On startups and advice
Giving and receiving advice is an extremely hard thing to do, even when both parties have the best intentions. In my startup career, I've frustrated many well-intentioned and extremely capable advisors over the years, by refusing to do things I don't understand the reasoning behind.
I think I recently had an insight that explains my instinctive reaction, and shows a better way to giving and receiving advice.
Imagine me playing a game of chess (and I'm really not good at chess), getting myself into a difficult situation, when suddenly Garry Kasparov enters the room. "Hey Garry, can you give me some advice here?" I shout. "Sure", he answers. He walks over, takes a look at the board, and tells me the next three moves he would make if he was faced with this board. He then walks off to wherever he was going to in the first place.
What good fortune, having Garry Kasparov play a few moves for me. Surely I'll destroy my poor opponent now. But wait -- why did he make those moves? And how do I make the most of the resulting situation? How do I defend against the weaknesses of the resulting position? How do I react to my opponent's various options? Well, Garry's not here now, so all I can do is to potentially make things worse for myself by trying to bring the board back to a situation I understand.
This is how a lot of advice-giving feels to me, having been both on the giving and receiving ends. People may suggest things I should do, but I don't understand why those options are better than others. And even if I follow them, I won't be able to explain to the team why with a convincing narrative. And even if they go along, we won't be able to make the most of the energy we put in, as we'll be essentially cargo-culting it.
If you're giving advice, the best you can do is not to suggest the "best move", or what you would do in the other's place. The absolute best is to suggest the best move that the other person can fully understand and exploit, even if they wouldn't have thought of it themselves. If you're particularly wise, you may suggest courses of action that will leave the receiver better off, but not for reasons they understand now (but will later). E.g. encouragement to start a startup was some of the best advice I ever received, even if my current venture ends in no big exit. This is because the process itself has made me immensely more capable and experienced than the alternatives would have.
If you're looking to receive advice, unless the advice-giver understands (or can be made to understand) the above, it follows that maybe the best advice wouldn't come from a Bill Gates or Elon Musk afterall, who think in terms we can't even begin to comprehend, but maybe from someone a little better than you, who's recently been where you were.
I should note in closing that all the usual defenses against bad feedback should still hold. Don't take one person's success as proof that everything they did was right, unless you've seen everyone else who's tried the same thing.