How to manage large distribution of stock in one company

When I made my first big divestment of company stock (to cash initially), I gave myself 2 years to average quarterly into the market. I didn't worry about opportunity loss over those next two years, which turned out to be a good thing as it was 1999, and I got better prices as time went on. I didn't worry about "getting the portfolio performing" in the short term, but rather focused building a good long-term portfolio. I did have a few years expenses already set aside.

If my company had been bought out by an acquiring company, and I had already had to pay cap-gains on what I owned, I would be strongly tempted to sell most of the acquiring company's stock unless I thought there was something very special about it.

I had already selected an asset allocation and a set of mutual funds to fulfill that allocation when I divested. Still - averaging in you have time to tweak things if you want to change some funds around. Once you are mostly invested, there tend to be significant tax consequences for selling an asset, unless the markets sell off strongly in which case you can tax loss harvest while changing funds.

Audrey
 
Well, I got to ER very early by doing the exact opposite - staying concentrated in company stock until it was big enough to diversify, pay my cap gains taxes, and retire.
I think you're one of the very few who didn't get pecked to death by black swans. I wish there were good studies & stats on the ratio of successes to flameouts in your situation-- 1:10? 1:20?

Same situation as the military-- a 20-year retirement looks like a pretty sweet deal as long as you overlook the ones who are killed or disabled.

I remember a story told by one of this board's members. He religiously executed his options and sold out as soon as they were available, for about a decade was regarded as an idiot, and then ER'd. He was at a co-worker's house one day, saw some paperwork she'd left on her table, and commented "Hey, your options are worth $7M! You could ER right now!!" Her response was "I guess I could, but I want to travel." She held on and she's still working.

I've been watching a lot of startup founders hold on to their stock. However their attitude is that they're going to keep it as long as they're in the business, and they're usually never going to retire in the first place.
 
I have owned my shares in the acquired company outright for almost four years, and I will be paying long term capital gains in 2010 on both the cash and stock components of the acquiring company's payment for those shares. My basis in the acquiring company's stock will be its price on the closing date (probably 11/30/10), so a quick sale would not result in much of a gain or loss.
It seems you have no short term capital gains liability. Why then wait one year if you feel it is unwise to hold 56% in one stock?

getting a high price for the sold stock, and paying a low price for the purchased assets.
./.
4. After 12 months, begin selling the stock in tranches when its price is high in order to fund ongoing dollar-cost-averaging into the desired asset allocation.
Of course, the opposite might also happen – your stock price is lower and the diversifying assets are all more expensive. Or, your stock price is unchanged but other assets have risen. Holding to convert short term gain into long term gain is not the same as holding and hoping for long term gain.

Not selling everything now because you don’t know what to do makes sense. Two things you can do now:
1. Use some of the cash to build a CD ladder to cover three years of expenses.
2. Allocate more of the cash to a money market account covering two years of expenses.
You can also get some very good ideas for asset allocations at bogleheads, here, and also reading a couple of books. William Bernstein is a great first step, and there are other authors also with excellent credentials. Efficient Frontier
 
I think you're one of the very few who didn't get pecked to death by black swans. I wish there were good studies & stats on the ratio of successes to flameouts in your situation-- 1:10? 1:20?
I think I was one of the few in the late 90s who wasn't retiring or suddenly wealthy because of a sudden and unprecedented run-up in my company's stock. My company was more of a sleeper. It seems that many folks experienced a sudden, unexpected run up of net worth in 98, 99, and hung on trying to maximize gains before exercising options. That was not my situation as I already owned all my stock outright with a very low basis. It just happened to coincide with the same time period. I had had co-workers who retired a few years before me, and a few years after. I think each person basically did so when they met their magic number.

I did divest as soon as I had enough to comfortably retire. Your example was of a person who had more than enough but hung on for various reasons. Maybe they weren't really ready to retire. I bet that happened to a lot of folks.

IMO the probabilities don't ultimately matter. Each situation is unique. You have to decide what kind of risks make sense in your own personal situation.

Audrey
 
as i work for a large "energy" company, I can't help but think, "what if I worked for BP?" (no debate on if BP is a "good company" needed, us peons have very little control or knowledge of what is going on elsewhere).

