Are You Overpaying Your Taxes?

Legal Tax Angles:

How to Save Taxes Without Going to Jail


It would be very difficult to find two families with exactly the same total income who also paid the same amount of income taxes. Some families rent while others own a home. Some families receive tax free medical benefits from an employer. Others have to pay for those expenses with after tax dollars or do without. Some families have learned how to get a tax deduction for many of their expenses. Other families have virtually no deductions. 

Two investors with the same total assets to invest will rarely pay the same taxes. Some investors will choose to buy tax exempt bonds. Others will invest in tax deferred annuities. Some investors will buy growth stocks instead of bonds. The most conservative investors will invest in fully taxable C.D.s and savings accounts. Some astute investors will decide to take money out of heavily taxed investments and use that money to pay off a home loan - even though it results in a loss of the home mortgage interest deduction. 

Some families put their children through college the hard way - with after tax dollars. Other families spend the time to learn how to legally transfer taxable income to their children so the income will be either tax free or taxed at a very low tax rate. Generally, this requires that the family has some business income (other than from a professional practice) or some investment income. 

There are many legal ways to defer the tax on long term capital gains for a long time. If you're selling a business, you often have a lot of ways to structure the sale to get the best result after taxes. 

But there's a catch.

To use these legal devices, you need to be aware of them and how they work before you need them. If you have sold a highly appreciated asset already, don't call your tax advisor to see if there is anything they can do to help you. The answer is almost certain to be "I'm sorry. It's too late. Why didn't you call me before you did the deal?". 

There are about 20 million businesses in the U.S. About 18 million of them are doing business as a proprietorship instead of as a corporation. These businesses often need to accumulate working capital for inventory and receivables with after tax dollars. Some business owners accumulate those assets with dollars that are taxed at federal and state personal tax rates of 35% to 50%. Others accumulate working capital at corporate tax rates of 15% to 20%. However, different tax advisors often have strongly diverse views on this subject. My view is that the best approach depends on when you think you will really need to "cash in" and convert your corporate assets into personal assets. It also makes a big difference whether you are likely to make $5,000 a year, $50,000 or $500,000.  

The federal estate tax has been called a "voluntary tax" because there are so many legal ways to avoid this tax with advance planning. However, few families will spend the time or money to restructure their assets to prevent the IRS from taking up to 50% in one generation, up to 75% in two generations and up to 91% in three generations. Basically, estate planning isn't done for your own benefit. It's done for your children. The current estate tax can be avoided until the death of both parents. Thus, the estate tax is virtually a tax on orphans. When you are both gone, the IRS gets a big chunk of what's left from your kids. That is, they will unless you are willing to spend a little time and money now to find legal ways to sidestep the problem. It's very easy to avoid the federal estate tax on a total estate of up to $3 million. Beyond that, it requires a little bit of effort. For estates above $3 million,  the federal estate tax can consume 40% to 50% of the total estate in excess of the available exemptions.   

The combined impact of various taxes can be hard to believe. When you compare the results of a long term conservative investment program, no family income shifting and no estate planning to a more tax enlightened approach, the difference can be dramatic.

Vern Jacobs

Copyright, 2003


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Caution:  While the information in this web site is believed to be from reliable sources and is believed to be accurate, it is not intended to represent legal, tax or financial advice for any reader of any part of this web site. Due to frequent changes in the laws, new court cases and differences of opinion among professional advisors, readers should not rely on this information without the help of a qualified professional advisor.