The fantastic Gilmore sells everything from potions and spell books to bags of holding and rare items like gate keys. The party having multiple dealings with Gilmore eventually bartered a deal with him advertising his store across the continent. This spread of Gideon's Glorious Goods has brought on such positive popularity that he is eventually capable of opening several successful branches across the globe. He accesses these through gate keys he sets up in the back room of each of his stores. Unfortunately after the chroma conclave attacked his stores were destroyed and he was forced to rebuild from scratch. Below is the link to one of our first inneraction with Gilmore.
On the non business side of things, Gilmore does for a long standing period of time have a intimate relationship of sorts with Vax'ildan. He and Vax go on for years enjoying each others company. Vax provides entertainment in his stories of adventures he and the party go on. Whereas Gilmore providing advice and companionship through hardships and what they may mean for the future. But like all good things their relationship came to a close. Vax fell in love with Keyleth and Gilmore grew busy building a franchise across the continent. Throughout all of this Gilmore still stands by Vax and Vox Machina supporting them financially and in midst of battle.
Throughout the years, Gilmore has stood by the Vox Machina party. Even when The party supported him spreading his business name far across the continent on their missions, and even named one of the party's babies after him.