My husband recently retired from a company adversely affected by the oil spill through no fault of its own. Last year the company did very, very well compared to its industry peers (and DH got a really nice bonus). This year the same company, same management, same good employees is at the bottom of the barrel and the employees won't get that bonus.

DH told me that when he told people he was retiring a number of people told him they had planned to soon retire but now couldn't. Why? Company makes matching 401k contributions in company stock. Many of them have held onto the stock all along and it now forms a large chunk of their 401k.

When DH and I got married I told him it was foolish to keep company stock in his 401k (this was pre-Enron but it was obvious to me). He groused a bit but over the years we would let the stock build up a bit but sell it before it became a significant part of his portfolio.

Since the oil spill the company stock went down but it had no real impact on him since he had so little of it. However for some people it meant they couldn't retire right now.
 
Marc, I don't see the short term tax liability if you are at basis, so why take the risk of holding 12 months. Anything that can go up 90% in 17 months can go down 90% in 17 months.
I don't see a need to average out or average in. If you lump sum out you can lump sum in without taking on equity risk, the only thing that happens is you exchange single company risk for a safer alternative of total market risk (assuming you buy vanguard total market fund, maybe an S&P 500 fund) and it sounds like you'll pay off some debt and set aside 5 years cash and cd's so again a much more stable set up.
The fact you want about 5 years of cash and cd's on hand suggests a much more conservative AA than someone who would hold 56% of portfoloio in a single stock.
Asset Allocation should be based on willingness need and ability to take risk. In your case you don't appear to have the need. So even if you're willing why do it?
To my thinking if you really feel you know the industry and the company and you want to be a gambler keep enough of the stock to represent 5 or 10% anything over that is tough to figure.
I would also repeat the advice to look at a hedge to ensure you protect what you have from now until this deal closes.
Plenty of fun figuring out exactly what AA and fund choices you might like but the easy choice is get rid of the single stock risk.

Good luck!
 
When I made my first big divestment of company stock (to cash initially), I gave myself 2 years to average quarterly into the market. I didn't worry about opportunity loss over those next two years, which turned out to be a good thing as it was 1999, and I got better prices as time went on. I didn't worry about "getting the portfolio performing" in the short term, but rather focused building a good long-term portfolio. I did have a few years expenses already set aside.
I'm reluctant to pursue a strategy that ensures that the portfolio will lose real value in the first couple of years due to inflation and withdrawals not balanced by sufficient dividends, interest, and/or growth. To get comfortable with it, I think I would need to develop a more quantitative understanding of the historical benefits of dollar cost averaging when compared with immediate deployment in dividend-yielding equities.
If my company had been bought out by an acquiring company, and I had already had to pay cap-gains on what I owned, I would be strongly tempted to sell most of the acquiring company's stock unless I thought there was something very special about it.
It’s clear from all the recent remarks that this is the consensus advice. I see now that I miscommunicated and caused many to think that the possible one-year wait was for favorable tax treatment on the entire asset. I was just thinking that it would be nice to be able to pay at the long term rate for incremental gains as I sold profitable tranches periodically to support a gradual transition into the desired AA. Plus I’m having difficulty letting go of the uncommonly high (8.4%) dividend yield. The idea that the portfolio can earn a year’s withdrawal, an inflation adjustment, and then some through the utter sloth and inertia of simply holding the stock they give me resonates emotionally even though I know it's not the smart play.
 
You are probably already aware that LT cap gains tax rate will likely be higher in 2011 as will the tax rate on qualified dividends. This should be factored into what you decide to do.
 
Really appreciate all of your ideas and advice - very helpful! I would like to clarify one point - this is not a stock option scenario. I have owned my shares in the acquired company outright for almost four years, and I will be paying long term capital gains in 2010 on both the cash and stock components of the acquiring company's payment for those shares. My basis in the acquiring company's stock will be its price on the closing date (probably 11/30/10), so a quick sale would not result in much of a gain or loss.

Also, I'm not receiving dividends today as I won't take possession of the acquiring company's stock until closing. The first dividend should be granted on 12/27/10.

