_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.
_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.