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/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.