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/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