Define success.

Jeff can define success however he wants. He can define it in terms of making money, or in terms of successful launches. Making money is hard - there is only so much demand for things in space, and some competition - making it questionable if the investment will pay off. However launching isn't as hard, and he can define metrics in that way and be successful for his purposes.

How is launching things into space any different from paying composers to write much, or painters to paint pictures - two things that rich people regularly did 300 years ago.