> Instead of trying to get the right answer, we set out to build a tool that could get an answer.
I'm curious though, from where did you get the numbers about the likelihood of an exit? I thought it was pretty interesting that a Series C is statistically less likely to make you money than a Series A, according to this.
Interestingly, data I found from 2010 was very different. It seems like more recently the popularity of early acquisitions (especially in biotech) and more robust seed funding have shifted the distribution of outcomes. It could definitely change again: success rates are by no means consistent.
Think of it as investment diversification.
Suppose you have $100k in the bank, and tldroptions.io says you have a 20% chance of receiving a $60 million payout. The geometric mean of your capital is then $360k: https://www.wolframalpha.com/input/?i=exp%28.2+log%5B60%2B.1...
It would take 62 million CA powerball tickets (each with different numbers, in the same drawing) to give the same result: https://www.wolframalpha.com/input/?i=exp((x%2F293000000)*+l...
Lottery tickets, unlike options, cost money up front. You still can't lose more than you pay, so the payoff curve is similarly non-linear, but unless you can trade options for cash options will always beat lottery tickets.
Lottery tickets are easy to diversify in that you can buy a variety of numbers. (The times when lotteries have become a net-positive buy the buyers takes advantage of this fact.) Employee startup options are more like buying one set of numbers over and over again. On the other hand, the odds of getting any payoff from options are somewhere around 15-30%, whereas the odds of getting any payoff from a California SuperLotto Plus ticket are ~4.3%. Because you can diversify ticket numbers, you could get the same odds of getting any payoff by buying 14 tickets with different Mega numbers, which would earn you $1 to the $14 you spent. If you could buy stock in many different startups, you would be called a "venture capitalist" and those folks on average do much better than people who play the lottery.
Finally, the maximum payout of a lottery ticket is capped and known ahead of time. The largest lottery win in the US was $656 million. On the other hand you don't know going into a startup what the payoff for that particular startup is going to be, and the largest exit of all time was Facebook at $104 billion. Just like with the lottery you don't know how many ways you are splitting the payoff, but unlike the lottery it's going to be based on the decisions of the board/founders, rather than random.
Basically, the lottery is a lot simpler than a startup, with few sources of actual uncertainty, and so there's no real risk involved. It is just gambling: you can do the math to figure out what edge the house has and figure out for sure that you shouldn't do it. Startup options, on the other hand, reflect actually-unknown unknowns, and so are more valuable to those who hold more-optimist-than-average beliefs about the probability of that particular startup succeeding.
That's only true as long as you're still working at the company. If you leave, you have to exercise, and then the worst case becomes negative.