Sold my dipshit company for $5m, where to invest?

The best thing you can do right now is taking a good 3-6 months to figure out what you want to do with this money, framed in terms of what you want to do in your life. Just park the money in a safe place (eg money market fund, treasury bills) and work things out. There's no need to rush into things, the money will still be there when you know what you want to accomplish with it.

After you've done that, you should have some idea of when/whether you plan to use the money, and how comfortable you are with losing some of it. To be honest, you're probably best off just choosing a reasonable mix of stocks/bonds/cash which reflects your goals/needs, then going on with your life. 5mil sounds like a lot, but in investment-land it's not an unusual amount for a family to have saved for retirement. You would be well off to check out the Bogleheads wiki and forum at http://bogleheads.org. The forum would be an excellent place to post any questions you may have.

With regard to specific allocations, here are some example mixes between stocks and bonds, and how those behaved over 40 years. It's not the best chart, but it should give you some idea. Note that the author is subtracting out an annual 1% management fee from those returns, which is completely bogus. Go with good index funds and you'll be paying 1/15th of that. http://www.fundadvice.com/images/stories/fundadvice_images/f...

Also, if you ultimately decide that you really want to get into real estate, you might want to consider REIT mutual funds/ETFs, rather than buying individual real estate properties and the risk/maintenance that comes with them.

An interesting dilemma is it not? As you're young and inexperienced you are not unlike the 3 or 4 folks who become millionaires under the California lottery each year.

So good news and bad news, good news is you have choices, bad news is commercial real estate is (by some estimates) the next thing to go into the crapper).

Lets say you had $5M clear to work with. Yes, the 2 - 4% "return" is currently 'safe' money (which is to say treasury bill equivalents) so take $2M and buy a treasury bill 'ladder', these things are sold by the government quarterly and you can buy them at all maturities, so you split $2M equally into 40 parts, buy 10 year T-bills with their 3.5% return and you end up with about $70,000 a year (in the US at least) which is tax free. (So that is like having a salary of $110K/year before taxes.)You buy a place to live and if you want, you create another income stream to cover the taxes for that place.

At that point you've insured you're not going to go homeless or hungry and you are left with between 1.5 - 2 million to be a bit more speculative with. Putting .5 - .75M into equities is a reasonable way to capture that growth and it gives you a way to augment some of your return. If you want to just "participate" then buying index funds on the S&P 500 can do that with minimal hassle.

If you go the Angel route you can invite people to tell you how they are going to change the world and sponsor some of them. I suspect you will learn a lot doing this, but I would not expect it to be particularly profitable.

You can find another niche, create a company to fill that niche, build it up and sell it too.

Oh and I don't think you want a 'broker' what you want is a Financial Advisor (There is a separate certification for them, they don't trade stocks directly so they generally have less conflict of interest when it comes to fees).

Sounds like a nice problem to have, hope you do better than the Californians (the Lottery here has depressing statistics about how some very large percentage of lottery winners have lost it all in 18 months, sad really).

I am curious--is that $5m after or before taxes, because it really matters?

Solid Advice, I was looking up T-Bills, and I think the return is 1.5% (http://www.bankofcanada.ca/en/rates/tbill.html)

Any advice on which firm to talk to about the financial advisor?

Hmm I used this page: http://www.treasury.gov/Pages/default.aspx and went to the 10yr note and looked at its return. So to be clear, I'm talking about US Treasury Bills and not Canadian Treasury Bills. If you have a relationship with a financial institution you can buy them 'directly' (which is to say you own t-bills as opposed to buy into a fund which invests in t-bills) at $10,000 each. (insert caveat about 'Goldman Sachs' which handles sales of t-bills to individual investors and takes a cut, grrrr)

I don't have a magic bullet for finding a good financial advisor, mine cold called me in 1988 when I was at Sun and convinced me to by some California Municipal bonds. Now going on 23 years later I still consult her for financial advice. I think its more of a style thing in terms of being able to talk with someone about what makes sense and what doesn't with investing.

To give you an example, I was waaaaaaaaaaay over invested in tech in the 90's. My advisor told me I was, but didn't push me to do something different. 2000 may not have had a y2k bug disaster but it was financially painful for me.

Some folks might blame their advisor for not being forceful enough and getting me out of tech, but I don't roll that way. I heard what she had to say, we talked about the pros and cons, and I went with 'let it ride for one more roll' (a reference to the game of craps).

I was less forgiving of a recommendation for a fund manager who turned out to be a total turd. But I'm a big believer in Iacocca's comment that if more than half your decisions are good then you are ahead of the game. So advice for looking for an advisor:

1) Interview them, ask them the 'hard' questions, like "did you suggest to anyone to invest in Madoff's schemes?" (note either 'no' or 'yes' has good follow up questions, "No? It was such a great return why not?", "Yes? Even when the returns were out of line with other investments?")

2) Know that the wider the diversification the closer to the mean you will get. If the S&P 500 has a return of X% and someone tells you they can guarantee you > 1.5X% return, then you know they are not being truthful :-) Doing about 50% better than the S&P 500 occasionally has sort of emerged for me as a good razor for becoming suspicious. (note that 'banks' make there boatloads of cash on volume, not because they beat the S&P by 50% but because they beat it by a small amount but on a lot of other peoples money, and FedRsrv money but that is a whole different rant)

3) Check for compatibility. Everyone is different in how they interact with each other, and money, like sex, is one of those things that often has some really strong notions that were burned into ones brain at an impressionable age which color the way you look at everything. Risk averse? Risk seeking? Money as a tool? Money as a game score? Do they define themselves by how much money they manage? Do you? Its perhaps the hardest thing to get right.