ESOP, Options, Restricted Shares holders: When do you sell?

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Ron Scott
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ESOP, Options, Restricted Shares holders: When do you sell?

Post by Ron Scott » Thu Sep 13, 2018 9:25 am

The BH approach to holding individual shares in your investment portfolio would motivate you to sell company equity as soon as you could and reinvest in your AA.

What’s your approach? And in retrospect, have you made more money following your approach?
Retirement is a game best played by those prepared for more volatility in the future than has been seen in the past. The solution is not to predict investment losses but to prepare for them.

mervinj7
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by mervinj7 » Thu Sep 13, 2018 11:34 am

I sell my company stocks as soon as they vest and reinvest according to my IPS. It simplifies my holdings, reduces risk, and allows me to follow the three-fund portfolio strategy. That said, I have NOT made more money following this approach as my company has done almost 2.5x better than the S&P 500 over the last 5 years. Though my coworkers may celebrate, I still sleep better at night (for now). YYMV.

PVW
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by PVW » Thu Sep 13, 2018 12:08 pm

I stopped participating in the ESPP because it has a 1 year holding requirement, the taxation is a pain (PA ESPP tax is designed to be difficult) and I have substantial company investments with options and restricted stock (and salary).

I sold ESPP shares when it was convenient - usually in large chunks. But I still have some ESPP shares that are a small percentage of my portfolio. Lazyness prevents me from selling them. I hold vested stock options that are a significant portion of my portfolio, but, to spread out the taxation, I've been selling them the past couple years and will sell the remaining next year because they will expire. I sell all restricted stock units as soon as they vest.

My company stock has averaged about a 20% annual return since I started. This is less than my average portfolio return. Hindsight says I should have held all my company stock. Foresight isn't as clear, but my conscience is.

Jack FFR1846
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by Jack FFR1846 » Thu Sep 13, 2018 12:17 pm

Company some years ago where I was granted a boatload of options: At year 1, 1/4 of them vested. Sold immediately. Paid off mortgage, bought my wife a car, bought an HDTV (early 2000's when that could cost $10k). Friend at company poo poo'd me and said he was holding and going to make a killing. Stock dove like Red October. Never came back. He remained on that submarine (under water) until leaving the company.

Today: RSU's: eTrade to sell on vest. ESOP: eTrade set to sell on vest. I don't play with stocks anymore. I don't care what the stock is. I take my money when it's offered and put it where it's needed.
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Whakamole
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by Whakamole » Thu Sep 13, 2018 12:40 pm

mervinj7 wrote:
Thu Sep 13, 2018 11:34 am
I sell my company stocks as soon as they vest and reinvest according to my IPS. It simplifies my holdings, reduces risk, and allows me to follow the three-fund portfolio strategy. That said, I have NOT made more money following this approach as my company has done almost 2.5x better than the S&P 500 over the last 5 years. Though my coworkers may celebrate, I still sleep better at night (for now). YYMV.
Same here.

When the company stock is doing well, it usually (not always) means the company is going well. I am already benefiting to a large degree by working for a company that is successful; at the very least more job stability, perhaps greater bonuses/raises/etc. Also the ability to concentrate; I've been at companies at times when there were impending layoffs, and it seemed like most were waiting for the pin to drop.

Letting it all ride on company stock is adding additional risk, a bad quarter can mean your job and your net worth both take a hit.

GuyFromGeorgia
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by GuyFromGeorgia » Thu Sep 13, 2018 12:52 pm

I do some of both. For me, it is about the percentage of company stock relative to my net worth. I try to keep vested stock <=5% of net worth, though sometimes it gets up to 7-8%. I never let it get above 10%, EVER. The interesting thing is that as I get older, my net worth continues to get significantly higher, and so that I means that ~5% worth of company stock is actually a large pile of $$. If things go to plan this fall/winter I might cash out and pay off my house. I'll vest more stock next year.

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Steadfast
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by Steadfast » Thu Sep 13, 2018 1:07 pm

I work for small biotech companies for which ESPP & options are a sizable piece of the compensation package, so I deal with this question a lot.

All of the ESPP plans I've participated in basically guarantee a purchase price 15% below market value during the purchase period. This is an amazing deal and I usually sell these relatively small lots upon acquisition, and take the short term capital gain hit in exchange for the ~15% guaranteed return. It's just a good deal. ESPP is incremental so this isn't a whole lot of money usually. Better to just get it done and move on.

