They Should Call It The Wash Sale Doesn’t Rule

They Should Call It The Wash Sale Doesn’t Rule

The only things keeping me going. (Jeez, my fucking hands look like Jack Kirby drew them)

Experts say that one of the most important things to establish in a fledgling website is a regular posting schedule – people apparently get burned out when they come back and find the same shit sitting there from last week.  This year, I’ve been pretty diligent so far, averaging what must be close to three posts per week, often on an easy-to-understand Mon/Wed/Fri schedule.  That shit ain’t gonna work this week, fo sho.  (Warning: The rest of this might be boring as fuck unless you enjoy taxes or being pissed at a former employer.  Feel free to head over to if this sucks for you.)

Why?  Because I have inexplicably become caught up in tax hell.  As you may be aware, I’m not just a blogger but a trogger, and the trading part of trogging requires some attention to detail and record-keeping.  I have been pretty obsessive and vigilant since the beginning of 2009 and so I thought tax records would be no big deal.  (You’re probably saying “for fuck’s sake, Chilly, why don’t you just get an accountant to do that shit for you?”  Two reasons: 1) I’m not sure an accountant could accurately sort through all this shit given that I have two brokers that apparently decided exchanging basis info would be a pain in their asses during the account transfer and; 2) I made some concessions when I got laid off.  Do I need a Porsche 911 that sits in a ($470/month) garage all the time?  No.  Do we need a maid when I can ostensibly clean stuff as effectively as she does?  No.  Do I need to pay an accountant a ton to try and sort out my trading records when I’m a fucking formerly-highly-paid finance professional?  No.)  Anyhoo, I was making some pretty rocking headway having tied down all my TARP broker transactions (through a whopping one month of 2009) and was ready to start ticking and tying (tieing?) the 100+ pages of transactions from my new broker (the excellent Thinkorswim).

I then realized that Thinkorswim had some helpful tax prep tools that were somewhat wasted on me given that the basis info got lost between brokers.  Looking through the TOS spreadsheets though, I realized there were some random line items for Wash Sale Adjustments.  Wait, what?  Fucking Wash Sale Rule applies for option trades??  (WSR just prevents one from taking a loss if they replace a sold security with a substantially similar security within 30 days before or after the sale.)  Dammit.  Helpfully, the IRS has never fully detailed how it works for options, so you are left to kind of guess, but if you do what I do – roll fucking dozens of positions from month to month – that almost certainly qualifies.  So my (in hindsight) not-that-stupid strategy of selling stock positions that had dropped significantly and replacing them with big options positions (not for tax purposes, but to conserve cash and lower downside during meltdown of 2008-2009) means I will have to make all kinds of weird adjustments and probably some judgment calls in the cases where i had massive losses on the stocks during the downturn.  Won’t be a major issue since I made decent coin in most of my names last year, but the few where I had taken a huge loss up front (thanks again, restricted list) are going to be problematic.

My SO is out of the country for a bit, so this weekend I was going to really buckle down and get some shit done: plow through taxes, write a couple of brilliant posts, maybe work at the soup kitchen Sunday morning.  Instead, I somehow slept for 20 hours from Friday night til Saturday night, made myself a batch of Yellowtail smoothies, threw on my snuggie and watched Kung Fu Panda four times in a row.

What preceded that funk?  The realization that my old employer, TARP I, had fucked me over one final time, and I had failed to realize what happened.  Modestly to their credit, TARP I had the policy of vesting all unvested restricted stock within 90 days of your termination date.  Mind you, this was winter 2008/spring 2009, so the meltdown in banking stocks had reduced the value of stock grants that were initially valued at hundreds of thousands of dollars to tens of thousands of dollars.  Whatever…fuck it, it’s just cash, I’ll go get some more.  Anyway, I just realized that the TARPsters made sure that instead of tens of thousands, that I got ones of thousands.  Motherfuckers.  Somehow, my shares vested in mid-January but they didn’t deliver them to my account until mid-March – by that point the piece of shit stock price had dropped another 70%.  To make matters worse, my gross income is overstated because of this (the tax effect is minimal because they take out shares to pay taxes, so its independent of the stock price, although you could go up a tax bracket due to this bullshit.)  I’m pissed because the place is so poorly run I’m sure their response will be “hey, buddy, feel free to go fuck yourself” but I feel that my W-2 is inaccurate so I might threaten them with the IRS.  Not that big a deal, but $8k is $8k, I’d pick it up if I found $8k sitting on the ground.  (Note: please don’t interpret this is as a call for sympathy – current, former and prospective investment bankers should receive probably the least sympathy of anyone in the entire fucking world.  This is just to illustrate the current frustrations in my bling bling world.)

This is all a long-winded way of saying there may not be a decent post this week.  As a peace offering though, here’s that crazy fucker’s review of Attack of the Clones.  If you haven’t watched the Phantom Menace or Avatar reviews, they are definitely worth the time.  (I’m not sure about all the references to being a serial killer, but the movie stuff is definitely hilarious.)




Chilly17 (possibly Chilly9 after taxes)

Time of this post: 4:24 AM (excuse the typos and nonsense)

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