It might be nice to see a breakdown of this goal from an epistemic vs instrumental rationality perspective. I.e. from an epistemic perspective, your terminal value is probably NOT to found a startup. It is probably something else: money? seeing an idea instituted? control over your daily activities? What are the best ways to achieve those things? "Found a startup" is probably only a tiny part of the answer to these questions.
From an instrumental perspective, evaluating business plans and estimating risk seems difficult but in a straightforward way. I don't see what new insights it would offer to the rationality community, unless you could provide some case examples as an exercise in identifying bias.
I can see another direction you could go with this. A community of rationalists should "win". If winning implies developing a comparative advantage at something, and business tells us comparative advantage can be translated into money, then why not monetize on our comparative advantage (if it exists)? You could ask what these businesses would look like. But I suspect they look like businesses do already: e.g. Google has a more rational way of evaluating relevance, and has turned that comparative advantage into profit.
There seems to be a non-negligible deal of overlap between this community and Hacker News, both in terms of material and members. For those not aware of HN, it's a news aggregator for people interested in startups, technology, and other intellectually interesting topics, with a reputation for high-quality material and discourse.
While rationality and LessWrong gets its fair share of attention over at HN, I haven't heard of much discussion about startups over here. Off-line, I've heard a claim that in terms of contribution to existential risk prevention charities, startups are suboptimal when compared to jobs in finance, but not much else other than that. I find this odd, as many of the contributors in this site seem to be prime founder material, and rationality should really be of use when working in a high-stakes ever-changing environment.
My intention with this post is simply to kickstart a discussion around startups and gauge the attitudes of fellow LessWrongers. Does anyone (else) aspire to becoming a startup founder in the next few years? Do you believe startup founding to be a viable means of contributing to groups existential risk prevention?