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?

The Cost Of Things: Tampons In The English-Speaking World

Assuming 40 years of menstruation, this means the Canadian government has been taxing the average woman $292.80 in their lifetime to have a vagina.

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.

Are You Ready For Some Fully Taxable Football?

Big news for NFL fans: in a move that multiple news sources call “largely symbolic,” the National Football League has decided to eliminate its tax-exempt status and become a fully taxable entity.

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.

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.”