Are you trying to say that stake.com are the ones losing?
However even when he has partnership with stake doesn't mean all the money he's gambling with are funded by stake.com, gamble with free money makes no sense because it looks like you aren't gambling at all because you aren't gambling with your money. If you want to talk about real gambler you have to make mention of gamblers that uses their own money to gamble, which means the person is a real gambler, but drake is a definition of a real gambler.
With the possibility that he's getting paid huge amounts of money with the partnership with Stake, and his music career being a success, I think that Drake isn't losing money and Stake isn't losing money either because Drake is advertising Stake and they're able to gather millions of people to get to their website. Maybe you guys are just saying that because you or me can't fathom how much money they're raking in profits, they're not the kind of money that's easy to earn in someone's lifetime, that's a definite thing. This loss might be big for us but this is just a cent to what Drake have in his total assets.