Well if you enjoy paying taxes on that 5k so you actually have 3.5k to invest there is a 1.5k difference. Not to mention with stock options if you hold them for more then a year it's considered long term capital gains vs short term (35% vs 15%). And there is quite a difference in the taxes you pay. So my way you only pay tax when you sell it hopefully at 15% tax. Vs your way you pay tax on it twice once as income tax at 35% for the initial 5k then another 15% at longterm capital gains when you sell. So close to a 35% tax difference. Uncle Sam thanks you for your contributions.