I’m terrified of taxes. I’m a partial/full owner of 3 different startups. Two of them have accountants on staff and the other one is on my own. The tax law is so complicated and I’m so scared that I will ruin my life by failing to report correctly.


  • Don’t worry. Prison is not so bad. You’ll get a nice warm bed to sleep in and three meals a day. Minus the occasional rape, you’ll do fine.

    Being serious though, you should consult a lawyer at the very least. Failure to understand the tax law is never an excuse as far as the IRS is concerned.

    The IRS will come after you hard and fast, like those guys in prison.

  • Basically make sure you don’t underreport. The IRS will normally not go hard on you as long as you don’t owe anything. If you try to pay fast and loose and try to short-change the IRS, then they’d make sure you regret it.

  • You might be missing a trick here… You part/own three businesses with two of them having accountants on staff. Pick up the phone and ask one of your accountant employees to help out. Problem solved.

  • You are lucky you live in the US. Taxes in my country (Argentina) are a complete nightmare, as not even accountants are always sure they are not skipping anything. And our version of the IRS takes so much money from you, you ultimately feel you are a feudal peasant working your ass off for an insatiable lord who won’t give you anything in return. I might as well shut down and start living on our version of food stamps, it’s a better quality of life for much less effort.

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