Risks often accompany available choices in decision-making, particularly where the monetary factor gets involved. Researchers have explored the pathways underlying risky decision-making for decades, but most of these pathways have explored the factors individually rather than through a holistic approach. The present study examines the role of personality, cognitive, and biological components in risky decision-making. Here, the Iowa Gambling Task (IGT) paradigm is used to study the targeted outcome variable (IGT payoff) in 281 healthy students. Two moderation-mediation models hypothesized sensation seeking and lack of premeditation as predictors of IGT payoff. Positive and negative moods prior to IGT administration were considered mediators, and age and gender as moderators in predicting payoff. The hypothesized models were tested using conditional process analysis. Results indicate that both predictors significantly negatively predict payoff while moderated by gender and age categories. Interestingly, the indirect relationships apply to 21–34 years old men and 21–25 years old women. These age and gender-specific findings in apparently healthy participants highlight the need for replicating the current research in different age groups and clinical populations involving maladaptive decision-making patterns.