It’s an interesting thought to de-couple risk from a small, nimble team — and although far less common, I would say such a thing exists. “Moderate-growth, tech-enabled companies” fit this bucket well.

For instance, a company that’s been bootstrapped and was once risky but it’s growth has tapered off and is now relatively predictable in terms of revenue. Perhaps the ambition of the founder isn’t to be Google, and thus he’s happy to keep a small, stable team of smart people.

Also:

“This advice forces hackers to become the worst type of VC investors: those with a portfolio size of 1.”

Not seeing the relevance of this statement in context with the rest of the paragraph. Either way, the nice thing about the worst-case scenario you painted is that surely it’s temporary :)

It seems hackers are attracted to meaningful and complex-enough issues with opportunity for growth + a sense of ownership in the work place.

This environment sounds much me to like a high-growth, high-risk startup. I’m sure there’s a window where all three conditions are met at once — but I don’t think that window exists very long.

JH