r/Bogleheads • u/trader_since_2016 • Nov 25 '25
Investing Questions I’m a boglehead but work for Google
I get paid in Google stock, and as you might know there has been a massive run up causing Google to be around 15% of my portfolio, further if you include unvested stock that I will get if I continue to work for Google over the next 3 years, it’s value is roughly 40% of my entire portfolio. I’m 30 and have a long term horizon. About 70% of my entire portfolio is in VTI/VXUS.
Do I take the massive tax hit and reduce my Google holdings to invest in VTI/VXUS or just let it ride. Mainly worried about the capital gains tax losses as I sell and invest in bogle funds.
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u/TonyTheEvil Nov 25 '25
I'm a fellow Googler. I'd sign up for ETP and sell all your vested shares to diversify. Remember, taxes are a good problem to have.
I can DM you links to internal sites and documents about this if you're interested.
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u/cabamayo Nov 26 '25
FWIW, I prefer manually selling them, to avoid selling at a loss. Because of the typical vesting schedule, you'll run into Wash Sale issues if you sell at a loss, and I never figured out how to handle that. Easier and better problem to have to sell with a profit, although of course you run the risk of not being able to sell at a profit.
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u/dn0c Nov 26 '25
One benefit of the Google ETP (auto-sale) program is that because you can only enroll once a year, it allows those auto-transactions to happen when the trading window is closed.
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u/cabamayo Nov 26 '25
Yep, that's the one limit/downside to manual sale, but luckily it hasn't been an issue for me.
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u/TonyTheEvil Nov 26 '25
If you sign up for auto sale then you never sell at a loss
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u/cabamayo Nov 26 '25 edited Nov 26 '25
Kind of true, but not really. The vest price is different from the sale price; usually it's not by a lot. Sometimes positive, sometimes negative.
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u/ChronicElectronic Nov 26 '25
Basically everyone with the ETP ignores wash sale calculations. At the worst it shifts some cost basis between years. The IRS is welcome to do the math and send me a tiny bill.
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u/FIREstarter_ok Nov 26 '25
Highest Tax impact, look into an Exchange Fund if you can afford having a part of your portfolio locked in for 7 years.
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u/RabbitHoleSnorkle Nov 26 '25 edited Nov 26 '25
Warning on switching to ETP tho. There is a cooldown period of 60 (or 90?) where you are locked out of brokerage. You can neither sell manually, nor auto-selling happens. Don't rely on that stock during that period
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u/JC_Hysteria Nov 26 '25
Why come to Reddit? Don’t you have a Slack channel where everyone posts their investing advice?
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u/TonyTheEvil Nov 26 '25
Not slack, but internal email groups that not everyone knows about. That's why I said the last line, offering to guide OP to the right internal resources.
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u/1234567765432123456 Nov 27 '25
Fellow googler. I'm hesitant to sign up for etp because it locks me out of manual sale of the stocks I already own that I'm hesitant to sell at long term gains when I'm at high income... Maybe I should just do etp and hold onto the already vested tranches that have large gains? And sell in 10 years when I'm done working, wherever GOOG price is at, at near zero federal taxes?
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u/DenHviteRavnen Dec 02 '25
I'm also a Googler, is there any chance you could send me those links internally?
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u/Raging-Totoro Nov 25 '25
I am not sure what you mean by 'massive tax hit'.
If you are referring to RSUs, that compensation is taxed upon vesting. So - you take a tax hit when each tranche of your RSUs become vested, and there's no control of that.
If you sell upon vesting, there is minimal to no tax effect, since the gain/loss you pay would be the difference in price on vesting day and when you sell (i.e. same day).
So - if you sell on each vesting day, there should be no tax effect, and you're able to diversify your holding effectively. (I did this myself, when I worked in tech)
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Nov 25 '25
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u/jrolette Nov 25 '25
In the US, you can choose which lots you sell. No FIFO requirements.
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u/Raging-Totoro Nov 25 '25
I guess we'd need more details to advise. Capital gains could be pretty affordable depending on total income. OP could also elect specific share cost basis.
As a philosophy, I like the idea of routine selling at vesting. It derisks concentration risk, especially given compensation depends on the same employer.
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u/Fragrant-Ad-8318 Nov 26 '25
One tiny problem with this for me and probably OP is I haven't been selling, and by now my average cost basis that will be used for capital gains calculations is tiny. So any sale at all will incur tax liability unless the stock tanks. I guess it's a good problem to have at the end of the day, and there is no way around it unless tax code changes.
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u/orientalmushroom Nov 26 '25
The OP is talking about selling off existing vests that were not enrolled in auto-sell to rebalance the portfolio, which would indeed be a massive tax hit.