My biggest concerns with a quick sale are knowing what to buy, making the purchases quickly enough to get the portfolio performing, getting a high price for the sold stock, and paying a low price for the purchased assets. If not for the single stock concentration risk, I would

1. Use some of the cash to build a CD ladder to cover three years of expenses.
2. Allocate more of the cash to a money market account covering two years of expenses.
3. Over the first 12 months, dollar-cost-average the remainder of the cash into longer term investments that improve the overall asset allocation.
4. After 12 months, begin selling the stock in tranches when its price is high in order to fund ongoing dollar-cost-averaging into the desired asset allocation.

I like this idea because it mitigates all of the "sell it all on Day 1" risks and lets me come up to speed more slowly and systematically.

Of course, the risk is real, which is why I'm so interested in all of your thoughts! :)

A few years before retiring from Intel I had 76% of my assets tied into the companies stock. Normally, for someone with a concentrated position. I'd discuss the use of covered calls and collars to slowly divest over time and minimize the tax consequences. Frankly you situation is much easier and Nords is right. You should sell a large portion of your position and do most of it before the end of the year. Set a goal to get your position down to 20% (max) <10% (preferred) within a year.

Lets exam the good reasons for maintaining a concentrated position.

1. You are officer of the company and you have corporate/sec regulations that make it difficult to sell.

2. Your position and/or tenure give you special insight into the companies future prospects that is better than an analyst.

3. There are tax advantages for postponing selling

A common but not good reason is
4. An emotional attachment to the company.

Now for me and many other people 2-4 are pretty common. In your case you haven't worked a day for the acquiring corporation so
neither 2 or 4 apply. In fact I'd argue that #3 taxes makes a strong case to sell now.

If Congress does nothing (and it seems pretty likely to me) the Bush cuts expire and capital gains jump from 15-20%, dividend income is treated as ordinary income. Even if Congress actually does something I find it hard to imagine that maintaining "tax cuts for the rich" is something that is going to pass. Even if they maintain the 15% capital gains rate and special rules for dividends, I suspect that somebody selling several hundred thousand (or more) worth of stock is going to be considered rich. So why not act this year and take advantage of the lowest capital gains we are likely to have for sometime.?

It seems to me that only two reason you have for not selling is fear that I sold at the right time and I don't know what to put the money in.
For the first one you certainly can apply dollar cost averaging to get you out of the position, but do it quickly 6-12 months. As for the second one, right now I hate all investment options, but I hate dividend paying stocks slightly less than the other choices, and the 5% Penfed CD doesn't suck too much. However all of other investment dilemmas you face, really pale compared to having more than 1/2 of your assets in a single company.

Finally a word about dividend stocks, when I first came on to this forum I thought dividend stocks were Nirvana, sure you need some cash and some bonds but dividend stocks were great because the gradually increased dividends. Even if the price dropped 50% you didn't care much because your income remained constant. This seemed true up until fall of 2008, when every bank stock I own slashed its dividend and even quasi-banks like GE followed suite, and finally Pfizer cuts its in 1/2. Suddenly my dividends don't look as good as bonds (except for GM bonds :)) and no where near as good as a CD.

Imagine if you were one of the founders of an small oil firm acquired by BP over the last year or so, AFAIK they would often give you a choice of BP stock instead of cash. You are comfortable collecting the prodigious dividend checks and enjoying your retirement until the spill happens. Now stock drops by almost 1/2 and the dividend checks? The stop for who knows how long. I bet plenty of those folks wish they had diversified.

To summarize in the words of Cramer sell sell sell. :)


BTW, I had very enjoyable few years as kid in Evansville.
 
I'm reluctant to pursue a strategy that ensures that the portfolio will lose real value in the first couple of years due to inflation and withdrawals not balanced by sufficient dividends, interest, and/or growth. To get comfortable with it, I think I would need to develop a more quantitative understanding of the historical benefits of dollar cost averaging when compared with immediate deployment in dividend-yielding equities.
I think you are unrealistic in thinking that real value loss is assured. You just don't know what will happen during the first couple of years. There might be deflation instead of inflation. There might be a market selloff instead of a gain. That is why people hedge their bets when investing a lump sum.

