In a previous post, I talked about some of the bookkeeping tips for poker winnings and tax accounting. That got me thinking about another kind of bookkeeping resource for poker grinders. Admittedly, I was single and semi-slobbish when I was a pro player, but contrary to the stereotype, I knew quite a few pros who had families or otherwise ran a tight ship at home even while juggling the poker lifestyle. Naturally, some had spouses who took care of the house, but others would make use of domestic workers to keep the place tidy. Everything from maids to nannies to personal chefs. Some of the more successful and established players might employ butlers or gardeners.

Indeed, some poker players undoubtedly used these workers to meet their logistical needs, while others could more easily afford to add the convenience that these employees provide. But it also makes me think of a study I was reading about in the news recently that spending money on time-saving services tends to create more happiness and value than spending money on things. This, too, is a great poker lesson that applies to other aspects of life. You have to account for your winnings and losses, as well as the time you spend at the poker table.

Household Employee Bookkeeping

These types of workers create a niche need for bookkeeping services among professional poker players. Due to the odd hours and somewhat unpredictable nature of the grinder lifestyle, it may be impractical to integrate common housecleaning and babysitting services into your schedule. Finding someone you trust to watch the kids late into the night isn’t easy. Someone who can housesit for the weekend while taking care of the dogs and doing handyman projects isn’t available on every street corner. For the perfectionist, detail-oriented, slightly anal poker player, you can also give these workers more individualized care instructions whereas commercial services tend to use their own “packages” with a predetermined list of services.

But crucially, no matter your personal motivation, the IRS will likely count these household workers as employees with W-2 filings, payroll taxes, and income withholding. Here’s the good news: Unlike regular business employers, you don’t need to track, file, and pay the payroll taxes every month. 1040 Schedule H enables you to do this on an annual basis. I recently talked to someone from the old network, and they recommend AMS as their go-to for payroll software and just general 1099/W2 type stuff. Don’t know if they are the best or worst, but it has worked well for me and my friend who recommended them. If you know of something that is better or cheaper, I’m all ears.