Options are different. These are generally granted in bigger chunks, and upon vesting you have to make the decision to pony up & sell or pony up & hold, depending on your view of the potential of the stock, and in light of short-term vs long-term capital gains tax rates. Although it goes against Bogleheads best practice, here is where I take more risk. Upon vest I usually buy the options and hold them until at least long-term capital gains territory. Once there, I reassess my view of the potential of the stock vs. reaping the return at the lower long-term tax rate (or reaping the loss if it goes that way, which of course can be used against other capital gains you may have via tax loss harvesting). Or sometimes split the difference, sell half keep half. This has worked out for me.

Restricted stock units are a whole other thing. It's just free money. In my industry, acquisitions are common, and when they happen unvested stock tends to get accelerated vesting. So, I generally sell vested RSUs and take my money straight away, because even my larger, unvested share pool will vest upon an acquisition and I'll get paid out there as well. This is a win-win but may be specific to my industry.
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by mak1277 » Thu Sep 13, 2018 1:34 pm

Steadfast wrote:
Thu Sep 13, 2018 1:07 pm

Options are different. These are generally granted in bigger chunks, and upon vesting you have to make the decision to pony up & sell or pony up & hold, depending on your view of the potential of the stock, and in light of short-term vs long-term capital gains tax rates. Although it goes against Bogleheads best practice, here is where I take more risk. Upon vest I usually buy the options and hold them until at least long-term capital gains territory. Once there, I reassess my view of the potential of the stock vs. reaping the return at the lower long-term tax rate (or reaping the loss if it goes that way, which of course can be used against other capital gains you may have via tax loss harvesting). Or sometimes split the difference, sell half keep half. This has worked out for me.
Just curious...why would you exercise the options if you're just going to hold the shares? Why not just leave them unexercised? I would rather just leave them be and not incur the tax today (not to mention being out the cash for the exercise price) upon exercise.

Anyway, for me, I have a mandatory holding requirement of company stock that I have to meet. Beyond that, I exercise and sell my options more or less immediately upon vesting, or at least within the same quarter.

Ron Scott
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by Ron Scott » Thu Sep 13, 2018 5:31 pm

mak1277 wrote:
Thu Sep 13, 2018 1:34 pm
Steadfast wrote:
Thu Sep 13, 2018 1:07 pm

Options are different. These are generally granted in bigger chunks, and upon vesting you have to make the decision to pony up & sell or pony up & hold, depending on your view of the potential of the stock, and in light of short-term vs long-term capital gains tax rates. Although it goes against Bogleheads best practice, here is where I take more risk. Upon vest I usually buy the options and hold them until at least long-term capital gains territory. Once there, I reassess my view of the potential of the stock vs. reaping the return at the lower long-term tax rate (or reaping the loss if it goes that way, which of course can be used against other capital gains you may have via tax loss harvesting). Or sometimes split the difference, sell half keep half. This has worked out for me.
Just curious...why would you exercise the options if you're just going to hold the shares? Why not just leave them unexercised?
FWIW, the strategy of exercising immediately upon vesting and holding the shares is done to be able to get capital gains treatment on incremental growth above the price at vesting.

For shares held in a "KSOP", in a 401K for example, a comparable approach is NUA.

Not BH by any means but I went into 7-figure debt to exercise and hold for several years and it paid off nicely. (Of course it only works if the stock continues to appreciate...but when the party is roaring, WOW!)
Retirement is a game best played by those prepared for more volatility in the future than has been seen in the past. The solution is not to predict investment losses but to prepare for them.

Ron Scott
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by Ron Scott » Thu Sep 13, 2018 5:31 pm

Double post
Retirement is a game best played by those prepared for more volatility in the future than has been seen in the past. The solution is not to predict investment losses but to prepare for them.

mak1277
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by mak1277 » Fri Sep 14, 2018 7:30 am

Ron Scott wrote:
Thu Sep 13, 2018 5:31 pm
mak1277 wrote:
Thu Sep 13, 2018 1:34 pm
Steadfast wrote:
Thu Sep 13, 2018 1:07 pm

Options are different. These are generally granted in bigger chunks, and upon vesting you have to make the decision to pony up & sell or pony up & hold, depending on your view of the potential of the stock, and in light of short-term vs long-term capital gains tax rates. Although it goes against Bogleheads best practice, here is where I take more risk. Upon vest I usually buy the options and hold them until at least long-term capital gains territory. Once there, I reassess my view of the potential of the stock vs. reaping the return at the lower long-term tax rate (or reaping the loss if it goes that way, which of course can be used against other capital gains you may have via tax loss harvesting). Or sometimes split the difference, sell half keep half. This has worked out for me.
Just curious...why would you exercise the options if you're just going to hold the shares? Why not just leave them unexercised?
FWIW, the strategy of exercising immediately upon vesting and holding the shares is done to be able to get capital gains treatment on incremental growth above the price at vesting.

