You bring up a good point, even though I enjoyed drinking / partying with a startup I worked at in college, an experience I wouldn't trade for anything - at 26

You bring up a good point, even though I enjoyed drinking / partying with a startup I worked at in college, an experience I wouldn't trade for anything - at 26 I draw serious boundaries between work "outings" / social groups and personal friend groups. Personally, if I ever had a startup there'd be no alcohol at work and work would be for work. The last thing I need is someone claiming someone said something off color at a work outing. Work friends also get messy when you leave a company for good or bad reasons.