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've heard this argument and logically it flows. I'm not sure of the premise. I'd much rather take advice from someone who has made a thoughtful study of life and business. Esp since I've gotten terrible advice from some folks who just got lucky.
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...)
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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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