I still have my doubts about how much the gain from that experience, that will lend value to any specific future potential investment, unless the firm that failed was in a very similar business. And you also have to consider that VCs frequently sit on multiple boards, and have routine "vc firm dealflow" stuff to deal with, so their attention gets spread around a lot.
Anyway, I don't mean to say that they don't have anything of value to add. But I will stand by saying "you claiming to be an expert in my business is a red-flag", barring some specific evidence to the contrary.
Instinctively I think "should be operators", but when I look at the backgrounds of the VCs I like the best, a lot of them were not operators, or were operators of pretty bullshit businesses in comparison to their VC careers.
Somebody said:
As a former investor, an entrepreneur that thinks he/she understands my business better than I do is a big red flag.
and I replied:
As an entrepreneur, an investor that thinks he/she understands my business better than I do is a big red flag.
To me, this gets to (or near) the heart of the thing. If you're a VC / angel, you're probably fairly smart, probably well connected, and probably have a modest amount of interesting experience in many things. But if you're not one of the VC / angel types who came from a background as an entrepreneur, why should I believe that you have much knowledge that will be specifically relevant to my business. And why should I think you are particularly well suited to judge my business?
msuster, sgblank, pg, and a few others, I would put a lot of faith in, based on their backgrounds... but most other VCs, I really wouldn't be looking to them for much besides: A. money and B. introductions / referrals. I almost certainly wouldn't be looking for product advice or marketing strategy, etc. from them (unless they had some proven background in that area).