The hierarchy of from whom founders should take advice: Founders who've done it twice > Founders who've done it once > Venture capitalists who've never done it > Business school profs > Everyone else
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I think the key is to look for people who've, over a long period, been in the area where you are seeking expertise and it is important that that area have some sort of filtering mechanism like getting fired, going bankrupt, or whatever. (I'm just rephrasing Taleb...)
For example, a guy who built a 10 million dollar business over 30 years will give you better advice than someone who, within a year, flipped his business for 20 million.
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Here's where I'll push back a bit: The been-there-done-that crowd is great but only gives good advice if they're thoughtful and insightful. Choosing one, I'll take the latter.
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My sample size is small, but I'll take the been-there-done-that crowd. There's a lot of bullshit false wisdom in the latter group and they deliver it with the same confidence.
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