DON'T LET THE HOUSEWIN YOUR TAX BILL TOO
Built for high-volume bettors, poker players, and advantage players juggling a dozen sportsbooks, W-2Gs, and bank statements. We organize and reconcile every document into one CPA-ready workpaper — with a full audit trail back to the original source — so your CPA reviews one clean package instead of forty PDFs.
Automated bookkeeping and document organization — not a substitute for your CPA. Your assigned preparer reviews and files the final return.
THE $10,000 SURPRISE
Starting TY2026, you can only deduct 90% of your gambling losses — even if you broke even for the year. That gap is called phantom income: taxable income that exists purely because of the new law, not because you actually won anything.
You won
$100,000
You lost
$100,000
You still owe tax on
$10,000
Break-even for the year. Not tax or legal advice — this is an illustrative example.
HOW IT WORKS
Upload everything
Drop in win/loss statements, W-2Gs, 1099s — from every sportsbook and casino you played at. PDF, image, spreadsheet, whatever you've got.
We read it for you
AI classifies each document, extracts the real gross figures (never guessed), and flags anything that needs a second look.
See your real number
Get your taxable income, phantom income, and net tax position instantly — reconciled across every book, no double-counting.
CPA reviews before filing
A licensed preparer reviews your workpaper and delivers a filing-ready package. Software does the grind; a human signs off.
BUILT FOR THE HIGH-VOLUME PLAYER
Not for someone who bets $20 on Sunday football. For players and preparers dealing with real complexity — and the CPA firms who serve them.
High-volume sports bettors
5–15 sportsbook accounts, hundreds of W-2Gs, thousands of wagers across multiple states. We reconcile it all into one ledger.
Poker & advantage players
Tournament payout sheets, casino win/loss statements, cash-transaction records — captured and cross-checked against what the IRS already has on file.
Gambling-focused CPA firms
Stop assembling PDFs, CSVs, and screenshots by hand. Get one organized, audit-ready package per client instead of forty scattered files.
Every number traces back to a document
If a return ever gets a second look, every figure in the workpaper links straight back to the original statement it came from — no "where did this number come from" scramble.
TaxPitBoss is automated bookkeeping and document organization for gambling taxes — not a substitute for tax preparation. Your assigned CPA remains responsible for reviewing and filing the final return.
KNOW YOUR NUMBER
Free to track. Your assigned CPA reviews before anything gets filed.