what are you selling today?

[Kuhndan]

I took a middle ground on my Berkshire stock. Sold the $460 calls. Pocketed the premium and potentially sell out at a higher price (although fingers crossed it doesn’t hit $460!)

[Saluki]

I sold some BRK recently, which was my largest and oldest position, until GOOG became larger due to the recent run up in price.  Not a lot, maybe 5% and I may sell another 5% of my higher cost shares depending on their earnings and the stock price. To answer the previous question, the insurance and other subsidiaries still look good bets, but GEICO has been struggling against Progressive, and the energy business suddenly doesn't seem as good as before if regulators or courts can take their pound of flesh at any time.  

 

With a recent ridiculous lawsuit payout for a wildfire where BHE didn't cut the power on a windy day, it's going to be put in a position to cut power more proactively in dangerous situations, but they are compensated/penalized for outages. So it will be damned if you do or damned if you don't.  Maybe the existing assets are okay, but it's definitely a disincentive to deploy more capital if the powers that be can change the rules of the game as they see fit. 

 

So two of the core assets have seen better days, AAPL is a big part of it's net worth and unless people buy into it's AI narrative, maybe that asset has it's incredible growth stalling out.  The railroad is a steady performer, but unlike car insurance, freight loadings are affected by the economy, so it's vulnerable to recession, although BRK itself tends to get great deals when Uncle Warren picks up assets that are beaten down, so the company itself is kind of a hedge/ballast in my portfolio.  

 

I have sold some VTS, ENPH and TAYD in my retirement account in the past few days when the resting limit orders were hit, which ran up a lot and I don't have to pay taxes on, but I don't have any great ideas on what to replace them with.  I don't want to buy GOOD ideas in my retirement account because I can't deduct the losses if I'm wrong, so I like to wait for no brainers there (like something I bought in my taxable account that drops a lot and I think will recover quickly, or something like OXY below $60 which has the Buffett floor).  

[Charlie]

Buffett at the annual meeting:

"The people who check the price daily have not made the money that the

people who have forgotten about it basically have over the years."

It pays to do nothing. 

 

 

[sleepydragon]

I have most of my assets in BRK. I checked yesterday , in my none-retirement account, my lowest cost shares were bought at $126. 

Over the years, I used margins to trade around other stocks. The stability of BRK gave me some assurance that I won't get margin called. My margin also has never exceeded 10% of my account.  As for how did I do with those tradings? I would say I am not as smart as I think I am.

[Charlie]

Don‘t interrupt compounding unnecessarily.

I got lucky that in 2011 I put everything in Berkshire.

The shares got cheaper and cheaper after Buffett bought all these nice assets in the big recession.

It didn´t make sense.

Since then I bought when it was cheap and nearly never sold.

Yesterday I was first time millionaire with my Berkshire shares.

It really pays to do nothing.  (Especially if you have the right partners.

The only thing you have to do is to recognize what you have and hang on).

 

The best advice on the topic, as usual, Munger gave:

"Don´t be so dumb to sell your Berkshire shares."

"Try to be non-idiotic, all day, every day." 

Edited July 17 by Charlie

[Paarslaars]

I always keep a core position in BRK but depending on it's price to book I go up and down. At 1.2 BV it used to be a 50% position, now at >1.5 it is about 10%.

[sleepydragon]

7 hours ago, Charlie said:

Don‘t interrupt compounding unnecessarily.

I got lucky that in 2011 I put everything in Berkshire.

The shares got cheaper and cheaper after Buffett bought all these nice assets in the big recession.

It didn´t make sense.

Since then I bought when it was cheap and nearly never sold.

Yesterday I was first time millionaire with my Berkshire shares.

It really pays to do nothing.  (Especially if you have the right partners.

The only thing you have to do is to recognize what you have and hang on).

 

The best advice on the topic, as usual, Munger gave:

"Don´t be so dumb to sell your Berkshire shares."

"Try to be non-idiotic, all day, every day." 

congratulation!

 

[73 Reds]

7 hours ago, Charlie said:

Don‘t interrupt compounding unnecessarily.

I got lucky that in 2011 I put everything in Berkshire.

The shares got cheaper and cheaper after Buffett bought all these nice assets in the big recession.

It didn´t make sense.

Since then I bought when it was cheap and nearly never sold.

Yesterday I was first time millionaire with my Berkshire shares.

It really pays to do nothing.  (Especially if you have the right partners.

The only thing you have to do is to recognize what you have and hang on).

