The 46-year-old entrepreneur co-founded Roc-A-Fella Records along with Jay and Kareem Burke in 1995, but Damon and the New York-born rap star split in acrimonious circumstances almost a decade later, and he still harbours regrets about the breakdown of their relationship.
Damon shared: ''I do miss the friendship. We were good friends. On a human level, of course we were friends, you miss the friendship.
''It was a camaraderie, we were both fighting for the same thing. There was ideals. I do miss those ideals - being around people that are honest and, you know, will do anything.
''[But as] you evolve, men ain't supposed to be wanting to hang out with other men as they get older.''
Damon admitted their lives were inevitably going to change as both men got older, with Jay ultimately marrying Beyonce and starting a family with the music icon.
Despite this, Damon still misses spending time with the chart-topping rapper.
Reflecting on the split, Damon told Us weekly: ''They're supposed to hang out with their girl and their family, so it has to happen regardless.
''But you still miss high school, you still miss camp, but I don't want to go back to it.''
Jay left the Roc-A-Fella label when he was offered the position of CEO and President of Def Jam Recordings.
The 'Empire State of Mind' hitmaker subsequently said: ''I don't really wanna talk about Dame or Biggs. I don't have nothing negative to say about them.''
Following the split, Kanye West was one of a handful of artists who decided to follow Jay rather than Damon.
Justifying his decision, Kanye previously said: ''Jay-Z know how to move in a room full of vultures. You know what I'm saying? As his little brother, I needed to learn that technique because I got something that God want me to give the world.''
Once a fire fighter, always a fire fighter.
Today (September 14th) marks the 25th anniversary since the album's 1993 release.
Labrinth has teamed up with Sia and Diplo to form a new supergroup: LSD.
The Struts teamed up with Kesha for a red and gold themed music video as part of their collaboration on 'Body Talks'.
Sometimes actors are not acting.