7/24/17: Emotional Rollercoasters

So here’s some fun: In trading (or, in anything else, really) “Cost Basis” refers to the average price you paid for a bunch of something. For instance, if I buy 10 shares of BLAH at $100, then I buy 10 more at $200, the cost basis for my 20 share position is $150/share. Nothing fancy.

Back in ’07-09 I daytraded for a living. It was absolute fucking hell. I made a lot of trades (probably 4 positions a day on average.) There were some BIG winners, and lots of slim losers slowly shaving away my capital. Looking back on it now I’m amazed I lasted as long as I did, given how bad my understanding of risk management was.

But one of my points is that I was trading the same money back and forth. I’d be in an out of a position sometimes in seconds, never really putting TOO much at risk.

It was exhausting not quite understanding what I was doing wrong. Blind spots like that are always a big pain in the ass.

Finally enough was enough and I got out and started working again.

I moved jobs a couple times, left the apartment in Brooklyn and moved to a house about half way between NYC and Albany, thinking to myself that I’d figure out wtf I was doing wrong and eventually come back to it.

Fast forward to the fall of…shit…2014? That sounds right.

I get a letter from the New York Department of Taxation and Finance. Well THAT’S never good news.

So I’m getting sweaty when I finally open this thing.

Now, if you want to take hallucinogens to achieve altered states of conscious, knock yourself out. But it will never compare to the buzzing in my temples, fucked up depth perception, and complete reevaluation of realities underpinnings as reading “You owe us $654,000.”

I MAY have actually had a cardiac event.

At this point in time (September ’14) I already had plans in motion to move cross-country under development. I didn’t know where or QUITE when. But that was irrelevant. The engines had been started and it was happening. Suddenly I had no idea what my life was going to look like for the foreseeable future. Would I be stuck in some wacky payment arrangement of some kind for the rest of my life, fruitlessly trying to whittle this down to nothing?

The dramatics of it all really just involved me hyperventilating a lot and not telling anybody why the hell I was so bent out of shape.

Now this was before I listened to a lot of audio books during my commute, instead spending a lot of time listening to country music radio, fantasizing about moving down south someplace. I’d been laughing at a commercial from this guy:

Finally I was damn near crapping myself and it came on and I just threw up my hands and said “fuck it” and I gave the guy a call. I talked with him a couple times over a week while his people got their ducks in a row and figured out wtf was going on.

APPARENTLY the state of New York retroactively decided that, for every trade I made (that is, for every position I entered and exited) my cost basis was ….drumroll please….


Meaning that if I spent $5000 on 100 shares of whatever at $50 each, then sold them immediately, the NYS Tax people decided I bought it for $0 and sold it for $5000. So my net gain wasn’t zero, it was $5000. Literally infinite profit. $5000 on which I obviously didn’t pay taxes because it didn’t exist. Now, if I traded that same $5000 five times a day…. I “magically” made $25,000.

So they thought I had a zero cost basis on more than 6.8 million dollars worth of trading activity.

It was a long slog. The company I had my trading account with had been bought at least twice. I was on the phone with them and they said there simply weren’t any records to get. FINALLY either Jerry or I got through to someone at the new firm who (this defies belief) found someone who had come over along with two levels of mergers from the original company and knew where the account transaction backups were, sitting on some old defunct server someplace.

So this guy saved my ass.

The CPA’s people got that info, put everything together and went back to New York.


It turns out…


Owed me more than $30,000.

Now, they won’t just write you a check like that. They’ll write some limit amount and take the reset out of your taxes going forward, a bit every year. Fine. Fine. It’s all fine.

So I had a party and blew half the cash. Stuffed the rest in the bank. I probably, now that I think about it, built my current desktop computer with it. The panic subsided, my step lightened, I went back to my master plan for getting the fuck out of New York. (Eventually I’ll tell that story. There’s no one alive who knows more than about 45% of it.)

Other concerns floated to the front of my mind. Life moved on.

I moved down here October ’15.

Took me a long time to get started. But again, I have a plan that’s under way now and I won’t be stopped. It’s going to take a while, but that’s okay. I’ll skip along the bottom. That’s fine.

I pull in to the parking lot tonight, not really minding the heat SO bad. I mean, at least I was moving. I toss out a bag of soda cans from my passenger seat on the way up to the lobby;

where I stop at the mailbox.

Oh, mail. I never get mail. (Seriously. I get like 1-2 pieces of “not an amazon package” a week.)

White envelope. Hmm.. I wonder….

I start making a noise like a cat horking up a hairball.

“Hey, are you okay?” A woman who lives in the building asks me, just having gotten her mail. I don’t even make eye contact, just show her the envelope. She takes a second to look at it, then goes wide eyed and sucks wind through her teeth. “Ouch.”


I just blink for a few seconds before catching an elevator up. I go up the 18 floors replaying the events described above something like 172 times.

I plop my stuff down at my desk and stare at the envelope.

“Fucking WHAT!?! I haven’t DONE anything. But I thought that before too, didn’t I. That means precisely dick.”

I hold my breath and use my trusty little EDC knife and slice the thing open.


In big, bold letters.

“Notification to Owner of an Uncashed Check”

Yeah. Apparently one of the checks got lost in my transit from New York to Nashville.

They’re going to issue me a new one.

Free money.

I’m going to fucking bed now.

I don’t think my heart can take any more good news today.