I’m assuming he is a man. Funny how he called his wife “spouse” and use “them” to describe her…
Also, he’s acting like a 3 year old baby not knowing what to do with his millions in the bank account… 
He can unload his worry to me, I am an adult who can handle this type of windfall.
He behaves like a greedy pig. I would sell $5M worth of stock, pays poor uncle Sam $2.5M and overpays for a SFH.
What a horrible way to squander away your fortune 
Did he only become rich after the IPO? Been poor for too long a time.
It’s better to build up gradually. But this guy is frugal, so he should be fine. we don’t have a dotbomb coming, whatever he does, he should be fine. The fact that he is worrying about money shows that he will be fine and his wealth will grow to higher ground.
The dot bombers that did not sell lost everything. This guy needs to diversify. Maybe $3m in RE at least
What a wimp. This person doesn’t deserve the 8M.
Who does?
He should buy at least one house in Hawaii.
Actually, he mentions spouse, not wife and by calling his spouse “them”, maybe his spouse is a he. I agree, this guy is chicken 
. Seems like he will have an anxiety breakdown soon… He’d probably be happier if he donated 1/2 away.
Sounds like there’s anxiety about waiting to sell for a lower tax bill vs. locking in the gains now. That’s what put options are for. The put options would be cheaper than the taxes.
you usually cannot trade options in the company you are working for (at least that’s how it has been with my current and previous companies)
There are restrictions, but you should be able to buy puts to project shares you own. That’s different than trading options naked.
People who know what they want to do. Either spend it all or have a solid financial plan. Wishy washy people stink.
You know, if you married one of these wishy washy types, you get to decide how to spend the money. The whole pot. 
Totally get how the poster feels in a way, and at the same time, I wish I had that problem, but waiting a year to not pay taxes absolutely makes sense, and at the same time, he/she could lose $2M if the stock price falls. The poster has every reason to be nervous.
Agreed, but they have to be done in the trading window don’t they?
Yes, but there should be a trading window every quarter. Ours is crazy short compared to most companies, but there’s one every quarter.
My mom said the same thing to me before…lol
Great minds think alike!! 