what? Steve died after icloud was already a thing, so I'm not sure how you're drawing that comparison. What other services was Steve giving out for free that other companies were not? Were you not there for when the original iphone was released and there was a lot of negative coverage over the price, and how apple lowered it months after release? Mobile me? Original macbook air? Your comment makes it seem like Steve somehow was throwing out money from the windows in Cupertino, as if he didnt answer to shareholders any more than Tim does now.
Steve was a unique guy. He had a way about him.
To use your analogy... Steve could have thrown money from the windows like confetti, and had the shareholders praising him the whole time. They would have believed him when he said trust me, it'll be fine, this will come back 10-fold. And, with the way Steve spoke, and the way he'd spin it, somehow it would.
Steve's unique position, was that he was brought back into a company that was dying. And, he helped it to not only recover, but to thrive. That gave Steve a huge amount of influence at Apple. Granted he could have eventually made enough mistakes to find himself booted out again. But, he had generally come back and done an amazing job. He had vision, and charisma. And, when he spoke, people listened. He may not have been right, but the way he spoke, you believed in him.
He was also at times humble when necessary. I don't specifically remember which speeches they were. But, I do remember a presentation of him humbly accepting some missteps, and promising to make it right, if we could take the lumps and move forward. A respectable characteristic.
I saw him make mistakes. I saw him do great things. There was a very human quality to him. And, you could see his vision. You could see his natural drive was to influence the world, take us to great places, and to bring us a new way of doing everything. He had a vision of the future, and that was his drive.
His successes gave him significant room to take a gamble, and the shareholders would go along with the idea.
Tim came into a less fortunate position in some ways. He came into a wealthy company that was already successful. His position is one to lose everything. So he is under tighter reigns. He hasn't proved himself to be the visionary that can likely succeed on a gamble that nobody understands yet. He has to tread the careful known path. And, in the end, that is very restricting. He can't announce a crazy thought, and say we're doing this. They'll tie his hands, afraid that he'll fail and resist the impulse change.
So, while the current trend is success, and money. The long term loss is there if you see it. Yes, they need to balance the books. But, without someone there to rock the boat, shake it up, and take a crazy gamble, they'll safely ride the rails next to all the other companies. A "me too" instead of suddenly rocketing off into the uncharted.
Crazy ideas are a gamble. But, crazy ideas are where the most amazing discoveries are made.