+21 @Simulated_Interest If you have enough wealth your goal should be to have a balanced portfolio. You want to have your finances arranged so that you have security and income. For the sake of the argument say you ended up with $100m after taxes. With that much you can afford to hire a team of advisors who will show you how to set up your investments so you accomplish your goals. The main thing to consider is the skill and motivation of your team. You'll need a lawyer, an accountant and a fund manager. Ensure none of them are working on commission. The lawyer and accountant will structure your investment vehicle (the trust you referred to, or whatever alternative they suggest) and do your tax planning. The fund manager (working directly with you as an advisor) can write the strategy for your investment vehicle and monitor the performance of the fund managers you place your money with. It took those people years of study and experience to get good at their jobs. You don't want to try to micro manage them. Your job is act as an asset allocation decision maker. Decide how much of your portfolio you want allocate to each fund manager you engage. Use several fund managers to spread your risk and create some competitive tension. You should be able to earn around 12-15% annually with a portfolio that large, so your annual income will be at least $10m after tax. You should be able to fulfill your dreams with that, so don't spend your time thinking about how to spend your winnings, think about how to invest it. For the nitpickers, 15% is way over the long term average stock market returns. I agree it's impossible (or extremely unlikely) for a retail investor to beat the market. A good team of investment professionals won't limit themselves to the stock market and can actively manage your money to bring in opportunities not available to retail investors. Once you have money its not that hard to continue to make money. It's the first $100m thats the hardest!

+16 @DavidBittner "when i win the lottery" lol