I don't have any close person who owns any betting company, but what I know of is that I have seen all these middlemen in the business bet in their shop but in rare cases. if at all, a betting company owner decides to place a bet on a different betting platform or company from his, then I think there is a reason behind that IMO, and that looks fishy to me and this act should attract some kind of questions because he should be patronizing his company in the first place.
If we have a friend like that who owns a huge business like a casino, then I'm sure we are not here now in the Bitcointalk forum because we are likely a businessman as well, and you know them, they are always busy. A middlemen might be different from the casino owner. They don't own a casino, but if they know someone who owns it, then maybe they can choose to play on that casino as a way of showing a support.
As for the casino owner, I think it's obvious that they will always play on the other casino because how can they earn a profit if they will only play on their own? Unless if they are only playing to get entertained. That way, they will never lose any of their wealth.
No, if we have friend who is successful in the casino business that doesn't mean we are also successful because no one will ever know each person fate and friendship will never be measured by the success they get.
Example, of course you have quite lot of friends and I sure some of them have achieved success but are still you are still here.
Don't assume that when you have successful friends we are also successful people, that not true.
And the activity of casino businessman may only be checking and monitoring how the business is running so that there is still time to gamble if they want to.
But I not sure they use their free time to gamble because people with huge wealth and successful businesses always have different ways to have fun and get entertainment.