Taxes & bookkeeping

Clean up a year of messy books before tax time

Export the year, have AI categorize to Schedule C lines with an 'uncertain' flag, reconcile to statements, and produce a summary for your preparer.

Real-world reports

• r/smallbusiness: using Claude instead of bookkeeping software (discussion of risks)

Self-reported results; not independently verified by us. Your outcome will differ.

Tools

• ChatGPT, Claude, Gemini or Grok (free tiers work; paid ~$20/mo helps with long files)
• Bank/card CSV exports
• Google Sheets
• QuickBooks/Wave

Steps

1. Export 12 months of every business account as CSV.
2. Give AI your category list (Schedule C lines) and 10 example rows.
3. Process month by month; require a confidence column and 'UNSURE' flags.
4. Review flags and a random 10% sample; reconcile totals to bank statements.
5. Match big expenses to receipts; list personal items mixed in.
6. Hand your preparer the summary plus open questions.

Copy-paste prompt

Categorize these transactions [CSV] into these categories [LIST matching Schedule C]. Output CSV: date, description, amount, category, confidence (high/med/low), note. Mark transfers and personal-looking items. Do not guess on unclear ones; mark UNSURE.

What to verify

Totals must reconcile to statements. You and your preparer decide what's deductible.

Legal & ethical notes

Not tax advice. Keep receipts per IRS recordkeeping rules.

Go deeper on money workflows with AI Money Playbooks: verify-first AI prompts for budgeting, bookkeeping, bills and taxes.

Official sources

• IRS Schedule C instructions
• IRS recordkeeping

Educational only; not legal, tax, medical or financial advice. Laws and prices change; check official sources.

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