For Calgarians, I know a girl who married to a founder of an Oil and Gas company (won't name it but its big). I know a few other small O&G company owners, but the money they have is "sneaky rich" as has been described - $20,000 allowances for their adult children etc.
I had a connection to the President of Clean Harbors. I got to go to a Patriots game in the Company's 48 person luxury box a couple years ago which was wild. I met Alan and genuinely seemed like a nice guy. Very down to earth as he grew the company from a rented backhoe. I think he had a big house on the cape and a massive fishing yacht as that was his hobby.
I know a few people who have went to the Richie Bros Island (yes the family owns an island)
A guy i used to work with knew a girl who was dating the son of Dennis Washington. He had some crazy stories about the money he had. The Washington's actually own the island next to the Richie Bros. island, and put a 9 hole golf course on the island - had to barge everything in and it apparently cost over 1 mil a hole.
Another random story, but i was in Cabo about 10 years ago and there was a massive yacht in the marina, complete with a regular size helicopter. My GF at the time was wondering how someone could afford something like that. I told her the story about the Washington's owning an island and building a private golf course etc. I remembered the name of the yacht and searched for it online... low and behold its owned by Dennis Washington
https://www.boatinternational.com/ya...-iv-yacht--247