What specialty do they serve? What size deals do they prefer? Don't approach an investor who has been cutting checks for $1M asking for $100k and vice versa. How big is their fund? What deals have they already done? How many successful exits? How many deals do they do in a particular year? How many deals have they done THIS year? How well connected are they? Have they ever co-invested with anyone? Are they young, hungry, and willing to get us into the new ways of raising? Or are they a seasoned veteran? Make sure to ask about the last deal they did? What can they bring to the table other than money? What is the likelihood they will be the first to say yes to your offer? The hardest investment is always the first one. Few are willing to take a chance until someone else has committed. How many times have they done follow on investments? Can they lead you to other investors that can help us raise more capital?