I would personally stay, the payout now is not nearly as large and potential upside you can have in the future. You are talking about possibility of building real wealth AND staying with the interesting new growing company where DH's input is appreciated and he is one of the founding members, so, rewarding in other sense. If you pocket the money now, then what? Will it be enough to retire? Sound like it's not enough. So, DH will have to look for other opportunities or get a regular job and be back into the grind of middle class. Why miss this opportunity, why should there be only risk? With risks can come greater rewards and sounds like he is already a part of this and the company is doing well. If the company is bought, what does DH really risk? Will he really lose all this money? I don't think it's likely. I am sure, they are trying to get rid of people on the cheap and ask them to sell out, so very few can make a real windfall.

In your situation, I will consider selling at least half of your holdings while you have some control. Cashing some of it out can make a difference for you, and after this exit point it seems you will lose control.

You obviously need professional legal and perhaps tax advice. Suck it up and pay for professional advice.

Anonymous wrote:If you don't need the money now.P, I would stay put. Sounds like the company is growing fast and once it's established your shares will be easier to sell individually as your need money, rather than all at once (with the resulting tax hit).

Yes, the tax hit is huge. DH is contemplating selling a fraction -- like .5%. And getting advice is tough b/c no one we know would make such a risky investment.

If you don't need the money now.P, I would stay put. Sounds like the company is growing fast and once it's established your shares will be easier to sell individually as your need money, rather than all at once (with the resulting tax hit).

I would sell now, but I am a 'bird in the hand is worth more than 2 in the bush' type person. I am hugely conservative when it comes to money, and I would always take the guarantee over the uncertainty.

So I think it's all a question of your risk tolerance, and if you're counting on this money for something. If you are counting on it, get it out now while the getting is good. If it would just be icing on the cake, let it ride.

This is a complicated question. Talk to a friend in VC or a financial advisor.

Here's one option: take the buyout, but also get some stock options in the company. The big company will like this as fewer owners, and your husband still sees an upside later on.