Investing General Discussion

Haus · 2026-05-13T21:37:26-0400

I'm struggling right now because we're closing at ATHs, my own company's stock is bouncing around it's ATH and has surged (and I'd out and out say spiked in the last couple weeks). Everything is coming up Milhouse.....

Yet the part of me that also had a lot of company stock options through the dot com crash keeps tapping me on the shoulder.

I honestly hope

M Power s chart and

Cad are right and I'm just stock doomering.

If my worst financial concern goes back to being how to diversify out of my outsized pile of company stock with minimum tax impact I need to be ready to tell myself to shut up and enjoy things.

M Power · 2026-05-13T21:43:47-0400

Haus said:
I'm struggling right now because we're closing at ATHs, my own company's stock is bouncing around it's ATH and has surged (and I'd out and out say spiked in the last couple weeks). Everything is coming up Milhouse.....

Yet the part of me that also had a lot of company stock options through the dot com crash keeps tapping me on the shoulder.

I honestly hope M Power s chart and Cad are right and I'm just stock doomering.

If my worst financial concern goes back to being how to diversify out of my outsized pile of company stock with minimum tax impact I need to be ready to tell myself to shut up and enjoy things.

A lot of wealth advisors would tell you that cashing out of company stock ASAP after vesting is the smart play because you have less control over company stock and it's much safer putting into S&P500 long term than chancing it. The company could fire you and make you have nothing depending on reasons. They can dilute your shares as well. Of course, this could blow up in your face if the company is a Google or Facebook but overall it's the smarter play. You do need to take taxes into account though if you're cashing out alot.

Gravel · 2026-05-13T21:51:29-0400

Haus said:
I'm struggling right now because we're closing at ATHs, my own company's stock is bouncing around it's ATH and has surged (and I'd out and out say spiked in the last couple weeks). Everything is coming up Milhouse.....

Yet the part of me that also had a lot of company stock options through the dot com crash keeps tapping me on the shoulder.

I honestly hope M Power s chart and Cad are right and I'm just stock doomering.

If my worst financial concern goes back to being how to diversify out of my outsized pile of company stock with minimum tax impact I need to be ready to tell myself to shut up and enjoy things.

Market trades within 5% of an ATH something like 85-90% of the time.

It's why time in the market beats timing the market. Human nature is risk averse and the market gives no shits.

As far as company stock, I'm not a fan. Because you already have a ton at stake in your company since your entire salary is already tied to its success. If the company goes tits up, not only is your investment cooked, so is your salary.

Haus · 2026-05-13T21:59:44-0400

M Power said:
A lot of wealth advisors would tell you that cashing out of company stock ASAP after vesting is the smart play because you have less control over company stock and it's much safer putting into S&P500 long term than chancing it. The company could fire you and make you have nothing depending on reasons. They can dilute your shares as well. Of course, this could blow up in your face if the company is a Google or Facebook but overall it's the smarter play.

I rode out the vesting of my shares. Last shares vested a couple years ago. At the time I considered that, but the fact that during the first year (pre-vesting schedule starting) my company shot up ~200% so I let it ride a bit longer.... between then and end of vesting (3 years later, 4 years total) it went up another ~225% and I got kinda paralyzed because I started worrying about how bad the tax raping would be.... In the 2 years since it's only went up another 20% or so. Feels like we're plateauing.

As for tax avoidance I'm debating now between if I plan on cashing and spending some of it pre-retirement, or if I am going to consider it "retirement money". If the former I start phasing it out opportunistically so it's only long term gains taxed (which all of it essentially is except some trickling extra I've picked up in the employee stock purchase program). If I'm going to hold out 6-7 years until I retire apparently I can avoid taxation more by locking it into Section 721 exchange fund. That locks it up until right about the time I plan on full on retiring.

Cad · 2026-05-13T23:13:01-0400

Gravel said:
Market trades within 5% of an ATH something like 85-90% of the time.

It's why time in the market beats timing the market. Human nature is risk averse and the market gives no shits.

As far as company stock, I'm not a fan. Because you already have a ton at stake in your company since your entire salary is already tied to its success. If the company goes tits up, not only is your investment cooked, so is your salary.

People always ask how do I know what the market is going to do? It might crash, it might never come back, it might...

Yea, it might. History suggests it won't. Just stick your money in there and leave it, and by magic, you get rich...

It's not that complicated.

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Investing General Discussion

Haus

I am Big Balls!

M Power

Bronze Knight of the Realm

Gravel

Mr. Poopybutthole

Haus

I am Big Balls!

Sheriff Cad

scientia potentia est