 

The best advice on the topic, as usual, Munger gave:

"Don´t be so dumb to sell your Berkshire shares."

"Try to be non-idiotic, all day, every day." 

+1   

There are some very talented stock pickers here;  I'm not one of them.  It takes too much time and effort.  It is far easier to recognize powerful companies with enduring competitive advantages and superior management.  Sitting on one's hands while owning shares in such companies is the best advice Munger could have given to most of us, who have neither the time, skills, and devotion necessary to trade our way to success.  

[nwoodman]

7 hours ago, Charlie said:

Don‘t interrupt compounding unnecessarily.

I got lucky that in 2011 I put everything in Berkshire.

The shares got cheaper and cheaper after Buffett bought all these nice assets in the big recession.

It didn´t make sense.

Since then I bought when it was cheap and nearly never sold.

Yesterday I was first time millionaire with my Berkshire shares.

It really pays to do nothing.  (Especially if you have the right partners.

The only thing you have to do is to recognize what you have and hang on).

 

The best advice on the topic, as usual, Munger gave:

"Don´t be so dumb to sell your Berkshire shares."

"Try to be non-idiotic, all day, every day." 

Awesome and congratulations.  I set up my retirement account around this time which was predominantly Berkshire also.  Still remember Buffett announcing he was doing buybacks like it was yesterday. Well done with the additions too, done right it makes this a double digit compounder

[Saluki]

1 hour ago, 73 Reds said:

+1   

There are some very talented stock pickers here;  I'm not one of them.  It takes too much time and effort.  It is far easier to recognize powerful companies with enduring competitive advantages and superior management.  Sitting on one's hands while owning shares in such companies is the best advice Munger could have given to most of us, who have neither the time, skills, and devotion necessary to trade our way to success.  

 

Besides your skill level and risk tolerance, there are a lot of other factors that come into consideration, such as when you bought your shares and if they are in a taxable account.  I'm reluctant to trim in my taxable account, but have done so lately.  I did sell off all my BRK in my retirement account though, and bought mostly FFH and Fairfax India.  I just checked and the FFH shares are up between 40-58% in less than a year, and I think they still have room to run. Fairfax India isn't doing as well in terms of stock price, but it's executing well and had been buying back shares at higher than the current price, so it still looks like a bargain. 

 

BRK (or a position in an index fund) is a great ballast for your ship, and you don't have to trade actively, but you should keep looking. Eventually, like with BRK, you may spot something that is really cheap, has great management and a long runway, and like Supreme Court Justice Stewart's definition of pornography you should  "know it when you see it" and take action.  Good luck. 

[73 Reds]

18 minutes ago, Saluki said:

 

Besides your skill level and risk tolerance, there are a lot of other factors that come into consideration, such as when you bought your shares and if they are in a taxable account.  I'm reluctant to trim in my taxable account, but have done so lately.  I did sell off all my BRK in my retirement account though, and bought mostly FFH and Fairfax India.  I just checked and the FFH shares are up between 40-58% in less than a year, and I think they still have room to run. Fairfax India isn't doing as well in terms of stock price, but it's executing well and had been buying back shares at higher than the current price, so it still looks like a bargain. 

 

BRK (or a position in an index fund) is a great ballast for your ship, and you don't have to trade actively, but you should keep looking. Eventually, like with BRK, you may spot something that is really cheap, has great management and a long runway, and like Supreme Court Justice Stewart's definition of pornography you should  "know it when you see it" and take action.  Good luck. 

Indeed; its like being married and spotting a great looking woman - there is no harm in looking!  But to your point, I'm always looking and FFH was in fact the most recent addition.

[thepupil]

I manage my money as well as that of my retired parents. Their taxable portfolio is ~50% basis / ~50% unrealized appreciation but the positions at the top (Berkshire / Google / Apple / Black Stone Minerals / Microsoft etc) are 5% - 30% basis with rest in unrealized appreciation creating significant tax friction for selling. Nevertheless as florida retirees, paying 15-23% on trims isn't so terrible and is portfolio is relatively tax efficient. 

 

My own portfolio is traded much more aggressively and is much more concentrated and far less tax efficient; on top of that I'm in a high tax state. My own taxable's portfolios CAGR is much higher than theirs (last 5 years = 25%/yr for taxable, last 5 years = 13% / yr for theirs). TO be clear, this is my main taxable account's CAGR and not my whole portfolio and reflects a very favorable time frame and is obviously not a sustainable return. Way too high. Will be much lower. On a longer time frame, I'm more like SPY +3% (of which I'm proud because as a value luddite, I do the whole "OP'd without tech" nonsense) but much of that +3% has likely gone to taxes. 

