After a long period of convincing people and especially the ones with the necessary mandate we got the mandate to go for LeSS at YSoft. Some of us went to public courses in Feb 2018, we got several preparation workshops going starting in Aug 2018 and finally flipped our first Area in Jan 2019. From that moment on we went on a rollercoaster with ups and downs which we would like to share. In this talk we take you with us from start till where we are today, not hiding the bad & the ugly part from it like consultants would.