>I used to trade options and had about 99.5% success on all my trades

Do you mean this literally or is that an exaggeration for effect?

I'm not sure how you'd do that unless all your trades are like selling a put with a $50 strike price expiring in a month when the stock is trading at $100.

It depends on how they measure profitability, but a 99% win rate isn't uncommon if you just write options.

Covered calls are a good example, you own the stock and sell calls with a strike that is in the money.

You make money on your option as it either expires worthless and you win getting to keep the premium you got paid to write the option or it expires in the money and you sell the shares to the option holder at the strike.

In both cases you can claim you didn't lose money on the option. But you did lose out on potential profit from your share as you were forced to sell them for less than they are worth on the open market and its very easy to get into a case where you would have been better off if you hadn't wrote the option in the first place.

If you manage your own money you can say you didn't lose on the option but you probably did on the underlying stock.

If the stock closes lower you lost money on the stock but make a tiny bit from selling the option.

If the stock closes higher than the strike you wrote you "make" money on the option from the premium but lose out on profit as you have to sell your stock for lower than what you could have in the market.

So again you can say the option didn't lose money but you are worse off than if you hadn't wrote the option, assuming it went up more than the premium you got from writing the option.

So amateur traders can fool themselves into thinking they are geniuses as their option leg doesn't lose money but the overall trade still makes them worse off than if they hadn't of sold the option at all.

> Do you mean this literally or is that an exaggeration for effect?

As a fellow options trader, I can confirm that it is spot on what is seen with SPY; it is not an exaggeration at all.

> 99.5% success on all my trades

Winning trades made $0.01, losing trades lost $10k.

Pennies in front of a steamroller