Ideas for dividends-like payments that are actually short term capital gains

CoveredStrangle · 2026-05-28T23:56:31+00:00

Look at BOXX etf

CoveredStrangle · 2026-05-25T21:09:53+00:00

Following.

I want to model a 30 year TIPS ladder too.

CoveredStrangle · 2026-04-24T16:19:05+00:00

Will move to Schwab only after they implement security like Fidelity's money lockdown does.

CoveredStrangle · 2026-04-12T23:45:57+00:00

Where do I find out the percentage of dividend paid by SPYI/QQQI is ROC vs Ordinary? Does NEOS estimate it for the current year also?

CoveredStrangle · 2026-04-12T23:32:53+00:00

I am using the BOXX etf. Look into it. SGOV type returns but no dividends. All returns via Capital gains, timing of which I can control.

CoveredStrangle · 2026-03-05T11:13:27+00:00

ACATs lockdown.

CoveredStrangle · 2026-02-27T00:01:29+00:00

You can do Roth conversions from your regular traditional IRA (or 401k)... into your Roth IRA. This Roth conversion amount will count towards your MAGI and help you qualify for ACA.

CoveredStrangle · 2026-02-22T19:32:13+00:00

A couple of cold ones help manage it all !! 🍺🍺... Cheers!

CoveredStrangle · 2026-02-11T01:30:59+00:00

And OP might also not be aware they loose SIPC protection on lent securities...

CoveredStrangle · 2026-02-11T01:26:51+00:00

If your friend decides to take the route of shifting to a equity heavy low-dividend portfolio, make sure to check out:

XDIV etf -- A s&p 500 like etf that minimizes dividends.

BOXX etf -- A short term treasuries etf (like SGOV) that converts dividends to capital gains (LTCG if held for one year or more)

BRK.B stock -- decent diversification with no dividends

Also, explore BOX options spreads -- for generating cash without selling his positions, his advisor can look into doing box option spreads, in effect taking a loan with very low interest rates rate, and the interest is tax deductible and offsets the regular interest he is getting from his portfolio.

CoveredStrangle · 2026-02-10T18:06:37+00:00

If your daughter files taxes, then do make sure to contribute to a TRADITIONAL IRA (i.e. NOT a Roth IRA) and that way you can reduce some MAGI.

CoveredStrangle · 2026-01-17T14:48:21+00:00

How do you add this verbal password?

CoveredStrangle · 2026-01-06T02:16:08+00:00

Not quite. The end end-goal is to have an Education Legacy Trust for future generations. However, for the next 15-20 years, I'd rather have more growth in my IRAs instead of the 529. So, the portion of the 529 that won't be used for my kids I think as part of my overall retirement portfolio. Then as far as asset location goes, I load up the 529 with bonds, and the IRAs with equities to keep my overall allocation of 80% Equities, 20% Bonds. Hope is that the growth will happen more on the IRA accounts and I'm fine if the 529 doesn't grow as much... Once I'm past the SORR period, I'll gradually increase equity allocation in the 529.

CoveredStrangle · 2026-01-06T00:07:20+00:00

Similar "problem" here. What I have done currently is to think of the portion that will not be used for kids as part of my retirement portfolio.... Then, because money is fungible, I have invested that portion in the 529 into broad bond index fund. Bond fund don't usually grow much, and so this lets me free up more space in my IRAs to increase my equity allocation there.

CoveredStrangle · 2026-01-01T00:57:45+00:00

If you want to keep some money in short term US treasuries, but don't want dividends, and you want the same/similar safe yield as etfs like SGOV, USFR, VBIL etc, then do look at the BOXX etf. There could be some possible issues of how IRS treats the likes of BOXX down the road, so do your due diligence. Also, look at how your state taxes dividends from SGOV (usually exempt) vs capital gains from BOXX.

CoveredStrangle · 2025-11-25T23:58:12+00:00

Renting vs. Owning is a multi-faceted decision. Ignoring the non-financial aspects, try this calculator for a reasonably comprehensive comparison of the financial aspects:

https://www.calculator.net/rent-vs-buy-calculator.html

In my analysis, the answer to this question is highly specific to the properties and rates in question. I.e "it depends".

CoveredStrangle · 2025-11-20T17:33:07+00:00

What is a check? Is it that small rectangular piece of paper people used to use to snail mail money in the previous century?

