Can I go to war with you?

I was brainstorming with angel investor Jeffrey Broer yesterday, and conversation turned to our previous investments. My portfolio is here, for those that want to take a look.

The learnings we discussed on what to look out for:

  • at least one failure
  • at least one success
  • a team
  • the team has competencies across marketing, tech, business, and design/UX

We didn't talk about styles, but on my side I strongly prefer to put in money AND time. For the investments that I've enjoyed, I've always worked closely with the founder and team to make things happen. When I go in, I want to contribute my whole commitment.

After this discussion, I realized I had another strong filter: "Can I go to war with this person?". In my Army squad, I distinctly remember this question as we were preparing to head to the sandbox. The Enlisted would then have a list of NCOs and Officers we'd prefer to stay with - not that we really had a choice, however.

So what does "Can I go to war with this person?" mean in the context of angel investing?: It means to me:

  • Can you make the right choices more often than the wrong choices?
  • Can you lead your team when needed, and know how to get out of the way when not? Can you tell the difference?
  • Do you have the courage to make the hard choices, the sacrifices, the dirty work to accomplish the mission?
  • Can you inspire?
  • Do you have integrity?
  • Can you drive longer, harder, faster?
  • Can you care about the right little things when it doesn't matter, because I know you'll definitely care about them when it does matter?