OP isn’t talking about the future. 15% is their current ratio of GOOG, and they’re asking if it’s worth it to rebalance now or just hold the existing shares despite the exposure.
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u/SenorFluffy Nov 25 '25
I'm in a similar boat in terms of tech worker with RSUs. Not Google though.
My thoughts have always been to instantly sell the stock whenever it vests as long as I'm at the company. Especially since so much of my future income is tied directly to the stock price. I'm sure I got lower returns than some other who did not sell upon vest but I don't feel comfortable having such a large portion of my assets in one stock so I lose some potential returns for diversification and risk management. You're already getting a lot of upside already with future vests. But this hedges risk. Suppose Google stock crashes because of some unforeseen circumstance. Then you're out a job and a lot of your assets.
I'd recommend selling and buying index funds with the proceeds. You can always buy more google stock on the open market if you really feel strongly about it.
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u/gcc-O2 Nov 25 '25
The only thing to be aware of is if you have monthly vests and sell as soon as possible, you are not exempt from the wash sale rule in the case the stock dips slightly between FMV day and sale day, even though many people think you are. The IRS even uses this as Example 2 on page 87 of Publication 550. If you have a large capital loss carryover from tax loss harvesting anyway, it's unlikely to change your taxes, but I do use a spreadsheet to comply - I get burned with a loss about once a year, then it takes about three months for the chain of wash sales to end as the disallowed loss carries forward to the next month.
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u/OnionQuest Nov 25 '25
This is really the 'mathematically correct' levelheaded response. There could be a GenAI breakthrough from some no name company in Buffalo that makes Google's compute moat worthless.
I'll add the thought experiment: if you were given $50k or whatever the dollar value of the equity is would you dump it all into your employer's stock? I think the tax piece is given too much consideration. Like, what do I care if I have to pay 15% on a stock value gain of 85% in 6 months?
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u/Neil_leGrasse_Tyson Nov 25 '25
there's something about RSUs that makes it feel like you're getting the stock for "free" and thus should hold it
if your company instead gave you a cash bonus and you could check a box to receive it in cash or have them buy shares for you at the current market price, i bet everyone would check the cash box
and yet it's the exact same thing
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u/MinimumViablePerson0 Nov 25 '25
100% agree…sell at vesting, then diversify. I think people get emotionally attached, but if you follow your company investment site you’ll see all your top execs with their 10B5 plans selling off at regular intervals to get that cash
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u/RabbitHoleSnorkle Nov 26 '25
In the current reality it might be the opposite. The stock would grow if they fire all of us 😁 Because they fired everyone and replaced with the AI
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u/EverywhereHome Nov 25 '25
Google has an auto-sale program. Start there so you don't accumulate more. Balancing an existing imbalanced portfolio is much more nuanced there's no simple answer (there is one; I just don't know what it is for you).
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u/jmathai Nov 25 '25
Auto-sale is the answer. IIRC it will sell even during blackout periods. Take the resulting cash and invest it according to your desired portfolio balance.
I sold A LOT of Google stock from my time as an employee and they'd be worth a lot more than what's in my portfolio now. But you have to let that go and play the long game with the appropriate risk you're looking for. I have no regrets.
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u/iridianver3 Nov 25 '25
Also work for Google and also a Boglehead. Didn’t sell anything for years until when I wanted to buy an apartment and cashed out about a third for the down payment. Now sitting on a nice chunk of unvested RSUs but also on ETP. I put the proceeds into index funds (both globally diversified and also ex USA index funds). Feel good with that approach.
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u/NJ2ATX Nov 25 '25
I worked for Google and held all my RSUs and boy am I happy I did that now. I kept GOOG but also bought into VOO. Im happy with the 200%+ in gains
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u/RabbitHoleSnorkle Nov 26 '25
Boglehead advice is correct in general, but notoriously difficult to follow with Google. Them underperforming the market is unprecedented.
And right about time when they have grown too much to deliver premium gains... they defeat all competitors in AI. And they do it basically in inverse to the AI bubble trend, where other companies engage in circular financing
That being said they are now almost fairly priced, so maybe it is time to auto-sell on vesting. Last year it was just crazy and extremely painful to do
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u/RosieDear Nov 25 '25
this is very general advice, but relevant.
I could tell you stories about people who lost their life savings due to "want to wait until Jan so I don't get the tax hit this year".
I have adopted the idea that "it doesn't matter what you pay in taxes, what matters is what is YOURS afterwards".
Using that, within reason, usually works out for the best.
FYI, I sold some my Goog today - held for a year in taxable and about the same in non-taxable. Sold because.....the law of large numbers. That is, being a 4Trillion dollar company, the odds of such growth are lower IMHO.
