The one boss I had like that was successful financially, but he cultivated a HORRIBLE work environment with his constant asshole-ish-ness, and eventually pushed out every talented employee with options. When the boss is the biggest crybaby in the company, there's no hope for positive employee morale.

On the other hand, I also worked for a much wealthier (low-7 figures vs. the mid-6 figure asshole) and dude was one of the best bosses that I've had. Positive, encouraging, forward-looking and knew how to maintain relationships. If he needed some help with something today I got him because of how much I liked working for him.