This paper draws on qualitative research on the experiences of men and women who work selling homeless street press across three cities: Melbourne, San Francisco and London. The sellers - or vendors - of homeless street presses, such as The Big Issue (Melbourne and London) and Street Sheet (San Francisco) have become common sights in cities trans-nationally, and mark a contemporary iteration of informal and marginal economic activity for those otherwise excluded from the mainstream and formal employment market. In this paper, I outline the ways in which these street presses constitute an important form of (informal and marginal) work, with strong affective dimensions, and which rest upon the contemporary dynamics of the work ethic and the 'learning ethic'. In the analysis presented, I suggest that this work practice is premised on the value not only of the product (the newspaper or magazine), but also of the exchange itself: the interaction between buyer and seller. Focusing in particular on the moment of exchange, the findings of this research reveal how vendors negotiate complex aspirations, expectations, needs and desires: expectations to be willing to talk about themselves and their 'personal story' with potential buyers; aspirations to move away from the stultifying experience of poverty; a need to generate income; a desire to engage in self-help and develop work skills; and a desire to connect socially with 'the public' and be a worker. Amidst these needs and desires, vendors cultivate entrepreneurial work practices premised on the performance of an 'authentically' homeless and 'deserving' self in public, on street corners.