Being loyal to a start up. As soon as I got those shares , should have cashed out and moved on asap.

Change jobs as soon as you can, easily blame it on being young and they never held it against me when I finally did learn that. And since you’re in your 20s, they will never let you retire there anyway. So why stay?

No. Jellyfin accounts are local. So you need to set them up on the server. No external auth system