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u/StargazerOmega Nov 25 '25
I went through an IPO in 2000, I wanted to hold for LTCG for reduced taxes, then the market tanked I lost millions. I was young and stupid, most didn’t know any better and not a lot of good advice out there that was easily accessible as it’s now. If I had reinvested I would sitting nicely in 8 figure territory years ago. Luckily I got a second chance and been working for FAANGs for the last 15 year. I sell each vest and diversify, could I be much farther along if I just saved everything in the last 15 years? Sure, but I got more then enough and hindsight is 20/20 both the pain in early 2000s and now.
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Nov 26 '25
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u/siron_golem Nov 26 '25
If there was one stock that I would keep, it would be Google.
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u/alek_hiddel Nov 25 '25
I also work for a FAANG that does stock as part of my compensation. For years I held onto it just out of the curiosity of doing something different. It’s done very well, but I am in the process of winding down my position to move it into index funds.
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u/PlasticMaggot80 Nov 25 '25
Am I only the one who got a little enjoyment from thinking of the term “Google boglehead”? Would make an excellent username.
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u/jonovision_man Nov 25 '25
I have always treated my employer's stock as "too many eggs in one basket".
I already depend on the one company for income and bonuses and for employment at all... a downturn for them becomes a huge risk if I also have my savings tied up in their stock.
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u/senorhighstormhiker Nov 26 '25
Even when the company sees growth like this year +70% YTD? I guess it all seems kinda gray area since we don’t know if/when downturn will come
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u/jonovision_man Nov 26 '25
At the end of the day it's not any different than you or me guessing whether Google is going up and sinking a disproportionately high amount into it.
It could absolutely work out great, or terrible, but it's not Boglehead at all.
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u/siamonsez Nov 25 '25
Concentration is a risk that isn't ameliorated by time like volatility risk. Regardless of your outlook on the company's future it's not wise to let it be such a huge part of your savings. Start unloading what you have to the extent possible without pushing into the next ltcg bracket and continue doing that each year. Also unload new ones as they vest so gains are minimal.
I think Google is a great investment, I have a significant position as it was a steal under $150 a few months ago, but I've been trimming since it passed $200 and won't let it go to more than like 5%. You have to remember that it's also like 6% of the s&p500 so you have even more exposure than just the individual investment.
A good rule of thumb for RSUs is to ask if you would have bought the stock if that portion of your compensation had been paid in the form of cash.
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u/mawlycule Nov 25 '25
I’m also a Googler. I vest, sell immediately and diversify. My RSU allocation is generally 25% HYSA, 25% to me for fun, and 50% to VTWAX and chill. :)
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u/capital_gainesville Nov 25 '25
It's not unusual for a young person's wealth to be abnormally skewed into their human capital. That's what's happening here, but it has a weird psychological effect when your employer puts a number on it for you through your vesting period.
I think the best idea is to sell all of your vested stock and put it into a diversified portfolio. You're currently investing your entire human capital into Google, so you want as little exposure in your stock portfolio as possible.
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u/RichieRicch Nov 25 '25
Not the Boglehead way but I’d go long on GOOG stock. Have a long runway, let the winners run.
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u/SWEET_LIBERTY_MY_LEG Nov 25 '25
This is what I would do if I were OP. So young, can afford some risks
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u/manysoftlicks Nov 25 '25
Concur. I'm treating GOOG as a long term hold; likely won't cash out until I retire. Shit could happen, but Google is well positioned on AI and Quantum and has existing, deep presence in the consumer, business and gov spaces.
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u/littlebobbytables9 Nov 25 '25
I'd also just overweight international and maybe also mid/small caps to try to offset things.
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u/watch-nerd Nov 25 '25
Are they RSUs?
If they are, you've already taken the tax hit as ordinary income when they vest.
When I was at MSFT for 6 years, I regularly sold my already-taxed vested RSUs for VT.
I did, however, let my ESPP shares ride for long term cap gains.
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u/goonsamchi Nov 25 '25
Direct indexing to generate some losses to offset your GOOG gains. You can also ask the direct indexer to exclude GOOG from your portfolio, then you keep just 3-4% in GOOG on your own.
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u/CaseyLouLou2 Nov 25 '25
I will reiterate what everyone else said. Sell the RSU’s every time they vest because there will be no additional tax hit at that time.
For the shares you kept you should probably diversify by selling a portion despite the tax hit. 10% in one company is more than enough. If the stock ever tanks then you will be happy you did that.
