He wasn't always an investor, and setting up a new fund/accelerator/etc. is closer to being an entrepreneur than the investor role of a random principal at a big VC.
Definitely. A 5 minute conversation with Dave will sound remarkably similar to a 5 minute conversation with other founders - he's always spread too thin, trying to raise money, figuring out the hustle, helping wherever and however he can.
Agree, however I just don't see where the fear of flying motif comes into play when you don't have all your eggs in one basket. Once a fund is raised it's typically for 10 years. There's a lot of hard steady work to do in those 10 years, but you don't really have a milestone to meet every 12-18 months otherwise you've failed and your business is over.
Actually, the milestone you have to meet every 12-18 months, in 500's case, is raising a new fund. Given their speed of investment and quantity, this is an incredibly herculean task. Definitely not easy, and very easy to fail - the failure mode here, of course, being not raising another fund. Sure, the first fund might do well, but 10 years later 500 will have failed as a VC if it has only raised one fund.
Yes and no. Is it entrepreneurship? Yes. Is it a startup in the Steve Blank sense of the word? No. It's a proven business model that works for those individuals that have a solid reputation and professional network. Is it more risk than being a partner or principal as a big VC? Yes.
Risk-wise, setting up and running your own fund is somewhere between starting a new business with an unproven business model and opting for a career path. IMHO it's not the risk profile described in this post.
The business model isn't proven - 500's idea of investing in a lot of companies and looking for lots of singles and doubles, rather than a few home runs, is unusual, unproven, and some would argue impractical. Whether that's true or not remains to be proven, but they've had some (minor) successes so far - sounds a lot like "the first few business deals" to me.