Some people believe businesses to be very difficult to determine the quality of ex-ante. I once held this opinion. On the basis of substantial experience, I believe I'd be much better at selecting successful businesses today than I was 15 years ago.
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The less polite way to say this is "A bet is a tax on bullshit." Here's a trade: Airbnb is the well-known private company I'm least directly conflicted about. I will donate $50 to a charity of your choice. If Airbnb IPOs, you donate $500 to a charity of my choice. Want in?
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How about I pick an AirBnB employee with equity, and we have an even bet over whether they see a windfall from an exit that recoups the reduction in salary they took for working at a startup? Obviously, some subjectivity there, but nothing that can't be agreed on in advance.
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And I will - for example, any trade which will enable me to get a better mortgage. Getting lenders to take account of Google equity vesting schedules was tortuous. I can't imagine what having a conversation about a random startup would have been like.
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Would you say there are significant expected value differences between the illiquid equity you have access to now and the illiquid equity someone who needs info from the internet to decide its value has access to?
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