Hello Guys & Gals....I’m looking to find the best way to optimize Tesla gains. I haven’t exercised options before only traded them, so any info on the best way to go about this is much appreciated.
Goal: End up with 100 TSLA shares (pre-split) from the call option gains with enough leftover to pay taxes.
Options; Current Price; Purchase Price
1x Oct 2020 1500c; $696; $62
1x Oct 2020 1800c; $461; $47
1x Nov 2020 1500c; $732; $200
All in taxable brokerage account, assume 32% short-term gains tax rate. Realize these are just paper gains at this point, but a man can dream/plan.
My thoughts:
If we see enough pump with S&P500 inclusion news, Battery Day, Q3 deliveries, Sell Oct 1800c and Nov 1500c and use gains to exercise Oct 1500c for 100 shares.
If SP reaches $2700 by mid-Oct:
Oct 1500c would be worth approx.: 1200
Oct 1800c would be worth approx.: 900
Nov 1500c would be worth approx.: 1200
Scenario 1: Selling two calls and using proceeds to pay taxes and exercise Oct 1500c
Required for exercising options: 150K
Total Value of 2 options: 210K
Taxes on 185K gain: 59.3K
Leftover after taxes: 150.7K
Scenario 2: Selling all Options and using proceeds to pay taxes and buy Shares
Required for 100 Shares: 270K
Total Value of 3 options: 330K
Taxes on 300K gain: 96K
Leftover after taxes: 204K
I approximated a little and it is a lot to ask, but if someone could please check my math and let me know if there is a better option than Scenario 1 or if i'm missing something, I'd be grateful.
Thanks Much!