Buy Borrow Die & Risk

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White Coat Investor
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Re: Buy Borrow Die & Risk

Post by White Coat Investor »

nvrmnd wrote: Tue Sep 26, 2023 2:02 pm Suppose your investment goal is to maximize the amount of money left to your beneficiaries,....
It's not really the margin call risk that gives me pause, but rather that if you plan on doing this any % of fixed income in your portfolio no longer makes any sense at all.
Yup. This is an unusual goal (and certainly not mine). Many of us take risk off the table when we no longer need to take it. We eliminate leverage risk from our lives by paying off mortgages etc. But if your goal is really to leave as much as possible, then it makes sense to keep risk levels high. Lots of equity risk. Lots of leverage risk. Work longer than you otherwise would. Work hard to get promoted. Start a side gig/business.

You would enjoy reading a book called The Value of Debt.
1) Invest you must 2) Time is your friend 3) Impulse is your enemy | 4) Basic arithmetic works 5) Stick to simplicity 6) Stay the course
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Taylor Larimore
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Re: Buy Borrow Die & Risk

Post by Taylor Larimore »

nvrmnd wrote: ↑Tue Sep 26, 2023 7:02 pm
Suppose your investment goal is to maximize the amount of money left to your beneficiaries.
nvrmnd:

Why not give your beneficiaries part of your money while you are still alive?

Best wishes.
Taylor
Jack Bogle's Words of Wisdom: “The enemy of a good plan is the dream of a perfect plan.”
"Simplicity is the master key to financial success." -- Jack Bogle
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Re: Buy Borrow Die & Risk

Post by whodidntante »

Taylor Larimore wrote: Thu Feb 01, 2024 10:31 am nvrmnd wrote: ↑Tue Sep 26, 2023 7:02 pm
Suppose your investment goal is to maximize the amount of money left to your beneficiaries.
nvrmnd:

Why not give your beneficiaries part of your money while you are still alive?

Best wishes.
Taylor
Jack Bogle's Words of Wisdom: “The enemy of a good plan is the dream of a perfect plan.”
The main advantage of death is that your heirs get a free step up in basis. You don't get that advantage if you gift while alive.
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Re: Buy Borrow Die & Risk

Post by whodidntante »

A variation on this idea is the Whodidntante Maneuver, where you short box spreads to generate a capital loss and get money, and use that capital loss offset capital gains from selling to deleverage. This effectively defers capital gains until death but without the downsides of a perpetually expanding margin loan. I have a spreadsheet showing this will work, but have not actually tried it because I am accumulating and have no present need for the strategy. Pretty sure I'll do it when I become a silver fox, though.
Escapevelocity
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Re: Buy Borrow Die & Risk

Post by Escapevelocity »

I hope that OP does not implement proposed strategy. I'd rather see taxes paid on a PAYGO basis considering LTCG rates are quite favorable and reasonable when viewed in the context of regular income tax rates. Also, I could foresee that step up in basis on death is curtailed at some point considering the need to close deficit which would blow up such a strategy.
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Re: Buy Borrow Die & Risk

Post by the_wiki »

Journeyman510 wrote: Wed Jan 31, 2024 8:31 pm I'm amused by this characterization of these ideas as schemes and motivated by greed.

I mean this is a site where people sweat the details on expense ratios, agonize over how to save money on razors, won't buy a car that takes premium gas, etc, because these savings can be reinvested in the market to generate more wealth in the long term.

Yet if you try to minimize tax liability it's complicated, time consuming, greed, etc. I mean there is a whole thread on frugality here, where folks talk about saving $15 per year by using loose leaf tea instead of prepackeged tea bags.


In this particular case we are talking about someone that has enough money to die wealthy already and considering adding significant risk for a chance to die with even more. That seems like a special case. If it was only time and complexity that is one thing, but this has the ability to implode.

Yes making your life harder to save $15 a year is a bit absurd too.
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Taylor Larimore
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Re: Buy Borrow Die & Risk

Post by Taylor Larimore »

whodidntante wrote: Thu Feb 01, 2024 11:01 am
Taylor Larimore wrote: Thu Feb 01, 2024 10:31 am nvrmnd wrote: ↑Tue Sep 26, 2023 7:02 pm
Suppose your investment goal is to maximize the amount of money left to your beneficiaries.
nvrmnd:

Why not give your beneficiaries part of your money while you are still alive?

