I only got partway into it due to time constraints but I want to go back and listen to the audio book (I realized I get through nonfiction much better in an audio format) - Lies My Teacher Told Me.
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Oh I personally couldn’t bear listening to that book in audio form. I quickly skip over large numbers of pages when it’s thing related to making toys and costumes for kids, high carbohydrate snacks and meals etc… No children here and we don’t eat sugar or grains here due to health reasons.
It feels like it’s taking a lot of time just skimming through it lol… it’s like what 1000 pages? Something catches my attention then I read that article and circle it.
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What do you all like for daytime/non drowsy cough syrup? DayQuil doesn’t seem to be strong enough and I have to talk to people all weekend at my home show.
Delsym is my go-to cough suppressant.
DayQuil went through a formula change a while back and now it’s much less effective. Behind-the-counter Sudafed is what I’d look for for general cold and cough symptoms (you need ID to buy it but it’s not prescription).
Hope you feel better soon!
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We have some allergy nasal spray that addresses post nasal drip which tends to be what causes long term coughs for us after other cold symptoms have been gone for a while, it’s a bit of a delayed effect so if you can get it today it should be working Saturday afternoon/Sunday. The label says Allergy Nasal Spray fluticasone propionate (glucocorticoid) 50 mcg per spray.
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I have a few questions related to selling company stocks that my husband gets as part of his compensation- any takers?
Questions
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If you also do this- how often per year do you sell the stocks? Or do you do it once the value hits a certain amount? I want a system for handling this going forward.
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How will this affect taxes and also do I need to get additional documentation for my taxes next year? ELI5 plz. Is there a smart way to do this for taxes? A dumb way?
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This sounds stupid but what exactly happens if I sell them? Like, will the site just ask me for a routing number and then the amount will show up in my checking account? Or do I have to put it in one of those holding account things? Or some terrifying third option I haven’t considered?
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Is there anything else I should know? Assume I know literally nothing about this because I don’t.
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I luv u. thx.
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Are these ESPP or RSUs? If ESPP (you purchased the stocks at a discounted rate) there is a slight difference in tax depending on when you sell. If you sell within 1.5 years (check the dates, it’s been a while since I’ve had to think about this) then it’s taxed as short-term capital gains at your income tax rate. After 1.5 years it gets taxed at 15% as long term gains. I believe RSUs (stocks given by employer, is taxed as income) get the tax taken out when they’re given to you so it doesn’t matter when you sell them.
If ESPP I would wait the 1.5 years to reduce taxes. If you just want to keep life simple then sell RSUs when you receive them. Marmalade didn’t believe in owning too much stock where you work but if you think it might eventually be worth a lot, you could also hold onto them in the hope that they’ll grow.
Your cost basis is the price of the stock when you acquired it. It’s a good idea to keep the documentation from the company (should be in the files in the broker) to have a record of this. You will be taxed based on the difference of the cost basis vs the selling price. If there is a loss, you can carry it forward to offset gains in future years. There are forms that will help you to figure this out in your taxes, BUT Marmalade says that TurboTax just downloads it all from the brokerage and calculates everything so it’s so easy these days. If you’re doing stock stuff and use TurboTax you’ll have to do the more expensive option, but it’s worth it for the simplicity.
Usually it goes into a cash account at your brokerage. The transaction will take a few days to settle when you sell the stocks, and then you can transfer from there to your personal account.
Hope this helps! Ask if there’s anything that’s not clear 
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Personally, I always preferred to sell my stocks as soon as I was allowed to. Is your husband required to only sell stocks during certain trading windows? For most folks I know, there are like 4 weeks per year where they’re allowed to sell stocks (right after the quarterly earnings reports).
My line of thinking was: we were already heavily invested in the company because I worked there; I already had financial exposure if things went bad (e.g. layoffs). I would rather have a diversified portfolio. Some people come up with a rule of thumb, like, no more than 5-10% of their net worth should be in their employer’s stock. And some people like to keep some company stock so that they feel “invested” (literally, haha) in the company doing well, and don’t want to miss out if it does.
So, when your husband receives the stock (aka “vesting”), that’s considered taxable income. His company should withhold taxes for that automatically for you, same as they would for any other bonus or salary.