 

I think given the tax inefficiency of my approach, their portfolio's risk adjusted after tax return is better than mine and their approach is probably where I'll shake out eventually. the result of my greater aggression has been compounding at a higher rate, but I've also been paying taxes as a I go whereas they build a favorable form of leverage with a DTL. It takes a pretty big delta in returns to overcome taxes. Nevertheless, I do not prioritize tax efficiency because a) so far more or less have paid for the increased taxes w/ better returns b) have built a (top 1% for age I suspect) amount of tax advantaged accounts from $0 over last 13 years so a portion of my investing will always be tax agnostic. 

 

Lately, I've introduced a tax overlay on my own portfolio where I'm long and short various indices, trying to generate $0 of net PnL but lots of gross positive and negative pnl. thus far this has been moderately successful and allowed me to sell all my highly appreciated berkshire with minimal tax friction, but it's also because I just haven't made that much money this year and paid lots of taxes in the past. 

 

long way of saying, I kind of get both sides of this debate. 

 

regarding berkshire, my view of the core businesses competitive position (Burlington vs UNP, GEICO vs Progressive, BHE/utes on an absolute basis) etc has dimmed relative to 3,5,7 years ago. My view of apple's valuation has as well, and the P/B multiple is quite healthy particularly considering just how much is in liquid stuff available at market outside of berkshire. the DTL is more likely to be realized / real as Buff dog trims Aapl, so you're paying quite a premium to an already rich valuation for a pretty big portion of the book. 

 

I've been at $0 of berkshire 2x in 13 years. I may regret it. it remains my parents largest position. I expect it to do okay from here over the long term. 

Edited July 17 by thepupil

[73 Reds]

1 hour ago, thepupil said:

I manage my money as well as that of my retired parents. Their taxable portfolio is ~50% basis / ~50% unrealized appreciation but the positions at the top (Berkshire / Google / Apple / Black Stone Minerals / Microsoft etc) are 5% - 30% basis with rest in unrealized appreciation creating significant tax friction for selling. Nevertheless as florida retirees, paying 15-23% on trims isn't so terrible and is portfolio is relatively tax efficient. 

 

My own portfolio is traded much more aggressively and is much more concentrated and far less tax efficient; on top of that I'm in a high tax state. My own taxable's portfolios CAGR is much higher than theirs (last 5 years = 25%/yr for taxable, last 5 years = 13% / yr for theirs). TO be clear, this is my main taxable account's CAGR and not my whole portfolio and reflects a very favorable time frame and is obviously not a sustainable return. Way too high. Will be much lower. On a longer time frame, I'm more like SPY +3% (of which I'm proud because as a value luddite, I do the whole "OP'd without tech" nonsense) but much of that +3% has likely gone to taxes. 

 

I think given the tax inefficiency of my approach, their portfolio's risk adjusted after tax return is better than mine and their approach is probably where I'll shake out eventually. the result of my greater aggression has been compounding at a higher rate, but I've also been paying taxes as a I go whereas they build a favorable form of leverage with a DTL. It takes a pretty big delta in returns to overcome taxes. Nevertheless, I do not prioritize tax efficiency because a) so far more or less have paid for the increased taxes w/ better returns b) have built a (top 1% for age I suspect) amount of tax advantaged accounts from $0 over last 13 years so a portion of my investing will always be tax agnostic. 

 

Lately, I've introduced a tax overlay on my own portfolio where I'm long and short various indices, trying to generate $0 of net PnL but lots of gross positive and negative pnl. thus far this has been moderately successful and allowed me to sell all my highly appreciated berkshire with minimal tax friction, but it's also because I just haven't made that much money this year and paid lots of taxes in the past. 

 

long way of saying, I kind of get both sides of this debate. 

 

regarding berkshire, my view of the core businesses competitive position (Burlington vs UNP, GEICO vs Progressive, BHE/utes on an absolute basis) etc has dimmed relative to 3,5,7 years ago. My view of apple's valuation has as well, and the P/B multiple is quite healthy particularly considering just how much is in liquid stuff available at market outside of berkshire. the DTL is more likely to be realized / real as Buff dog trims Aapl, so you're paying quite a premium to an already rich valuation for a pretty big portion of the book. 

 

I've been at $0 of berkshire 2x in 13 years. I may regret it. it remains my parents largest position. I expect it to do okay from here over the long term. 

