For the love of all that is holy I sure hope that you're not missing out on free money trying to time a correction, and are holding large hedges against a sudden crash you seem certain is eminent.
The amount of money that's been made on bubbles in the last 30 years far exceeds what's been lost. It's strange to see that trying to call the top hasn't died as a hobby after how much sheer energy has been spent being wrong about it.
Bearish bets are expensive even if you time them perfectly. Most of the time you just piss your money away on theta or borrowing costs even if the security in question doesn't even go up.
I've only ever had one grand slam bearish bet and I placed it in March of this year. I think a lot of idiots get excited by that kind of success and chase recreating it to their ruin.
Learned my lesson this year, probably only lost about $6000 while waiting for the crash that never came. Even if it does, I still have made money since.
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.
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.
The amount of money that's been made on bubbles in the last 30 years far exceeds what's been lost. It's strange to see that trying to call the top hasn't died as a hobby after how much sheer energy has been spent being wrong about it.