Once he sells the stock, the difference of (sales price - value at vesting) is considered capital gains or a capital loss depending on if the price went up or down in the meantime. Sometimes companies will withhold taxes for the capital gains, sometimes not - my last employer didn’t, for example, but my partner’s current employer does. If they don’t withhold, remember to set some money aside for tax time. If you have a big capital gains in a year, AND nobody is withholding taxes for you when you sell your stocks, you might need to pay estimated quarterly taxes.
Also, if the capital gains are going to be really big, it can be worth it to wait until you’ve held the stock at least for a year. That way the taxes will be “long term capital gains” and the tax rate will be much lower.
BUT filing taxes for it should be easy regardless: the brokerage will give you a 1099 at the end of the year. Usually it’ll be a 1099-INT and a 1099-DIV.
This depends on how his company has it set up! Usually the stock account will be at a brokerage like Schwab, Morgan Stanley, etc. Once you sell stock, the brokerage account will now have $$$ in it instead of stocks. The money will sit in the account unless you do something with it. (It’s usually not FDIC insured there. Transfer it out!!) You should be able to set it up to make a bank transfer to any checking account. The transfer from stocks to $$$ can take a few days.
I think you’ve asked all the main questions! Congrats on the stock comp. 
If you run into more questions feel free to PM me!
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@AllHat Do you know what kind of stock he has?
My understanding is RSUs basically get double-taxed - they get tax taken out when they’re given to you, but they’re taxed again when you sell. And for the tax when you sell, short-term vs long term still applies. This info based on information I got from my brokerage (Fidelity) and personal anecdote of selling my RSUs immediately after they vested and getting a massive tax bill lol
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The double-taxation thing can really surprise people! My understanding is that it works like this:
Let’s say you had received RSUs valued at $5 per share. And then sold them at $7 per share.
The green dots would be taxed as income, when you receive your shares, even if you don’t sell them.
The blue dots would be taxed as capital gains once you sell.
You’re not actually paying double-taxes on anything, though - each dot gets taxed exactly once.
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Ooh thank you!! Very much appreciate the clear explanation
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Thank you lovely people! Obligatory disclaimer/reminder that I went to art school. Elementary questions ahead:
Summary
We definitely did not purchase these at a discounted rate. These stocks were given to us as part of his salary/benefits package. Can I assume they are RSUs?
I don’t know! I’ll have him check with HR but it looks as if I can sell them anytime through the website. I will double check on this, though. The main reason I didn’t sell any earlier is because the amount was so small (like $1200) but now it’s around $6k so I feel like I should do something with it.
Is it silly to do this based on dollar amount? Like once it’s over $5k or $10k? That would be easier for me than figuring out a percentage. Thoughts?
Thank you! This is good to know.
Ok, I think I understand- is this what Meowmalade was saying about the “cost basis”? Basically, it matters because it can help me figure out taxes, correct? I’m afraid to ask but how does one figure out how much they will owe on something like this?
Is there a rule of thumb I can use? Like, how big? Haha. Sorry I have no frame of reference for this. Is it based on the percentage increase in value? Or…how would I know, basically, if I should wait or not.
Ok, thank you! I think I understand this part now.
ETA: Also please no one feel pressured to respond tonight! This isn’t urgent
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No questions are too elementary! I like infodumping on this kind of thing, lol.
Summary
Definitely the most likely case but I would still ask for clarification. There are other, more obscure structures too.
Oh that wouldn’t be silly at all! $5k or $10k would be totally reasonable IMO.
Yep, “cost basis” is the technical term, it means “how much the stock was worth when you received it”.
For calculating it: it will be taxed at the same rate as regular income if you’ve held onto it for less than a year (aka “short term capital gains”). So for me, that means I set aside like 30%ish of the cash from the sale to pay my state+federal taxes.
If you’re going to hold it longer than a year: the rate will probably be 15% for federal and possibly as low as 0% for state.
Capital Gains Tax: Meaning, Rates and Calculator - NerdWallet
Haha, this really depends on your personal preference for risk! And on how big the difference in taxes would be.
If you have almost no gains, I would sell immediately and not worry about it.