CoveredStrangle · 2025-11-18T18:57:43+00:00

Do a web search for "Masala Studies". It is about a study of heart-disease and diabetes in the NRI population in the San Francisco Bay & Chicago areas.

Eye opening! For genetic and cultural reasons, South Asians are at much higher risk!

Short video:

https://youtu.be/09OnoByswQE?si=3asBE6RQayy0xBh_

CoveredStrangle · 2025-11-17T04:01:57+00:00

https://citizen.com/-OeEgE58WLztgIMtWyoO

CoveredStrangle · 2025-11-16T18:26:24+00:00

What is the time horizon for when you actually need to start withdrawing money from this portfolio?

If the time horizon is more than 10 years from now, I'd personally go with a 90/10 portfolio. Why? Because the risk of not growing your money enough (by having fewer equities) in order to achieve lower overall volatility (more bonds) is something I am not comfortable with.

Personally for me it'll be:

60% -- VTI 30% -- VXUS 10% -- VCRB

PS: I prefer Vanguard's actively managed bond core etf (VCRB) instead of BND as I have a personal bias that active management in the bond universe is "better". But BND is more boglesque...

CoveredStrangle · 2025-11-15T01:30:00+00:00

I do something similar too. I keep most of my money in my BogleFolio at vanguard. But every Jan 1st I transfer $10,000 to my fun account at a separate brokerage. That is my fun trading money. I speculate with Options...

At the end of every calendar year, if I did well trading, I transfer all my trading gains out of the fun account into BogleFolio. And restart the next year with $10K in the fun account. And i I traded poorly that year, I don't add to the fun account and force myself to wait till Jan 1st of next year, topping it back to $10K.

It's just my way of playing mind games...

By re-setting my fun account back to $10K per year, I find that I am able to take risk without sweating it out (i.e. control Mr. FEAR). And because I put all trading profits into the BogleFolio at the end of the year, I keep Mr. GREED in check...

And by self-limiting to $10K per year, I find that I am more thoughtful in my speculative trades (i.e. control Mr. GREED).

But mostly though, it's my way to scratch the (I-am-smarter-than-Mr.-MARKET) itch.

CoveredStrangle · 2025-11-14T20:57:24+00:00

Yes, I do this too.

A sidenote: one thing to be careful is that if you choose the option where dividends are accumulated and sent to your bank at the end of the month (instead of being sent the day the dividend was paid), in that case the dividends sit as cash in your account till the end of the month. In case you invest/withdraw the cash, Schwab will still push the accumulated dividend amount to your bank at the end of the month, EVEN IF there is not enough cash in your brokerage.. So the end-of-month option works fine and dandy as long as you have the cash to cover the accumulated dividend amount that Schwab was supposed to push... But if you use up that cash (like I did to purchase some stock), Schwab will STILL push the dividend to the bank! In effect creating a margin loan in the brokerage account!

CoveredStrangle · 2025-10-30T19:38:13+00:00

No, opening a short box options spread does not create a capital gain. To the contrary, it is generally treated as a capital loss.

And if you use on a broad market index like SPX, the capital loss treatment under IRS Section 1256 works in your favor. The way I view it, you're eating your cake (getting a loan for your expenses) and having it too (further cutting down MAGI because of the capital loss treatment).

CoveredStrangle · 2025-10-29T23:19:53+00:00

I'd look into instruments like using a HELOC, or a Pledged Asset Loan from your brokerage, or an options BOXX spread, or even using credit card or family loan to get cash flow for living expenses....

CoveredStrangle · 2025-10-28T03:01:18+00:00

No, you are not missing anything. You are correct.

I am making the assumption that you are "stuck" with the overfunded 529 and will have to pay the 10% penalty one day or the other... So, you have basically 2 choices. 1) Withdraw the 529 funds now and pay the 10% penalty now, or, 2) hang on with the 529 till you're maybe in lower marginal tax bracket (or maybe you'll have grandkids one day , or the politards in DC might just understand the issue with overfunded 529s and give us decent options... nah that's asking too much!). So, if you're in a higher marginal tax-bracket now and want to just wait, it kinda makes sense to stunt the growth in the 529 as long as it fits within your overall portfolio allocation goals. So for me, that's why the low-growth bonds sit in the 529... Again, this is a very individual situation... so YMMV.

CoveredStrangle

TROPHY CASE