Any time you take money out of a retirement account (for whatever purpose), you need to be sure that you won’t get hit with penalties for early withdrawal. In addition, your plan to have the 401(k) plan buy the stock of your company seems overly convoluted if your company is not publicly traded and therefore does not have a market value.

The simplest solution is most often the most elegant one, and 401(k) rules as to how the plan gets established are very complex. You should definitely speak with a financial advisor or other retirement-plan specialist to make sure you don’t run afoul of the rules.