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_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 te

_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.

throwaway9191a 6y ago
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.
compsciphd 6y ago
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.
- lostdog 6y ago
  I don't mind working for less on something I'm passionate about. But, if we do get lucky and the startup goes to the moon, I expect to do well! And that's why I can't work at startups anymore. It's fundamentally unfair that VC's capture all the upside. I'm can no longer bring myself to donate half my compensation as funding and only get the measliest of common stock options in return.
  - compsciphd 6y ago
    if the salary you are getting sufficient, then they are taking a lot more risk than you are. most startups fail, as long as you are getting paid an amount that is sufficient for goals and are working on what you want to work on, you are taking on minimal risk. And most startups that do well, the employees do also do well (not necessarily as well, but they also took on less risk). A startup that sells for 250 million after raising 300 million, did not do well. A startup that basically went bankrupt and had to be recapitalized after you left, did not do well.
- fatnoah 6y ago
  >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. 100% agree. The experience gained was the invaluable part of working at a startup. That said, every startup I've talked to pitches the equity as the big thing, and not the experience. I.e. "...and these options would be worth X at our current valuation."

throwaway9191a 6y ago

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.

compsciphd 6y ago

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.

lostdog 6y ago
I don't mind working for less on something I'm passionate about. But, if we do get lucky and the startup goes to the moon, I expect to do well! And that's why I can't work at startups anymore. It's fundamentally unfair that VC's capture all the upside. I'm can no longer bring myself to donate half my compensation as funding and only get the measliest of common stock options in return.
- compsciphd 6y ago
  if the salary you are getting sufficient, then they are taking a lot more risk than you are. most startups fail, as long as you are getting paid an amount that is sufficient for goals and are working on what you want to work on, you are taking on minimal risk. And most startups that do well, the employees do also do well (not necessarily as well, but they also took on less risk). A startup that sells for 250 million after raising 300 million, did not do well. A startup that basically went bankrupt and had to be recapitalized after you left, did not do well.
fatnoah 6y ago
>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. 100% agree. The experience gained was the invaluable part of working at a startup. That said, every startup I've talked to pitches the equity as the big thing, and not the experience. I.e. "...and these options would be worth X at our current valuation."