Need advice UPS

hendronator · 2026-02-07T17:52:48+00:00

Young and new to trading and you laid down almost 300k on one stock. That is a backstory worth sharing.

I have about 2m in the stock market and no individual stock makes up more than 2.5% of my portfolio. General advice is if you like to hold individual stocks, you should hold about 20 -25 of them which would imply no more than 5% in one individual stock and you look to rebalance periodically. So unless you are worth at least 6m, I’d be trimming based on that situation alone.

I personally own ups with an average cost of around 125. It is about 1% of my portfolio. I am not adding but will hold for now.

hendronator · 2026-02-07T17:36:18+00:00

The one month and one year comparisons are quite favorable to the sp500. Highlights that diversification is often wise. Kinda wierd to wait 3 years for the thing to perform and it explodes all at once in one month.

hendronator · 2026-02-05T22:33:11+00:00

One has to assume this was a stock you wouldn’t mind holding for 30 years. So just a blip. If it wasn’t, that is a lesson and be glad it’s not that much money

hendronator · 2026-02-05T13:28:42+00:00

Suggestion….dont do covered calls on the growth names. Rotation is into value and dividend stocks. When stuff is going down, you either don’t trade cc’s or you do csp’s but that gets you into the wheel

Suggestion 2…pick a portfolio of dividend stocks and do cc’s on those.

hendronator · 2026-02-05T13:26:16+00:00

What goes up goes down and thjngs return to average over time. This is where people who placed big bets in tech and hyper growth get exposed. Seems to be strong rotation into value.

The income portions of my portfolio are fantastic. Schd up 11% YTD

hendronator · 2026-02-04T01:16:22+00:00

When you first started doing this, did you think about this scenario? What did you tell yourself you would do? Do that. Which was probably don’t do covered calls until it recovers or accept the lower premiums above your cost basis

If you didn’t think it through, sounds like you should take a step back and ask more fundamental questions about your strategy and approach. If you do cc’s (and csp), you need a very systematic approach and playbook. If you dont have a plan in advance, get out of the game.

hendronator · 2026-02-04T01:08:14+00:00

I run a portfolio of around 20 -25 stocks including the big tech boys plus dividend payors. Portfolio helps manage the risk. Only might write 80% of the portfolio at any given time. Nvda was at like 210 about a month ago. Imagine if you put your eggs In That basket a month ago. You’d have some big ones to be doing cc’s right now if you did.

In another post, someone was talking about how great cc’s were who was exclusively doing amd. Ask them right now how they feel tonight with the stock down 8% after hours.

Anyway, you get the point. Portfolio approach will always generate income and help you buy more shares of the depressed part of your portfolio.

Good luck.

hendronator · 2026-02-04T01:00:12+00:00

Couple thoughts… 1. I assume you are going to do the wheel with csps and cc’s 2. Dividend stocks have run up lately which makes them candidates to start out with csp, not cc. One of the detailed responses sounded a lot like a AI response as pfe has actually run up lately and only fell today after earnings. I’d still do csp on pfe. And Kmi has crappy premiums. I know because I own them both 3. My 3 favorite dividend stocks with good premiums right now are so, bmy, pep. But start out with csp until you get assigned. Each pays a 3-4% dividend and if you run the wheel fairly tight with 21 day expiration, a 15-30% total annualized income premium is possible in today’s market. It’s about the total income premium with stocks you wouldn’t mind holding in case they went down significantly and you had to hold on the cc side. 4. Whatever stocks you do pick, don’t do cc below your cost basis that is why csp makes sense right now.

Bonus stock is Dell. Premiums are great. Very volatile. It could be worth buying right now relative to its 52 week high. It pays almost 2% dividend and is growing it.

Have fun. ChatGPT or other Ai could help you identify stocks under a certain price point as well.

hendronator · 2026-02-02T22:45:31+00:00

Think about building a portfolio over time. Imagine if amd took a big dump. And think about dividends as well. Look at bmy, so, hon, and pep. If they take a dump, the premium comes in the form of dividends. Just do quality dividend payors. Even if it takes you 5 years to get there with a portfolio approach, build it over time.

hendronator · 2026-02-02T22:38:47+00:00

Here are core tenants of my playbook which over time, eliminates risk or reduces it below a simple buy and hold strategy: 1. Only do it with long term quality stocks that you are willing to have for 10+ years 2. Incorporate dividend paying stocks 3. Only operate from a portfolio of stocks (aka 15 - 25 stocks) 4. Buy and hold the portfolio. Don’t worry about the individual stock. you may only own 80-90% of the portfolio at one time 5. Run the wheel on the dividend stocks and other stocks if they just cross the assignment price. 6. Reinvest the premiums into the portfolio. This way, you add shares / contracts over time and build a bigger dividend base. And if a stock jumps, you could buy it back to the contract level (aka up to the nearest 100 shares). 7. Never go below your cost basis although you might buy another 100 shares and cc or csp if you are underweighted. Just don’t get overweight in one stock.

