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Your argument is treating the future as knowable and certain, while not accounting for the value of risk. I guess you'll feel pretty bad if you pay for car ins

Your argument is treating the future as knowable and certain, while not accounting for the value of risk. I guess you'll feel pretty bad if you pay for car insurance for 40 years, and never have a crash. If the 100% upside is guaranteed, then sure, you should hang on. But if "anything can happen" then cashing out 10% now, and providing a "can't fail" safety net, is well worth it. The reduction of risk of "losing it all" is well worth the 10% premium. And if the (somewhat unlikely) big exit ever happens you still have 90%.

kelnos 2y ago
> If the 100% upside is guaranteed, then sure, you should hang on. Overall agreed, but that's not even always true! If you're -- for example -- under crushing levels of debt today, you very well may want to take that $500k now, even if that $50M is 100% guaranteed in 5 or 7 or 10 years. Or even if you aren't in debt, but would find it a huge quality of life improvement to be able to have a down payment for the house you'd really like to live in now, and not have to wait 5 or 7 or 10 years.