The letter collection of Lapo da Castiglionchio the Younger offers important evidence about the dynamics of early-Quattrocento literary patronage. Like his more successful humanist peers, Lapo used Ciceronian expressions amicitia (friendship) when writing to the brokers whose help he needed in order to win a comfortable post. For most humanists, such formulaic assurances of devotion constituted only one aspect of letters that included discussions of philosophy, current events, and classical scholarship. Lapo, by contrast, focused his collected letters almost solely on these formulae, thus mocking their prevalence and emphasizing the difficulties of finding a job as a humanist.