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Didn't both Soros and Taleb move from "well-off" to "squillionaire" by going short?

• User23 6y ago
  If you time a short bet perfectly then yes you can make multimegabucks, but arguably you'd have better odds playing the powerball. Soros and Taleb are both great examples of survivor bias attributing their success to personal virtue. Edit: What I'm trying to say is most people most of the time will be better off making long bullish bets. For example I bought some deep out of the money AAPL calls in June of this year and I'm quite pleased with how that turned out. It more than paid for the mistakes I made. The way I see it is think like a venture capitalist. Place 20 bets that pay out 100-1 and try to arrange for at least one to pay out.
• nemo44x 6y ago
  Taleb didn’t use an “all-in” short strategy. I don’t know the specifics but he describes in his writings using a “barbell” strategy made up of about 90% very safe investments and about 10% high risk. For instance, 90% long treasuries and 10% in various options. The idea is we live in a world of extremes today and something will happen but we don’t know what or when. So keep yourself liquid while sizing bets appropriately (Kelley Criterion in essence) and profit when the black swan event occurs. The additional, important benefit is you are liquid while almost everyone else is getting margin calls. This is an opportunity with many advantages such as buying low. In essence lose a small amount often to win a large amount at some point. Similar to VC strategies or blackjack professionals when you could get away with counting.