BackgroundCurrently available behavioral and dietary weight‐loss programs lack magnitude and sustainability compared with bariatric surgery. A novel dietary weight‐loss program was developed to assist participants in achieving sustainable diet changes by building knowledge and skills in food self‐selection. Although the approach worked, a large variation was observed in outcome among participants.ObjectiveDetermine factors affecting weight‐loss outcomes among participants to further improve the efficacy of the program.MethodsParticipants attended 19 dietary educational sessions during a 1‐year intervention which included prescribed homework. Changes in weight, diet, and body composition were assessed.ResultsParticipants (n = 22) achieved mean body weight loss of −6.49(8.37%, p < 0.001) from baseline at 12 months. Nine participants (41%) achieved weight loss >5% of initial bodyweight; two reached a Body Mass Index 25 kg/m2. A large divergence in weight loss among participants was observed; successful (n = 9) achieved −12.9(9.6)% while unsuccessful achieved −2.03(2.78)%. Dietary protein and fiber density by 24‐h records showed a significant and inverse correlation with weight loss (%) throughout the program. Weight loss at 3 months and 12 months showed a strong correlation (r = 0.84). Participants with self‐reported depression lost significantly less weight than those without depression at 12 months (p < 0.03).ConclusionsDivergence in weight‐loss outcomes among the participants is likely due to a difference in successful dietary implementation. Intra‐cohort analysis indicates early weight‐loss success and early dietary implementation was predictive of long‐term success.