Document intelligence for gamblers

THE IRS ALREADY HAS YOUR W-2GS AND 1099S.
MAKE SURE YOUR RECORDS MATCH.

Every payer already sent your W-2Gs and 1099s straight to the IRS. LedgerWager uploads, reads, and reconciles every gambling document you have — win/loss statements, bank records, PayPal, Venmo — into one clean, audit-ready package before your CPA ever opens a file.

Think of it like Plaid, but for every gambling document you own.

Automated bookkeeping and document organization — not a substitute for your CPA. Your assigned preparer reviews and files the final return. New for TY2026: also calculates the 90% gambling-loss deduction rule.

Reconciliation status

203 documents read
4 duplicates flagged
43 W-2Gs matched to ledger
CPA package ready
Taxable income$99,111

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.

Read the full breakdown of how this works →

HOW IT WORKS

The full document-to-CPA-package workflow, end to end — not just a calculator.

1

Upload everything

Win/loss statements, W-2Gs, 1099s, bank statements, PayPal, Venmo, credit cards — from every sportsbook, casino, and payment method you used. PDF, image, or spreadsheet, whatever you've got.

2

AI reads & extracts

Every document is classified and every transaction extracted — the real gross figures, never guessed, with the source document linked to each one.

3

Duplicates & gaps flagged

Re-imported files, double-entered transactions, and missing months or documents are caught automatically — not discovered after you file.

4

Sessions built, W-2Gs matched

Deposits, withdrawals, wins, and losses are grouped into gambling sessions and cross-checked against every W-2G and 1099 for that book.

5

See your real number

Get your taxable income, phantom income, and net tax position instantly — reconciled across every book, no double-counting.

6

CPA package, human sign-off

One click builds an audit-ready package — reconciliation report, workpaper, and every source document. A licensed preparer reviews before it's ever filed.

See exactly how W-2Gs, casino reports, and your return all tie together →

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, bank/PayPal/Venmo records, and 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.

LedgerWager 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.