If you plan a dividend investment strategy instead of a total return approach, that is another matter. But prudently investing for dividends requires an experienced stock investor and a lot of hard work researching and then tracking. There are a few on this board who are experienced in this. And many of them avoid stocks with an unusually high dividend yield as it often signals a serious problem such as the dividend is likely to be cut in the near future - but you have to know enough to evaluate the company's risks and evaluate it with respect to other companies in the same business. I think you are unrealistic to think you can pick winners right off the bat unless you are an experienced stock investor.

Audrey
 
The idea that the portfolio can earn a year’s withdrawal, an inflation adjustment, and then some through the utter sloth and inertia of simply holding the stock they give me resonates emotionally even though I know it's not the smart play.
Yes, but can it survive?

A portfolio can also earn a year’s withdrawal, an inflation adjustment, and then some when it is allocated among asset classes that combined offer much of the upside while limiting the downside, and with substantially greater survivorship potential.

As to the high dividend, two comments:

High yields, whether in dividends, bonds, or savings accounts, are always a sign of increased risk. The higher the number the greater the risk, no exceptions. Nothing wrong with that as long as you are capable of assessing and accepting it.

Over a 50 year retirement plan dividend growth is much more important that current yield.
 
I don't have a lot to add to the discussion except to say that VA Collector's story about his devastating losses from just this scenario still haunt me (and I'm not exaggerating).

I cannot imagine going through the same thing and would do whatever it took to diversify out of a possibility of experiencing the same nightmare. Nords is right; investor psychology is a huge part of what we do as investors (or as investment professionals).

I've used Va Collector's story countless times to talk about these very real risks and the heartbreak that can come from not mitigating them to the best of your ability.
 
I didn't see the very high yield before I posted. In my mind a generous dividend in this environment is 5%, 8.4% activates the flashing yellow lights, and "if it looks too good to be true it probably is" sign.

I check Morningstar database of the 10,000+ stocks they cover only 141 have a dividend yield of >8%. Now while there are probably a number of those 141 which have good prospects of maintain their dividends (and I've even own some of the names in the past, like shipping companies and oil MPs). Looking at the list their are lot of troubled companies, in many case the M* analysts believe that the companies will have trouble maintaining the dividend. Obviously you want to check out all of the information about the company.
 
I'm reluctant to pursue a strategy that ensures that the portfolio will lose real value in the first couple of years due to inflation and withdrawals not balanced by sufficient dividends, interest, and/or growth. To get comfortable with it, I think I would need to develop a more quantitative understanding of the historical benefits of dollar cost averaging when compared with immediate deployment in dividend-yielding equities.
It’s clear from all the recent remarks that this is the consensus advice. I see now that I miscommunicated and caused many to think that the possible one-year wait was for favorable tax treatment on the entire asset. I was just thinking that it would be nice to be able to pay at the long term rate for incremental gains as I sold profitable tranches periodically to support a gradual transition into the desired AA. Plus I’m having difficulty letting go of the uncommonly high (8.4%) dividend yield. The idea that the portfolio can earn a year’s withdrawal, an inflation adjustment, and then some through the utter sloth and inertia of simply holding the stock they give me resonates emotionally even though I know it's not the smart play.

Best of luck (seriously!). Keep us posted on how it works out. Just be clear that one should not confuse a good outcome with a good strategy.
 
The issue you have to deal with is not the likelihood of a bad outcome but the consequence if the price falls and does not eventually fluctuate back up.

As I see it, this is the sole issue. All else is noise. If you gamble, and that is what you will be doing if you decide to let it ride- perhaps a short odds gamble, but a gamble none-the-less- then you have (according to you) a good chance of coming out richer than if you sell right away. However, if you lose you are screwed.

Worrying about what you will do with the money, whether you will DCA, etc., is way down on the list of things to think about.

Also, many of these issues can be finessed by hedging your position as suggested by Brewer and I believe others.

Ha
 
Thanks again, everyone, for investing so much time and effort helping me see this decision more clearly. Your stories and passion are very convincing. And reading VaCollector's story really made me swallow hard. The upside isn’t nearly enough to warrant assuming the downside risk. That said, there are no storm clouds anywhere near this company or sector at this time, and I’m not going to pay to hedge my risk while I wait to take possession of the stock in December. I’ll sell it soon thereafter, dump it all in a money market fund, and begin dollar cost averaging into a planned asset allocation over the next 24 months.