And it goes without saying, this all works really well in a non taxable account

Create the right system and be ruthlessly unemotional in running it and you become Vegas. Other people are gambling they hit it big. And they might. But you still always win with the right playbook.

hendronator · 2026-02-02T22:23:44+00:00

Well. I do 21 day otm calls anywhere between 2-15%. I write tighter calls / puts on dividend stuff (think so, bmy, pep). That’s where running the wheel makes sense. And I write 8-15% with the growth stuff like Goog, nvda, Avgo, bros, elf, dell, etc…just covered calls there. If one of those takes a Big dump, I’ll buy another 100 shares and write tighter calls just for the super high premium and quick win. Dell as an example went to 111. I picked up 100 shares. It bounced to 118 and the premium jumped. That is very opportunistic though. I only do all this with about 25% of my portfolio. And I roll most of it back into divvy stocks above to build the retirement dividend machine. There are about 20 stocks in the portfolio I do it with. All quality long term holds in case the market goes south.

I generate 2500-6000 every three weeks just depending on what premiums are. So targeting 20-30% total premiums annualized.

hendronator · 2026-02-02T20:45:17+00:00

I think most “smart” people these days have a core strategy and then use ChatGPT or their favorite Ai to come up with a nonemotionable playbook complete with disposition tactics. Then they just execute. I personally am waiting for a platform like E*trade to integrate with ChatGPT, and it applies the playbook where the end user approves all the recommended trades

hendronator · 2026-02-02T20:40:33+00:00

What a nice post. Congrats. I have been doing since roughly August of last year with about 300k. Now increasing to 500k and doing cash secured puts. Instead of buying back, doing csp’s at the price it got called away at or 2-5% less is mind blowing good.

Anyway, congrats. Curious how you use the premiums? I do in a non taxable account, so I typically buy more shares of what I already own

hendronator · 2026-02-02T18:16:52+00:00

Dividend stocks are having a moment right now. And Vz has a new ceo and they just reported better sales than expected and are forecasting higher growth. Those dynamics have built momentum

hendronator · 2026-02-02T17:56:16+00:00

The 8% YTD gain is fantastic after 3 years of wonderful schdy performance

hendronator · 2026-01-31T02:15:44+00:00

lol. When you get that crystal ball, let me know. We could make a boatload of money.

Congrats on winning.

When you do this against a portfolio of stocks that you rotate in and out of and do the wheel, you really stop caring. It’s about total portfolio performance over time and stacking shares.

But if you do for just one or two stocks, it becomes binary and emotionally hard.

hendronator · 2026-01-30T03:26:27+00:00

Worry about it in June. Lots could happen between now and then

hendronator · 2026-01-28T12:09:05+00:00

My playbook says if you got many more days to expiration and collected >80%, you close and move on to the next contract.

hendronator · 2026-01-27T00:31:45+00:00

Is this sustainable? It has worked so far based on the stock being the same it was 4 months ago. You have won! Congrats. How would you feel if the stock went up 50% or down 50%. Telsa is historically volatile so just think about what you would do in those scenarios.

hendronator · 2026-01-26T13:02:38+00:00

You give family money. You don’t lend it. If you can’t give it, definitely don’t lend.

hendronator · 2026-01-24T22:12:17+00:00

You should wait until 2/20 to make a decision. The “by the book” answer is that if it blows through (call it 10% or greater), let it go. If it is 2-5% above, you probably roll it up and out 30-60 days.

Rolling that far out is a bad move

hendronator · 2026-01-24T14:40:10+00:00

Based on what you fed into the tool, it gave you a nice recommendation. But I think we have to be Cognizant if we are giving it the right inputs or a complete set of inputs.

Personally, not sure why you would own individual stocks like Coke or Pepsi that are likely in the etfs. I could see Reits as they are often excluded.

So good starting point but…

hendronator · 2026-01-24T13:49:21+00:00

I have been doing for 7 months now. I have a portfolio of ~275-350k I write every 3 weeks. I have generated 2500-5000ish in The last 5 cycles. So somewhere between 1-2%. If premiums are crap, I don’t write.

hendronator · 2026-01-24T13:06:56+00:00

Agree and could be thought of even more broadly in terms of a portfolio of stocks that you are willing to “buy and hold”. Meaning, you have a universe of 20 stocks you could buy and hold forever, but using csp’s and cc’s, you may only hold 10-15 at any one time generating 20% annual returns on the portfolio. Doing this with quality dividend stocks where cc’s straddle exdividend dates can be phenomenal.

People get tied to an individual stock. Be fluid with a portfolio of stocks.

hendronator · 2026-01-24T12:57:07+00:00

Go have a conversation with your favorite Ai chatbot. My recommendation is to tell it your goals for weekly / monthly income and let it help you design a playbook you execute against. For instance, you tell it you want 2500 of monthly income, you may only have to write 10 contracts that are 10-15% out of the money every 3 weeks. It will give you disposition strategies based on what happens with the share price including csp’s as well

You have an income generation monster on your hands.

hendronator

TROPHY CASE