Mile - Gig Worker Tax Deduction Assistant

Inspiration

Gig and delivery drivers are the group most likely to miss deductions they're legally owed. Professional tax prep is expensive and generic tax software just plugs numbers into a form but it doesn't reason about a driver's actual situation or tell them what they're allowed to claim and why.

What it does

A guided intake asks a rideshare or delivery driver about their actual work including vehicle type, mileage, phone use, equipment bought, health insurance and returns a list of deductions they may be eligible for. Every deduction shown is grounded in the real text of IRS Publication 463 (car and travel expenses) and Publication 535 (business expenses), with a plain-language explanation and a citation back to the specific section it comes from. A free-text field also surfaces related guidance pulled from the same source material using TF-IDF retrieval, so the tool can point to relevant rules even outside the structured questions.

Every output carries a standing disclaimer: this is an educational estimate, not filed tax advice, and users are told to confirm with a licensed preparer before filing.

How we built it

React + TypeScript on Vite, no backend. Deduction eligibility runs through a deterministic rule engine not an LLM because getting numbers like the standard mileage rate ($0.725/mile for 2026) right matters more than sounding fluent. A small TF-IDF and cosine-similarity index runs client-side over a corpus of paraphrased IRS publication chunks, each tagged with its real Pub 463/535 section, powering the free-text retrieval feature.

Challenges we ran into

Deciding what not to build was the hardest part: we scoped to one filer type (rideshare/delivery drivers), federal deductions only, and no e-filing, so the deduction logic could be genuinely correct instead of broadly approximate. We also had to draw a hard line between numbers the tool can compute exactly (mileage, phone allocation) and expenses that legally require the user's own receipts (actual vehicle expenses), rather than faking a total for the latter.

What's next

Server-side retrieval over the full text of Pub 463/535 (not just our paraphrased chunks), a downloadable/printable summary a user can hand to a preparer, and expanding filer types beyond rideshare/delivery drivers.