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Ask HN: Employees who exersised stock options: how did it go?

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Re: Ask HN: Employees who exersised stock options: how did it go?

#22
I did an early exercise (83b election) when I started at a startup a few years ago, paid about $30k to exercise all my options, granting me about 0.3% ownership. Five years later, AWS made our product obsolete, and company was acqui-hired, all regular share holders were wiped out, so I lost my $30k (and worked for five years at well below market). Oops.

Re: Ask HN: Employees who exersised stock options: how did it go?

#23

Worked at company for 4 years. About a month after I left, the company was acquired. Fortunately, I could still exercise my options. I paid around 10K to exercise my options and got about 70k once the sale was finalized. Honestly, I was expecting more but I'm not complaining.

I left about $20k in options on the table when I left a company that was acquired about 4 months after I left. My coworker who stayed ended up doing great, but not because of options. The company put him on a $100k-per-year retainer for 4 years to stay on and help port the project.

Retainers are often much better for the little people.

Re: Ask HN: Employees who exersised stock options: how did it go?

#24
post #19

Bought $10K of options before I quit. 20 years later the company has gone public and has a market cap of several billion. My options? "Extinguished" in some "event" 18 years ago. My guess is that's the event where they screwed as many employees as they could.

Is it even legal? You spent money on your options, if they get extinguished, you should be compensated in some way

Re: Ask HN: Employees who exersised stock options: how did it go?

#25

Worked for a startup in 2000 which Sun Microsystems bought. My options get switched to Sun options, and had a strike price higher than the value of the shares. Right before the options were set to expire, I got a call from someone at Solomon Smith Barney (remember that) who was like "I know the answer is no, but do you want to exercise these?" lol That job, and especially my time at Sun, super kickstarted my career (…

pardon my ignorance, but what exactly does exercising stock options mean?

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Re: Ask HN: Employees who exersised stock options: how did it go?

#26

Worked at a company almost 2 years, exercised my stock options (only $2k, it was my 2nd junior position and I didn't negotiate for equity at all). 4 years later I have no idea how much they're worth, if they even still exist, or if there's been any liquidity event. If I had to guess based on the company's revenue, they're probably worth about 4x what they were when I exercised, but I'm planning on holding off on tryi…

what exactly does equity mean in this context?

compensation in the form of stock

Re: Ask HN: Employees who exersised stock options: how did it go?

#27
post #19

Bought $10K of options before I quit. 20 years later the company has gone public and has a market cap of several billion. My options? "Extinguished" in some "event" 18 years ago. My guess is that's the event where they screwed as many employees as they could.

Is it even legal? You spent money on your options, if they get extinguished, you should be compensated in some way

He can write it off as a total loss.

Re: Ask HN: Employees who exersised stock options: how did it go?

#28
post #5

The problem is that you never know when a liquidity event will happen, and not all outcomes involve you at least breaking even. The company I have my exercised options with hasn’t gotten acquired, hasn’t gone public, it just hobbles along failing to make a profit year after year receiving round after round of funding by investors who just hope to turn the company viable. I was only able to buy a few hundred bucks of…

> They probably only make sense for people working for Microsoft, Apple, Google, Amazon, and the like. Having worked at Google, I'm pretty sure that most of us only took stock because that was simply "how it was done"; it saves the company money versus paying you in cash (I guess! not an expert here). There is an infinite amount of paperwork that results from being paid in stock, and while it's obviously worth it for…

>My advice is to find an accountant your first year at a FAANG and let them handle everything. Don't do it yourself.

If you do go with an accountant, treat it as a learning experience so you can do it yourself or at least go over their work before submitting it. You'll be surprised at how often accountants make mistakes or leave money on the table.

Re: Ask HN: Employees who exersised stock options: how did it go?

#29

Worked for a startup in 2000 which Sun Microsystems bought. My options get switched to Sun options, and had a strike price higher than the value of the shares. Right before the options were set to expire, I got a call from someone at Solomon Smith Barney (remember that) who was like "I know the answer is no, but do you want to exercise these?" lol That job, and especially my time at Sun, super kickstarted my career (…

pardon my ignorance, but what exactly does exercising stock options mean?

Options aren’t stocks. They are an option to buy the stocks. Exercising your options means buying the stocks. They options contract has a price for stocks set up front. Ideally the price of the stock has risen over time so when you exercise the option to buy the stocks, you are buying the stocks at a lower price than their current market value. Thus you make money.
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