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I've heard this strategy referred to as "picking up pennies in front of a steamroller" - it works until the CEO is discovered to be a fraud, goes to jail, and s

by vgt 4y ago

I've heard this strategy referred to as "picking up pennies in front of a steamroller" - it works until the CEO is discovered to be a fraud, goes to jail, and stock loses 80% of its value in a week. Then you lose everything on a single position. Market makers do this as a free way to cover delta risk in that direction. If you have +100 delta, selling 100 "units" (way out of the money options) is a nice way and doesn't carry any other greeks. I've seen speculators do this, but they're playing with fire. I've seen an investor risk 9 digits to pick up $50k a minute before strike expiration, not realizing that the actual settlement is the next day (so adversarial events can still happen).

moneywoes 4y ago
If the expected value is positive that means in the long run it should be fine right?
- vgt 4y ago
  I am not a fan of Taleb these days (he went off the deep end in conspiracy land), but it's worth reading his "Black Swan" book. These tail risks are impossible to predict, and volatility of volatility of these events is incredibly high. So your expected value is better to think of as a "very broad range with a positive mean" - are you comfortable with this?
- mikeyouse 4y ago
  In the long run, we're all dead...
- NovemberWhiskey 4y ago
  If you have infinite capital, and the market is infinitely liquid, sure. c.f. martingale betting strategies.
NovemberWhiskey 4y ago
>"picking up pennies in front of a steamroller" ... generally that refers to the strategy of writing (far) OTM options. Like: the Dow is currently trading at about $49.44; and the bid/ask on a Nov 18th put with a strike of $40.00 last traded at $0.04. So you can write 25,000 of those and get $1,000 in premium. Those are the pennies. You can't lose any money unless the Dow actually below $40.00 because those options will expire worthless. However, if the Dow goes to $39.00 ... then you'll be on the hook for $25,000. That's the steamroller.
- ivanche 4y ago
  Just a correction that the steamroller is $1,000,000 in this case - 250 contracts x 100 "shares" x $40.

by vgt 4y ago

moneywoes 4y ago

If the expected value is positive that means in the long run it should be fine right?

vgt 4y ago
I am not a fan of Taleb these days (he went off the deep end in conspiracy land), but it's worth reading his "Black Swan" book. These tail risks are impossible to predict, and volatility of volatility of these events is incredibly high. So your expected value is better to think of as a "very broad range with a positive mean" - are you comfortable with this?
mikeyouse 4y ago
In the long run, we're all dead...
NovemberWhiskey 4y ago
If you have infinite capital, and the market is infinitely liquid, sure. c.f. martingale betting strategies.

NovemberWhiskey 4y ago

>"picking up pennies in front of a steamroller" ... generally that refers to the strategy of writing (far) OTM options. Like: the Dow is currently trading at about $49.44; and the bid/ask on a Nov 18th put with a strike of $40.00 last traded at $0.04. So you can write 25,000 of those and get $1,000 in premium. Those are the pennies. You can't lose any money unless the Dow actually below $40.00 because those options will expire worthless. However, if the Dow goes to $39.00 ... then you'll be on the hook for $25,000. That's the steamroller.

ivanche 4y ago
Just a correction that the steamroller is $1,000,000 in this case - 250 contracts x 100 "shares" x $40.