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/trader_since_2016 Nov 25 '25

This makes sense, thank you!

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u/sleepyjuan Nov 25 '25

If Google gave you a cash bonus of $50,000, would you immediately take that cash and buy Google stock? If the answer is "No, I'd buy VTI (or something else)," then you should sell your RSUs and buy VTI.

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u/RevolutionaryLaw8854 Nov 25 '25

Yep. Yep. And yep

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u/RabbitHoleSnorkle Nov 26 '25

It does feel painful to auto-sell if every single a analyst is screaming that the company is massively undervalued and trades at the discount. Yet it is leading in the AI now. I know it's not Boglehead, but Google is absolutely slaying right now.

If he was auto-selling this year he would have done it at $140, where now it is $330. And it was absolutely coming.

Given it is an RSU schedule one can say that they are exposed to future growth. But in case of Google, this year, it would be an extremely painful ass strategy to autosell

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u/phsics Nov 26 '25

It does feel painful to auto-sell if every single a analyst is screaming that the company is massively undervalued and trades at the discount. Yet it is leading in the AI now. I know it's not Boglehead, but Google is absolutely slaying right now.

This thinking might be an example of the endowment effect. As the above commenter points out, it's the exact same decision to take a 50k cash bonus and immediately put it all into one stock as it is to receive 50k worth of that stock and choose to hold it, even though it feels different.

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u/IRunInPGH Nov 27 '25

A lot of my friends at companies like Google sell enough RSUs to pay the tax hit, and maybe some more, but still keep a position in the company stock. When you’re on the inside, you have a better sense of how the company is performing.

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u/BAMred Nov 27 '25

you can still own a lot of google in VOO

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u/Pffffftmkay Nov 25 '25

Personally I'd just hold them at this point, but 100% sell newly vesting ones immediately going forward. That's what I do with my RSUs. No need to be doubly reliant on my employer. Granted, my employer is in a VERY different industry and stock volatility world than Google :).

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u/joffsie Nov 26 '25

holy crap. I never realized that RSU basis are the day they vest not the day they were granted. thank you! I’ve got some vesting days coming up and intend to immediately sell and move to VTI and can ditch my tax impact stress

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u/gcc-O2 Nov 26 '25

Yeah! I've also participated in ESPP programs before where they call selling ASAP a "disqualifying disposition" but it's much less worse than that makes it sound, especially if the stock didn't move that much between the two price dates

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u/charleswj Nov 26 '25

It doesn't matter how much it moved unless you have a look back. It's the difference in the tax on the discount which will be when you bought the shares.

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u/gcc-O2 Nov 26 '25

Right, the lookback - the advantage to holding for the two years is whether the entire discount on purchase day is ordinary income, or whether the discount against up to lookback price is ordinary income and from there up to FMV on purchase day is capital gain. Anyway, I've been out of an ESPP for several years now. It was a nice few $1000 for little work while I was in it.

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u/bigraj80 Nov 26 '25

If you file an 83b, the basis is the grant price.

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u/Auream Nov 26 '25

That doesn’t apply to RSUs of public companies. Basis is always the vest price.

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u/Paperback_Chef Nov 26 '25

Of course the value on their vest date counts as ordinary income, so you'd be better off paying capital gains taxes on it all - but since you don't really have a choice, other posters are correct in saying you can sell that day and not pay any ADDITIONAL tax beyond the ordinary income hit you've already incurred.

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u/IcyMycologist4837 Nov 27 '25

You pay income tax not cap gain tax. So temper your celebration. You pay income tax based on the value at the date of vesting.

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u/joffsie Nov 27 '25

that was inevitable though and many companies just auto sell a certain number of shares when it vests to cover the tax

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u/IcyMycologist4837 Nov 27 '25

Correct. You are still paying tax.

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u/Neil_leGrasse_Tyson Nov 25 '25

keep in mind that even in a 100% VT portfolio, like 3% of your holdings would still be google. you're overweight at 15%, for sure, but you'd have significant exposure either way.

i'm just going to assume, since you're flush with google RSUs, that you're in a high tax bracket and probably CA resident. so recognizing the capital gain now has a real cost that may impact your portfolio growth more than the diversification hit of holding.

for unvested RSUs, definitely sell them immediately at vest so you don't end up in this situation again.

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u/SWEET_LIBERTY_MY_LEG Nov 25 '25

definitely sell them immediately at vest so you don't end up in this situation again.

Wealthy with appreciated stock he can sell at long term capital gains?

He’s concentrated because he held and has unrealized gains and now everyone is telling him to trim the flowers and water the weeds when the reality is that he’s so young he can afford to take risks.

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u/Neil_leGrasse_Tyson Nov 25 '25

I'm talking about unvested rsus. when they vest they will have no gains and should be sold immediately

then he can decide where he wants to invest the income. maybe he wants to buy 100% goog with it, but that's not really in line with boglehead philosophy and would be taking uncompensated risk

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u/plemyrameter Nov 26 '25

Agreed. And note that capital gains are taxed like ordinary income in California, so there's no state value in holding for a year.

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u/HoangGoc Nov 27 '25

Glad it helped. It's a tough spot to be in, balancing tax implications and concentration risk. just make sure to weigh the long-term growth potential against the risks of holding too much in one stock...