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You can help him most by being the realistic one in his circle. As the advisor to an undergraduate fraternity chapter, I see it daily; their eyes are bigger than their stomach. Much of the time this is a good thing, they rarely say "that wont work." but conversely, often they are too optimistic and not realistic about what it takes to achieve a goal.
I used to work in student affairs in college and at least three times a week a guy or group of guys would come in wanting to start their own fraternity. They were successful about 1 in 1,000 times.
The group I advise started as a colony and after twelve years of membership in my org, I wasnt ready for the amount of hard work it took.
I'd suggest you be supportive, yet keep him real about challenges/obsticles/heartbreak he could face.
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