taxes

man with lots of rolled coins at bank

I have almost $5,000 in rolled change sitting in my basement. If I cash them in, will the IRS question where it came from? Could I get in trouble?

Most people have a jar of spare change somewhere. You took things a little further. Over the years, loose coins turned into rolls, the rolls turned into boxes, and now there's nearly $5,000 sitting in your basement. It sounds harmless enough—until you start wondering what happens when you finally try to turn all that metal into money. Could a giant pile of change raise questions you weren't expecting?
June 23, 2026 Jesse Singer
sad man at casino table

I lost big at the casino last week. If the IRS taxes gambling winnings, can I write off all my losses?

You walk into a casino hoping for a lucky night. But while you might know that the IRS wants its share when you win, the bigger question for most of us is: can we write it all off when we lose? The answer is more complicated than most gamblers realize.
June 18, 2026 Jesse Singer
Concerned older man looking at the camera

My wife handled all our taxes, and after she died I found out we owed the IRS thousands. Is there nothing I can do?

Found out you owe the IRS after your spouse handled taxes? Learn about innocent spouse relief, your options, and how to handle unexpected tax debt.
June 16, 2026 Allison Robertson
Canadian and American Lottery winners

Americans should know that Canadians don't pay any taxes on lottery winnings. So why do you have to give so much of your winnings to the government?

You hit the jackpot. Life-changing money. But then reality kicks in—if you’re in the U.S., a big chunk disappears before you even see it. Meanwhile, Canadians keep everything. So what’s the deal with that?
May 27, 2026 Jesse Singer
older woman, happy rich man

I make $85,000 a year and pay over 30% in taxes. I heard some billionaires pay under 5%—do I really pay more than a billionaire?

It sounds completely backwards. You earn a solid middle-class income and see a big chunk go to taxes every year. Then you hear that one of the richest people in the world is paying a much lower percentage. Is it true? Is it fair?
May 26, 2026 Jesse Singer

I want to quit my job but I’d have to repay my signing bonus. I paid tax when I got it, but I’ll have to reimburse the full amount. What can I do?

Repaying your signing bonus can be a strong mental barrier to leaving behind an unsatisfying job.
May 26, 2026 Alex Summers