Lesson I learned and the hope that others can learn from my mistake since we are nearing the end of the year —- Last year (2015) I had a very good DFS baseball season. At one point in September, I won a couple tournaments ($27 and the $9), and finished 2nd in a high-dollar tourney ($1060 – after winning a ticket to this tourney). I withdrew some, but not all of the money because I mistakenly had thought I would receive a 1099 for the amount of the withdrawal minus the deposits I had made – in 2015. I thought I would withdraw some in 2015, and some in 2016 – thus splitting the taxes owed over 2 years……WRONG!
After DK had first credited back my deposits, I was sent a certified check (around $50k). I put a chunk into savings to pay what I had thought my taxes were going to be for 2015, I paid down debt, and the wife and kids had a really good X-mas.
After January 1, 2016 – I went against all lessons in bankroll management, and was thinking I should play higher-dollar buy-ins. I was playing in $300/$333 tourneys when I had no business playing in those. The only time I would have been in those was if I had won a ticket to them. Took me all of about a couple weeks to run through the bankroll I had left in my account after withdrawing back in Sept of 2015.
No worries, right? I still had the money set aside for what I had thought was going to be enough for the taxes that I would owe. Fast forward to when I got the 1099 from DK —- the amount on the 1099 is actually your NET WINNINGS for the calendar year – yikes! Not the amount of the withdrawal minus the amount of the deposits in the given calendar year. No worries, right? I still had the rest of the money in my DK account since I used proper bankroll management and didn’t stray from my comfort zone — OOOOPS!
This mistake is from a guy with an MBA in Finance….stupid mistake…..I know tons of tax guys and instead of asking them for advice, I made a huge mistake!
Lesson of my story – don’t get caught up thinking you know everything and jump out of your comfort zone. Proper bankroll management doesn’t guarantee success, but it sure helps to lessen the blow when that cold streak hits……