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I'd say this precisely mirrors my journey through day trading.

You start out with the naive mindset, thinking you can make money by finding strong undervalued companies and investing in them with stocks/LEAPS.

Then when you've lost enough money trying that, you move on to technical analysis, thinking you can time the momentum and price action of "predictable" securities. Still thinking it's the "market" you're trying to figure out.

Then once you've lost enough money trying that, it finally hits you. I've been the sucker all along! The way you make money at this is by realizing it's all a game that you're playing against other individual people, not some abstract "market". You buy lots of the underlying stock of something that's trending and start selling OTM "lottery ticket" contracts to the hapless fools (of which you used to be), and you finally start winning.




> You buy lots of the underlying stock of something that's trending and start selling OTM "lottery ticket" contracts to the hapless fools (of which you used to be), and you finally start winning.

I'm relatively new to the stock market and still learning, can you confirm I understand?

You buy (say) n * 100 of the underlying, then you just sell OTM options. There's no link between the the underlying and the option, it's just collateral for the options in case the purchaser decides to exercise?

Your upside is that you make the premium + the strike price. You lose out if the share goes up past the strike + premium, but you win if it goes down, or not up enough?

So for example with ABNB, last trade 203.25. You buy 100, sell one option bundle for Mar'19 '21 202.5 strike for $15.60 per share.

If the share price goes above $218.85, you lose out on the difference, but you still get to keep the premium + strike, so you didn't really "lose" anything, you just didn't make as much.

If the share never goes above $218.85, you keep the shares, and are up by the premium price (in simple terms).

Is that the gist? Are there any other mechanics of this I've missed out? It seems Interactive Brokers will let me sell a call option without owning the underlying (edit: it seems there's a separate "write option" tool), so I guess if the option owner decides to exercise your broker somehow either just take the shares out of your account or makes you buy some?

How far out do you sell OTM options for?


>"Your upside is that you make the premium + the strike price. You lose out if the share goes up past the strike + premium, but you win if it goes down, or not up enough?"

You still "lose" in the short term if the underlying goes down more than your premium covers. That's the risk you take on writing calls; the underlying can technically go to zero. But so long as it's a decent company with real earnings or growth potential, over time stocks always go back up.

>"If the share price goes above $218.85, you lose out on the difference, but you still get to keep the premium + strike, so you didn't really "lose" anything, you just didn't make as much."

Exactly. Although you technically still "lost", even if you didn't lose money, because you took on the risk of holding the underlying for longer than you collected in premiums (theta value of the option). But this, along with "cash secured puts"[0] is the basis of the "wheel" strategy. It goes like this:

Pick a strong stock you're generally bullish on long term and would be fine with owning -> Sell cash secured puts -> When the underlying drops to the point of your CSP hitting the money, get assigned at a price you wanted to buy it at anyways, keep the premium, and now you own the underlying -> Sell covered calls on the underlying until it rises to the point of being exercised -> Get exercised, keep the profit + premium -> Start over from step one.

>"It seems Interactive Brokers will let me sell a call option without owning the underlying (edit: it seems there's a separate "write option" tool), so I guess if the option owner decides to exercise your broker somehow either just take the shares out of your account or makes you buy some?"

That's a "naked call"; the black tar heroin of options. You can do it, but it's incredibly risky. Stocks can technically go up infinitely, meaning you're taking on infinite risk for a finite return. The GME debacle is a great example of how dangerous that can be for an individual. One huge overnight price movement can completely bankrupt you.

>"How far out do you sell OTM options for?"

It really depends on the underlying. That's why it's so important to follow a stock, and get to know how it trades over a few months before playing options on it. A general rule of thumb is ~%20 OTM on monthlies puts you in the sweet spot of premium/risk though.

[0] https://www.optionsplaybook.com/option-strategies/cash-secur...


This is super helpful, thanks!


There is an old saying, two kind of people enter the market in the morning, one with money and the other with experience. They switch postions by day end.




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