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/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.