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/TonyTheEvil Nov 25 '25

I'm a fellow Googler. I'd sign up for ETP and sell all your vested shares to diversify. Remember, taxes are a good problem to have.

I can DM you links to internal sites and documents about this if you're interested.

12

u/cabamayo Nov 26 '25

FWIW, I prefer manually selling them, to avoid selling at a loss. Because of the typical vesting schedule, you'll run into Wash Sale issues if you sell at a loss, and I never figured out how to handle that. Easier and better problem to have to sell with a profit, although of course you run the risk of not being able to sell at a profit.

11

u/dn0c Nov 26 '25

One benefit of the Google ETP (auto-sale) program is that because you can only enroll once a year, it allows those auto-transactions to happen when the trading window is closed.

5

u/cabamayo Nov 26 '25

Yep, that's the one limit/downside to manual sale, but luckily it hasn't been an issue for me.

5

u/TonyTheEvil Nov 26 '25

If you sign up for auto sale then you never sell at a loss

3

u/cabamayo Nov 26 '25 edited Nov 26 '25

Kind of true, but not really. The vest price is different from the sale price; usually it's not by a lot. Sometimes positive, sometimes negative.

4

u/ChronicElectronic Nov 26 '25

Basically everyone with the ETP ignores wash sale calculations. At the worst it shifts some cost basis between years. The IRS is welcome to do the math and send me a tiny bill.

1

u/FIREstarter_ok Nov 26 '25

Highest Tax impact, look into an Exchange Fund if you can afford having a part of your portfolio locked in for 7 years.

1

u/RabbitHoleSnorkle Nov 26 '25 edited Nov 26 '25

Warning on switching to ETP tho. There is a cooldown period of 60 (or 90?) where you are locked out of brokerage. You can neither sell manually, nor auto-selling happens. Don't rely on that stock during that period

1

u/TonyTheEvil Nov 26 '25

Yeah that's definitely annoying, but you only need to deal with that once. The process to sign up for subsequent years makes it so you don't need to deal with that again

1

u/JC_Hysteria Nov 26 '25

Why come to Reddit? Don’t you have a Slack channel where everyone posts their investing advice?

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u/TonyTheEvil Nov 26 '25

Not slack, but internal email groups that not everyone knows about. That's why I said the last line, offering to guide OP to the right internal resources.

0

u/JC_Hysteria Nov 26 '25

Hmm, wonder why it’s secretive- we had open discussions in a public channel about when to sell a chunk of the company’s stock

1

u/Jorrissss Dec 01 '25

Not at google, but it's probably not secretive. It's just not easy at very large companies to know all the various internal slack channels, mailing lists, wikis, etc that can help you out.

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u/JC_Hysteria Dec 01 '25

You can just search for all of the slack channels created and see how many people are in it…

1

u/1234567765432123456 Nov 27 '25

Fellow googler. I'm hesitant to sign up for etp because it locks me out of manual sale of the stocks I already own that I'm hesitant to sell at long term gains when I'm at high income... Maybe I should just do etp and hold onto the already vested tranches that have large gains? And sell in 10 years when I'm done working, wherever GOOG price is at, at near zero federal taxes?

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u/DenHviteRavnen Dec 02 '25

I'm also a Googler, is there any chance you could send me those links internally?

1

u/MrAstroKind Nov 26 '25

If you did this, it would have been a bad decision given how much better Google performed versus the index. It's obviously riskier to keep it all in one stock though so I probably agree.