown area during this time.

According to Fleischmann's father, he was seen outside the Fuel Pizza restaurant down the block after he left the saloon, and his image was captured on surveillance tapes. An employee there remembers Fleischmann coming inside the restaurant at 2:30 a.m. He was alone and ordered two slices of pizza. The employee didn't see him leave. A cab driver thinks he saw a man fitting Fleischmann's description walking on north Davidson Street at 3:25 a.m., but he couldn't say for sure whether the man he saw was Fleischmann.

The last time Fleischmann used his cellular phone was at 3:30 a.m., when he called his roommate and his sister. They didn't answer and he didn't leave any messages. Since then his cellular phone has been turned off and there has not been any activity on his bank accounts. He left his debit card and his coat at the bar, and left his car parked at a friend's home, but he is believed to have been carrying his black leather wallet, his car keys and approximately $6 in cash. He was reported missing the next day when he did not show up for work at Fidelity Investments, a health care recruiting agency where he was employed as an executive. He lived in a condominium with roommates. His roommates are not considered to be suspects in his disappearance.

Fleischmann is described as a responsible man and it is extremely uncharacteristic of him to leave without warning. At the time of his disappearance, his mother was undergoing treatment for breast cancer and he kept in close touch with her as a result. He was not having any personal or financial problems at the time of his disappearance, and appeared to be in a good mood the day he went missing. Fleischmann is a 2006 graduate of Elon University, where he majored in business administration and was a member of the Kappa Alpha fraternity. His case remains unsolved. His parents believe he was probably murdered.