While cooperation and risk aversion are considered to be evolutionarily advantageous in many circumstances, and selfish or risky behaviour can bring negative consequences for individuals and the community at large, selfish and risk-seeking behaviour is still often observed in human societies. In this paper we consider whether there are environmental and social conditions that favour selfish risk-seeking individuals within a community and whether tolerating such individuals may provide benefits to the community itself in some circumstances. We built an agent-based model including two types of agent—selfish risk-seeking and generous risk-averse—that harvest resources from the environment and share them (or not) with their community. We found that selfish risk-seekers can outperform generous risk-averse agents in conditions where their survival is moderately challenged, supporting the theory that selfish and risk-seeking traits combined are not dysfunctional but rather can be evolutionarily advantageous for agents. The benefit for communities is less clear, but when generous agents are unconditionally cooperative communities with a greater proportion of selfish risk-seeking agents grow to a larger population size suggesting some advantage to the community overall.