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As sole proprietorship, your basis should be whatever you invested in your assets, such as office furniture, computers or anything you used in the trade. The only valuable thing for a potential buyer should be your customer list or the reputation of your personal service. I agree that it is easier to assign a selling price than a costs to those items.

You are very likely to pay regular tax on the gain on the equipments and etc, but capital gain tax on the customer list and goodwill. For 2010, long term capital gain rate is still 15%, expecting a change to 20% in 2011. You are right that New York, just like many other states, does not provide favorable rate for capital gain. New York rate is 6.85% while our rate here in California is 9.3%, considering yourself lucky still Well, I take it back, you are subject to New York City tax as well (another 2 or 3%), so probably we even then.

I know you are probably seeking an exit strategy for retirement. It is very hard to sell a business in the form of sole proprietorship because all assets and debts are tied to you personally. Even the value of goodwill is hinged on your personal service. Without you, the goodwill vanish quickly, and customer may be leaving as well.

To solve both problems, have you thought about converting your business into a LLC? Then you can take in new partner(s) who are interested in taking over the business. The incentive is that your presence will help maintain the critical on-going relationship with the customers until certain expected date. Within the LLC, you can gradually give up ownership percentage, and you can structure the payments to you in any form or time. In other words, you can control your payment flow suitable to your tax circumstances.

This is similar to installment sale. One drawback for installment sale is that seller has to rely on the capability of the successor, but this idea is different, when the partners (buyers) come on board early (before your full retirement), you are pretty much still involved. You can cash out gradually when you are still in control. If they bring in investment to the LLC, that will strengthen the business value and the health cash flow too. As far as the form of payment, you have many options, salary, right out distribution, payment to life insurance, contribution to retirement plants, etc.

Anyway, just consider this my wild brainstorming effort for you, you may work this out with your advisors of course.

When your mother passed away, the value of her total assets was fixed. Such estate, including money in banks, value of her house, and other investments, will be subject to estate tax (Form 706). For 2009, if her total estate is less than $3.5 million, the estate tax due should be none.

Obviously, you are her estate administrator according to her Will, your job is to distribute the money to all her children according the detail of her Will. In general, there will be no tax impact on all of you who are inheriting. You do not even need to report that, because, in theory, Uncle Sam already gets the share from estate tax return.

In 2000, the company I worked for as an employee for almost 20 years
“fired” all of their employee agents and allowed them to become
independent contractors, thus I dont know where I could start looking
for any basis. Prior to 2000, I used Form 2106 Employeed Business Expenses to declare business expense and Schedule C from 2000 to date.

My question is this…if I receive a lump sum of about 25% of the sale
price and structure a secured settlement with the buyer for, say 7
years, I want to find the most legitimate ways to minimize or avoid,
if legally doing so, any capital gains.

Also, I read that NYS taxes capital gains the same as ordinary income, wow,
I will get killed since I can’t establish any basis and I need cash to pay off outstanding debt and some back taxes.

Are there specific clauses, stipulations that must be in the sales
contract (non-compete, good will, etc) that would help me decrease any
CG taxes or, for that matter, if I omit certain clauses, would I be
liable for more capital gains?

Where the IRS imposes a 15% capital gains tax, what about NY State and
NY city?…I am a sole proprietor and age 62 and I am in about a 28%
tax bracket. From what I understand, I will pay regular taxes on any
income I earn for the year of sale but only pay the CG taxes on the
sales proceeds.

Of course I have intentions of seeing a tax professional but I need to
get some idea what I’m looking at before I even meet with prospective
buyers. Any advice or avenue of directions is greatly needed and appreciated.