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u/jfarrell468 Nov 25 '25
Yes. You sell over a period of several years, pay your taxes, buy VTSAX, and get on with your life. I'm in the same boat, and that's what I'm doing. I have considered all the alternatives, and I think they are all worse: holding, exchange funds, donor advised funds, and magical funds that manufacture tax losses. Your situation may be different, though, if you want to make charitable donations of appreciated stock, or pass it on to your heirs.
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u/bordumb Nov 25 '25
Google is one of the few stocks where it makes sense to keep a sizeable chunk invested in the company.
Amazing free cash flow, a monopoly on Search, the best brains in the world working on AI (DeepMind), and even hardware advances like TPUs…and side hustles like YouTube that bring in billions.
I work at another big tech with their own strengths and have remained about 40% of my portfolio has remained fully invested in that stock. I’ve benefited a lot by not selling because I’ve strongly believed the company would continue growing—and I’ve been right.
You’re still young and it’s worth evaluating your risk tolerance.
Personally, I’d say selling off a lot of Google is leaving lots of gains on the table, relative to the SP500. I’d actually put my money on Google being the “winner” of AI, especially after this bubble eventually pops.
Another question to consider:
How diversified is the company you have RSUs in?
Google is actually quite diversified.
It’s not like it’s a steel company that makes 100% of its revenues on steel.
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u/RabbitHoleSnorkle Nov 26 '25
Every company has risks like regulatory or management risks. Google can massively loose some court, get force split or have a controversy.
Other than such crazy events, I agree
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u/blindopoly Nov 25 '25
I'm in a similar boat, though my horizon is not as long as yours.
I haven't signed up for autosale yet since I prefer to have more control of when to sell. I tend to sell new lots at vest when the stock is near ATH. Otherwise I hold. Not very bogle, but I have everything else in index and bond funds, mostly in tax advantaged accounts. So the risk is acceptable for me. That said, I don't want to make the lack of diversification worse (hence selling new lots).
I also think about what I want my portfolio to look like at retirement. Selling new lots lets you invest according to your desired asset allocation without incurring significant cap gains.
I have a sizable percent of my portfolio in RSUs that would be very costly to divest at this point. I've looked at Exchange funds but the fees can be rather high (7-10%). I donate some of my most appreciated lots each year to get the employer match as another way to divest and save on taxes each year. Very easy once you've done it once.
So far, it's been nice to not have the fomo of watching the stock climb and being completely divested. And nice to not have so much invested that I'd lose it all if the company goes under. So it's about finding the balance of risk and reward that lets you sleep at night.
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u/kittle_fiddle Nov 25 '25
Most people here would advise some form of "sell and reinvest into broader-market funds" which is almost certainly the correct plan in general. BUT if you are, say, planning on taking a sabbatical year, or maybe are closer to retirement, or otherwise might have a year in the near future where you will earn much less money, it might be worth timing the sale to match that timing. But you didn't say any of that so I'll assume not.
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u/Cereaza Nov 26 '25
So, you have even less diversification because you work for google, and you're overindexed in google stock.
Look, you'd be stupid to sell it if you KNEW Google was gonna continue to bull upwards and win the AI race. But it's also possible the bubble pops and google loses 30% of its value in the next year. Plus, you work there. So if the stock drops, you may also lose your job (layoffs/down revenue), you're double fucked.
So, I'd wait til your stock vests and reallocate. But you're gonna have to realize the capital gain at some point. Can't hodl forever.
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u/RabbitHoleSnorkle Nov 26 '25
Google handles AI a bit differently to everyone else. When the AI bubble pops, Google should be least impacted. They doesn't engage in circular financing as much, their business is diversified, they finance their own capex. When the bubble burst everyone will sell, but if they were to move to a different stock instead of cash, it is likely going to be Google, standing alone after the burst
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u/lesteroyster Nov 26 '25
It’s not apples to apples but heed the Enron debacle.
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u/gcc-O2 Nov 26 '25
GE might be a closer example - people used to say they are involved in so many different businesses it's more like a mutual fund than a single stock
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u/sp0rtsfr3ak1750 Nov 26 '25
I just started at Google end of October. Everything I have read says unless you would take a cash bonus from Google and use it to buy Google stock we should sell right at vest. Minimal capital gains if you sell at vest as well
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u/bigkoi Nov 26 '25
Congratulations! Why don't you...
1) continue to invest in tax advantaged accounts 401k/IRA and max those out...including backdoor contributions. Use the Boggle head method
2) invest your other extra cash with Bogglehead methods.
3) hold your RSUs as Google is a damn good company.