If you have very very big gains relative to the cost basis, I would consider holding for a year if you’re willing to gamble on it. IDK what my threshhold for that is though. Gut instinct? 50% of the share value?
One year I had a really weird grant where the cost basis was $15/share but the fair market value was $60/share by the time I was allowed to sell. 
So…most of the tax I was going to pay would be on the gains, and the bill would have been much bigger if I had paid short term gains instead of long term. But on the flip side, who knew if the stock price would still be that high in a year! I ended up selling half immediately and half of it a year later. By then the stock price had dropped a little, but not too badly. So it ended up working out. If the stock price had dropped back to $15 I would have kicked myself for not selling!
One thing I do want to stress is that a lot of these choices are relatively small optimizations/gambles with imperfect knowledge. The biggest, most important thing is to make sure that your overall balance of [stuff invested in company] vs [stuff invested in the general market] feels good to you. I have had coworkers who had literally never sold any of their company stock and didn’t otherwise invest in the stock market. Other than that, any of the choices you’re looking at are perfectly reasonable ones!
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Thank you!!!
Oh ok, good to know. I will ask. Thank you!
Sweet.
Got it!
Perfect!! Thank you.
Cool, this works for me, haha!
Ok, that’s very good to know! I feel better. A very tiny percentage of our money is in company stocks and we’re actively investing in other stuff so I think we’re ok.
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There have been good explanations for the other stuff, but as someone who has to fight with Turbo Tax every year because they screw up RSUs (for the record they screw up ESPP too, but the RSUs tend to have a bigger effect)–the 1099 you’ll get will look like every other 1099, ex.
1099 snip
However if you upload that directly to Turbo Tax and do nothing else, like you would a normal investment, you will get double taxed. The other form you need is the release form, which should look something like
Release snip
I’m sure the look varies based on brokerage, but you should get one every time RSUs vest. When doing taxes, after uploading the 1099, go back and click that this stock sale is a special situation, and then walk through filling in the details about shares released and shares traded for taxes…once you’re at that page it’s pretty clear what to do, but you do have to go back and tell it that it’s not a standard stock sale. And when I’ve looked in the past HRBlock was worse and TaxAct didn’t seem to know what I was talking about, but I also gave up after some poking around because I know how to make Turbo Tax cooperate…if nothing else if you’re doing your taxes yourself, I’d plan on extra time to figure out how to input the extra info.
For the other questions…for myself I generally sell RSUs as soon as they vest (or as soon as I remember they’ve vested, it happens every couple of months which I have a harder time keeping track of than when it was once a year), but my company also does ESPP which gets me to about the max amount of stock I’d want to hold at the company I work at (for me <5%, but you could pick a dollar amount just as easily). ESPP I sell ~18 months later to hit the 1yr after purchase date/2yr after grant date qualifications for long term capital gains, and if you want a rant about those tax forms, I can do that too . That sounds less useful to you, though.
One other thing–if you do decide to hold on to vested RSUs for some amount of time and the company in question gives dividends, don’t forget to log into your account every now and again and either reinvest or transfer them wherever you want them. Every year there’s a post from someone at my company who has just logged into their brokerage account and is shocked to find some amount of money sitting there from dividends that they didn’t realize they were receiving (or didn’t realize that they weren’t DRIP/auto re-investing if that’s your preference…I don’t do that both because it would be more stock in the company I work at and also involve rant #3 about tax forms).
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He could also ask his boss. In my prior roles, anyone who was heavily involved in preparing for the companies quarterly earnings call, in business development/acquisitions, or business forecasting was usually restricted. Also VPs and executives who generally knows how the company is doing at any given moment. These people usually can’t sell for a few weeks before each earnings call so the market can react to the news and adjust the company’s stock price before they sell. Otherwise it could be considered inside trading.
Generally I would say that I always sold my RSUsmas soon as they were available to sell. It was just easier to have that rule than any other arbitrary rule.
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So I should have already been getting this document? I’ve definitely not seen a release like this before.
Thank you, good to know since I use turbotax too.
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His boss is c-suite so I’m assuming she might be restricted? Not sure if he would be, though. Is there a reason I shouldn’t have him ask HR?
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No real reason. At my company HR wouldn’t necessarily know right off the bat, they might have to look into it but my boss would know.
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