I'd have no trouble taking money from friends who have been around the startup block a couple times. These people don't need me to protect them from themselves.

I'd have no trouble taking money from friends who have been around the startup block a couple times. These people don't need me to protect them from themselves. Asking directly seems tacky, but they'd know I was looking (some I'd be going to for help finding investors!), and if they expressed interest, that'd be fine. Those definitely fall into my latter category of "successful entrepreneurs". I agree that you can take investment from them - because they know what it's like to run a business!