Best wishes.
Taylor
Jack Bogle's Words of Wisdom: “The enemy of a good plan is the dream of a perfect plan.”
The main advantage of death is that your heirs get a free step up in basis. You don't get that advantage if you gift while alive.
Bogleheads:

IRS Gift Tax Regulations are often misunderstood. The only requirement in 2024 is that we must report (not pay) any gifts over $18,000. Most of us have a lifetime gift exemption of $13,610.000 without paying a gift tax.

https://smartasset.com/estate-planning/ ... -and-rates

Best wishes.
Taylor
"Simplicity is the master key to financial success." -- Jack Bogle
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whodidntante
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Re: Buy Borrow Die & Risk

Post by whodidntante »

Taylor Larimore wrote: Thu Feb 01, 2024 11:59 am
whodidntante wrote: Thu Feb 01, 2024 11:01 am
Taylor Larimore wrote: Thu Feb 01, 2024 10:31 am nvrmnd wrote: ↑Tue Sep 26, 2023 7:02 pm
Suppose your investment goal is to maximize the amount of money left to your beneficiaries.
nvrmnd:

Why not give your beneficiaries part of your money while you are still alive?

Best wishes.
Taylor
Jack Bogle's Words of Wisdom: “The enemy of a good plan is the dream of a perfect plan.”
The main advantage of death is that your heirs get a free step up in basis. You don't get that advantage if you gift while alive.
Bogleheads:

IRS Gift Tax Regulations are often misunderstood. The only requirement in 2024 is that we must report (not pay) any gifts over $18,000. Most of us have a lifetime gift exemption of $13,610.000 without paying a gift tax.

https://smartasset.com/estate-planning/ ... -and-rates

Best wishes.
Taylor
Many people misunderstand capital gains taxes, which is what I was talking about. Gift taxes are not relevant to my point.

If you sell shares while alive to gift money, you're going to have to pay capital gains taxes.
If you gift shares while alive and then the recipient sells, the recipient will have to pay capital gains taxes.

It is possible to avoid this tax by dying with appreciated shares.
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Lee_WSP
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Re: Buy Borrow Die & Risk

Post by Lee_WSP »

I think it’s a pretty simple analysis. Is the interest rate paid higher than that of the investments.
Journeyman510
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

Escapevelocity wrote: Thu Feb 01, 2024 11:16 am I hope that OP does not implement proposed strategy. I'd rather see taxes paid on a PAYGO basis considering LTCG rates are quite favorable and reasonable when viewed in the context of regular income tax rates. Also, I could foresee that step up in basis on death is curtailed at some point considering the need to close deficit which would blow up such a strategy.
It depends on your tax situation. If you are in the highest tax bracket in CA then your combined capital gains rate is 38%.
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

the_wiki wrote: Thu Feb 01, 2024 11:25 am
Journeyman510 wrote: Wed Jan 31, 2024 8:31 pm I'm amused by this characterization of these ideas as schemes and motivated by greed.

I mean this is a site where people sweat the details on expense ratios, agonize over how to save money on razors, won't buy a car that takes premium gas, etc, because these savings can be reinvested in the market to generate more wealth in the long term.

Yet if you try to minimize tax liability it's complicated, time consuming, greed, etc. I mean there is a whole thread on frugality here, where folks talk about saving $15 per year by using loose leaf tea instead of prepackeged tea bags.


In this particular case we are talking about someone that has enough money to die wealthy already and considering adding significant risk for a chance to die with even more. That seems like a special case. If it was only time and complexity that is one thing, but this has the ability to implode.

Yes making your life harder to save $15 a year is a bit absurd too.
How does it potentially explode?

Worse case is I'm forced to liquidate the underlying securities in the first year of this which will then if have to pay the capital gains taxes. Best case is that I whittle down all of my capital gains. Likely outcome is somewhere in the middle.

Could you explain the worst case that would constitute an implosion?
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

whodidntante wrote: Thu Feb 01, 2024 11:12 am A variation on this idea is the Whodidntante Maneuver, where you short box spreads to generate a capital loss and get money, and use that capital loss offset capital gains from selling to deleverage. This effectively defers capital gains until death but without the downsides of a perpetually expanding margin loan. I have a spreadsheet showing this will work, but have not actually tried it because I am accumulating and have no present need for the strategy. Pretty sure I'll do it when I become a silver fox, though.
This is exactly what I'm going to try out. I'm going to start small to test things out. Then go from there.

Would love to see the spreadsheet.
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

Lee_WSP wrote: Thu Feb 01, 2024 12:08 pm I think it’s a pretty simple analysis. Is the interest rate paid higher than that of the investments.
Exactly. This is a form of arbitrage. If you do a short box instead of a margin loan then you can use the cost of the capital to offset capital gains which has the effect of lowering the implied interest rate.
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Re: Buy Borrow Die & Risk

Post by the_wiki »

Journeyman510 wrote: Thu Feb 01, 2024 2:09 pm
the_wiki wrote: Thu Feb 01, 2024 11:25 am
Journeyman510 wrote: Wed Jan 31, 2024 8:31 pm I'm amused by this characterization of these ideas as schemes and motivated by greed.

