This paper explores the intersections of age and masculinities in small information technology (IT) firms in Canada. The IT workforce, although demographically young, does not entirely comprise younger workers but is dominated by men and is ageing. Despite the infamous ‘nerd’ stereotype of IT workers and its associations with immature age and masculinity, perceptions of age and ageing in the industry have not been considered in the context of masculinities. To what extent are conceptualisations of IT work shaped by notions of age and masculinities? How do perceptions of age and masculinities correspond to occupational trajectories and responsibilities in IT work settings? To address these questions, this paper reports an analysis of qualitative semi-structured interviews with 76 employees of small IT firms in Canada. The findings indicate that the dominant frameworks for describing the nature of IT work are metaphors and analogies with sports, the military, entrepreneurial drive and craftsmanship. This paper focuses on the allusions to sport, war and ‘being driven’, and argues that the discursive ties to these masculine arenas normalise, or make ‘natural’, the affiliation of youthfulness and technical ability. The corresponding intersections between age and masculinity suggest that older workers are marginalised in small IT firms.