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Whoops, I meant buy not sell. That is the market makers won't buy a deep in the money call option with a positive extrinsic value. If you sell one with a negative extrinsic, they'll just immediately exercise it.

Well, even its own pre-IPO investors are supposedly trying to constructively sell it via shorting.

Ah makes sense. Looking at the threads looks like either: Broker won't allow the trade (more likely) The market makers will not sell the options at a price at or above intrinsic value. Meaning, you either can't buy them or you get insta-assigned if you do.

Lyft options are currently under heavy put-call parity violation, with Oct '18 ATM puts being nearly double the cost of calls. My understanding at the high level is that this is caused by hard to borrow fees on shorting. Meaning you can't trivially arbitrage this by going short lyft, short ATM...

To close this out, my thoughts align with elt894: Gainskeeper explicitly states they cannot handle this, though I see a whitepaper suggesting their institutional product can. I contacted Tradelog; they can't handle straddles. Tradelog even notes that you can't even import 6781 part 1 info into...

Schwab. What do you mean by "supports" options? TurboTax can definitely report gains/losses on them after import (albeit some bugs around exercising them); what it can't do (and traderslog's extensive documentation doesn't cover this making me assume it can't) is generate a form 6781 from the...

Not following how tradelog solves my issues. I already have my forms prepared; the issue is importing into my main tax software. Specifically, Tradelogtalks about using form 8453 to paper attach 8949 to an efiled return (sane enough), but that doesn't work for form 6781 (8453 doesn't support...

I've used TurboTax much in the past, but it's limitations are catching up to me: There's no way to batch import form 6781 transaction lists. E.g. I have an Excel file describing all of my identified straddles (entries for 6781 part 2), but there's no way to input this in without typing each in...

I have highly appreciated put options I'd like to gift to my child to minimize capital gains taxes. [1] Unfortunately, I haven't found brokers (checked both Vanguard and Schwab) that allow UTMA accounts to hold unprotected puts [1]; therefore, they'll reject inbound transfers. [2] Anyone know...

Well, you can take no risk.. Just have to accept no return. E.g. long stock, long atm put, short atm call. :)

Whoops, missed that detail. Ya, put is not a LEAP, so will have a short term holding period at expiry. Clearly in a situation where exercise is superior to selling separately (time value is almost nil at this point).. but the donation rules appear unclear.

I'm not even sure if there's a strategy behind this.. it's much too complicated with the different expiry. No, worse case is stock flat until long options expire and then moves rapidly in either direction. Unlimited losses in fact are possible if it surges upward.

You can actually do this pretty accurately from some basic probability theory. Basically, earnings day is "high volatility" (3x+ a normal day) and every other day is normal. An option expiring after earnings day will have its IV be a weighted combination of "high" and normal. So the volatility...

I have: Stock that has been held well over a year with large cap gains. Deeply in the money put options on stock with very large cap gains. (Puts purchased after stock held a year when stock was a lot higher) If I understand correctly: If I sell the stock and put individually, stock is LTCG...

Yup, this helps a lot and was a great recent find, but the interest rates can get so high it starts exceeding what I'm willing to pay. (Thus low margin requirements remain key to minimize interest fees)

As you noted, this is discussed at my sibling thread (This particular thread is just on low margin requirements). To close out this question, pledging stock held in one custodian to another broker is basically impossible. * Custodian generally has zero incentive to even allow this. [1] *...

It should only be sucking away available margin buying power. In that sense, I guess what you are being charged is just the cost it would take to get a loan (from a bank) to regain that margin power. Which is very person dependent and might not even be possible. Point is I'm trying to...

There's no margin fee typically (or anywhere?) with writing naked calls; the naked calls just eat into available margin BP. BP goes to 0 = margin call!

At the risk of this being an essay, I'll respond to everyone's helpful suggestions. (and maybe find some brokers to call in the meantime) 1. It's pretty expensive due to the high implied volatility (in my mind too high) 2. Given that I see IV as too high, the calls are actually more...

180 day post IPO lockout bans selling, but not hedging. Share transfers also blocked until lockout ends. Want to hedge as currently have a very concentrated portfolio in a single stock. (E.g. this is the same sort of thing Mark Cuban famously did with his Yahoo stock.. except his deal size was...