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First, congratulations!

Now, to business.. If you sold company stock, and live in the states, you now owe about $1m in taxes, or a little less depending on what state you live in.

Your very first job is to sit down with an accountant and get your 2010 taxes estimated. Then set aside the money for this. Seriously, do it today. Then lock in your head "I sold my company for $4m." It will help you in the future days to remember that.

If it was an asset sale, you got f-ed, and now owe a lot of tax money. Live and learn.

Next, let's talk about 'more money than I can ever spend'. If you keep your current spending rates, and you keep your money in a completely 'safe' vehicle that exactly matches inflation, you have about 94 years of spending ahead of you at your current rates, and at 15% cap gains tax on the 'earnings'.

It is nearly psychologically impossible for a newly minted 20-something millionaire to keep at their current level of spending. Since you do not already have a plan for this money, I would say that it is 100% likely you are not the sort who can go about his business without some change in lifestyle. So I would suggest that you expect either to keep working or get good at investing.

Along with the books recommended here, I would strongly recommend you pick up one called "How To Retire Early and Live Well on Less than a Million Dollars." It's written by a financial writer who decided to do what the title says in the 1970s. He talks through a number of items and considerations that financial advisors will not think about. Simple example: what's the proper amount of real estate leverage for someone who needs some income, and wants to be able to hold on to the building in a real estate crash? This is not typically discussed in most investing books.

It is not unreasonable, based on all this, to put almost all of this money into a one year, low-risk, locked-away investment just to give yourself time to think, plan,and get on with a new part of your life.

Now, if you built this company up, and are now unemployed, expect to be depressed. You should consider (along with some celebrating) doing some fun things (I like to travel), and also learning some new skills.

You will need some new friends, because your old ones will all still be working,and won't be able to hang out most of the time. You might want to find a new hobby, or pick up an old one.

Finally, enjoy! Sounds like a great experience.




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