I mean this is a site where people sweat the details on expense ratios, agonize over how to save money on razors, won't buy a car that takes premium gas, etc, because these savings can be reinvested in the market to generate more wealth in the long term.

Yet if you try to minimize tax liability it's complicated, time consuming, greed, etc. I mean there is a whole thread on frugality here, where folks talk about saving $15 per year by using loose leaf tea instead of prepackeged tea bags.


In this particular case we are talking about someone that has enough money to die wealthy already and considering adding significant risk for a chance to die with even more. That seems like a special case. If it was only time and complexity that is one thing, but this has the ability to implode.

Yes making your life harder to save $15 a year is a bit absurd too.
How does it potentially explode?

Worse case is I'm forced to liquidate the underlying securities in the first year of this which will then if have to pay the capital gains taxes. Best case is that I whittle down all of my capital gains. Likely outcome is somewhere in the middle.

Could you explain the worst case that would constitute an implosion?
Read the 4th post in this thread by randomguy

Basically the longer you do this, the more expensive your loans get and the faster your debt grows. If you end up with a significant portion of your wealth in debt, you could run out of borrowing room or have a margin call after a market dip.
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

His post makes a few assumptions. One that you are using margin. I will be using short box spreads. The cost of the loan (interest) is a capital loss. I have significant capital gains in the 7 figures. As I accumulate losses I can sell some my gains (tax free) and use those proceeds to pay down the debt to keep it manageable.

In my case, my household income is 1.5m and we have plenty left over from that to pay down the debt to keep it manageable.

The amount of debt is only troublesome if the rate is higher than what you make in the market AND the ratio of your debt to the liquidation value of securities is high.

Let's say I do have to bite the bullet and pay off my debt. I would only be out the "interest" which is a capital loss. So yeah I could loose some money if it implodes in the first year but I'd still be not that far off from where I would have been. So the risk is manageable (for me). Now if it happens a few years into my loan term then I very well have accumulated addition capital gains which I could offset with my capital losses and come out ahead even if things implode.

So my question is can we still call it an implosion if I made money?
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Re: Buy Borrow Die & Risk

Post by afan »

The risk is that market movements reduce the value of your assets while your debt continues to grow. If the market crashes you may not have so much in the way capital gains.

If you do this for years and the total debt, including accumulated interest, are large compared to your assets, then it could implode. If you continue this for years but your debt never comes close to your asset value, then you remain safe.

I suggest looking at where you will be if the market drops by 80%. It rarely happens and may not happen in your lifetime. But you do not want to be wiped out if it does. Would a major crash take your assets below your debt level? Would it leave you solvent but force a margin call? You can avoid both outcomes by limiting your ever-increasing debt to a small part of your networth.
We don't know how to beat the market on a risk-adjusted basis, and we don't know anyone that does know either | --Swedroe | We assume that markets are efficient, that prices are right | --Fama
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Re: Buy Borrow Die & Risk

Post by afan »

Lee_WSP wrote: Thu Feb 01, 2024 12:08 pm I think it’s a pretty simple analysis. Is the interest rate paid higher than that of the investments.
It would be simple if we were dealing with known fixed rates. But no one knows what the interest rate on the debt or the returns on the investments will be. A strategy could look great when interest rates are low and there are high returns in the market. That same strategy can blow up if the interest rates on the debt go high and the market goes low.
We don't know how to beat the market on a risk-adjusted basis, and we don't know anyone that does know either | --Swedroe | We assume that markets are efficient, that prices are right | --Fama
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Lee_WSP
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Re: Buy Borrow Die & Risk

Post by Lee_WSP »

afan wrote: Fri Feb 02, 2024 10:44 am
Lee_WSP wrote: Thu Feb 01, 2024 12:08 pm I think it’s a pretty simple analysis. Is the interest rate paid higher than that of the investments.
It would be simple if we were dealing with known fixed rates. But no one knows what the interest rate on the debt or the returns on the investments will be. A strategy could look great when interest rates are low and there are high returns in the market. That same strategy can blow up if the interest rates on the debt go high and the market goes low.
It's still simple. We just don't know what the particular outcome will be.
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nvrmnd
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Re: Buy Borrow Die & Risk