For shares held in a "KSOP", in a 401K for example, a comparable approach is NUA.

Not BH by any means but I went into 7-figure debt to exercise and hold for several years and it paid off nicely. (Of course it only works if the stock continues to appreciate...but when the party is roaring, WOW!)
Is getting capital gains treatment worth losing the earning power of the exercise money? Plus, if you exercise and the price goes down, you lose. If you just wait to exercise you can never lose. I'm unconvinced that this strategy makes sense.

Ron Scott
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by Ron Scott » Fri Sep 14, 2018 8:05 am

mak1277 wrote:
Fri Sep 14, 2018 7:30 am
Ron Scott wrote:
Thu Sep 13, 2018 5:31 pm
mak1277 wrote:
Thu Sep 13, 2018 1:34 pm
Steadfast wrote:
Thu Sep 13, 2018 1:07 pm

Options are different. These are generally granted in bigger chunks, and upon vesting you have to make the decision to pony up & sell or pony up & hold, depending on your view of the potential of the stock, and in light of short-term vs long-term capital gains tax rates. Although it goes against Bogleheads best practice, here is where I take more risk. Upon vest I usually buy the options and hold them until at least long-term capital gains territory. Once there, I reassess my view of the potential of the stock vs. reaping the return at the lower long-term tax rate (or reaping the loss if it goes that way, which of course can be used against other capital gains you may have via tax loss harvesting). Or sometimes split the difference, sell half keep half. This has worked out for me.
Just curious...why would you exercise the options if you're just going to hold the shares? Why not just leave them unexercised?
FWIW, the strategy of exercising immediately upon vesting and holding the shares is done to be able to get capital gains treatment on incremental growth above the price at vesting.

For shares held in a "KSOP", in a 401K for example, a comparable approach is NUA.

Not BH by any means but I went into 7-figure debt to exercise and hold for several years and it paid off nicely. (Of course it only works if the stock continues to appreciate...but when the party is roaring, WOW!)

Is getting capital gains treatment worth losing the earning power of the exercise money? If you just wait to exercise you can never lose. I'm unconvinced that this strategy makes sense.
This strategy is certainly not recommended for the average executive. But if you are willing to take risk AND live in a company with great assets, great management and a great story, the difference between paying ordinary income tax and cap gains can be huge. And if you are willing to take even more risk, and borrow money to finance an exercise-and-hold, you have the opportunity to realize additional growth on the shares you would have sold to finance the exercise. This is a power play.

My attitude at the time was that of an entrepreneur who believed in his opportunity. All in. And that is just not the BH way...
Retirement is a game best played by those prepared for more volatility in the future than has been seen in the past. The solution is not to predict investment losses but to prepare for them.

inbox788
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by inbox788 » Fri Sep 14, 2018 8:03 pm

PVW wrote:
Thu Sep 13, 2018 12:08 pm
My company stock has averaged about a 20% annual return since I started. This is less than my average portfolio return. Hindsight says I should have held all my company stock. Foresight isn't as clear, but my conscience is.
Are you saying "my average portfolio return" exceeded "20% annual return" during the same period? What years? A BH portfolio?

If switching horses got you more, how does keeping the old horse help?

Anyway, it's not so much about performance as much as risk management. Diversification away from putting all your eggs (job & investments) in one basket. On the performance side, we tend to remember the big winners and regret holding on to them, but more easily forget the average performers and losers. Google? Yahoo? Altavista? Infoseek? Then there's Facebook, Twitter, Snapchat, Linkedin, Myspace, Friendster, Geocities, etc.

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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by AlphaLess » Fri Sep 14, 2018 8:24 pm

Could someone working for a public company please clarify how these things work, or comment on whether my understanding is correct:

1. ESPP: periodically, say, every month, you are allowed to purchase stock, at 5% discount (for example) to some closing price. Company incentivizes you to buy at a discount, and there are parameters as to how much you can buy, e.g., 3% of total pay per year (and this needs to spread out over time).

Vesting: is there such a thing, or as soon as you buy, you can sell.
Considerations: short term vs long term capital gains when selling.

