I think having a set of balls and taking the chance would be the most important part. All of the other stuff is important too but generally they make it because of being different and taking over a segment of the economy.
I would be surprised if it isn't a stock swap. It isn't taxable to the Pilot shareholders if Bershire acquires Pilot by exchanging Pilot stock for BRK. If the principals want liquidity, BRK is easy enough to sell in the open market. There are also accounting advantages to BRK for using their stock as currency instead of cash.
berkshire has a bunch of cash though. more than it knows what to do with. in the past buffet has liked to use cash.
I know a guy down in the place I grew up that started a trucking company from nothing... He's a multi millionaire now and no shit, he'll be wearing overalls just about every time I see him.