The Funny Side of Desiree Oakman, Enrolled Agent
Who is Desiree Oakman, Enrolled Agent, IRS Tax Attorney (Naperville IL)
Desiree Oakman is smart. But in the tax resolution and tax planning fields, she is really smart. And she’s funny, in ways you would never expect. Here are just a few moments from an earlier interview, where Desiree shares some stories during her career.
What are some of the craziest things you have seen so far working in this field?
Desiree:
“Okay …
Can I Be a Tax-Free Church?
“Before, I never really liked the “crazies”. But tax planning and representation always have their stories.
“There was this guy who became a minister online. At least, that’s how he described it. He set up a church with only one member, his wife, who gave him thousands of dollars wanting to get a tax write-off. So, it was like they selectively created a “home church”.
‘It was interesting. It sounded like a scam. Everyone was listening for the scam. But the guy wanted me to prep the “church’s” tax return. Naturally, we asked more questions, to learn more.
“There were no other members, no services, no advertisement. There was no operation. They were not even trying to move money around. The only source of income for the body was from the minister’s wife. It looked like the minister was making a considerable amount of money. Maybe. It’s not for me to say.
“Was it a crazy tax dodge? Was the minister just spending his wife’s charitable donation, to achieve a big tax exemption for the family?
“The guy floated through several tax return locations, I think trying to find somebody willing to take his church as a client. Other tax professionals told this guy that he didn’t have a real church. But maybe they were wrong. Again, it’s not for me to say.
“If you are wondering, yes, it’s possible to create a tax-exempt church with no congregation, no operation. As a career Tax Professional, I had to research it. I can’t tell whether THIS ONE was legitimate.
“Still, the guy seemed generally surprised that we didn’t want to advise on his tax exemption or prepare the organization’s Form 990 tax-exempt return. I remember thinking, orange is not my color. Plus, I have no interest in wearing the matching bracelets from federal prison. Haha.
Don’t Judge Me (or My Business)
“Before that church guy, there was another funny situation where we had a client who wanted a professional tax opinion on her “trade or business expenses”. We got into the entire discussion that any expenses claimed had to be ordinary and necessary, paid to conduct her business.
“This client was a stripper. I guess we call them exotic dancers (but she liked being called an erotic expressionist). Still a stripper. Who am I to judge?
She wanted to take a tax deduction for her “boob job” (her words, not mine). I thought, ‘Yeah, sounds legit to me’. So, we took that one.
“The creativity of people still amazes me.
Wait! Please Stop Talking
“There was also the couple setting up their cannabis business, which was not legal at the time. Sometimes you have to tell someone to stop talking. For me, I don’t want to be the witness that they were committing a crime (at the time). There are some things that you cannot unhear. But that was a while ago.
“I am pretty cautious when taking on clients that are (or will be) subject to IRS criminal investigations. But now, since joining Tax Law Offices, we have a system to protect attorney-client privileged communications.
“So now, gimme the crazy. Let’s figure it out!”
Certified Tax Coach, Desiree Oakman is a Treasury Circular 230 licensed tax professional. Contact her at Tax Law Offices, 312-212-1000.