Jim McIngvale, the mattress king of Houston, places bets with the underdog at the SuperBowl to cover his rebate of $3000. to any customers who buy mattresses from him if his team wins.

Mattress Mack Finally Wins a Big One, Cashes $3.46M Super Bowl Bet

In this instance, his team won, but this just barely covered the rebates he had to shell out, and is a means of self-insuring because no insurance company s willing to cover all of his potential losses against the rebate offer.

He didn't too well in 2019, or 2020:
https://www.truepassage.com/forums/s...ress#post40914

In any case, this year at least, he's doing a lot better than the Canadian (former) mattress king, Alan, the millionaire of Louis Theroux's BBC Las Vegas documentary fame, who ended up a broke Uber driver.