Taking such risk in gambling requires tolerance and I'm sure I will never engage in such, just imagine you never won any of those games and your friend at the other hand had the money, this is very risky even with little amount I can't afford  Losing such.
Although gamblers are meant to take risk but the risk depends on what you want, if you bet with high amount and the day turns to be your lucky day then you've taken a risk that worth celebrating but if you stake with high amount and still loss you will still bear the pains that's what makes gambling a risky game. I have learnt to avoid taking higher risk ever since I lost to some random game I had high hope. You should be happy you won all games and you should avoid taking higher risk with huge amount.