Thanks for that!  I don't view the issue as so much of a debate; rather its more a question of style and comfort level, as well as investing to one's strengths.  To me, buying FFH a few years back well under book value was equivalent to buying single family homes at the height of the financial crisis.  Whereas buying improved real estate for less than the cost of construction while getting the land for free was simply too good to pass up, buying FFH after Covid was at its core acquiring some fine assets well below cost with a steward at the helm who has grown book value at more than 18% per year since inception.  

[Xerxes]

11 hours ago, Charlie said:

Don‘t interrupt compounding unnecessarily.

I got lucky that in 2011 I put everything in Berkshire.

The shares got cheaper and cheaper after Buffett bought all these nice assets in the big recession.

It didn´t make sense.

Since then I bought when it was cheap and nearly never sold.

Yesterday I was first time millionaire with my Berkshire shares.

It really pays to do nothing.  (Especially if you have the right partners.

The only thing you have to do is to recognize what you have and hang on).

 

The best advice on the topic, as usual, Munger gave:

"Don´t be so dumb to sell your Berkshire shares."

"Try to be non-idiotic, all day, every day." 

well done !!

[bizaro86]

2 hours ago, thepupil said:

 

Lately, I've introduced a tax overlay on my own portfolio where I'm long and short various indices, trying to generate $0 of net PnL but lots of gross positive and negative pnl. thus far this has been moderately successful and allowed me to sell all my highly appreciated berkshire with minimal tax friction, but it's also because I just haven't made that much money this year and paid lots of taxes in the past. 

 

 

 

Would you be willing to share more on this? I'd really love to do something similar, because if I could buy something that went up 50% and and something offsetting that went down 50% quickly and with certainty it'd be a huge win.

 

In Canada you can donate appreciated securities and take the deduction at fair market value while not paying tax on the gain, while losses are still deductible.

 

I've sold some real estate this year and am donating a portion of the proceeds anyway, so if I could combine that with some bonus tax efficiency I'd love to do so.

[dealraker]

11 hours ago, Charlie said:

Don‘t interrupt compounding unnecessarily.

I got lucky that in 2011 I put everything in Berkshire.

The shares got cheaper and cheaper after Buffett bought all these nice assets in the big recession.

It didn´t make sense.

Since then I bought when it was cheap and nearly never sold.

Yesterday I was first time millionaire with my Berkshire shares.

It really pays to do nothing.  (Especially if you have the right partners.

The only thing you have to do is to recognize what you have and hang on).

 

The best advice on the topic, as usual, Munger gave:

"Don´t be so dumb to sell your Berkshire shares."

"Try to be non-idiotic, all day, every day." 

I first began interacting in the mid 90's online with Berk investors stating I had $500K of both Berkshire and AJ Gallagher.  Not interrupting this, now together rounding out to $30 mil or so.  In the mid 90's I was by far the least financially successful in a close family of 7 first cousin men and pretty much obsessed with wanting to be a part of their world, one of business ownership and community (volunteer and financial contributions) involvement.  I'm there now and just loving it.  I grew up in a world view of many successful men who preached  never selling a good business.  It was a culture I loved slowly becoming a part of.

[Junior R]

45 minutes ago, dealraker said:

I first began interacting in the mid 90's online with Berk investors stating I had $500K of both Berkshire and AJ Gallagher.  Not interrupting this, now together rounding out to $30 mil or so.  In the mid 90's I was by far the least financially successful in a close family of 7 first cousin men and pretty much obsessed with wanting to be a part of their world, one of business ownership and community (volunteer and financial contributions) involvement.  I'm there now and just loving it.  I grew up in a world view of many successful men who preached  never selling a good business.  It was a culture I loved slowly becoming a part of.

Did you hold any other stock?

[dealraker]

2 hours ago, Junior R said:

Did you hold any other stock?

I mention 1st cousins, relevant because all of us lost our fathers (they were brothers) by 20 (some long before 20), thus our close connections and some of us (4) are in the builders supply and millwork business together (where we have a relatively large investment portfolio also).  I hold all the stocks I inherited in 1975 that haven't collapsed or been merged or bought and basically except my tax free account (which I have shared info about and described here on several occasions) I hold all the stocks I've ever bought.  Angela and I own over 150 stocks in taxable accounts and retirement accounts.