Post by nvrmnd »

whodidntante wrote: Thu Feb 01, 2024 11:12 am A variation on this idea is the Whodidntante Maneuver, where you short box spreads to generate a capital loss and get money, and use that capital loss offset capital gains from selling to deleverage. This effectively defers capital gains until death but without the downsides of a perpetually expanding margin loan. I have a spreadsheet showing this will work, but have not actually tried it because I am accumulating and have no present need for the strategy. Pretty sure I'll do it when I become a silver fox, though.
It's hard to be sure you would generate a capital loss though, the stock could go down or sideways for a long time. I once thought I had a genius idea of doing this and just taking the cash from the short-sale and using that. But then I learned that you have to keep all that cash in your brokerage as collateral.
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

nvrmnd wrote: Fri Feb 02, 2024 11:47 am
whodidntante wrote: Thu Feb 01, 2024 11:12 am A variation on this idea is the Whodidntante Maneuver, where you short box spreads to generate a capital loss and get money, and use that capital loss offset capital gains from selling to deleverage. This effectively defers capital gains until death but without the downsides of a perpetually expanding margin loan. I have a spreadsheet showing this will work, but have not actually tried it because I am accumulating and have no present need for the strategy. Pretty sure I'll do it when I become a silver fox, though.
It's hard to be sure you would generate a capital loss though, the stock could go down or sideways for a long time. I once thought I had a genius idea of doing this and just taking the cash from the short-sale and using that. But then I learned that you have to keep all that cash in your brokerage as collateral.
This is not correct. The box short is a synthetic loan. The "interest" on the loan is a capital loss. The loss is known at the time you execute the trade. It can never change regardless of what the underlying asset does (usually you want it to be an index like spy and European styled option). If you do it with a stock then it will be a US styles option and one of the 4 legs of the option can be exercised early which would blow up the box spread.

And yes, in some cases you can withdraw the cash. You typically need a portfolio margin account instead of the normal reg t account.
Last edited by Journeyman510 on Fri Feb 02, 2024 12:10 pm, edited 1 time in total.
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

afan wrote: Fri Feb 02, 2024 10:42 am The risk is that market movements reduce the value of your assets while your debt continues to grow. If the market crashes you may not have so much in the way capital gains.

If you do this for years and the total debt, including accumulated interest, are large compared to your assets, then it could implode. If you continue this for years but your debt never comes close to your asset value, then you remain safe.

I suggest looking at where you will be if the market drops by 80%. It rarely happens and may not happen in your lifetime. But you do not want to be wiped out if it does. Would a major crash take your assets below your debt level? Would it leave you solvent but force a margin call? You can avoid both outcomes by limiting your ever-increasing debt to a small part of your networth.
The key is to not let your debt grow infinitely. You must maintain a debt ratio of assets to debt.

There is nowhere to hide in an 80% drop. If you are in VOO you are still screwed. If you want to protect yourself from an 80% drop then keep cash in your mattress.
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

White Coat Investor wrote: Thu Feb 01, 2024 10:20 am
nvrmnd wrote: Tue Sep 26, 2023 2:02 pm Suppose your investment goal is to maximize the amount of money left to your beneficiaries,....
It's not really the margin call risk that gives me pause, but rather that if you plan on doing this any % of fixed income in your portfolio no longer makes any sense at all.
Yup. This is an unusual goal (and certainly not mine). Many of us take risk off the table when we no longer need to take it. We eliminate leverage risk from our lives by paying off mortgages etc. But if your goal is really to leave as much as possible, then it makes sense to keep risk levels high. Lots of equity risk. Lots of leverage risk. Work longer than you otherwise would. Work hard to get promoted. Start a side gig/business.

You would enjoy reading a book called The Value of Debt.
I bought the book last night. It's a quick read. I'm halfway through it. It aligns with most of the tenants I came up with myself. The key being maintaining the right debt ratio.

When I took corporate finance many years ago, I learned that it is valuable for companies to have some debt. It directly enhances EPS. This contradicts the notion by the average consumer that most debt it bad. I always wondered why this disparity exists.

So I was greatly amused when the author started off with this fact in his book. Then he mentioned his finance professor and textbook. It was the same textbook I used. Then he mentioned he went to wharton just like I did!

I plan on reading his two follow on books next. One key difference in my thinking is that asset backed loans have a pretty high interest rate right now and can only offset investment income. I don't have much investment income. I have a lot of capital gains. This why I'm interested in the box spread short because it will offset capital gains and has a lower interest rate than any alternative.