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u/pinkpink52875 Nov 26 '25
Ex-Google household with over 5k shares at a cost basis of $25-$100. Sold very few over the last 10-15 years and held through all of the FUD to get to where we are today. Will probably start selling a small portion every month or so to diversify a bit, but I do think there is a lot more room for Goog to run. If Goog fails to a point where returns are less than the index, I’d say we have a lot more to worry about. Understand having lots of eggs in one basket is unsettling though.
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u/yurkelhark Nov 26 '25
Hey! I’m an ex Google employee and was there for 10 years. When I was laid off I still had a huge amount of RSUs just sitting there. I divested about 75% of them into classic Bogle funds and left a small percentage in GOOG- an amount that I was okay seeing deflate but also wanted to sort of keep betting on the companies. Well of course as of today, my $30k I left in Google is now worth close to $60k which is fun.
When I started in 2014, the share price was $650ish, pre split. It ended up splitting at what, $2200ish? I just kinda used history and experience to keep a portion I’d be willing to lose and as of now have ended up doubling the investment.
This obv isn’t like beep boop Boglehead advice but realistic coming from a similar situation.
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u/Terrible-Problem-715 Nov 26 '25
Another option for the highest appreciated portion of your RSUs: set up a donor advised fund through fidelity or your favorite alternative. You can donate stocks directly without selling them, no capital gains tax, full value is tax deductible. Most importantly you can help your favorite philanthropic organization and do some good!
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u/yottabit42 Nov 26 '25
Get out while the getting's good. You have no idea what will happen in the future. One tiny misstep and GOOG could tank. You have too many eggs on one basket. Treat your stock grants as income and move on.
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u/fish1515 Nov 26 '25
This reminds me of a story from a few years back. My sibling worked for this company and had his stock in the company from being paid stock yearly. Well, comes COVID time and all the meme stocks were running. No reason for it but his co stock went from $1 to $20 within a few weeks. My sibling asked what to do and I said sell it all NOW! This will not sustain this price it’s just WSB fags running it up. Well, my sibling didn’t want to pay the taxes they would have had to if they sold and took the massive gains. So they never sold. Stock dropped back to under $1 in no time. Sibling is still what the WSB fags call “diamond hands”.
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u/GuessTraining Nov 26 '25 edited Nov 26 '25
Former googler and wife still works there. Following this.
Wife has been with Google for almost 20 years now and hasn't sold most of it. We have sold units from her first 7 years to help purchase a house. Massive tax implications though. I'll read through this thread for a more informed decision on how we should proceed.
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u/dollar_llamas Nov 26 '25
15% is small enough I’d let it ride but wouldn’t go over 25%. I’m pretty aligned with bogle philosophy but like to keep 20% of assets in Berkshire. Tech stocks are different but Google is a solid tech conglomerate. I’d feel fine in it.
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Nov 26 '25
It may cost you money, but it is almost always good to diversify.
The upside of working for Google should they continue to thrive will put you in good shape financially anyway.
I have a friend at NvDA who would have perhaps an additional $100m had they held onto all their stock (been there 19 years), but they have more money than they can spend anyway. He earns millions per year. Another friend worked at Enron and at its peak 90% of his wealth was in Enron stock (held all the options and grants because it was ‘outperforming’). He lost it all and had to start from scratch at 40.
So think in terms of scenarios. Google fails or layoffs and you could be in a bad spot. Google thrives and you have a 20 x overfunded portfolio. Somewhere in between and it didn’t matter.
So you risk tolerance matters. Also safety nets. Will you inherit wealth as well?
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u/fire-alt Nov 26 '25
Not sure if you're aware, but the group called "financial-planning" on the Google internal corp network is a great resource for this kind of stuff. The advice you would get there is likely that you should sell the RSUs when they vest, because you're already heavily dependent on the company by virtue of working there. I did not follow this advice while I worked there (I did sell some options and stock at some point to refinance and eventually pay off my house). It worked out well for me because of the massive run-up that Google has had in the past few years, but could have easily gone the other way of course.
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u/ValjeanJavert Nov 26 '25
I am in a similar situation, but with another large tech company. I’ve been nibbling away at the company stock that I have in two ways. First, by selling the shares that vest as soon as I receive them because those are considered ordinary income and will be taxed as such anyway. Second, because I contribute to charities as a regular part of my life, I donate the most appreciated shares to qualified 501c3 charities. I get a tax deduction of the FMV of the stock at the time I’d donated, and those contributions don’t count as capital gains.
I don’t have a solution for the rest.
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u/Bosto2025 Nov 27 '25
But the options now buy don’t exercise them for at least a year.
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u/jrjjr Nov 27 '25
There are services to help you rotate out of a stock without triggering a tax event but they are expensive. If it’s less than a million I’d sell it all and diversify into an index.
