What do I look for in a founder

I have been asked a number of times what type of founders will succeed or will I invest or even remotely spend time with. I have spoken and talked about this in bits and pieces over the years. To summarize, they tend to possess a few of these traits below:

  • Ability to speak to anyone sincerely: Mirroring oneself to speak at a level to a 3 year old or a 70 year old (Shows empathy, sincerity)
  • Stubborn but listens with a little curiosity, craziness and humbleness: Some level of fearlessness, going against the grain (Shows the love of risks, chaos, and challenges)
  • Grit: Hustles and perseveres (Shows staying power, never ever give up)
  • Obsess with the product or the market he or she is in (Shows passion or domain expertise)
  • Someone I would like to get drunk with (Shows the ability to be a total package ok maybe not)

Lastly, to be all of the above and not come across as a total asshole.