I have a roofing contractor friend, high school drop out, has a firm grasp on business doing $50-$100mil In sales.
If "$50-100mil" is meant to per year that seems just a little far fetched for a "roofing contractor." Assume the average roof job costs $100,000 (a number I'm pulling out of thin air; I've no idea how much it does, but I can't imagine it's more than $100,000 unless your roof is made of gold), then he's doing between 500 and 1,000 of those a year, which works out to
more than a roof job per day, 7 days a week, 365 days per year. Unless you live in a place where the rate of roof failures is unusually high (or your buddy does a shitty job) at a rate of 500 roofs per year, he'd probably run out of roofs to repair relatively quickly.
For reference,
Kiewit Corporation, "one of the largest construction and engineering organizations in North America" with over 22,000 employees which handles things like highway interchanges, dam spillways, bridges and more had revenue of $1.2 billion (and a profit of about $580 million). I just find it hard to believe that one of the largest construction companies in North America would only do 10x in revenue compared to your "roofing contractor" buddy.
Something smells.