I wish I had 20k extra to max…
My mortgage + property tax + HOA is over $5k 
I need a raise
Huge benefit of Po life. I think mine average to about $1,100 (no escrow so used some back-of-envelope guesses) for a moderately nice house.
Used to do this when it was available. Would max out the ESPP (cost was 15% less than lower of beginning or end of period, which ever was lower) with a deduction from each paycheck. I would then donate to my Church, usually around 10-15K per year. They hated getting the stock and would sell as soon as they got it. I guess the record keeping for the treasurer was a bit unwieldy but I didn’t have to do anything other than initiate a transfer to the Church. I got the full charitable donation.
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I’ve maxed out an ESPP for the last few years. I sell within days though, so I didn’t replace any other investments with it. I don’t do single stock investing and definitely not in my own company’s stock. Instead I just make quick money off the 15% discount. I’ve been happy with it and plan to continue going forward.
The taxes are slightly confusing the first couple times. The discount flows through your W-2, but the brokerage includes the discount in the 1099-B numbers, so you have to adjust it for your tax return or you’d be double taxed on the discount. No big deal once you figure it out.
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My understanding is that you only get a break on the discount if you keep it long enough and there’s a loss. No desire to find out if that’s accurate.
I do the max on ESPP. An old employer did twice a year, I think 10 or 15% discount. New employer does 4 times per year but only 5% discount. It’s basically a raise with some slight market risk (slight lag between when price is set and I receive shares). I always sell ASAP.
At my old firm I was shocked at how many actuaries held onto company stock, even if you intend to keep it invested. I think most just couldn’t be bothered to sell it regularly.
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Do they let you sell?
I would think that the goal of an ESPP is to encourage stock ownership amongst the rank and file. Don’t they limit your opportunity to sell it off?
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Research has shown that very few ESPP participants sell their shares immediately. Adding a restriction to when the ESPP shares can be sold would be a turn off
When I discovered the ESPP at the first employer that had it I figured as much and didn’t participate in the first offering I had the opportunity. Then I chatted with a coworker about it and it caused me to look more deeply into the rules and discovered you’re allowed to sell it immediately, same with my new employer that also has an ESPP.
Nearly all charities will sell stock as soon as they receive it. AFAICT that’s SOP. Did they tell you they hated it?
I’ve never experienced anything other than gratitude from charities receiving stock donations. Maybe possibly a gentle reminder that they do have to pay transaction fees on the donation, but that’s about it.
A lot of employers do have restrictions, but some do not. I’ve had both.
Good point. I hope I don’t need to hand in my credentials. 
I think the treasurer didn’t want to do the work to sell it, regardless of how much work it might have been. There may have been record keeping too. I think I was the only one doing this so it was always a one off at that time.
Ah, yes, getting an account set up for the first time is a hassle. But the charity can set up an account with a brokerage firm that will automatically immediately sell anything and everything deposited into it. Type up some instructions for would-be donors and have a notification sent to the financial secretary every day that money is in their cash brokerage account so they can transfer it to their operating account.
Not that much more difficult on them than writing them a check… maybe even simpler. It’s just the initial setup that’s time consuming.
The first company I worked for lost virtually all of its value during the financial crisis. Luckily, I wasn’t invested, but know several people that lost a ton.
Then I joined a small company that was growing like crazy. The company wasn’t publicly traded and shares were completely illiquid (could only cash out through recapitalization / acquisition or if we left the company). From the time I bought shares until the company sold (5-6 years later), value went up 8x. I had a decent chunk but am still kicking myself for not buying more haha.
Based on my observations, you have a 50/50 chance to get rich or go bankrupt.
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New question, closely related.
Gifted stock in the case of an IPO: Counted as taxable income? I think it is. But information online is scarce.
I’m not following your question. You have IPO access and buy the shares yourself and then gift them to someone else?
Generally when you gift shares of stock the recipient inherits your basis and is then taxed when they sell the stock, based on the original purchase date (for determining long-term vs short-term) / price.
It’s essentially as if they purchased the stock themselves, from a tax perspective.
But if you gift them more than the gift tax limit then you trigger gift tax reporting.
I’m not sure why any of that would be different for an IPO than shares bought on any other day.
But maybe I am misunderstanding your question.
“Gifted” was the wrong term, it’s “Restricted Stock Unit”. Stocks given to employees for “free”, not counting taxes. I’m pretty confident I figured it out, have emails out to HR to confirm some things.
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I’m far from an expert here, I’m exercising options at my company now (we are not yet public) and trying to parse this all out. I don’t think it counts as income unless it would cause you to hit the AMT, in which case you would be on the hook for taxes. I’m not quite clear on what happens above the AMT, let’s say this causes you to exceed the AMT limit by $100, are you just responsible for some tax on that $100, or are you responsible for paying the full amount - basically bumping your income above AMT and paying the tax that way? I’m a little lost here, this seems relevant:
Topic No. 427 Stock Options | Internal Revenue Service.
If your employer grants you a statutory stock option, you generally don’t include any amount in your gross income when you receive or exercise the option. However, you may be subject to alternative minimum tax in the year you exercise an ISO. For more information, refer to the Instructions for Form 6251. You have taxable income or deductible loss when you sell the stock you bought by exercising the option. You generally treat this amount as a capital gain or loss. However, if you don’t meet special holding period requirements, you’ll have to treat income from the sale as ordinary income. Add these amounts, which are treated as wages, to the basis of the stock in determining the gain or loss on the stock’s disposition. Refer to Publication 525 for specific details on the type of stock option, as well as rules for when income is reported and how income is reported for income tax purposes.
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