Small business owner Kyle Ray doesn’t have the budget to hire a full C-suite.
“Basically my entire leadership team is AI,” the Geek Window Cleaning founder told Business Insider. “It’s not a massive company, so I can’t afford the salaries for those kinds of people. But I can pay 40 bucks a month for Claude and ChatGPT.”
This tax season in particular, he’s leaning into AI’s capabilities, and using what he calls his “AI CFO” despite having a CPA.
Ray, who grew Geek from a side hustle to a six-figure business, uses a handful of AI and software tools. For tax questions, though, he turns to ChatGPT.
For one, he asks it to surface tax strategies that could save him money. He said AI helped him think through whether some sales reps could qualify as independent contractors rather than W-2 employees.
“Anytime you’re a business owner, you’re like, ‘Can this person be a 1099 contractor, or do they have to be a W-2 employee?'” Ray said. He said that structure can be more favorable from a tax perspective because employers generally don’t owe the same payroll taxes on contractors.
He also uses AI to help him prepare for conversations with his CPA. One of his favorite questions for ChatGPT is: “What questions am I not asking that I should be asking?”
He’s using it to double-check what he’s paying for, too. Ray said he’ll prepare his own taxes using ChatGPT as an assistant, then compare those results with what his accountant produces. From there, he brings any discrepancies or new ideas back to his CPA.
“And they’ll be like, ‘Oh yeah, I didn’t catch that,’ or, ‘Oh, you’re right. You can do that.’ Or they’ll say, ‘No, you can’t do that because x, y, z,'” Ray said. “So it’s just a good way to inspect what you expect.”
One of the biggest benefits of working with AI tools, he said, is accessibility. Rather than having to schedule and prepare for a call, “it’s available whenever.”
Still, his CPA gets the final say.
“I wouldn’t trust it 110%,” he said of AI. “I think it’s a good idea to always have someone look it over.”
That’s especially true when AI moves from explaining tax concepts to offering advice tailored to a specific business, CPA Amanda Han said.
AI can be especially helpful for explaining basic concepts, such as what depreciation is or how an S corp works, she said. However, if you’re asking, “Is an S corporation good for me? That’s probably still a question for a CPA rather than AI.”
Han said she and other CPAs use AI tools in their own practices. It can be useful for tasks like surfacing relevant court cases, she said, but it still falls short when it comes to applying that information to an individual client’s situation.
“Ultimately, the applicability of a specific court case to a specific client is really the part that’s not really there yet for AI,” she said. “That still needs a human touch.”
Han said AI is best used for lower-stakes tasks that don’t require much judgment, like organizing transactions or helping business owners draft questions for their CPA. But people shouldn’t assume it’s always right.
“Double-check, and always use your own judgment,” she said, adding that if something sounds too good to be true, it probably is.
For Ray, AI’s appeal goes beyond tax help: It’s readily available.
“CPAs — their time is valuable, and during tax season is when they’re the busiest,” he said. “So they have less time to sit there and just hold your hand. And ChatGPT will hold your hand 24/7.”