I'm curious what aspects of his theories you didn't agree with?
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White Coat Investor
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Re: Buy Borrow Die & Risk

Post by White Coat Investor »

Journeyman510 wrote: Fri Feb 02, 2024 12:26 pm I bought the book last night. It's a quick read. I'm halfway through it. It aligns with most of the tenants I came up with myself. The key being maintaining the right debt ratio.
Yes, that's my takeaway too. It's all about the ratio and the intentionality and making the debt as "good debt" as you can.

Journeyman510 wrote: Fri Feb 02, 2024 12:26 pm I'm curious what aspects of his theories you didn't agree with?
I'm not sure that I disagree with a lot of it so much as I just don't need to take leverage risk any more to meet any of my goals.
Journeyman510 wrote: Fri Feb 02, 2024 12:26 pm I plan on reading his two follow on books next. One key difference in my thinking is that asset backed loans have a pretty high interest rate right now and can only offset investment income. I don't have much investment income. I have a lot of capital gains. This why I'm interested in the box spread short because it will offset capital gains and has a lower interest rate than any alternative.
Be careful with methods of leverage that involve fancy financial instruments you learned about in business or finance school. This thread is worth a read for why I give that caution:

viewtopic.php?t=5934

Like your box spread plan (that I admit I don't fully understand yet) this guy had a very smart and sophisticated method of leverage that worked...until it didn't. Reading it now (pay attention to the dates) is a fascinating study. It was even more fascinating to watch it unfold in real time.

Be careful with debt. It has ruined a lot more lives than it has created wealthy people.
1) Invest you must 2) Time is your friend 3) Impulse is your enemy | 4) Basic arithmetic works 5) Stick to simplicity 6) Stay the course
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Re: Buy Borrow Die & Risk

Post by comeinvest »

Journeyman510 wrote: Fri Feb 02, 2024 12:26 pm I bought the book last night. It's a quick read. I'm halfway through it. It aligns with most of the tenants I came up with myself. The key being maintaining the right debt ratio.

When I took corporate finance many years ago, I learned that it is valuable for companies to have some debt. It directly enhances EPS. This contradicts the notion by the average consumer that most debt it bad. I always wondered why this disparity exists.

So I was greatly amused when the author started off with this fact in his book. Then he mentioned his finance professor and textbook. It was the same textbook I used. Then he mentioned he went to wharton just like I did!

I plan on reading his two follow on books next. One key difference in my thinking is that asset backed loans have a pretty high interest rate right now and can only offset investment income. I don't have much investment income. I have a lot of capital gains. This why I'm interested in the box spread short because it will offset capital gains and has a lower interest rate than any alternative.

I'm curious what aspects of his theories you didn't agree with?
What do you mean by asset backed loan? Something like broker margin or a pledged securities loan, and deduct it against dividend income in lieu of the standard deduction?
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Re: Buy Borrow Die & Risk

Post by Journeyman510 »

White Coat Investor wrote: Fri Feb 02, 2024 2:58 pm
Journeyman510 wrote: Fri Feb 02, 2024 12:26 pm I bought the book last night. It's a quick read. I'm halfway through it. It aligns with most of the tenants I came up with myself. The key being maintaining the right debt ratio.
Yes, that's my takeaway too. It's all about the ratio and the intentionality and making the debt as "good debt" as you can.

Journeyman510 wrote: Fri Feb 02, 2024 12:26 pm I'm curious what aspects of his theories you didn't agree with?
I'm not sure that I disagree with a lot of it so much as I just don't need to take leverage risk any more to meet any of my goals.
Journeyman510 wrote: Fri Feb 02, 2024 12:26 pm I plan on reading his two follow on books next. One key difference in my thinking is that asset backed loans have a pretty high interest rate right now and can only offset investment income. I don't have much investment income. I have a lot of capital gains. This why I'm interested in the box spread short because it will offset capital gains and has a lower interest rate than any alternative.
Be careful with methods of leverage that involve fancy financial instruments you learned about in business or finance school. This thread is worth a read for why I give that caution:

viewtopic.php?t=5934

Like your box spread plan (that I admit I don't fully understand yet) this guy had a very smart and sophisticated method of leverage that worked...until it didn't. Reading it now (pay attention to the dates) is a fascinating study. It was even more fascinating to watch it unfold in real time.

Be careful with debt. It has ruined a lot more lives than it has created wealthy people.
Thanks for pointing me to that thread. It was like reading a suspense novel.

Maybe I should start a thread to chronicle my box spread thingy.
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nvrmnd
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Re: Buy Borrow Die & Risk

Post by nvrmnd »

New video by Ben Felix on the topic of bonds vs equities LONG TERM, which seems to align with my thoughts in the OP

https://www.youtube.com/watch?v=JlgMSDYnT2o
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