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I'm happy to post these things, without identifying companies. I'm sure you could find them on my resume or linkedin but there'll still be some ambiguity.

Company A, 0.05% or 9000+ options vested, IPO, post-lockout sale at net ~$300k, was an early engineering employee

Company B, <0.001% or 10000+ shares vested, very late engineering employee, not liquid yet, hypothetical value in low-mid 6 figures

Make sure you do proper tax planning, taxes take an enormous bite, even with long term capital gains.






What do you mean by tax planning?

If your company IPOs they will withhold shares for you. Only thing to watch for is depending on your income they might underwithold. There isn’t much more to it than that.


I was taxed at the time of my grant, and then again on the gain when I sell. Had I put them in a self directed IRA i could have bypassed 6 figures of cap gains tax.

You can’t contribute in-kind to an IRA.

Actually that’s a great point. Depending on your company and your role in the company I’m sure there are ways to get around that, but that would require your company to play ball and get creative with you.

The ole mitt Romney.

My experience was significantly different. My advice is to consult a tax attorney and accountant with experience in these matters, don't trust the company to do it for you.

It depends on what form your equity is in. If you have options, you're responsible for taking care of your own taxes. (And the exercise+hold AMT mess is something to watch out for, though it's a little more difficult to fall into that trap now since the AMT exemption amount was raised.)

Even if you have RSUs (where taxes are customarily withheld), the company will withhold at the minimum statutory rates, which may not match up with your personal tax bracket.


Yes mentioned the company might underwithhold. I’m just suggesting it isn’t quite as complicated as it is being made out to be, from personal experience.

Anyone with a six-figure sale is nearly certain to end up owing more than they withhold (assuming you sell, which you probably should).

If a company hasn't IPO'ed, an 83(b) election may also make sense.


The IPO is a taxable event. You’re taxed at the IPO price, and your company should withhold shares based on that price.

After whatever lockup you have some fraction of shares remaining. When you sell those and if the price is greater than the IPO price then you have capital gains on whatever shares you still hold.

You still owe tax from the IPO. My point is the company will withhold shares from you, but you might need to pay more if they underwitheld for the IPO. This has nothing to do with your capital gains from selling your remaining shares.


The IPO is not a taxable event.

Parent is presumably referring to RSU releases at IPO which are taxable. You are correct that options and shares are unaffected.

https://www.amafinance.org/ipo/overview/


It's income, which in the USA is generally taxable.

You only pay tax when you sell your shares or exercise options.

IMO an 83b election only makes sense if you have negligible exercise costs. Otherwise, it's a lot of risk to take on an exit that may never profitably happen.

Eh, it generally can make sense if you can get QSBS, as that is so favorable.

All said, the better companies offer partial recourse loans to early exercise.


My point is that most employees at most startups are going to join after the earliest days, with option grants that will have exercise prices that entail a 4- or 5-figure outlay to exercise. Maybe this is just the east coast, but I've never worked at a company that makes loans to allow for early exercise. I'm not sure I know anyone who has had this situation. Even early exercise is relatively rare here.

This is days later, so not sure if you'll see this, but could you explain what QSBS has to do with it?


Exercising options has tax consequences.

Depends if you signed 83b or not. If you’re early you should always do that.

You can't always, not all companies allow early exercise.

If you've been at a private company for a while you may have options that have vested approaching the ten year expiration with a large spread between strike and the fair market value.

If these options are ISOs then exercise has a lot of tax consequences to get right (AMT particularly to save some money). If you have NSOs you've still got a lot of tax to deal with on exercise, but you don't have to benefit of getting some tax free below AMT.


What tax-planning resources did you find useful?

Consult an experienced tax attorney and CPA in your state. For a six figure sum the taxes make the cost of an attorney and CPA a rounding error.

I'm recently found out that California treats capital gains as normal income. No fun.

There are fewer than 10 states that don't tax capital gains at the same rate as ordinary income.

Most states tax capital gains at the same rate as ordinary income.

And then 10 states don't tax income at all.


Sounds like a great reason to relocate to a state that is more reasonable about income taxes than CA.

imo the cap gains treatment from CA is pretty normal compared to the majority of states.

The part where CA chases your stock grants/options for years after you leave the state is a bit less reasonable to me. (But I'd guess some other states do the same)


Right, the taxation mechanism is typical, but it's the amount that's onerous. CA has the highest state income tax rate in the nation. If states are going to tax capital gains as income anyway, it's all the more reason to move to a state with low or non-existent state income tax.

I'm curious, why shouldn't they?

Short term capital gains, yes.

I don't know about California, but NY State definitely treats long term gains as regular income too. You take the net capital gains number from your IRS Schedule D (total gains minus total losses) and copy it onto a single line on your NY tax form that gets added directly into your NY gross income. (There's no mention at all of long term vs. short term on the NY tax form - capital gains is just a single line item.)

(Everyone, including the IRS, treats short term gains as regular income.)


Long term capital gains as well



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