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Startup Investing | My Favorite First Meeting Questions

As an early-stage startup investor, I look for self-aware, determined, capable, passionate CEOs who are entrepreneurial by nature and have a track record of making the seemingly impossible possible.

I like to use the first meeting to ask some fairly unconventional qualitative questions to better understand whether a startup CEO meets these criteria.

Here are 18 of my favorites:

1) Can you give your best example of something seemingly impossible that you made possible?

2) Can you give an example of a time that you thought you were up for a challenge, but had to give up?

3) What did you learn from that experience?

4) What is the most interesting thing you’ve learned about yourself from this startup experience?

5) What is the most interesting thing you’ve learned about yourself from working with your co-founder(s)?

6) If you could start your business all over again, what is one thing you would do differently?

7) If a million dollars showed up on your doorstep, and you could choose to invest it in one thing to improve your business, what would that one thing be?

8) If you were an investor considering an investment in your company, what is the biggest hesitation you'd have to overcome?

9) In the unlikely event that your company fails, what will be the most likely reason?

10) What is a piece of advice that a mentor or an authority figure gave you that you are most thankful that you ignored?

11) If you were your own mentor, what's the most important advice you'd give yourself?

12) If you could change one thing about yourself to make you a better CEO, what would that be?

13) If you weren’t doing this, what would you be doing?

14) Knowing what you know about our fund, if you could choose only one person or thing from our network or program to access, what would that be?

15) What questions should I be asking?

16) What questions do you have for me?

17) How do you think this meeting went?

18) What is one thing our fund could have done to have improved your experience with us to date?

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