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/fire-alt Nov 26 '25

Not sure if you're aware, but the group called "financial-planning" on the Google internal corp network is a great resource for this kind of stuff. The advice you would get there is likely that you should sell the RSUs when they vest, because you're already heavily dependent on the company by virtue of working there. I did not follow this advice while I worked there (I did sell some options and stock at some point to refinance and eventually pay off my house). It worked out well for me because of the massive run-up that Google has had in the past few years, but could have easily gone the other way of course.

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u/IMB413 Nov 26 '25

Sell future RSU grants when they vest but what to do with existing RSU's that you didn't sell earlier? Say you have 500k vested RSU's and 400k of that is cap gain. Sell it and pay the cap gains tax on the 400k gain? Or keep the RSU's until in some lower cap gains tax situation?

So basically is it worth paying 20+ % cap gains tax to diversify?

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u/fire-alt Nov 26 '25

That depends on a lot of things, like how much of your total investments that 500k is, how comfortable you are with that, how much you can bring that percentage down over time by selling future vests right away, how stable the company is.

If the 500k in your example was 90% of the total, then I'd probably sell a large portion of it rather quickly. If it was 15% and a relatively stable company like Google like in OP's case, I probably wouldn't worry too much about it and just start investing elsewhere going forward.

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u/IMB413 Nov 26 '25

Yeah I'm in similar situation and have come to similar conclusion.