My biggest loss was a Rolex Moonphase Watch I bought on ebay for $14000 last year, which turned out to be a very good fake and even confused a couple of Christies Specialists. So I learned my biggest lesson, if it is too good to be true walk away. Rolex Moonphase in Steel Case with Black Dial usually goes for > $250000 and I should have known better before paying $14000 for it.
Here is my advice on investing your money, start slow, study your market, keep a diverse portfolio, target 10-15% per year return, if you reach that you are already ahead of inflation and increasing your networth. With practice you will get better at it.
Getting good at investing takes time and effort, but its well worth it, for me antiques were a hobby which turned into good investments, for you it might be stocks, land, startups, commodities etc. But same principles apply to all of them, you have to be passionate about your investments, know your market, learn from your mistakes, never put all eggs in one basket and walk away if its too good to be true.