This is a question that I will be indirect on because I don’t like to pick favorites for our students. What we do is give advice on what are key criteria for making decisions like this and so here they are:

1. Is this someone you see working with for a long time?
2. Is this someone you really want on your side when there is a problem?
3. Is this someone who has enough money that if they lose all their money on this investment, it won’t kill them or really hurt them too bad?
4. Are they respected by others in the investment community? This is very important. They should have made investments before, successful and unsuccessful. It is important they are well respected because this will dictate the possible list of investors going forward. If you get a “C” or even “B” quality (“A” being the best) as an angel, you odds of getting “A” quality investors will be dramatically decreased, really hurting your odds, valuation and terms & conditions of future funding. If you get an “A” angel investor, your world of potential investor is much bigger and much better. This has a disproportionate effect on your ultimate success so work very hard to get a good initial investor. It sets the tone for essentially all future rounds.
5. Angel’s terms and conditions should be standard. No special terms.
6. Angel should be strictly an investors. They should be looking for an operating or consulting role for which they get paid. This is a real red flag to me.
7. Make sure the angel has time for you. There will need to be communication and if they don’t have time, that is a signal that you are not important to them.
8. Look at their other investments and see if there are synergies in their portfolio with what you do. That is a significant plus.
9. Check references on the angel, ones that you find not the ones they give you. Find out what they are like after the money is in your bank account. How do they react in good times? Bad times? Find out how they rate with others, i.e., reputation? Find out who to avoid for sure. Find out how what specific value add they bring. Be very specific – who will they introduce you to? what specific knowledge do they have?
10. Valuation is not as important as the other dimensions above but it does figure into the equation of who you chose. However, maximize for the long term and not just the first round. I developed a model when I was fundraising that showed that if I took an “A” quality investor at a 20% lower valuation, it was much better in the long term than taking a “B” investor with the 20% higher valuation.

There are a lot in Boston and may other people want to name them in their posts but I don’t want to play favorites. It is always the choice of the entrepreneur and my job as an educator is to teach the entrepreneurs how to think about a problem/opportunity and not do it for the entrepreneur – so this is the most direct answer you will get from me.