I guess my argument is that there are products that people want, that aren't financially viable under the current model

I think Plan A is evidence of that -- investors want to fund hockey stick growth, because they want one win to pay for 99 losses

But that shouldn't be the only way to grow a company, and retain skilled engineers. You may be right that it would have been the best strategy at the time, given the flood of investment money into tech.

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Some kind of "bootstrapped" path sounds more appealing and sustainble to me, and perhaps more likely to lead to a high quality product (or at least I don't think it would lead to an inferior product)

That's what Plan B sounds like. I am not sure that a cloud OS designed to be self-hosted is ever going to make revenue justified by Plan A (though I'd be happy to hear an argument otherwise!)

That is, there's the question of what happens if Plan A succeeds, and the company don't find revenue.

I guess that's sort of what happened to Docker -- the company shrunk, and lost a bunch of people. Some people may see that as a net positive outcome, but it seems a bit inefficient to me. And I think better tech could have won there ... i.e. it's not clear that the tech that got a lot of VC investment is the one that we should be using

I see a similar dynamic with say Github Actions -- they give a ton of computing resources for free, because it's subsidized. But that actually prevents better companies from forming!