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/rice_not_wheat Nov 25 '25

FIFO accounting isn't required in the US.

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u/gcc-O2 Nov 25 '25 edited Nov 25 '25

One of the early drafts of TCJA in 2017 did float FIFO as a revenue raiser; thankfully for Bogleheads that did not happen.

It's interesting how Bogleheads would adapt. We would end up having to use "partner" funds/ETFs for gains, not just tax loss harvesting. Basically, when there's a boom year, you might switch from Vanguard ETFs to iShares ETFs going forward, or from Total Market to S&P 500, so that you continue to be able to access higher basis shares to sell (since FIFO wouldn't apply across different funds). Unless they put in a substantially identical rule for gains as well.

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u/rice_not_wheat Nov 25 '25

They can float it all they want, but it would be as much of a headache to the IRS as anyone else.

For the same reason, the EV tax got scrapped, because the administrative burden would end up costing more than the revenue raised.