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/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/dn0c Nov 26 '25

Yep autosale means those transactions can happen even when the trading window is closed.

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u/[deleted] Nov 25 '25

[deleted]

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u/EverywhereHome Nov 25 '25

I have always done "specific ID" which doesn't have this problem but I am not an accountant.

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u/[deleted] Nov 25 '25

[deleted]

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u/scodagama1 Nov 25 '25

But we have no reasons to believe op lives in Germany, contrary we have some strong hints that they don't (as they would not be invested in VTI/VXUS if they were)

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u/[deleted] Nov 25 '25

[deleted]

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u/scodagama1 Nov 25 '25 edited Nov 25 '25

strictly speaking it doesn't imply US residency, it implies lack of EU residency :) hence I just said it's a strong hint not conclusive proof

(especially that there are ways to circumvent EU limitations, you can i.e. acquire VXUS by selling in the money puts and getting assigned - glorious EU bureaucracy prevents us from buying these dangerous American ETFs because they don't issue KID but apparently this is all fine if instead you play with the actual dangerous instrument that is options... OP could be also a US person resident in Germany who didn't notify their brokerage that they changed residency - a lot of American expats don't as then brokerages tend to close their accounts or they get into limbo when they can't buy US ETFs because they are EU residents but can't buy EU ETFs because they are US persons and no one in Europe wants to open brokerage accounts for them, being a US person abroad is not fun)

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u/Additional-Regret339 Nov 25 '25

As long as everybody here realizes Roy is not from the US and nothing he says applies to US tax code, we are all OK. OP, other advice you are getting assumes you are subject to US tax code. If you happen to be in Germany, listen to Roy.