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I'm currently at a unicorn SaaS startup. I have 11,500 ISOs, about 7000 of which I've vested and exercised (I've got about 1.5 years left till I'm fully vested)

I'm currently at a unicorn SaaS startup. I have 11,500 ISOs, about 7000 of which I've vested and exercised (I've got about 1.5 years left till I'm fully vested). My strike price is $1.50, which to me is a bargain, especially since there was a tender offer last year of around $14. There are ~70M outstanding shares. Other stats: $60M ARR, 120% NRR last year, almost 100% YoY growth during 2021, raised $110M at 40x revenue last year, high NPS, company still has over $110M in the bank, TAM is in the tens of billions, current market penetration is <5%, planning to go public at $200M ARR. So the potential upside is huge. Work environment is great, I have a great boss and a decently challenging/significant role. I'm a senior engineer making around $170k/year. I'm curious what you all think - is it worth the risk of staying until I vest? The alternative would be to join a public software company and increase my salary significantly (which would help so much right now - we need a larger house for our kids).

staplers 4y ago
You can do a lot more with liquid capital than options. Guaranteed money is worth more than maybe money, especially if you have a family. If you truly believe they're valuable, then invest when they ipo.
molsongolden 4y ago
Extremely simplified thought exercise with very rough possible #’s: Vesting 2,875 shares per year 2,875 @ $(14-1.50)= $36k/yr Assuming IPO @ $200MM ARR, public cloud SaaS benchmark rev multiple was roughly 20x last year before the crash. That’s a $4B valuation, ignoring dilution from here to there: $4B/70M shares = $57/share 2,875 @ $(57-1.5) = $160k/yr That’s assuming the market recovers to a similar level, ignoring further dilution, assuming the company continues executing and doesn’t hit unforeseen difficulties, etc. Can you make that much with less risk by changing jobs? - Another consideration might be diversification if your vested options represent a large % of your portfolio. - Another consideration, “work environment is great” isn’t something that everybody can say and this might be worth more than the raise.
- unicorn_eng 4y ago
  That's really helpful, thank you!

staplers 4y ago

You can do a lot more with liquid capital than options. Guaranteed money is worth more than maybe money, especially if you have a family. If you truly believe they're valuable, then invest when they ipo.

molsongolden 4y ago

Extremely simplified thought exercise with very rough possible #’s: Vesting 2,875 shares per year 2,875 @ $(14-1.50)= $36k/yr Assuming IPO @ $200MM ARR, public cloud SaaS benchmark rev multiple was roughly 20x last year before the crash. That’s a $4B valuation, ignoring dilution from here to there: $4B/70M shares = $57/share 2,875 @ $(57-1.5) = $160k/yr That’s assuming the market recovers to a similar level, ignoring further dilution, assuming the company continues executing and doesn’t hit unforeseen difficulties, etc. Can you make that much with less risk by changing jobs? - Another consideration might be diversification if your vested options represent a large % of your portfolio. - Another consideration, “work environment is great” isn’t something that everybody can say and this might be worth more than the raise.

unicorn_eng 4y ago
That's really helpful, thank you!