Bookkeeping Tips for Grinders: Document Your Losses to Offset Your Winnings

Come tax time, you’ll need to collect, organize, and report your various income and tax forms to the IRS and state government. But long before the filing forms start arriving in your mailbox, you need to keep reliable documentation of different aspects of your gambling and poker activities. For the time being, I’m going to side step the various ethical and legal issues that come with reporting various types of poker winnings. (If you’re interested, you can read more about these issues here.) Instead, I want to focus on the biggest and most common mistake you can make: Failing to document your poker losses and legitimate business expenses.   

Here’s the deal: When you’re in a Las Vegas casino or some other institutional poker setting, that institution is going to document and report any winnings of a certain size. What they’re not going to report is any losses and expenses you also incur. Crucially, these losses and expenses can be used to offset your gross winnings and taxable income. If you play in casinos, these expenses include basic travel expenses. If you play online, these expenses include your computer, internet charges, and other telecommunication costs. You can even deduct the cost of any poker books and training materials that you purchase.  

Depending on your circumstances, tax filings can get incredibly complicated. Poker tax accountants cater to this crowd. Don’t let an institution give you excuses about providing these filing forms. Nowadays, comprehensive accounting software must include support for Form W-2G. You have every reason to expect to receive this form in a timely manner.