Obesity is particularly hazardous for people with multiple cardiovascular risk factors and existing cardiovascular disease, although few studies investigate experiences and perceptions of weight loss in this population. This study provides an understanding of participants' knowledge, attitudes, and experiences of managing multiple risk factors and/or existing cardiovascular disease of participants who were undertaking a weight loss program. Thirty-five participants were recruited from the first 50 completing a multicomponent group-based weight loss intervention designed to follow cardiovascular disease and diabetes disease management programs. Four focus group interviews were conducted using a semistructured interview schedule. Data were analyzed using an inductive approach, and themes developed. Participants found the process of weight loss to be complex, dynamic, and challenging, as the conflicting needs of existing health conditions, social support, ambivalence, and time limitations required careful balance. In response, participants determinedly developed and tested strategies based on simplified principles, establishing routines for new health habits and portion control, and going back to basics in food selection. Therefore, weight loss programs for this population need to be specifically tailored to support patients' efforts and strategies.