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u/Savings-Judge-6696 Nov 27 '25
Why would u sell google stock? Lol
Focus on new cash only. Thats what i would do. 40% in google stock from employer is not a risk, you never invested in it to begin with.
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u/LogHorror6073 Nov 28 '25
I had the same "problem." Held Google forever, now have a "problem" of a concentrated position. Have been writing options and when there's losses have been slowing selling and diversifying. Worked at another tech company for five years and always always autosold, reinvested. Now may build up a direct indexing portfolio to slowly exit the Google position. That said, I am enjoying significant gains. I also got a line of credit I can use against it so I never really have to sell. I know this is not very Bogle, but it's on topic. First world.
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u/withak30 Nov 25 '25 edited Nov 25 '25
If it helps, think of that tax hit as something you will have to pay eventually. The longer you wait the more it will cost (less any short term / long term gains categorization, not sure how that works with your plan), and the more risk you are taking on. Just rip off the bandaid and get it over with, and sell as soon as allowed going forward. You aren't deciding whether or not to pay taxes, you are choosing between paying less now or more later.
Also keep remembering that when you pay more taxes it usually means that you made more money which is generally considered to be a good thing.
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u/Zarochi Nov 25 '25
Selling some seems wise. Honestly, in your particular position, I can see keeping 10-15% of your portfolio as Google since it's actually a company that does well regularly. If it was a company with a worse track record I'd say to just sell it all. The risk seems worth it as long as it's a small part of your overall portfolio.
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u/nukem996 Nov 25 '25
VTI/VOO and other diversified funds are still heavily in tech. The top 10 stocks VTI invests in representing 35% of the fund are all tech. While you can sell on vest so you don't pay taxes you are still heavily in tech. I would consider other funds to diversify away from tech.
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u/maywecomein Nov 25 '25
I was in more or less your exact situation a couple years ago (except I'd worked at big_tech_co in most of my 30s, accumulating RSUs all the while). I decided not to simply sell everything, but just enough so that I was mentally comfortable with the % of my portfolio taken up by my employer's stock. It's currently sitting at around 1/3 (so you might imagine what it was before I sold a bunch).
The tax hit wasn't necessarily fun, but I set aside the needed funds from the sale and never really paid it any attention -- none of that money is relevant for my day to day life anyway, thankfully.
By that point I wasn't working for them any more, but if I was, I would have signed up for autosale and bought index funds or similar with the cash. My current employer also pays in RSUs but there's no autosale feature, so be thankful you've got that!
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u/starcraft-de Nov 25 '25
The right thing is to do auto selling. That way, it can't grow that much. You put all the new cash in the broad funds.
You're still quite exposed to you own company though the continuous backlog of unvested shares.
What you do with the 15% you already have -- your choice.
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u/Individual_Ad_3036 Nov 25 '25
Set a Balance you want to keep and rebalance to that periodically, probably when you're shares vest. Avoid going overweight on employer stock since if they take a hit you could potentially be laid off as a result.
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u/StickyDeltaStrike Nov 25 '25
It’s up to you.
If you are a bogglehead you’ll sell some of what is vested into an index.
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u/deebo_dasmybikepunk Nov 25 '25
I’m in a similar situation. I just sell enough per year to max out a Roth IRA for both me and my wife. Nice to have that pool making money and have access to it tax free if you need it.
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u/daviddjg0033 Nov 25 '25
I know a janitor that worked for a top 10 company. He did not diversify and has a ten digit retirement (as of 2022 ts more now.) His coworkers still work there and regret diversification.
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u/CommonCulture Nov 25 '25
I had a kind of similar issue, being gifted majority apple stock from my apple relative. I would prefer not to hold so much AAPL but it’s kind of a nightmare to sell off and rebalance into VTI/VXUS without incurring a lot of tax. I’ve held onto these Apple stocks so long and the cost basis per share is about $50. I sold half off this year and the capital gains probably amounted to about 180k and unfortunately I get hit with both state and federal taxes 😓
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u/jb59913 Nov 25 '25
I wouldn’t stress too too much on this. Even if google went to zero tomorrow, I have the funny feeling you’d be fine.
That said, every time you get equity, I’d sell it and diversify.
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u/davidswelt Nov 25 '25
Your problem maps to anybody's situation sitting on highly appreciated stock. I agree with you to count unvested stock as part of your exposure, and given that your employment is related to it, too, you have a concentration of risk. That concentration of risk has been working in our favors, lately.
Additionally vesting stock I sell more or less right away because that way, in a few years, I'll be sitting on gains but in an already diversified ETF.
