On a visceral level, does this fire you up? Or feel like settling?
Would you want to be in a foxhole with these people? Eye contact, handshake feel.
If you could only make ONE bet, would it be this one?
Does this complement our existing investments? Fill a gap?
Could you confidently explain this to investors at the next meeting?
10 = no suspicion at all. 1 = something feels off. Trust your spider sense.
Right time in the cycle? Market conditions favorable? Or are we chasing?
How does this compare to other deals you've seen recently?
Can you sleep well after wiring the money? Or will it keep you up?
In 5 years, would you kick yourself for not doing this deal?
Do you feel well-informed? Or are there big unknowns?
Question weights are relative within the section.