Edited July 17 by dealraker

[Red Lion]

On 7/16/2024 at 9:18 AM, Saluki said:

With a recent ridiculous lawsuit payout for a wildfire where BHE didn't cut the power on a windy day, it's going to be put in a position to cut power more proactively in dangerous situations, but they are compensated/penalized for outages

ridiculous or not the writing is on the wall, and whoever invests in utility companies should certainly beware. 

[73 Reds]

14 minutes ago, dealraker said:

I mention 1st cousins, relevant because all of us lost our fathers (they were brothers) by 20 (some long before 20), thus our close connections and some of us (4) are in the builders supply and millwork business together (where we have a relatively large investment portfolio also).  I hold all the stocks I inherited in 1975 that haven't collapsed or been merged or bought and basically except my tax free account (which I have shared info about and described here on several occasions) I hold all the stocks I've ever bought.  Angela and I own over 150 stocks in taxable accounts and retirement accounts.

150 stocks - Wow!  I have enough trouble keeping up with 5.  As someone who has held my earliest shares since not long after you inherited yours, is there a particular reason why you've never sold any of those stocks?  Surely they all could not have turned out to be great holdings(?)

[dealraker]

9 minutes ago, 73 Reds said:

150 stocks - Wow!  I have enough trouble keeping up with 5.  As someone who has held my earliest shares since not long after you inherited yours, is there a particular reason why you've never sold any of those stocks?  Surely they all could not have turned out to be great holdings(?)

73 Reds, as I've stated here many times, time and price have informed me which businesses were the best, not my personal trading expertise.  I have many stocks in the 100-and-way-up-from-there "bagger" status and yes some crumbs that I have written about here too...you know the go to zero types LOL.  I inherited about $47,000 of stocks in 1975 by the way.   Even then not a lot of money.

 

For decades around here basically everybody either owned or traded Coke and Pepsi for instance.  Counting the spin off of YUM which gave me a bunch of stocks, the outcome of holding Coke and Pepsi since 1975?  Well, I remember the local business titans discussing holding Coke and Pepsi...and I also remember the guys who in the upcycles decided to buy and sell Coke and Pepsi - a repeated pattern.  Luckily I was drafted into an investment club that began in 1954 where for decades I was the youngest member.  These men bought and held and they were the cream of the crop locally in financial matters.  

 

Yea, in the long run the men/women and their heirs who held instead of traded?  Well, these families have one HELL of a lot of money.  

 

This is one hard issue to discuss for me and I'm not good at it.  I find that so few people understand the longevity of holding stocks...and that the web is a place where the time frame focus for owning stocks is hyper short.  

[73 Reds]

7 minutes ago, dealraker said:

73 Reds, as I've stated here many times, time and price have informed me which businesses were the best, not my personal trading expertise.  I have many stocks in the 100-and-way-up-from-there "bagger" status and yes some crumbs that I have written about here too...you know the go to zero types LOL.  I inherited about $47,000 of stocks in 1975 by the way.   Even then not a lot of money.

 

For decades around here basically everybody either owned or traded Coke and Pepsi for instance.  Counting the spin off of YUM which gave me a bunch of stocks, the outcome of holding Coke and Pepsi since 1975?  Well, I remember the local business titans discussing holding Coke and Pepsi...and I also remember the guys who in the upcycles decided to buy and sell Coke and Pepsi - a repeated pattern.  Luckily I was drafted into an investment club that began in 1954 where for decades I was the youngest member.  These men bought and held and they were the cream of the crop locally in financial matters.  

 

Yea, in the long run the men/women and their heirs who held instead of traded?  Well, these families have one HELL of a lot of money.  

 

This is one hard issue to discuss for me and I'm not good at it.  I find that so few people understand the longevity of holding stocks...and that the web is a place where the time frame focus for owning stocks is hyper short.  

Well, you - or I found a fellow Compadre.  Not that it started that way in my case, but it turned out that way almost by default.  When you bang your head against a wall so may times and it always hurts, you try something different to avoid the pain.  Just like for so many here, Buffett's and Munger's lessons resonated.   BTW, been there/done that with enlarged prostate - common in men our age.  Had a Turp some years ago and doc discovered cancer.  Fortunately radiation treatment seemed to work - PSA has been in normal range for several years.  Still go every 6 months for checkups and after 5 years only annually.  Good luck with your upcoming surgery.

[Saluki]

16 minutes ago, dealraker said:

 

 

Yea, in the long run the men/women and their heirs who held instead of traded?  Well, these families have one HELL of a lot of money.  

 

This is one hard issue to discuss for me and I'm not good at it.  I find that so few people understand the longevity of holding stocks...and that the web is a place where the time frame focus for owning stocks is hyper short.  

