VC is particularly idiosyncratic in that your founders often ask for your advice in truly difficult situations. Some VCs have been successful founders or operators and hence can draw on that experience. But some of the most successful VCs come from diverse backgrounds, like consulting, journalism, or law. And others have only ever been VCs.
In fact some of the most challenging board members for me have been very successful young founders who thought their own experience was almost always transferable to this very specific situation and, worse, who loved hearing themselves talk. A strong one-sided recommendation based on past experience is often more harmful than providing clarity by simply structuring the problem.
For me, the coaching analogy holds up quite well (which is why I trained as a professional coach a few years ago). You're not the athlete, but you do understand the game and your job is to bring out the very best in your founders and their teams. That's why I always talk a lot about the "Company" (capital-C). Many conflicts in early stage startups are resolved when you ask all parties to put the Company and its interests first.
The best board members are more than knowledgeable about the market, building a product, recruiting and retaining a world-class team, raising capital, and so on. They are more than an amalgamation of career experience and good judgement. They are wise and this wisdom is quite hard to put your finger on. You know it when you see it, but you often don't see it before you get to the difficult situation.
My thesis is that it is some combination of knowledge of the deepest and the highest truths. Deepest in that they conform to our heart's true desire. Highest in that they align with the nature of all things. And hence wisdom answers questions that our culture usually relegates to the private: what is right and wrong, what is the purpose and meaning of life, how to live and act well. Clarity in this realm in particular is becoming rare.
Thankfully there are two complementary paths which I believe lead you to wisdom. One is to observe the nature of all things using reason (see my post from yesterday). The second is by way of your conscience. The intelligibility of all things shows you the pattern you are meant to live by. And your conscience, the "aboriginal Vicar" of your soul (John Henry Newman), whispers to you what is right (if you can only listen). Both paths require contemplation and some absence of existential fear. There's a leap required there somewhere (I want to write about this in the future).
Wisdom sits at the mysterious intersection of predestination and free will. That from the vantage point of the grand story, the narrative is effectively written, but from the individual's perspective in time, the choice is irreversible and consequential. And thus each act of ours rings through eternity: all things that have happened have led up to it, and nothing that follows will be forever the same. How is that for drama?
Wisdom then aligns the will of the individual with the nature of all being. Someone much wiser than me once said (I'm paraphrasing because I can't find the quote): "freedom is doing what you ought." Now isn't that counter-cultural?