A viable strategy for a conservative individual investor with a substantial Tesla stake and a desire to 'live off' the shares is IMO to always have both free cash besides having the majority invested in the stock, and decide situationally whether to write calls or puts:
- When the share price is rising and you think it will go up more in the short term, write a few (cash covered) puts but don't deplete cash:
- best-case (TSLA goes up as you expected) you keep the premium and much of your portfolio goes up in value,
- worst-case (TSLA goes down and your puts get exercised) you'll increase your portfolio size on a down-leg and keep the premium.
- When the share price is rising and you think it will go down a bit in the short term, write a few (shares covered) calls:
- best-case (TSLA goes down a bit as you expected) you keep the premium,
- worst-case (TSLA goes up against your expectations) you get exercised and get cash for a part of your portfolio (you keep the premium), which cash you can either store or use up to write puts (see above)
- When the share price is dropping and you think it will go down more in the short term, write a few (shared covered) calls:
- best-case (TSLA goes down a bit more as you expected) you keep the premium,
- worst-case (TSLA goes up against your expectations) you get exercised, you get cash for a bit of your portfolio but you keep the premium.
- When the share price is dropping and you think it will bounce, write (cash covered) puts up to your cash limit:
- best-case (TSLA goes up as you expected) you keep the premium and the rest of your portfolio appreciates,
- worst-case (TSLA goes down further than you expected) you get assigned shares and you max out your stake, but you keep the premium.
Also note that there's a few limits and special cases to observe:
- Don't go negative cash (margin) - if your cash dedicated for this position is gone your position is maxed out and you ride out the bottom. Once you think there's a temporary top you can start writing calls again, maybe even re-balance into cash a bit.
- Don't divest shares below a 'core shares' percentage - which, if you are otherwise a long term Tesla investor, should be at least ~50% of your assets. Even if you timed everything wrong you'd still ride out the past 6 months with 50% of your assets in TSLA, and you'd also earn quite a bit of extra cash writing puts all the way up.
- Never write naked options. Always cover the worst-case with cash or shares.
- You can also, obviously, whenever you think the time is right, buy shares from cash at any moment you think is appropriate. Increasing your stake by buying shares is not a problem, but divesting shares should never be panic or price drop driven, it should be by writing calls.
- A special exception if you think there's a rock-bottom reached, then you can sell shares to buy straight call options and leverage up without the risk of margin.
- Obviously there's plenty of tail risks remaining: a recession might wreck havoc, and single-company investments are always risky: near really high price levels you could consider buying wealth insurance against black swan events, covering your position: for example the 2021 $250 puts are just around $15 right now - you only pay Theta in essence. Just 6 months ago these were going for $100 ... $200 puts go for half of that and $150 puts go for $4, and you could buy 200% of them to protect against a black swan event at $300 effective protection price. These kinds of per year wealth insurance costs would normally be much lower than option writing premiums earned.
Note how in
every single case you get to keep the premium,
even if you are wrong, and that none of the outcomes will reduce your stake below your limit or will deplete your cash below zero. So you can take advantage of big breakouts and big drops as well, in accordance with your bullish thesis, which hopefully you'll be able to subscribe to for yours.
"Being wrong" won't have a wealth decreasing effect if the stock otherwise goes broadly up according to your bullish thesis - the worst effect is that you might run out of cash to write puts against, or run out of non-core shares to write calls against. You can still always write the other type of options to recover your ability to swing-trade, and to earn premiums.
(I suspect this trading plan is similar to what the unmentionable Tesla investor who left this summer was doing in essence, with millions of dollars worth of TSLA position.)
Selling covered calls when you think the stock will go higher in the short term is a bad idea - selling calls is effectively a profit taking method.
Nevertheless, not advice.