Aero99, you're certainly right that everyone who has succeeded had to listen to many people tell them "it'll never work". I would certainly encourage this guy not to succumb for that reason.
It is, however, and entirely different thing to have people saying "I have been there - and it sucks!". A regular conversation of the individual owner / operator Part135 outfits I knew was just how few charter services were honest-to-God profitable stand-alone business. So many dreamy eyed pilots wanted to be in the business, and all were willing to offer the services at breakneck prices, that noone could make a buck. It seems to be a permanent fact of life in that industry.
As was pointed out you'll work your guts out for a month in a Baron or Navajo to carve out the profit you'll make in one Learjet run across the country (which will make you tons of money all month til it sits for 28 days waiting for some hideously expensive part that's not available, then you're broke). There could be a whole new conversation on just capital alone.
This guy mentions something about a special angle - it's not as if there are no profitable Part 135 operators out there. Plenty have the right situation, but I bet it is a tiny fraction of the ones out there. Maybe he's got something unique that other operators don't.
Also Aero99 - you're right, being a pilot or not isn't much of an issue as to wether or not you can run a charter operation. I started mine with about 700 hours, and didn't make IFR PIC until my first year in business. In fact, the problem is that too many of the people that start up these outfits are pilots rather than business people. Heck - in some ways I was able to think farther outside the box and make some really cool innovations to our market because I didn't know that "that's not how it's done".
In retrospect, it would have been nice to have had more experience in both business and 135 flying. The learning curve would not have been nearly so costly.
Sure did have a lot of fun though...Whatever you do, find, beg, borrow, or kidnap someone with a lot of experience in a successful operation to help guide you.
Good Luck.