"It's like a videogame," said the 33-year-old owner of Brass Taxes, a boutique accounting firm in Crown Heights that caters to the young, hip, and creatively-employed.
"When your parents would try to play Nintendo, they were so terrible at it and it would take so long, and you would watch them fumble with things that are like nothing for you to do because you played all the time."
Most young taxpayers are like that — otherwise intelligent adults reduced to mashing buttons and cursing at a screen as they flail through a DIY 1099. But while even W2-holding wage earners suffer over their returns, for non-standard taxpayers of the striving, self-made stripe, filing is more like a root canal.
"Seventy-five percent of people sit down and say ‘I'm terrible at this and I don’t know anything,’" Garofalo said of the freelancers and artists who file through his home office on Franklin Avenue. "A lot of what I talk about when I meet with people is how can this be less sh---y going forward?"
Despite his clients' unusual list of deductions — fake severed heads, costumes and movie stubs, to name a few — Garofalo isn't what you'd call a 'creative accountant.' He just happens to be an accountant for creatives.
"I have a lot of people that write for TV, and it doesn’t occur to them that going to movies and watching Netflix is a business expense for them," Garofalo said. "Because we’re trying to make the thing we love the focus of our income as well, things we love become business expenses, and it becomes difficult to delineate what’s legitimate."
Before he became a financial consultant to the soon-to-be stars, Garofalo, too, was a freelancer, earning a living as a video editor while writing and performing as a comedian. It wasn't until the recession hit in 2008 and he found himself searching for a day-job to help make ends meet that he turned to Uncle Sam.
"This was my nightmare job," Garofalo said. "I thought becoming an accountant was what happened if you didn’t make choices. If you grew up middle class and never pursued your passions you’d end up as an accountant."
Five years later, he's approaching the IRS's highest level of agent certification, with a roster of more than 600 clients.
"I think I had a natural ability to market toward my demographic — I knew how I would talk myself into it," Garofalo said. "It’s in the complexity that you get to deduct the expenses you’re allowed to deduct. We’re screwing future us who’s entitled to that money because we want the anxiety to go away."
In fact, he said, helping cool people make the most out of their money has proved surprisingly rewarding.
"I’ve never had people hand me money and be grateful in this way, where it’s a deep, sighing 'thank you,'" Garofalo said. "You get a year’s worth of anxiety balled up into an hour, and we digest it. Even if they owe a bunch of money, it’s down to one number. It’s not an invisible, frightening thing in the back of their head."
While owing the IRS is never fun, it doesn't need to be a root canal.
"I see everybody, and everybody is anxiety-ridden about money," Garofalo said. "It doesn’t need to suck so much."