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 […]

Who is the Poker Inspector?

Hi, my name is Drew, and I was a poker grinder in the truest sense of the word. I played poker for a living for the better part of five years during and just after grad school. I made enough to live on, but not especially comfortably, and while I did have a decent chunk […]

How to Use Data to Pick Your Spots

Many successful poker pros spent months, or more often years, being a grinder. The term can mean a few different things. In one sense, it refers to the mental grind and general stress of earning a living by playing poker. Indeed, it’s tough enough to consistently make the best decisions possible at the poker table […]

Projecting Weakness vs. Allowing Strength

Whether it’s pocket aces or flopping the nuts, one of the skills that’s important to develop as a poker player is what to do when you have a monster hand. The primary calculation here is how to extract the most chips. (Depending on the situation, you also need to be mindful of getting blind-sided. Just how stone-cold are your […]

What Poker Teaches Us about Luck

No doubt, there are dozens of different ways I could talk about the intersection between poker and luck. But one of the things that’s always resonated for me, and continues to resonate, is how often bad luck first appears to be good luck, and vice versa:     “When the gods wish to punish us, they answer […]

Picking Your Spots: At the Poker Table and in the Stock Market

Everybody runs hot and cold at different times, that’s just randomness and noise doing its thing. But the key is knowing that by consistently making good decisions, starting with picking your spots at the poker table, you can increase your advantage over your opponent so that, given a large enough sample size, you’re showing a […]