Welcome to WebmasterWorld Guest from 220.127.116.11
Forum Moderators: LifeinAsia
I'm in talks to sell my largest website to a major corporation.
Because I've worked full-time on it since 2010 and generated very high revenue every year, while taking all of my deductions yearly on my tax returns,You're confusing the issue- the website is an asset owned by your business, annual deductions deal with the operations of your business.
And one accountant warned that if I take a capital gain with a zero cost basis that I will likely trigger an audit,Huh? Why on Earth would the IRS audit you when you paid the maximum possible taxes on a transaction? Best case scenario (for them) is the audit determines you were right. But it's much more likely an audit would determine a higher basis, resulting in a low tax.
but at the same time he said I cant claim expenses over the years that I've already taken deductions on.That's certainly true.
when I have questions of this kind, I simple write my IRS's office. Explaining the situation simply, and they always answer me precisely, and giving arguments to the interpretation they have.In the U.S., write 3 letters to the IRS and you'll most likely get 3 different answers. :) Especially if it is more than just a little complicated.
I do what they tell me to do, and I keep preciously their answer, in case one day I have to explain why I did such or such thing.That will probably keep you from being charged with intent to avoid taxes, but most likely won't help you avoid penalties, and it definitely won't let you avoid interest on any tax differences.
Is the website considered a company asset if I've always filed normal taxes with a schedule C for deductions.Irrelevant. All forms of businesses (corps, LLCs, sole props) can have assets. Even individuals have assets. However, depending on how you have been deducting your expenses all along can affect things. I found this interesting read about amortizing/deducting website design costs [lansingbusinessnews.com].