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Agreed. We'll cover liquidation preferences in Part 2. In general, I like to look at the "lottery ticket" value of the options. What are the options worth if e

by nivi 18y ago

Agreed. We'll cover liquidation preferences in Part 2. In general, I like to look at the "lottery ticket" value of the options. What are the options worth if everything works out? Especially when the startup can afford to pay a reasonable salary, I think of the options as a free lottery ticket.

mattmaroon 18y ago
I'd like to hear more about exercising options early. I had no idea that could be done. Not that I'll ever be in that situation, but I'm just curious how that happens. Sounds like a bit of a legal hack. Did you mean with the 83b form?
- nivi 18y ago
  You exercise the options before they vest and the company maintains a right to repurchase the options that expires over time. From the perspective of the company, it is like reverse vesting. Talk to a lawyer for the myriad details but if you ever hire someone who knows his stuff, he will want to exercise his options immediately.
  - abstractbill 18y ago
    I did exactly this when I joined justin.tv - it's not very difficult to arrange. The hardest part was actually finding a CPA who had any availability to work with me, and who I felt I could trust (he came recommended by a friend). It's obviously important to keep in mind that to exercise your options you'll need some cash. If your share is big and the company has been well funded already, you might need a lot of cash. And you need to be prepared to lose it all if the company fails.
  - prakash 18y ago
    Can you please write a post that covers this? Thanks, Nivi!
sanj 18y ago
I believe that "lottery ticket" thinking is really dangerous. It leads to making really awful financial decisions. At many companies, people don't do enough math to realize how little their options are worth. And so slog it out for years thinking it is a good deal. And many companies will argue that paying below market is justified because they're giving you options. If you do the math, you might find out that the lottery ticket, spread out over 4 years, diluted by liquidity preferences and successive rounds don't come close to the aggregate bonuses from a 'regular' job. True story: At my last startup, as I was leaving, I created a spreadsheet that took everything into account (liq. pref., multiple rounds, etc.) so you could plug in the options you had and an acquisition price and see what you'd make. I went and showed it to some folks to make sure I'd done all of the crazy math right. It turns out that a. No one quite knew, because b. No one else had done it and that c. Everyone wanted a copy of the spreadsheet

by nivi 18y ago

mattmaroon 18y ago

I'd like to hear more about exercising options early. I had no idea that could be done. Not that I'll ever be in that situation, but I'm just curious how that happens. Sounds like a bit of a legal hack. Did you mean with the 83b form?

nivi 18y ago
You exercise the options before they vest and the company maintains a right to repurchase the options that expires over time. From the perspective of the company, it is like reverse vesting. Talk to a lawyer for the myriad details but if you ever hire someone who knows his stuff, he will want to exercise his options immediately.
- abstractbill 18y ago
  I did exactly this when I joined justin.tv - it's not very difficult to arrange. The hardest part was actually finding a CPA who had any availability to work with me, and who I felt I could trust (he came recommended by a friend). It's obviously important to keep in mind that to exercise your options you'll need some cash. If your share is big and the company has been well funded already, you might need a lot of cash. And you need to be prepared to lose it all if the company fails.
- prakash 18y ago
  Can you please write a post that covers this? Thanks, Nivi!

sanj 18y ago

I believe that "lottery ticket" thinking is really dangerous. It leads to making really awful financial decisions. At many companies, people don't do enough math to realize how little their options are worth. And so slog it out for years thinking it is a good deal. And many companies will argue that paying below market is justified because they're giving you options. If you do the math, you might find out that the lottery ticket, spread out over 4 years, diluted by liquidity preferences and successive rounds don't come close to the aggregate bonuses from a 'regular' job. True story: At my last startup, as I was leaving, I created a spreadsheet that took everything into account (liq. pref., multiple rounds, etc.) so you could plug in the options you had and an acquisition price and see what you'd make. I went and showed it to some folks to make sure I'd done all of the crazy math right. It turns out that a. No one quite knew, because b. No one else had done it and that c. Everyone wanted a copy of the spreadsheet