bryan wrote: ↑Mon Sep 11, 2017 7:21 pm
I've noticed that the last six months I've been more lax with keeping my non-automated mint accounts in sync in mint. One reason is being conservative so that my networth does not take a dive in the graphs (e.g. if I update the value of my Bitcoin, I would have to update it again to be lower in the event of a crash..).
Well, I guess I've had the opposite "problem"!
Bitcoin
Been a big fan of Bitcoin from the moment I learned about it in 2013. It took a day or two to see the huge implications, and then another few weeks to see even more. After about a month you begin to see the flaws, limitations, and negative implications/drawbacks. Today all of that is still true (and pandora's box is
most assuredly open), but the experiment has been a wild one. For instance, engineers in arms have rage quit or started their own competitors over a difference of opinion and direction (e.g. use cases); governance has been hairy featuring techno-tyrants vs the capitalists (and oh yeah, also the mob with flaccid pitchforks..).
Flash forward to current day.
I find it interesting that the doubters think Bitcoin is in a perpetual bubble (been at least 4 years now?) and haven't wanted to even bet $100 on it, whereas you have hedge funds willing to bet millions.. Again, cash-settled futures should be quite interesting.
The rise has been pretty crazy for the emotions. The first rise in 2013 was crazy as well.. losing sleep watching the ticker; but things really settled down after that crash. Hitting 7, 8, 9k was nice and expected and I mostly didn't mind (clearly I didn't go all in when it was pennies or a couple bucks..)*; but once it hit 10k, I started thinking about options to decrease my exposure. Especially since this rise in price has been exponential in the short term.. I started thinking about tax implications and how to optimize. Meanwhile the price is going up $1k each day

... flashbacks to 2013. Eventually I just realize that in the last X hours, the price has already gone up 15+% and basically paid for my taxes.. so I should just figure out how much to divest and get moving!
[*] funny how I had friends that went through this same thing in 2013, and if instead of being smart and taking some risk off the table ("I can retire and travel and do what I want") they had stayed in, they would be looking at insane amounts of money.. Wheaton Levels of Capital/Risk and all..
For now I've cashed out >$100k with not much thought to strategy, other than selling the coins that I bought at the highest prices (to avoid some tax)*. I've also looked into donating Bitcoins to my own Donor Advised Fund to avoid tax completely for my cheapest coins and to get a significant (~30% of my AGI) deduction**, but I'm not so happy with how the DAF provider's bitcoin donation process works (basically they treat it like some crazy complex foreign asset*** that takes a few days to handle, as opposed to a very liquid asset e.g. foreign check or a stock). Vanguard Charitable is still in the "actively looking into it" phase.
[*] apparently part of the tax bill is supposed to do away w/ Spec ID? Only allow FIFO or AvgCost?
[**] because this year may be the last foreseeable year where itemizing makes sense.. might as well
[***] the guy on the phone literally said it was an art..

cmon man! It's more liquid on GDAX than most stocks on NYSE! Shit's automated too (they use Coinbase, apparently)!
It looks like I won't be able to contribute BTC to the DAF until next week. I could donate BTC
directly to a charity, but I don't feel confident that I want to do such a large donation in one year, you know? Then again maybe that would give me some nice perks w/ the charity? Also, you can name the DAF a fun or interesting name! At least CME got delayed a week (if my theory of a Dec futures price crash is correct).
I've been looking at the exchanges' trade views much too much the past few days.. the initial part of the sell I did was for a pretty good price (the procrastination worked in my favor!) but I didn't think to set some limit orders for overnight, in the event of a run-up (and of course BTC hit its all time high that night while I was sleeping..). I have a few limit orders in place in case it runs up again.. but I'm trying to now really fine-tune my plan of how much I should divest now (stay within 15% tax LTCG, at least?) versus next year (who knows what the price will be... at least to harvest some gains? Will I want to sell more than the 0% LTCG or have any other income?).
The common advise seems to be 1) get FIRE money completely out of BTC, 2) sell off 20%-50% of BTC, and my own advise: 3) if you were 5% allocated and now over-weight, shift to a ~10% allocation.
Opinions welcome.