 

I'm listening to an audiobook now, not related to investing, and the author is very good at phrasing things. I've been writing down some quotes because I like them.  He was talking about his dad trying to explain entropy to him, and why it was so hard to grasp.  He said that "where there is no mental model, there is nothing that the human mind can hold on to. Math is a mental model for abstractions."  Which is why you can explain it easier to people who are good at math. I think investing is like that too. 

 

It's difficult to come up with a metaphor for the buy and hold forever method, but the coffee can anecdote is a good one.  I remember reading about the Busch family and they invested in a lot of things (timber, real estate, amusement parks) but only with the money that was spun off from the beer business.  They never wanted to sell the main tree of financial life.  I think it's the same with the Walmart heirs, the Johnson family, and some others.  And the opposite is true of the Vanderbilt's where there are only a handful left with respectable money, and one of them earned it on his own. 

 

The closest metaphor I could come up with is a Banyan Tree. The original tree doesn't grow to the sky forever, but it drops a root from one of its branches and just keeps moving out indefinitely.  BRK doesn't pay a dividend, but most of the other large caps do, and I think that even if I don't add to large positions like JOE, they will grow on their own and eventually be joined by other ones that are smaller now and I'm still buying while I have a paycheck, and eventually I'll have a big beautiful banyan tree as far as the eye can see. 

[dealraker]

2 minutes ago, Saluki said:

 

I'm listening to an audiobook now, not related to investing, and the author is very good at phrasing things. I've been writing down some quotes because I like them.  He was talking about his dad trying to explain entropy to him, and why it was so hard to grasp.  He said that "where there is no mental model, there is nothing that the human mind can hold on to. Math is a mental model for abstractions."  Which is why you can explain it easier to people who are good at math. I think investing is like that too. 

 

It's difficult to come up with a metaphor for the buy and hold forever method, but the coffee can anecdote is a good one.  I remember reading about the Busch family and they invested in a lot of things (timber, real estate, amusement parks) but only with the money that was spun off from the beer business.  They never wanted to sell the main tree of financial life.  I think it's the same with the Walmart heirs, the Johnson family, and some others.  And the opposite is true of the Vanderbilt's where there are only a handful left with respectable money, and one of them earned it on his own. 

 

The closest metaphor I could come up with is a Banyan Tree. The original tree doesn't grow to the sky forever, but it drops a root from one of its branches and just keeps moving out indefinitely.  BRK doesn't pay a dividend, but most of the other large caps do, and I think that even if I don't add to large positions like JOE, they will grow on their own and eventually be joined by other ones that are smaller now and I'm still buying while I have a paycheck, and eventually I'll have a big beautiful banyan tree as far as the eye can see. 

Superb example, the banyan tree.  I'm often looking at my investment accounts and seeing a few "stocks" with business names I've never heard of.  Didn't know they were being spun off and have no clue until I do some investigation.

 

The goal for us is of course as mentioned many times, to create a sustainable model for those who follow if they choose to use it.  So far our method model is spoken about by them - as the next generations choice too.  

[thepupil]

9 hours ago, bizaro86 said:

 

Would you be willing to share more on this? I'd really love to do something similar, because if I could buy something that went up 50% and and something offsetting that went down 50% quickly and with certainty it'd be a huge win.

 

In Canada you can donate appreciated securities and take the deduction at fair market value while not paying tax on the gain, while losses are still deductible.

 

I've sold some real estate this year and am donating a portion of the proceeds anyway, so if I could combine that with some bonus tax efficiency I'd love to do so.

 

 

 

example: I went long about $xxxK notional of $VT via (synthetic long, short put long call) and short the same of SPX via futures options expiring in december. so long world / short US, not the exact same security, but about 65% or so pretty similar since world is 65% US. I'm invested mostly in US in all accounts including tax advantaged so being short US for this trade wasn't a concern. I lost $xxK on the short SPX leg and was up $xxK on the $VT leg at time I closed out the SPX short and realized $xxK of losses. I then re-established a similar short position in a slightly different US based index (even though 1256 contracts don't have wash sales so this was not necessary). Assuming the $VT leg is still profitable at expiry, I can choose to exercise in December (which will require borrowing a bit of money) which will build the gain into the VT shares but allow me to control timing of realization. there's a number of iterations. 

 

I think the "right" way to do this would be to diversify across tons of highly correlated pairs including individual stocks, but I'm optimizing for pre-clearing as few things as possible at my employer.