Last week, one of my colleagues was sounding a little tense as he set out to work on his taxes.

Radio producer Josh Woo fills in here as a director on the Marketplace Morning Report, and during the 2014 tax year, Josh won big on a TV game show. Four years earlier, Josh had also won prizes on another show, “The Price is Right,” and a dozen years before that, when he was just a kid, Josh won $2000 on Jeopardy.

With Josh’s tax return now signed and delivered, I wanted to see if, with all this experience, he managed to avoid the classic mistake of forgetting to pay estimated tax on extra income. 

Click on the multimedia player above to hear more on what Josh’s big win means to him this tax season.