One of the biggest shocks that a lot of small business owners face when they are first starting out is the sudden change to the complexity of the tax rules that they have got to follow. While most businesses do not have to pay all that much attention to things such as Sarbanes Oxley when they are first starting out, there is a very big jump from being an employee (who can simply hire someone to look at the taxes that are automatically withheld from them by their employer, and then figure out from their deductions how much they are going to get back) and being the owner of a business (even if they are just a sole proprietor) and having to pay their estimated taxes every three months. Going quarterly is quite a shift.
Think about how passively most people go into the whole tax situation. A lot of people maintain the habit of spending everything that they make, almost as soon as they have made it. Some people even live the precarious lifestyle of owing money on bills, and having to delay their payments until they have been paid by their employers. While this is something that you can do, come tax time it can lead to a lot of pain if you are self employed or own a business.
After all, small businesses often do not have investors who will simply give them money if they need it. Often, as the owner, you are the only investor. And while you might not be making money on the corporate level, you have got to record the deductions which bring down your adjusted gross. You have also got to keep in mind that if you have any employees (including yourself) who are drawing any W-2 style income, you have got to pay FICA taxes on those at around eight percent of what your employees make. There is no deducing your way out of that.