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RowanE comments on Saving for the long term - Less Wrong
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I would suggest an option 5), complementary to 4) - you work a normal-ish job, have an otherwise normal retirement plan that you put a much larger-than-normal fraction of your income into, and retire at a totally abnormal age. The go-to example of this approach is Mr Money Mustache. Past a certain level of income, most people are spending most of their money on what are essentially positional goods, and if you can resist the urge to buy what all your peers in the same income bracket are buying, you can save a big chunk of your income, and if you can get as high as 2/3rds you can retire in about 10 years. Should be much more comfortable, both in terms of risks and in terms of actual comfort, than spending 10-20 years on failed startups until you get one that succeeds.
Hm, that has the opportunity cost of me not spending the next 10-20 years working towards startups. That seems like a pretty big opportunity cost to me, and it seems that there's a high likelihood that I'll retire comfortably regardless of whether or not I save (because of 1, 2 and 3).
So your proposal has the benefit of a marginal increase in retirement security, but has the cost of me not working on startups for 10-20 years. What do you think of these tradeoffs?
Well, I'm not very optimistic about the idea of spending 10-20 years working on startups, I didn't comment on it because I thought it had been addressed enough by others, but I suppose I'll add some thoughts on it: The "75% of startups fail" is from a group already selected for being confident enough that they're startup founder material that they actually go and make a startup. A single failed startup might be the best way of getting the experience you need to make a successful startup, but a track record of multiple failed startups is probably a bad sign, and even if it's not necessarily evidence you're "not startup founder material", that kind of track record will probably affect you negatively.
Although, really my misgivings aren't from any particular argument like that, I just have a feeling that the calculation in 2) must be hopelessly naive, and that's followed by the picture of an impoverished person who once had lots of potential declaring, to the dismay of his family, that with four failed startups under his belt he's going to try founding a fifth one, and this one will be a success for sure.
I mean, maybe all the patterns that option 2) is matching to in my mind are actually totally inapplicable, but it would take an awful lot to convince me the opportunity cost of not following a predictable path to retirement in 10 years was worth it.