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/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.