Did you know that only one person raised their hand at the first RubyConf when the attendees were asked, "Who's getting paid to write Ruby code?" Or that _why the lucky stiff was at the second RubyConf and came off as a preppy surfer dude? Or that Rubygems as we know it today was coded up in the bar at the third RubyConf, but that was actually its second incarnation? As one of the few people who has been to every RubyConf, and the only person to speak at each of them, I can't think of anything more fun for the tenth incarnation than to take a trip down memory lane. I'm going to talk about RubyConfs past, my own personal highs and lows as a ten year serial presenter, and what it all can teach us about the past, present, and future of the Ruby community that we know and love.