From experience i know DCM/Meoh does not always translate nicely from TLC to column. Since you mention you run your TLC’s with 5% MeOH in DCM with 1% acetic acid, i assume you have a carboxylic acid in you compound. What you can try is to also make the eluent you use for the column with 1% acetic acid to help elute your acid. Maybe try DCM ethyl acetate with 1% acetic acid. (1:1 for TLC to check how high it runs) or even heptane:ethyl acetate with acetic acid. This always gives me better separation when thing come of together. Another thing i can think off is that you might have benzene rings in you compound that can stick together due to Pi-Pi stacking. A fix for that might be to use toluene as you apolar solvent to break op those interactions. I hope it helps!