The IRS Doesn’t Want You Writing Them $100 Million Checks

My question is, why are people writing $100 million checks?

Chicago Passes Amusement Tax Ruling, aka “Netflix Tax”

Why shouldn’t we pay taxes on our monthly Netflix bill the same way we pay taxes on Steam games?

Five Fixes For Next Year’s Taxes

Having a large return can be fun, but it also means that you loaned the government your money interest-free for a whole year.

One Way the Tax Code Punishes Domestic Partners

At the beginning of 2014, I put my partner on the medical coverage I receive though my full-time employer. It was a godsend, as going without health insurance and trying to buy your own health insurance in New York City are both surefire paths to the poorhouse. For domestic partners who aren’t married, or for those forbidden from wedding by law, it is perhaps the best work perk you can come by.

Heavy Taxes On The Rich? 52% Say Yea

“redistributionists” are a plurality of this country, outnumbering almost 2:1 the free-market true believer Ayn Rand-types.

When Paying Taxes Leaves You Temporarily Broke

In which I share my 10 emotional responses to paying my taxes and having $41.51 left over.

If You’re Doing Your Taxes at the Last Minute, You’re Not Alone

I was walking home from work the other day when I realized that it had finally happened. I had reached the day where I couldn’t reasonably put off doing my taxes any longer. That got me thinking, how many other jerks are in the same boat? So, in an almost perverse fit of procrastination, I started digging around online for somedata. Instead of, you know, firing up TurboTax.

Last Minute Taxes Reminder! Complete With Help

Ask a CPA: Selling a House and Tax Deductions

My wife and I lived in a home for more than 10 years. In August of 2014, we moved out and put it into service as a rental. We intend to sell the house when our current tenants move out (their lease is up at the end of August of 2015, but we’ve told them they can move out earlier if they want and they’ve indicated that they may).

An Update From the Wealthy Retiree

“I agree that my federal taxes are too low. I don’t think someone living off of dividends and capital gains ought to be paying a lower rate than a middle-class wage earner.”