the ability to ask good questions is an indispensable skill

The ability to ask good questions is one of the most useful skills you can develop. Boring questions get boring responses.

One of the first considerations is to have nothing in the way of having intellectual insecurities. Have no shame. Ask people to explain things that are obvious to them but not to you.

This page will definitely be updated with different sections, since asking questions is multi-faceted and can involve a variety of variables. We'll start with questions of curiosity.

1. I've taken to heart your advice on your site about picking an industry you're truly interested in and "doing the work". In the case that the industry is very nascent and there's really no rulebook, what strategies would you use to "pave the way"?

2. What's the trade-off between switching companies and switching roles, versus moving horizontally within your current company, despite not being as interested in the product?

3. I've received advice to "apply broadly", but am opposed to this shotgun approach because I think your interest in a product peeks out during an interview. What is your opinion of such an approach?

4. You've talked a little about your work history on your site. What about investment banking turned you off from that, and why was product the next transition for you?

5. I see now that you're not a PM. What changed and what made you decide you wanted to become a VC?

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