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Connect Claude to your files for tax and bookkeeping workflows
Sam Leon, CPA and owner of The Millennial CPA, a solo tax firm (on The Successful Bookkeeper podcast). Note: he is also building TaxWeave, an AI platform for tax firms
Claude, connected to files on his computer, summarizes documents, categorizes transactions and builds QuickBooks rules. He never uploads anything with Social Security numbers, EINs or last names, and checks outputs by hand.
From $17/mo (checked prices)
Medium · or we do it from $497
Claude
The problem
A solo tax practitioner wanted to save time on document-heavy work without exposing client data.
What happened
Self-reported: he says that's where his time-saving workflows started. No figures given.
Told by the owner Source: The Successful Bookkeeper podcast (2026-09-14) · Added 2026-10-14. Results as reported by the source; we haven't independently verified them.
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How to set it up yourself
- Strip SSNs, EINs and names before anything goes to AI.
- Start with summaries and transaction categorization.
- Save instructions in a Claude Project and review them when models change.
Tools used
Claude
AI assistant for writing, long documents, analysis and coding help.
From $17/mo billed annually ($20 monthly) (checked 2026-10-13)
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Checked prices: Claude: from $17/mo billed annually ($20 monthly) (verified 2026-10-13)
Rather not do it yourself?
We'll set this up in your tools, in your voice, tested. Single use case $497. Satisfaction guarantee: we'll fix it until it works, or refund your setup fee. Terms. We reply within 1 business day.
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