I just threw out the rest of my first start-up's stuff. It was a big box of flyers we had printed and wanted to distribute among students. Most of the flyers had handwritten codes on them that would allow people to try out our product, http://partycode.de/ for free. We hand-wrote them because it was cheaper.
Back then, I wasn't afraid of ordering 5000 printed flyers. I also wasn't afraid of throwing out the first batch because I had a spelling error on them, and ordering a new batch. I wasn't afraid of an evening of writing codes with friends.
But throwing them out...
I had kept the stuff for a year, before I finally liberated myself. It's not that I didn't know that it was over, after all, I had shut down all work on that enterprise, as well as the next one, but still, throwing away all that stuff that I worked so hard for felt strange.