I like talking to entrepreneurs who are excited about starting and growing new business ideas. I have some good experience with bootstrapping several companies I've started and have gown with very little capital investment as I am a true believer in lean startup.
I believe that you can do a lot more with cultural capital then with financial capital and have had some success building high performing teams that work very well together and get results.
Absolutely enable it! I know the folks at Sheepdog do this as standard operating procedure for all client domains
Great Question! I know entrepreneurs who have faulted on both sides of the equation. From my perspective it's easier for the folks on the "not trying hard enough" side self-identify as being so with the help of good advisors, mentors, & peer group. If you don't have that then get them!
The other case is much more difficult. I've seen the most amazing victories snatched from the jaws of defeat that seem nothing short of miraculous. That's what makes it difficult. I've also seen people dig a hole so deep they won't likely get out in less than 5 years and it's truly devastating to them and their families (if they have them). If you are in this spot ask your advisors, mentors, & peer group to be very blunt with you and listen to them carefully, and take notes!