The first time I was ever asked to invest in something, my college roommate wanted $300 from me to buy Elvis posters at the dollar store, mark them up to $10, advertise them in the back of some weird magazine and make $200.  Of which I would get $20.  

Interestingly, I ran through all of the same filters then that I have learned to do now when considering whether or not to invest:
-Proximity.  I want to be close to the team so that I can help in person whenever necessary.  Could I have helped him? Sure- we lived in the same apartment.  
-Team.   I knew him really well- love him to this day.  I knew he was just as likely to buy beer with the money.  
-Deal Terms.  hmm, 10% of the profits.   Not exactly what I was looking for.  
-Vision.  Could this lead to a huge business where I would rake in cash every month? Nope.  It was a very small vision.   

I said no.  

I started angel investing roughly a year ago and have made 7 investments and am on the verge of making a few more.  One cratered and the rest are going strong and I’ve learned a ton in making the investments.  The biggest mistake that I’ve made is not getting to know the entrepreneurs enough prior to making the investment- not because I have some great ability to discern whether or not they will be successful; rather that I need to understand the commitment to the Big Vision of the entrepreneur.  Vision trumps team for me- if it isn’t huge, then the entrepreneur likely lacks the confidence to 
pull it off regardless of what the vision is.  It is also unlikely to get huge if the vision isn’t huge!   Of course I need to believe that the team in place can execute that vision, but that really is secondary to me.  

I’m happy to say that the investments I’ve made that are still “alive” all have huge visions of changing their particular world.  I think they will.  I’ll try to help.