3년간 400만 달러 RSU 받는데 어떻게 할지 너무 고민돼요 🤔

With $4M in RSUs, I'd be spending less time trying to predict the stock and more time thinking about diversification and tax planning before the first shares vest.

Hire a CFP at a firm that specializes in clients like you. You're young and have a long run way ahead of you, this is the way to go.

You should work with a CFP to develop a real plan. Not Reddit 

Pulling in 7 figures and asking reddit for financial advice. Lol

1. Any capital gains Tax is due when you sell (taxable event)
2. I would sell and diversify because that is a lot of net worth to have in one basket.

Put a 10b51 plan in place with the plan administrator so you can liquidate during the blackout periods, sell everything, make estimated tax payments and invest in diversified assets.

Unless your answer is “I would put $4M of my own money into this AI company” you should follow my advice.

What the fuck

Doesn't have to be all or nothing.. maybe plan to sell 50% total to start? Either do so by selling 100% each time they vest until you've sold 50% of the allotment or sell half of what vests each time?

First, find an amazing CPA or tax professional. Second listen to them

Def diversify. You can diversify 3 and keep one invested and if the company hits it big you’ll be set up for life even beyond what you are already.

You will need to understand how your company handles taxes at vesting. Do they sell to cover, do they withhold shares to cover? Typically they will sell or withhold at a rate lower than what you will ultimately pay in taxes so you will have to supplement that at the end of the year. As for whether to diversify or not, every person is different. I see a lot of peers who do nothing because they are not comfortable with executing on their own. They have built huge positions in their company stock and feel stuck now because of the taxable gains. My advice is to sell all or the majority at vest. You pay next to nothing in taxes and it allows you to diversify. Ask yourself, if you were given that much $$ in a cash bonus would you put it all in your company stock? Your monthly vests already have “skin in the game” with your company stock.

Two things...

1. Typically they'll withhold shares at vest time for tax purposes. So the $4M (at current prices) you're expecting to get over 3 years will probably be haircut be 30-40% (or more) to pay the feds and CA. Just warning in advance. And if they ***don't*** withhold, that still counts as income so you'll have to pay that amount when you file. Oh, and $4M over 3 years just bumped you up several tax brackets... Congrats lol!
2. RSUs set their cost basis at vesting date, not grant date, so if you sell them immediately upon vest, you should have low/minimal capital gains issues. Granted I don't know what sort of blackout periods you have, and that might not be an option, but unless it moves REALLY hard between vest date and the open selling period, it still shouldn't be a huge issue.

Overall, though, this is the sort of money I'd say to sell most/all of it and diversify. This is the kind of wealth that will set you and your family up for an early retirement. You'll be kicking yourself if you hold it all and your AI lab company fizzles and you've watched all that paper wealth go away. 10 years ago I watched my ESPP stock go 4x in a rapid period--was afraid to sell due to cap gains, and gave it all back when the stock dropped back to where it was before it happened. My ESPP/RSU went parabolic this year, however, and I'm not going to make that mistake again. It's the difference between "am I going to be able to afford to retire at 65?" and "I think I can comfortably retire in my mid-50s..."

hire my CFP office we're in norcal

I immediately sell my RSUs and transfer proceeds to my Roth.

So it's $4m over 30 months or roughly $133k/month?

You're going to be on the hook for a lot of taxes because RSU's are taxed at vest. It's effectively income, think of it as similar to a cash bonus, it's compensation. I've worked at companies where they automatically sell a number of shares to cover estimated cost of taxes at vest and you get credited the remaining shares. And at others where you have an option to pay cash to cover estimate if you wish to retain the shares.

Perhaps you had grants before this retention so you already know how it works?

If all of your net worth is tied up in this equity, I think the smart move is to diversify out.

Here's an oversimplified example. Let's say the value of the RSU's goes 4x. You could have had $16m pre-tax; or you could have $0 if it goes bust. Now suppose you sold out of 3/4. You'd have $3m pre-tax (plus any investment gains) and $4m pre-tax or $7m - or if it goes bust you still have $3m+.

In reality, the RSU value could either go bust or explode before those 3 years elapse. Me personally, I'd sell out the initial batches to lock in value in SP500. I'd probably want no more than 25% RSU weight, but that's going to differ for many.

Also note that the first tax you get on RSU is because the value of the shares given to you is considered income. If the RSU's appreciate in price, you will also pay a captial gains on that profit when you sell. So let's say at grant, the shares are valued at $100/share. But when the first vest comes in, the value per share is $125. You're going to have income of $125/share which is taxed as ordinary income. Fast foward 2 years later and shares are $250. If you sell shares from this first batch, you will be taxed at $125/share capital gains.

I'm in the same boat, but further along. I'm in AI and recieved lots of RSUs.

Often companies only withhold 20% on vest. Your likely in the 37% bracket. This means, if that is the case, you'll likely owe money on those vesting events even if you don't sell.

Definitely hire someone to help you set up mechanisms to soften this.

Secondly, selling will also trigger another event in which you'll be taxed on. If you're in California, you'll also be taxed at a higher rate here because California doesn't treat short or long term capital gains differently.

Timing your sales will be important as well...

The reality is you're likely going to get use to writing uncle Sam some big checks soon.

Having things set up properly can soften the blow though, so hire someone to guide you thru this. Ask around at work for a reference.

Also, selling alot now and diversifying isn't necessarily the answer. I was told that initially, but I believed in the company and held all shares. The shares are up 100x+ now. So think that over some.

For every vest, you'll still have upside potential on your unvested RSUs as long as you work there. So, the general advice is always sell on vest and diversify into something simple.

Yeah well not to brag but my employer matches 6% of my 401k contributions.

RSU so it is already a public company? Which public company can issue $4m RSU and worth more in the future?

This is a tough call. You will definitely have some big tax bills if you diversify.

But taxes are usually a sign of success. Congratulations on your success.

Personally, I would look to diversify 80%. Bill Gates did this with his MSFT stock, and ended up with a tiny net worth compared to if he had stayed concentrated. I don't think he has any regrets.

I keep my single stock investing to 5% of my portfolio, even though I am doing well (over 80% annualized for the past 4 years, and taking profits, so a lot of it is "house money"). But most of these are high beta stocks, and when the market crashes by 40%, I expect my stocks to crash by 80%.

Be prepared for this, however your future selves might travel back in time to coach you (include the ones from the alternate universe where your AI lab stock is up 10,000% and the the universe where it went down 90%+).

If this is hard for you, I would recommend diversifying at least 20%, with every vesting moment.