Well, if you put $14000 into the Dow last year (and this is not the same as buying one of each share of the DOW, since they have all sorts of price-weighted adjustments due to stock splits and other adjustments), then 89% losses from the top would put you at $1540. This would be a loss of $12,460. Sort of like investing in juniors! (OK, I didn't need to say that...)

I think back in 1929 the index was simply a basket of stocks, without all the modern adjustments, so from the high of $381 in Sept of that year, down to the low of about $42, for a loss of $339, that would be a loss of about 17 ounces of gold at the 1932 price of $20. Today, 17 ounces of gold at $880 would mean a loss of $14,960. As the price of gold goes higher, this would actually magnify the apparent loss. One could argue that gold could be 3 times higher from these levels, so you could easily call it a $45,000 loss on a $50,000 investment stake. Now we're talking price terms we can agree is a significant loss!