2. RSUs: restricted stock units. These are awarded to mid-to-upper management, in form of bonus. Let's say you get a $20K bonus. $10K is awarded as cash. $10K is awarded as RSUs.

Vesting: say, 3 years, cliff vesting (i.e., can not sell anything for 3 years, and at 3 years plus 1 day, you can sell everything).
Income / taxes: taxed at ordinary income, when vested. OUCH. This seems like a TERRIBLE incentive.

Say, you get $10K worth of stock at $100 (100 shares). In 3 years, stock is worth $200. So you are happy. But when it vests, you have to pay income taxes against $20K ordinary income (at, say, 33% marginal rate).

Is there anyway to 83(b) this thing??

3. Restricted stock options. Offered instead or as an optional alternative to RSUs. Say, you receive a $20K annual bonus. They give you half, $10K, in cash. The other $10K is offered as RSU or options. You choose options.

Stock is trading at $100. How many do you get? I assume someone does some pricing of company LEAPs, and decides the purchase price, say $20. At that price, you get 500 options

What is the options expiry? 7 years from issue, 10 years from issue?

Say, they vest according to some schedule: cliff at 3, or 1/3 every year, to 3rd year.

What are the tax consequences?
Once vested, you get hit with ordinary income?

When vested, can you sell the option, vs exercising them?

If anyone can comment on my answers, and questions, I would appreciate them.
"You can get more with a kind word and a gun than with just a kind word." George Washington

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corn18
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by corn18 » Fri Sep 14, 2018 8:31 pm

I get RSU's and sell immediately and invest according to my AA. RSU's are just more income to me. If I think about them any other way, I get cornfused and am liable to do something stupid.

TN_Boy
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by TN_Boy » Sat Sep 15, 2018 9:50 am

Ron Scott wrote:
Fri Sep 14, 2018 8:05 am
mak1277 wrote:
Fri Sep 14, 2018 7:30 am
Ron Scott wrote:
Thu Sep 13, 2018 5:31 pm
mak1277 wrote:
Thu Sep 13, 2018 1:34 pm
Steadfast wrote:
Thu Sep 13, 2018 1:07 pm

Options are different. These are generally granted in bigger chunks, and upon vesting you have to make the decision to pony up & sell or pony up & hold, depending on your view of the potential of the stock, and in light of short-term vs long-term capital gains tax rates. Although it goes against Bogleheads best practice, here is where I take more risk. Upon vest I usually buy the options and hold them until at least long-term capital gains territory. Once there, I reassess my view of the potential of the stock vs. reaping the return at the lower long-term tax rate (or reaping the loss if it goes that way, which of course can be used against other capital gains you may have via tax loss harvesting). Or sometimes split the difference, sell half keep half. This has worked out for me.
Just curious...why would you exercise the options if you're just going to hold the shares? Why not just leave them unexercised?
FWIW, the strategy of exercising immediately upon vesting and holding the shares is done to be able to get capital gains treatment on incremental growth above the price at vesting.

For shares held in a "KSOP", in a 401K for example, a comparable approach is NUA.

Not BH by any means but I went into 7-figure debt to exercise and hold for several years and it paid off nicely. (Of course it only works if the stock continues to appreciate...but when the party is roaring, WOW!)

Is getting capital gains treatment worth losing the earning power of the exercise money? If you just wait to exercise you can never lose. I'm unconvinced that this strategy makes sense.
This strategy is certainly not recommended for the average executive. But if you are willing to take risk AND live in a company with great assets, great management and a great story, the difference between paying ordinary income tax and cap gains can be huge. And if you are willing to take even more risk, and borrow money to finance an exercise-and-hold, you have the opportunity to realize additional growth on the shares you would have sold to finance the exercise. This is a power play.

My attitude at the time was that of an entrepreneur who believed in his opportunity. All in. And that is just not the BH way...
Another risk of the borrowing money is a major stock market crash. Even if your company is indeed a winner (a fact which an insider doesn't actually know, though they often believe they do), a major crash will almost surely take your company's stock with it, leaving you exposed to the risks of borrowing.

I think the risk of holding to get LT capital gains is pretty high. If I had a big win, I'd sell and take the money upon exercise. If the company continues to prosper and the stock continues to rise, you will keep on making lots of money off the options as new ones are granted. I don't know if the tax laws have changed, but it used to be that some exercise and hold scenarios could leave you with a big tax bill if the stock never recovers, even though you actually lost money ....

