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If you live in a state that will tax the capital gains, move to a state that will not tax them. Depending on your situation, maybe worth it.

I second the All-ett. I've had one for a few years now (leather outside, nylon inside. It's been great, and very thin. I got tired of my old thick wallet, so I got this. I think I have the "International wallet", but check out their site, they have several choices. http://www.all-ett.com/i...

I don't know your company's prospects, so you'd have to make a best guess as to their likelihood of success (being acquired, etc). I can offer my own story. I was in a similar situation, the main difference was my strike price was very low (like 20 cents). I started exercising my ISOs as soon as the...

One book I read that really made me grow some brain cells was The Alchemy of Finance by George Soros. It's dense reading, but I learned a lot.

Try using Indeed.com's salary tool - http://www.indeed.com/salary

It tells you salaries for a job title and location. If the results are in your favor, you can use this as a reference point in your negotiations.

Thanks for these comments - I'll have to double check the safe harbor stuff. The capital gains happened this month (October 2012). I have had no withholding in 2012 at all - I haven't had any job income this year. I started a business in January that hasn't turned a profit yet (it is just starting t...

I plan to use the safe harbor to make an estimated tax payment by Jan 15 of 110% of my tax last year, plus a bit more to be safe. My taxes last year were much lower and more "normal" (under $40k).

Due to a long-term capital gains in, I owe $1.1M in US taxes, but I don't have to pay it until April 15, 2013. I can put it in a high-interest savings account such as Amex Savings (0.90% interest). But is there another low-risk place to put it where it might earn 1.5% or even 2% or more? Thanks!