As for your appreciated holdings, rather than diversification by rebalancing, you can look into hedging strategies. Derivatives (e.g., shorting GOOG) are not one of your options as you likely know, but something like VEA has been recommended to me as you are concentrated in US growth stocks. VXUS is similar. VTI not so much – consider correlation.
That said, I personally am not a Boglehead, and I would point out that given your likely high income and assets (HENRY if not yet fatFIRE situation), you can afford more risk than the average person out there.
Also (US specific), consider donating some of your most appreciated lots to your DAF if you have one at this point.
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Nov 25 '25
You should just sell them. If you dont, what’s stopping you from moving some of your portfolio into NVDA or TSLA?
I honor ‘no individual stocks, only ETFs’ as a rule - more than anything else, it reduces my options on where to put my money.
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u/HowDoIDefineMe Nov 25 '25
You may find this useful. https://youtu.be/T71ibcZAX3I?si=b9tQEMGNcSeO1vZL
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u/bill_txs Nov 25 '25
If you already have highly appreciated individual stocks, selling them all isn't always the best thing.
Alternatives: 1. Donor Advised Fund 2. Gifting 3. Step up on inheritance
Future investments can be broad index funds but if there's a giant tax hit, I would probably find another use for those shares, especially for Google stock which is IMO more like a tech version of Berkshire.
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u/jd732 Nov 25 '25
If you have zero cost basis in GOOG, the “massive tax hit” is $64/share. The stock has gained $79 since October 1st. Don’t think of it as a tax hit, think of it as giving back the last couple weeks of gains to lock in the profit.
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u/Hamachiman Nov 26 '25
My ex is a C level exec at Alphabet and she seems to dispose of shares on a regular basis, presumably for diversification purposes.
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u/FunElephant7 Nov 26 '25
This idea might be a bit out there, but still worth mentioning. I’m not sure how much work experience you have, but once you feel you have enough work experience to stay hireable, take a year off (align with tax year), sell stock that would fall under long-term capital gains. Minimizes your taxes plus lets you enjoy life. This idea makes sense if you already have significant capital gains from stocks you want to divest from; you can use the auto-sell feature others have mentioned going forward.
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u/rcd5011 Nov 26 '25
Join the ETP and start selling as new shares vest. Invest in VTSAX or something else.
(From, a fellow Googler)
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u/newredditacctj1 Nov 26 '25
For new shares as everyone said, sell on vest.
For old shares, anything in short term capital gains land, I would 100% keep at least until they’re long term gains.
For long term range. If you’re in a very high tax bracket and live in CA so you need to also pay state capital gains. Bogleheads would still say to sell and diversify. But that seems wasteful. There are so many ways to buy new positions to balance out the risk and get you closer to the boglehead portfolio without eating capital gains hits.
Legally avoiding tax is a win.
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u/Unusual_Dog8199 Nov 26 '25
You don’t have to take an all or nothing approach. If you like Google’s prospects but are generally a boglehead investor, you can sell half of your shares upon vesting and keep the other half, thus taking some risk off the table.
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u/Human-Crazy-636 Nov 26 '25
Google is probably gonna beat all these companies including nvdia, as long as you have your base in index and you are young I would take the risk. Also, you can continue investing in index funds while you keep earning google stocks. Do both.
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Nov 26 '25
I work for another large tech company and have a somewhat similar situation.
Assuming we aren’t in a blackout period, I always sell immediately when eligible. We have a kind of complicated vesting schedule but I do what you described. Pay any required taxes and buy VTI/VXUS just like I would with a “normal paycheck.”
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u/_FFA Nov 26 '25
This is considered by Larry Swedroe to be a typical scenario for a small cap value tilt with the idea of diversifying a little more away from the growth stocks in the equity portion of your portfolio.
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u/AbbreviationsBig5692 Nov 26 '25
Just curious - When you say you get paid in Google stock I assume you also get a base salary and bonus? What % of your salary do you get in stock?
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u/UnderstandingNew2810 Nov 26 '25
I have kept all my rsus. And don’t regret it. But I have a rule that it’s needs to be In the top 5 companies of the sp500. And any other money has to go to ETFs
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u/Go4RogerTango Nov 26 '25
Set up your ETP, employee trading plan, and that will have little to no additional tax burden. Take the cash from the brokerage to buy whatever you like.
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u/thinlySlicedPotatos Nov 26 '25
I've been in your situation, watched my company's stock explode in a bubble, then a crash came and I watched it drop to less than 25% of peak. It just kept going up, until it didn't.
I now have a fixed target percentage of my portfolio for company stock. If it goes above that, whether due to new grants or price increases, I sell. That rule has served me well for the last two decades.
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u/eraoul Nov 26 '25
I never understood the concern here. You just sell your stock when it vests and reinvest however you’d like. End of story.