It's rolling the dice. I'd agree that it is not very "bogleheaded." I once worked for a company that started in the dot com days and is now a fortune 500 company. Depending on when you tried the exercise and hold versus exercise and sell, you could do a lot better, or worse, than the market. For example, there was a seven year stretch (yes I'm cherry picking dates) where it underperformed the US market with quite a bit more volatility. But that was later in the stock's life, when it was less of a high-flyer (albeit still a high-beta stock).

The concentrated risk works out fine if you really have a winning company and the market is running well (90s, 2010 to now). Those risks are less fun when both those facts are not true. All that said, especially if someone is younger and willing to take a risk, making a bet on a company you believe in is not the worst idea in the world, though I still wouldn't borrow money to buy more. And I'd be really clearheaded about the company prospects; many younger employees don't truly grasp the risks.

PVW
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by PVW » Sat Sep 15, 2018 2:32 pm

inbox788 wrote:
Fri Sep 14, 2018 8:03 pm
PVW wrote:
Thu Sep 13, 2018 12:08 pm
My company stock has averaged about a 20% annual return since I started. This is less than my average portfolio return. Hindsight says I should have held all my company stock. Foresight isn't as clear, but my conscience is.
Are you saying "my average portfolio return" exceeded "20% annual return" during the same period? What years? A BH portfolio?
Ugh, I said the opposite of what I meant. The return on my company stock is well above the return of my portfolio.

I don't know what my portfolio has returned, but it's a Boglehead portfolio of roughly 80% stock, 20% bond. My company's stock has averaged 20% return over the past 10 years or so - the stock is almost 8 times higher than when I started. My portfolio has not done this well (but still pretty good).

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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by TigerNest » Sat Sep 15, 2018 3:23 pm

I sell my restricted stock as soon as it vests.

I have plenty of exposure to my company's stock performance through my unvested stock with 4+ year holding requirements. I don't need to add to it by holding on past when I have to. It's also a significant portion of my net worth (~40% if I counted it in the total), so it's important to diversify when I can.

TigerNest
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by TigerNest » Sat Sep 15, 2018 3:28 pm

To add, when I was in my 20s, I got stock options that quickly were deep in the money and worth $12,000 but had a 4-year cliff vesting requirements. I planned to use it to pay for graduate school.

2 months before they vested, the stock cratered on a bad quarter and they ended up worth $1,100. Nothing I could do about it, but that has shaped how I deal with company equity ever since.

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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by drk » Sat Sep 15, 2018 7:05 pm

corn18 wrote:
Fri Sep 14, 2018 8:31 pm
I get RSU's and sell immediately and invest according to my AA. RSU's are just more income to me. If I think about them any other way, I get cornfused and am liable to do something stupid.
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by TomatoTomahto » Sat Sep 15, 2018 7:18 pm

corn18 wrote:
Fri Sep 14, 2018 8:31 pm
I get RSU's and sell immediately and invest according to my AA. RSU's are just more income to me. If I think about them any other way, I get cornfused and am liable to do something stupid.
Yes. OP asked how this worked for us. One company, thank heavens we sold as soon as we could; big win. Another employer’s shares went up after sale, but less than the first company went down. Third company, too early to tell.

We have no qualms about continuing to sell at vesting.
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Re: ESOP, Options, Restricted Shares holders: When do you sell?

Post by inbox788 » Sat Sep 15, 2018 7:34 pm

PVW wrote:
Sat Sep 15, 2018 2:32 pm
inbox788 wrote:
Fri Sep 14, 2018 8:03 pm
PVW wrote:
Thu Sep 13, 2018 12:08 pm
My company stock has averaged about a 20% annual return since I started. This is less than my average portfolio return. Hindsight says I should have held all my company stock. Foresight isn't as clear, but my conscience is.
Are you saying "my average portfolio return" exceeded "20% annual return" during the same period? What years? A BH portfolio?
Ugh, I said the opposite of what I meant. The return on my company stock is well above the return of my portfolio.

I don't know what my portfolio has returned, but it's a Boglehead portfolio of roughly 80% stock, 20% bond. My company's stock has averaged 20% return over the past 10 years or so - the stock is almost 8 times higher than when I started. My portfolio has not done this well (but still pretty good).
Sounds like you lucked out and work for a company that's performed more like AMZN than SNAP. I think there's some survival bias creating the perception that keeping these programs outperforms the market. If there was some alpha, some sophisticated investors would have already have exploited it. The main benefit IMO is the discount/subsidy, which the employee should absolutely exploit, but beyond that, I don't believe there is added benefit.

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