When someone asks me a question like this I always look for the “good reason” and the “real reason”.
It seems to be that starting and doing six businesses is far from failure. And 49 is young. So it sounds totally rational (the good reason) that he is calling himself a failure and trying to figure out what’s next.
But my guess is there’s a real reason. He might simply not like doing businesses and has another passion he wants to pursue. That’s the real reason and its right below the surface.
So he’s looking for excuses (calling himself a “failure”) to break his pattern instead of simply saying “I want to do X” where X might be something totally different from doing a business. Maybe he wants go to chef school. or be a photographer. Or move somewhere super cheap and paint landscapes.
Don’t forget: you can give yourself permission to do anything you want. Even when you are walking towards the altar you aren’t married until you say “Yes”.