Probably just burning through savings or an inheritance. It's hard to see money flowing out of your pocket when you are drunk and preoccupied with girls.
All you see is people telling you how great things are so you can't see the losses, or see them somewhere but end up believing things are great as other people tell you so things must turn around soon.
Can't let all those happy campers down, especially if you have come to know bar regulars, so you maintain the illusion until you are forced to sell. Then do so quietly by making an excuse like a medical issue or whatever so you don't look like a loser and elicit pity from others. No real loss, people forget quickly and move on even quicker.