[rcxdude]

I think the main trick is balancing the two. Companies that take any +ev bet, no matter how big, will tend to explode spectacularly eventually (SBF famously had this philosophy, for example).

Skunkworks is a decent example of how this can work: you set up a subset of your larger company to operate more like a startup. But importantly this isolation both limits the risk to the company as a whole as well as isolating the subset from the bureaucracy of the larger organization.

[ronfriedhaber]

I tend to agree. This is just the intersection of two age-old problems; Kelly Criterion (pareto-optimal sizing of bets) and Organizational Management.