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Prepare your own tax return with ChatGPT as a cross-check, then bring the differences and better questions to your CPA

who Kyle Ray, founder of Geek Window Cleaning, interviewed by Business Insider

The problem

A six-figure service business can't afford a CFO, and at tax season the CPA is too busy to walk the owner through every question, so missed deductions and structure questions go unasked.

What happened

Per Ray, comparing his ChatGPT-assisted return with the accountant's turns up points the CPA either agrees with ("I didn't catch that"), confirms, or rules out with a reason. He pays about $40/mo for Claude and ChatGPT and says he wouldn't trust it 110%: the CPA still gets the final say. No dollar savings are published.

Quoted in the source: Kyle Ray, founder, Geek Window Cleaning. Source: Business Insider: This founder uses AI as a 'CFO' during tax season. His CPA still gets the final say (Kyle Ray, Geek Window Cleaning) (2026-03-28) · Added 2026-10-15.

How to set it up yourself

1. What Geek Window Cleaning does: Ray works through tax questions and a draft return with ChatGPT, then takes the differences and new questions to his CPA, who decides.
2. In ChatGPT, select New project in the sidebar and name it "Taxes {YEAR}". Upload last year's return, this year's profit and loss and payroll summary (remove Social Security numbers and bank account numbers first), then open ••• > Project settings and paste the prompt below as the instructions.
3. Ask it three things in separate chats: the questions you should be asking your CPA, the tax strategies that may apply to a business like yours (for example contractor vs employee status), and a line-by-line draft of the return from your numbers. Ask it to mark every item "CONFIRM WITH CPA" and to name the IRS form or rule it is relying on.
4. When the CPA's return arrives, upload it to the same project and ask for a table of every difference with a one-line reason. Email that table and your question list to the CPA. Don't file or change payroll classification on ChatGPT's word alone.

Copy-paste prompt

You are my tax-prep assistant, not my CPA. My business: {BUSINESS TYPE} in {STATE}, structure {LLC / S CORP / SOLE PROP}, revenue about {REVENUE}, {NUMBER} workers. Using ONLY the files I uploaded, 1) list the 10 questions I should ask my CPA this year, 2) list tax strategies that may apply, each with the IRS form or rule it depends on, 3) compare my draft numbers with the CPA's return and table every difference. Mark every item CONFIRM WITH CPA and never invent a number that isn't in the files. My question: {QUESTION}

Tools used

Some tool links may be affiliate links. Disclosure

Checked prices: ChatGPT: from Free $0; Go $8/mo; Plus $20/mo; Pro $100/mo (verified 2026-10-14)

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