In the meantime, I’m going to spend my time reading some of the links and books that you all have recommended. I need to figure out what to buy, how to manage the taxes, and why dividend investing is harder than total return investing. :)
 
In the meantime, I’m going to spend my time reading some of the links and books that you all have recommended. I need to figure out what to buy, how to manage the taxes, and why dividend investing is harder than total return investing. :)
On the latter:

Dividend investing pretty much requires owning dividend-paying stocks directly. Total return investing is easily done via mutual funds. It's a lot harder to manage a portfolio of stocks than of mutual funds. The former requires research, frequent monitoring and (hopefully) not-as-frequent tweaking. The latter can be done with simple annual rebalancing, otherwise forget about it.

Audrey
 
i just dumped all my company stock today. it went into my normal allocation, almost doubling bonds (currently 8%, 15% will go into bonds). I also got into a new fund, VINIX.

curious thought as i walked through the office building to my assigned cell, i work in the old enron building.

feels good. i enjoyed reading this thread. and although not directly related to the OP, it pushed me to do what i have been wanting to do for the last 6 months.
 
Dividend investing pretty much requires owning dividend-paying stocks directly. Total return investing is easily done via mutual funds. It's a lot harder to manage a portfolio of stocks than of mutual funds. The former requires research, frequent monitoring and (hopefully) not-as-frequent tweaking. The latter can be done with simple annual rebalancing, otherwise forget about it.
Ah, I understand now. Yes, I'm convinced that I need to follow the total return approach in the near term. I just bought

http://www.amazon.com/Investors-Manifesto-Prosperity-Armageddon/
http://www.amazon.com/Four-Pillars-Investing-Building-Portfolio/
http://www.amazon.com/Bogleheads-Guide-Retirement-Planning/

and hope to use them to set a safe and profitable course in December.

Currently I'm interested enough in investing that after retirement I may carve out 1-2% of the portfolio - most of it taxable but some of it tax-advantaged - and try as a hobby to recreate the asset allocation of the overall portfolio using individual equities and fixed income investments in hopes of beating the market safely.
 
I also recommend this: Amazon.com: The Informed Investor: A Hype-Free Guide to Constructing a Sound Financial Portfolio (9780814472507): Frank Armstrong III. His other later books might be worth a look.

It helped me design my portfolio. At the time I was designing my long term portfolio, Frank Armstrong's material was available on the web free. It was really good in terms of how-to nuts and bolts portfolio design and withdrawal strategies.

I still probably made something too complex in terms of allocation - a lot of asset classes. You can keep the fund selection simple with a few judicious balanced funds, or a balanced fund as a base, and a diversified bond fund if more bonds needed, and a foreign equity fund for a little more equity diversification. Simpler is usually better.

Audrey
 
Just in case anyone wonders how this all turned out ...

Closing was 12/2, and the stock was registered and delivered to my new deal-created Computershare account on 12/6. Computershare was willing to sell it as early as 12/7 for the low low price of $25K - they exact a substantial per-share commission. As someone accustomed to the $7/trade Scottrade price, I just couldn't bring myself to do it and elected instead to transfer the shares to my new Vanguard account. As luck would have it, the stock rose most of the week and reached a new 52-week high on 12/15, the day before it arrived in my new Vanguard account. Yesterday (12/16) I sold it all and immediately bought the equity portion of my asset allocation, which today is

VMLUX (11%) Limited Term Tax Exempt
VWIUX (29%) Intermediate Term Tax Exempt
VTI (24%) Total US
VBR (6%) Small Cap Value US
VNQ (6%) US REIT
VEU (18%) International - Europe, Pacific, Emerging
VWO (6%) Emerging

The sale price was 23.5% above the level established when the 8/17 acquisition deal was struck, so I benefited greatly from the four-month lock-in period.

What a relief to shed the single stock risk!

Anyway, thanks once again for cluing me in to a simpler, safer investment approach. Your comments, the recommended books, and bogleheads.org have been very influential.
 
Glad it worked out and you were able to allocate in a more diversified way.
 
Glad it worked and that looks like an excellent AA. (I wish I could convince myself to have 24% international.)

It is also nice to know that boards advice is sometimes followed.
 
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