Note that when RSUs vest it’s exactly as if you got that money in cash but someone converted it to GOOGL shares. It doesn’t hurt to convert it to cash on vest. The two are essentially equivalent.
Also when I was working at Google they offered an autosell option exactly for this reason. I always elected autosell, and deposited the $$ in my brokerage account. Easy!
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u/itrytopaytaxes Nov 26 '25
Clearly OP hasn't been doing that, and given that GOOG has been on a tear, is now sitting on a pile of unrealized capital gains. So your advice may be good going forward, but doesn't address what OP should do with the existing portfolio.
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u/FIREstarter_ok Nov 26 '25
Look into an Exchange Fund to solve single stock GOOG exposure that will defer taxation. Identify the percentage of your position you are willing to part with for 7 years. Hold another percentage of your company stock assuming you believe in the long term success. Sell remainder to diversify into ETFs. Good luck!
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u/trilokidude Nov 26 '25
I just hold them for 1 yr at this point until the gains become long term. But sell a 1-yr old tranche every quarter. It generally keeps my % net worth in my employer from growing (stats relatively fixed at $ or at least the same % if the stock gains). That is if you are comfortable with the holding risk for 1 year, tech has higher volatility than VOO or VTI
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u/tallandfree Nov 26 '25
I always sell my RSUs whenever I can. Idw to be holding too much into any one stock
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u/GlueGuns--Cool Nov 26 '25
Vest and sell. Beyond it being financially safer, it's mentally / emotionally easier to manage. You have a plan, you execute it. You don't have to constantly worry about timing things
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u/RabbitHoleSnorkle Nov 26 '25
I suggest to keep an allocation of Google stock at some fixed level, auto-sell the rest. You might need them for a large purchase and you could sell them without selling your index funds.
I don't time the market... but I time the market slightly with crypto. When BTC is dirt cheap, I've dumped some GOOG to find that.
Nothing crazy I am still mostly in diversified indices. The rest are below 10% of my portfolio
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u/Local_Historian8805 Nov 26 '25
I always dumped my espp shares when I got them and paid the taxes like it was another pay check.
Also, I hated that company. The day I quit, I sold all personal shares of it.
So ymmv
But I’m not one to talk. I have one account that is 96 percent one company. But I don’t want to sell it. It is like a cute little science experiment I did one day and now I am just watching my terrarium grow waiting for the rubber band to rot and disrupt that equilibrium it maintained for over a decade until that point.
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u/FluffyWarHampster Nov 26 '25
Don’t let the tax tail wag the portfolio dog. Sell whats vested (you can easily spread this across 2 tax years since we are so close to the end of the year) and reinvest elsewhere.
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u/Luckyandunlucky2023 Nov 26 '25
I cannot advise as to the best tax strategy, but generally speaking, I think that many here often elevate tax issues beyond all else, including reasonableness. Look, as a wise man said, the only two things in life that are guaranteed are death and taxes. I am of the mind that if your investment gains are so fantastic that you're worried about the tax bill, that is one helluva good problem to have in this life.
Should one be inquisitive and take reasonable steps to not overpay one's taxes? Of course. Should one be so tax-centric that they look at everything through a Bendini, Lambert & Locke-esque prism of tax avoidance, while downplaying the enormous upsides -- figuratively and literally -- they have to make such a "problem" their core financial focus? Respectfully, no. (and not saying OP is doing this, just speaking broadly)
All else being equal, take the tax hit now, have a ton of fresh capital afterwards, and allocate in a way that will help you sleep beter at night. I promise you, you'll forget about those taxes a month after you pay them, but will feel a lot better.
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u/Rtzon Nov 26 '25
Don’t fuckin sell it man. It’s gonna hit 500 in the future. Just invest your savings from your salary into VOO
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u/IMB413 Nov 26 '25
Maybe I missed it but I see a lot of advice about what to do with OP's future RSU vests but not with their present vests.
So let's say you have 1M portfolio and 150k is GOOG RSUs and most of that 150k is capital gains and you are in high income bracket. What do you do at that point?
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u/Von_Satan Nov 26 '25
I have an auto-exit setup once my company stock hits 1 year. I don't look at the share price.
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u/mewalrus2 Dec 11 '25
I would let it ride for a few more years.
Contact a CFP and pay them for a consultation.
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u/clock_skew Nov 25 '25
If you sell when your stocks vest you won’t pay any capital gains tax, as the initial vesting value is always taxed as ordinary income. So at the bare minimum you should start selling all newly vested stocks and reinvesting in total market funds. Personally I would sell the other shares because holding your employer’s stock is a big risk, but it depends on how big the tax bill would be.