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Sure, I can relate :). Have a few thoughts: $20k to $5-10m is incredible. That implies 250-500x valuation growth (for example you joined at series A with $20m

Sure, I can relate :). Have a few thoughts: $20k to $5-10m is incredible. That implies 250-500x valuation growth (for example you joined at series A with $20m valuation and the company is worth $10b), which means you hit a unicorn within the unicorns! Was the company QSBS-eligible when you exercised? There are huge potential tax savings there. Your shares were NSOs, correct? There are weird potential issues with 83bs and vesting ISOs. It's worth thinking through how to factor your paper money into your investment portfolio. You could model it as $0 and have an otherwise standard asset allocation (e.g. whatever WealthFront recommends for your risk profile). Alternately you could include it as a huge illiquid stake in a US tech company -- as if your portfolio was 80% in GOOG -- and mitigate your overexposure in the other 20%. Or something in between.

luckystartup 10y ago
Yes, I was very lucky. I was actually one of the first few employees, and I joined about a year before they raised their series A. Now they are a unicorn, and hopefully on their way to an IPO. I don't know if I would say I joined a "unicorn within unicorns". Every unicorn has at least 10 early employees with the same story, and according to this list [1], that's at least 1,850 people. I don't think the company was QSBS-eligible. At least, I've never heard that acronym while reading through all of the paperwork. And yes, the shares were NSOs. I don't really have an investment portfolio, apart from these shares. I've been working as a part-time freelancer while I try to build my own startup ideas, so I'm not really saving for retirement. The IPO should only be a few years away, so I'm just going to wait and see what happens. If everything falls apart, I'll try a few more startup ideas. If those fail, my backup plan is to spend 4 years working full-time, living frugally and saving as much money as possible, and then retiring in a country with a very low cost-of-living. I can save around $130k per year as a remote software engineer, and I only need $500k to retire comfortably. [1] https://www.cbinsights.com/research-unicorn-companies https://www.cbinsights.com/research-unicorn-companies
- trefn 10y ago
  You should read more about QSBS: http://www.andersentax.com/services/for-private-clients/business-owners-and-entrepreneurs/qsbs/ http://www.andersentax.com/services/for-private-clients/busi... Under certain circumstances, QSBS (Qualified Small Business Stock) rules will significantly decrease your tax burden.
- 01181008 10y ago
  QSBS is a tax thing, not a specific company thing. On the face of it (tech company, exercised very early) it seems like you'd be eligible. The company lawyers should be able to tell you the QSBS eligibility period (something like "options exercised before MM YYYY, when TECH CORP's gross assets exceeded $50 million")

luckystartup 10y ago

Yes, I was very lucky. I was actually one of the first few employees, and I joined about a year before they raised their series A. Now they are a unicorn, and hopefully on their way to an IPO. I don't know if I would say I joined a "unicorn within unicorns". Every unicorn has at least 10 early employees with the same story, and according to this list [1], that's at least 1,850 people. I don't think the company was QSBS-eligible. At least, I've never heard that acronym while reading through all of the paperwork. And yes, the shares were NSOs. I don't really have an investment portfolio, apart from these shares. I've been working as a part-time freelancer while I try to build my own startup ideas, so I'm not really saving for retirement. The IPO should only be a few years away, so I'm just going to wait and see what happens. If everything falls apart, I'll try a few more startup ideas. If those fail, my backup plan is to spend 4 years working full-time, living frugally and saving as much money as possible, and then retiring in a country with a very low cost-of-living. I can save around $130k per year as a remote software engineer, and I only need $500k to retire comfortably. [1] https://www.cbinsights.com/research-unicorn-companies https://www.cbinsights.com/research-unicorn-companies

trefn 10y ago
You should read more about QSBS: http://www.andersentax.com/services/for-private-clients/business-owners-and-entrepreneurs/qsbs/ http://www.andersentax.com/services/for-private-clients/busi... Under certain circumstances, QSBS (Qualified Small Business Stock) rules will significantly decrease your tax burden.
01181008 10y ago
QSBS is a tax thing, not a specific company thing. On the face of it (tech company, exercised very early) it seems like you'd be eligible. The company lawyers should be able to tell you the QSBS eligibility period (something like "options exercised before MM YYYY, when TECH CORP's gross assets exceeded $50 million")