Nick Fountain

People go to incredible lengths to pay the smallest amount of taxes, sometimes in legal ways, sometimes in less than legal ways, in the shadows.

And it's not always clear which is which.

Figuring that out, that used to be the job of Carolyn Shank.

She spent nearly two decades at the IRS.

And she says the way the IRS uncovered the newest, hottest tax crimes ran the gamut.

I'm shocked y'all still do that.

That's incredible.

Then, of course, there are the times when people reach out to them and say, I've got information.

I'd like to whistleblow.

Have you been in one of those interviews?

She says the bag thing is just a term of art.

Sometimes, though, people are afraid to talk even anonymously.

Carolyn says one time, after a long day at a conference, she got to her hotel room.

She says she changed rooms and the documents, they turned into a case.

Can you say any more details about it?

Yeah, come on, guys.

Right.

The case I wanted to talk with Carolyn about came from a much less dramatic tip.

And it really paints a picture of how hard it is to draw a clear line between what is OK and what is not when it comes to taxes.

Carolyn first heard about this questionable tax move in 2021.