People differ greatly in their financial risk taking behaviour. This heterogeneity has been associated with differences in brain activity, but only in laboratory settings using constrained behaviours. However, it is important to understand how these measures transfer to real life conditions, because the willingness to invest in riskier assets has a direct and considerable effect on long-term wealth accumulation. In a large fMRI study of 157 working age men (39.0 ± 6.4 SD years), we first show that activity in the anterior insula during the assessment of risky vs. safe choices in an investing task is associated with self-reported real-life active stock trading. We then show that this association remains intact when we control for financial constraints, education, the understanding of financial matters, and cognitive abilities. Finally, we use comprehensive measures of preferences and beliefs about risk taking to show that these two channels mediate the association between brain activation in the anterior insula and real-life active stock trading.