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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?

#51

Post by throwaway099910 »

Worked as a sw dev for a small B2B startup in the midwest that was acquired by a much larger player in the space.

I was an early employee and stayed for many years, knowing that my options may be worth little or even worthless in a liquidity event.

After the acquisition last year, my pre-tax payout ended up around $80K. Not a life changing amount, but more than I was expecting. And it gave me a nice chunk to deploy toward investments.

I knew I wouldn't become rich and I'm happy with how it turned out.

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

#52

Post by wildmindwriting »

I did an 83b when stock options were granted since I was a very early employee. Paid $30 for 30,000 shares, which then went through a 10-to-1 split, so I had 300,000 shares. But, in the end, we went bankrupt and I received nothing. Wasn't out any real money and the experience alone was worth it.

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

#53

Post by cvhashim »

daenz wrote: post #47
kabdib wrote: 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.

Name and shame, please.

Why is this downvoted?

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

#54

Post by squirrel »

Early employee at a UK startup that started in 2001. In 2007, exercised options for a cost in low five figures. Company loaned me the money to exercise and I continued to work there. When I left in 2012, I paid off the loan with cash. Company sold in 2018 and the ROI was substantial - received a sum in the high six figures.

In the next company, I bought shares outright during one of the investment rounds for a few thousand pounds, and later, in an acquisition, I had the opportunity to sell my shares again - for £0.

Lessons learnt: be patient (I held options or shares in the first company for 17 years!) and don't bank on shares as the route to riches.

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

#57

Post by fatnoah »

_Startup 1_ Joined in 2000 as employee #35 and left in 2004. Exercised options for ~$300. Company acquired in 2014 and options worth $0. Reported a long term capital loss that year.

_Startup 2_ Joined in 2005 as employee #3 and left in 2011. Never exercised options. Company still going today w/no plans to grow or sell.

_Startup 3_ Joined in 2011 as a Principal Eng and promoted to VP Eng in 2014 and had option for a little over 1% of the company. Company was acquired in 2016. Value of my options was $0.

After 17 years, I was done with startups.

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

#58

Post by throwaway9191a »

fatnoah wrote: post #57

_Startup 1_ Joined in 2000 as employee #35 and left in 2004. Exercised options for ~$300. Company acquired in 2014 and options worth $0. Reported a long term capital loss that year. _Startup 2_ Joined in 2005 as employee #3 and left in 2011. Never exercised options. Company still going today w/no plans to grow or sell. _Startup 3_ Joined in 2011 as a Principal Eng and promoted to VP Eng in 2014 and had option for a l…

I've got 3 in the bag that match your #2 experience. I would love to know how common this outcome is.

My overwhelming experience is that companies rarely "fail". A good idea just chugs along with an owner making well into the 6 figures. Somebody else (like me) built the infrastructure that allows the owner to outsource the maintenance development work.

This became my reason for doing CTO as a service type solutions. A lot of people were doing this 5 years ago or so, which makes me think your #2 is fairly common.

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

#59

Post by PopeDotNinja »

Joined a company in 2000, got 14_000 shares at $4.75/share. Company went public that same year, and stock climbed to over $50/share. I was a black box QA Engineer w/ barely any work experience and I was sitting on ~$750_000 USD of paper money. By the time I started vesting & could sell, the stock price was down to about $12/share, and I started selling everything I had vested. I ended up w/ maybe $25K in cash. A few months later the stock was at $2/share & it never back above my stock price.

A few years later I joined a company that gave me about 15_000 options at $7/share. Less than a later, the stock was over $55/share. I made pretty good money on that one.

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

#60

Post by compsciphd »

fatnoah wrote: post #57

_Startup 1_ Joined in 2000 as employee #35 and left in 2004. Exercised options for ~$300. Company acquired in 2014 and options worth $0. Reported a long term capital loss that year. _Startup 2_ Joined in 2005 as employee #3 and left in 2011. Never exercised options. Company still going today w/no plans to grow or sell. _Startup 3_ Joined in 2011 as a Principal Eng and promoted to VP Eng in 2014 and had option for a l…

I've repeated this many many many times. You don't work at a startup to maximize your net worth. You'd be better off working almost anywhere else and come out on average with a higher net worth.

you work at a startup because the salary is sufficient for your needs/goals and its work you want to be doing and dont think you would be able to do elsewhere (at least with the same ease). If either of those 2 choices aren't being met, you probably shouldn't be working at a startup. If both are met, you might not be caring that you aren't maximizing your net worth and hence why are willing to work there.

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