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> Between '99 and '09 you would actually lose money

You would have made a profit (albeit a small one) if you invested every year from 99 to 09, using the yearly figures on wikipedia.

> From the peak of the '99 bubble till around today we have about 2% yearly return on the S&P 500 (excluding dividends)

Using March 99 as the peak, it's 2.5% ignoring dividends and ~4.5% if you include them.

Source: https://dqydj.com/sp-500-return-calculator/

> Over long periods, dollar cost averaging, you'll do OK. Don't rush in at a top and obviously don't sell at a bottom, something a lot of people end up doing.

This is a very important point (though lump sum investing tends to outperform DCA), there's a big difference between how you might feel now while stuff is going up quickly and how you might feel when everything is falling apart. Selling low is a historically bad move. Far worse than buying high (http://awealthofcommonsense.com/2014/02/worlds-worst-market-...).




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