I also believe that the fundamental insights there are not particularly Deep Magick but rather are teachable. For example: ceteris paribus, if you don't have a billion dollars or the best distribution machinery around to subsidize you, B2B >>>> B2C for software companies.
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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That’s a massively less favorable bet for me which refutes nothing I’ve said. (I offered definitive and successful disproof by counterexample.) I would accept an even bet on any technical Airbnb employee with employee number <= 1000 and the opportunity cost “$250k minus cash”
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No. See my other reply. I don't care about bragging rights on Twitter, I care about financial planning and the ability for me to do stuff in life. If you want to get nuanced, I'm willing to relax my statement to "equity has uncertain value, and the distribution is left shifted".
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Privately traded equity may indeed have non-zero value, but that value is highly uncertain, so cannot be relied upon for anything. Keep a stash of it somewhere, maybe see some upside some day. But it's effectively a lottery ticket. Maybe you know the RNG is compromised. I don't.
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