i had the really good fortune of starting series B (coincidentally weeks before there was a C round) at a unicorn startup.
at the time i was overly-optimistic about its outlook and when countering pushed for more shares instead of higher base.
i bought all my shares before leaving a few years later and made out really well on the acquisition -- i think the sale_share_price was 50 x my_strike_price.
here's the thing though, retrospectively i still don't think i'd ever advise someone to do what i did. there are so many factors that had to line up exactly right for this to be a positive outcome for me:
* joined with particularly low valuation with company in a strong position
* happy enough to stay n years and vest all my shares
* was able to borrow $ from family to outlay the huge cost to buy what were at the time essentially worthless options
* survive getting absolutely KILLED on taxes, i think my AMT obligation when i exercised ended up being almost 2x as much as the cost of buying the shares (it uses a company filed valuation to set current fair-market-value which was completely theoretical since the company was private when i exercised)
i joined a fortune 50 company when i left and pushed for high base and a large performance bonus. i did the math on what my earnings would have looked like over time if i had spent my years working with big-co-pay vs. lower startup pay + good options outcome and even with a crazy lucky outcome i don't think the extra $ i earned was worth the high risk.
my partner and i both agree it wasn't worth it, especially when we reflect on how many early mornings, long nights, and weekends i had to work to make it happen.
at the time i was overly-optimistic about its outlook and when countering pushed for more shares instead of higher base.
i bought all my shares before leaving a few years later and made out really well on the acquisition -- i think the sale_share_price was 50 x my_strike_price.
here's the thing though, retrospectively i still don't think i'd ever advise someone to do what i did. there are so many factors that had to line up exactly right for this to be a positive outcome for me:
* joined with particularly low valuation with company in a strong position
* happy enough to stay n years and vest all my shares
* was able to borrow $ from family to outlay the huge cost to buy what were at the time essentially worthless options
* survive getting absolutely KILLED on taxes, i think my AMT obligation when i exercised ended up being almost 2x as much as the cost of buying the shares (it uses a company filed valuation to set current fair-market-value which was completely theoretical since the company was private when i exercised)
i joined a fortune 50 company when i left and pushed for high base and a large performance bonus. i did the math on what my earnings would have looked like over time if i had spent my years working with big-co-pay vs. lower startup pay + good options outcome and even with a crazy lucky outcome i don't think the extra $ i earned was worth the high risk.
my partner and i both agree it wasn't worth it, especially when we reflect on how many early mornings, long nights, and weekends i had to work to make it happen.