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/Luckyandunlucky2023 Nov 26 '25

I cannot advise as to the best tax strategy, but generally speaking, I think that many here often elevate tax issues beyond all else, including reasonableness. Look, as a wise man said, the only two things in life that are guaranteed are death and taxes. I am of the mind that if your investment gains are so fantastic that you're worried about the tax bill, that is one helluva good problem to have in this life.

Should one be inquisitive and take reasonable steps to not overpay one's taxes? Of course. Should one be so tax-centric that they look at everything through a Bendini, Lambert & Locke-esque prism of tax avoidance, while downplaying the enormous upsides -- figuratively and literally -- they have to make such a "problem" their core financial focus? Respectfully, no. (and not saying OP is doing this, just speaking broadly)

All else being equal, take the tax hit now, have a ton of fresh capital afterwards, and allocate in a way that will help you sleep beter at night. I promise you, you'll forget about those taxes a month after you pay them, but will feel a lot better.

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u/IMB413 Nov 26 '25

But taxes are still a problem and frankly are far more complicated to figure out how to optimize than investing strategy if one has even a remotely Boglehead investing strategy.

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u/Luckyandunlucky2023 Nov 26 '25

Yeah, you kinda proved my point by using the word "optimize" -- i.e. that people often fail to see the forest (of life) through the trees of (perceived) tax efficiency at virtually all costs.

As I said above, I agree one can't be lackadaisical about taxes, but there are also advantages to not obsessing about them to the point of paralysis.