The only thing I know for certain about early-stage companies is that there will be uncertainty. Even the best opportunities often twist, turn and pivot thousands of times before they produce a return for their investors.
As an angel and the Chief Investment Officer at MergeLane, I focus most of my angel investing diligence on the team. I look for founders that are tenacious enough to break through walls and clever enough to figure out how to go around them.
When I meet with entrepreneurs, I rarely ask conventional questions. Sure, I look at the pro forma, review their business model, check out the competitive landscape, etc., but I typically send those types of questions by email.
When I talk with them, I want to learn how they think and what makes them tick. These are my favorite questions to that end:
- If you had unlimited capital and resources, and could choose to do one thing to improve your business, what would that one thing be?
- What would you try now if you couldn’t fail?
- If you were an investor considering an investment in your company, what is the biggest hesitation you’d have to overcome?
- What was the best compliment you’ve ever received?
- What would your last employer say about you?
- If you were your own mentor, what’s the most important advice you’d give yourself?
- If we offered to invest a million dollars in your company, would you take it? Why or why not? If yes, what would you do with it?
- In what ways might you be contributing to the challenges you are experiencing?
- What are you currently tolerating or putting up with in your business?
- How do you think this meeting went?