Secondary markets have a coextensive history with the world wide web – from email lists to message boards, people have consistently used the web to facilitate the exchange of used goods, job ads and apartment listings. As a way of tracing the socio-technical trajectory of secondary markets, this article offers an extended comparison of two online platforms: craigslist and VarageSale. The former represents one of the earliest and most stable platforms for the online secondary market, whereas the latter is a newcomer that both critiques and seeks to improve on older visions of peer-to-peer exchange. By comparing the monetisation strategies, aesthetics, marketing and user policies of these two platforms, this article generates a historical discussion of key shifts in the online sharing economy specifically and online interactions generally. In particular, this article argues that the gap between these two companies illustrates a transition towards monetisation and away from anonymity, and demonstrates the difference between anonymity as a tool versus anonymity as a way of being.