[torkins]

Sure, the guys at tastytrade.com put a ton of effort into educating people and providing a platform (dough.com) that provides this information. I think it has some organizational issues, but my way to start would be to start with the 'Where Do I Start' series they have.

In short, that site largely revolves around the fundamental premises of a random-walk view of prices, and using the time-decay of selling options to reduce the cost basis of holdings over time. There's a lot of treatment and research on correlation of different assets (equities, different kinds of commodities, currencies). My advice if you follow this is to start small and stay actively engaged without getting over-confident at early success. There is a lot of getting used to the mechanics and learning the products so that you can make it a manageable part of your life, time-wise. Also you need to make sure you properly understand the relevant notional values you're dealing with so you can do proper sizing.

BTW quick answer to your first question, here's a sample basket of lesser-correlated assets that the typical index funds that all boil down to being long the market. One of the cores of having a random-walk view of things is that the choice of direction (long/short) is less important than the strategy & cost basis reduction (all of these have liquid option markets):

Long S&P (/ES or SPY) Long Gold (/GC or GLD) Short Bonds (/ZB or TLT) Short WTI Oil (/CL or USO) Long Euro/USD (/6E or FXE)

[ericd]

Thanks! I'm not sure how shorting bonds/oil is like being long the market? I've always been under the impression that going long had an upward bias, and buying options had a downward bias (but maybe selling them gives some upward bias), so that playing with options was a bit like playing at a casino, where the odds are biased in the favor of the house.

[torkins]

I'm not saying shorting bonds/oil is like being long the market. I just picked a set of underlying assets that are much less correlated than e.g. S&P & Nasdaq. The directional choice (long/short) is really a choice of the investor. Correlations between products are not stable over time, so picking one vs the other is similar to a price bet (i.e. normally distributed). The main point is that the underlying assets are not highly correlated, and that they have liquid derivatives markets that can be used to reduce cost basis.

You may or may not make money on your directional choices, but the core strategy is to be short option premium to make your expected value positive, and to have low internal correlation amongst your assets to reduce volatility in your portfolio.

I'm not 100% sure I understand what you're trying to say re: upward bias/downward bias. However, buying options do have a negative expected value so I agree about that. Selling options is the strategy, and conceptually is similar to selling insurance. Limited profitability, positive expected value. Just like an insurance company, you keep your risk diversified to reduce volatility and keep positions small enough to prevent busting out during drawdowns.

I'm not suggesting buying options (except as part of a spread)

[ericd]

Ah ok, I see what you mean. Yeah, I meant expected value with the bias parts.

Thanks for the explanations!