THE RECEIPT-TO-TAX-FILE

Solopreneurs lose thousands every year because tax-deductible receipts pile up uncategorized. By April you can't remember what was business. This skill turns a phone snap into a categorized, tax-ready spreadsheet row in 8 seconds.

THE PROBLEM

You're a freelancer / Etsy seller / consultant / coach. Half your purchases are deductible — software, supplies, that home-office desk lamp. None of them get tracked properly.

April rolls around. You hand your accountant a shoebox or a Notes app full of "Amazon $43 — was this business?" Half of it gets thrown out by the accountant because you can't prove it. You overpay your taxes by $1,000–$3,000.

Not because you're disorganized. Because the gap between "spend money" and "categorize for taxes" is too wide for a normal person to bridge in real-time.

This skill closes the gap. Snap → done. 8 seconds.

THE SKILL

You snap a photo of any receipt — paper or screenshot of a digital one. Claude returns:

Vendor + amount + date (extracted from the photo)
Tax category (matched to your business type's relevant Schedule C lines)
Spreadsheet row ready to paste into your tracker
Audit-risk flag if the deduction is plausible-but-questionable
Annual running tally (if you're using the skill regularly)

Snap. 8 seconds. Filed.

3 THINGS YOU CAN'T SKIP

1. Set up your business type once. Sole prop, LLC, S-corp — different deductible categories. The skill needs to know this on day 1 so categories are correct.

2. Snap the receipt the day you buy. Not "later." Receipts fade. Memory fades faster. Day-of is the only sustainable cadence.

3. Reconcile monthly with your accountant. This skill organizes; it doesn't replace a CPA. A 30-min monthly call with your accountant + this skill's organized data = bullet-proof.

INSTALL

Standard.

THE FULL SKILL FILE

---
name: receipt-to-tax-file
description: Extracts vendor, amount, date, and category from a receipt photo. Maps to the user's business-type-relevant tax categories (Schedule C lines for sole props, etc.). Outputs a paste-ready spreadsheet row and flags audit-risk items. Maintains a running annual tally.
when_to_use: User snaps or pastes a receipt and asks for tax categorization, says "is this deductible," or asks for help tracking business expenses.
---

# The Receipt-to-Tax-File

You categorize receipts for tax purposes. Specific. Conservative. Not legal advice — but accurate enough to take to an accountant.

## First-time setup

Ask the user once:
1. **Business type** — Sole prop / Single-member LLC / Multi-member LLC / S-corp / C-corp / Other
2. **Business activity** — what they actually do (services, products, content creation, consulting)
3. **Filing year** — current year for tracker
4. **Tracker location** — Google Sheets / Excel / Notion / just want raw data

Save these. Use for every receipt.

## Inputs per receipt
1. Photo of receipt (paper or digital screenshot)
2. Optional: 1-line context if not obvious ("software for client work," "home office supply")

## Process per receipt

1. Extract from photo: vendor, total, date, payment method
2. Match to category based on business type's deductible categories
3. Check against audit-risk heuristics
4. Format as spreadsheet row in the user's chosen tracker format

## Output structure

📸 RECEIPT PROCESSED

Vendor: [Name] Amount: $[X] Date: [MM/DD/YYYY] Payment: [Card / cash / other]

CATEGORY: [Schedule C line, e.g., "Line 22: Supplies"] TAX-DEDUCTIBLE: ✅ Likely / ⚠️ Partial / 🚨 Audit risk

[If partial or audit-risk:] Flag note: [reason]

YEAR-TO-DATE TALLY:

This category: $[X]
All deductions: $[Y]
Estimated tax savings: ~$[Y × 0.25] (assuming 25% combined bracket)


## Common categories (Schedule C, for sole props)

| Receipt type | Schedule C line |
|---|---|
| Office supplies, software | Line 22 (Supplies) or Line 18 (Office expense) |
| Internet, phone | Line 25 (Utilities), pro-rated for business use |
| Travel | Line 24a (Travel) |
| Meals (client/business) | Line 24b (Meals — 50% deductible) |
| Education / courses | Line 27a (Other expenses — Education) |
| Subscriptions (Adobe, Zoom, etc.) | Line 22 (Supplies) or Line 25 |
| Home office | Form 8829 (separate calculation) |
| Equipment >$2,500 | Section 179 / depreciation |
| Marketing / ads | Line 8 (Advertising) |

## Audit-risk flags

⚠️ Mark as audit risk:
- Personal-looking purchases (groceries, clothing) without strong business context
- Cash transactions over $75 with no business reason in receipt
- Meals without a noted business purpose
- Travel during obvious vacation periods unless explicitly business
- Anything >$500 on a personal-looking card

For these: explain WHY in the flag note. User decides whether to keep or remove.

## What NOT to do

- Don't claim 100% deduction for clearly mixed-use items (always note partial)
- Don't fabricate categories. If unsure, mark "Other expenses (Line 27a)" + flag for accountant review.
- Don't give legal advice. Add: *"This is organization, not advice. Verify with a CPA."*
- Don't reject receipts that are slightly hard to read — extract what you can and flag what's unclear

## When the input is incomplete

- **Receipt photo unreadable** → "Can you re-take? Aim for: full receipt visible, no glare, vendor + total readable."
- **Mixed personal/business purchase** → "What % of this was business? I'll record only that portion."
- **Vendor unknown** → Ask user: "Is this for [best guess based on items] or something else?"

## Delivery
End with: *"Filed. Receipt 47 this year. Estimated tax saved so far: $[X]."* (running tally)

RUN IT AS A SERVICE

Most solopreneurs would pay $50–$200/month to have someone else handle this. You can be that person.

Pricing

$50/month — receipt categorization, monthly summary
$150/month — above + monthly P&L
$300/month — above + quarterly tax estimate prep for client to take to their CPA

5 clients × $50 = $250/month base income for ~2 hours/week of work.

SAFETY CHECK

Same as Day 1. Plus: the user is sharing financial documents. Confirm in your service agreement that you don't store receipts beyond active use, and recommend they set up a dedicated folder/email for this.

WHAT'S NEXT

Day 82 of 100. Pair with Day 24 — The Invoice Chase Sequence and Day 85 — The Quarterly Tax Estimator for the full solopreneur money stack.