I don't recall hearing about Jobs ever meeting financial morons like him. He cared more about the products and I doubt he had the slightest interest in or patience for Wall St or even lawyers and financial people within Apple unless they were working on something he wanted or of direct relevance to the products. Sadly I think this demonstrates just how different Cook is from Jobs and it worries me a little.
Tim Cook just seems to try to keep people happy. There are a lot of conflicts going to crop up because of this. The Apple employees regularly state that they don't put much importance on money and yet the cash hoarding, tax setups seem to run counter to that but is part of their fiduciary responsibility. Their employment almost requires that they operate counter to their core values. At the same time, a lot of the major stockholders likely primarily care about money and the major ones have a say in how the company is run. So people who don't care about money yet have a responsibility to care about it because of the people whose only interest in Apple is money are not going to see eye to eye.
I'd say one difference between Tim and Steve is that Steve wouldn't try to keep everyone happy, he always had teams competing for success. Tim prefers collaboration. When a stockholder would have something to say, I'd expect Tim to try and work it out. Steve would most likely just wear his values on his sleeve and let people deal with it e.g doing a good job should be its own reward and if financial success is a result then so be it. Steve was asked about how he felt when Apple surpassed Microsoft's market cap and what he said was:
"It's surreal, but it doesn't matter very much. It's not what's important. It's not what makes you come to work in the morning. It's not why any of our customers buy our products so I think it's good for us to keep that in mind and just what we're doing and why we're doing it.
Apple was about 90 days from going bankrupt in the early days and it was much worse than I thought when I went back but I expected that all the good people would have left and I found these miraculous people, these great people and I tried to ask this as tactfully as I could but "why are you still here?" and a lot of them had this little phrase "I bleed in 6 colors", which was the old Apple logo and it was code for 'because I love what this place stands for'"
People who are involved in finance don't all understand this because they put a price tag on everything. The documentaries about the stock traders that caused the financial crisis talk about how they would go to prostitutes, have it billed to their company cards under miscellaneous expenses and then go home to their families. How they would take cocaine all night long and get up to go to work the next day making risky trades but taking no responsibility. These kind of values (or lack thereof) don't align with the people who work at Apple.
I don't think that people who have these disparate natures can reconcile this because it's like trying to explain to someone why you prefer chocolate ice-cream over strawberry. Everyone lives their lives to reach positive states of mind. Some people see everything as material and therefore subordinate to the common exchange currency of money and that's a valid way to look at things but has the side-effect of placing money first. Other people see that money is a byproduct of things that are of genuine value and it's the latter that comes first. When doing a good job because that's the goal results in financial success, both groups are happy. When a point is reached where doing a good job doesn't give the same financial reward because of inherent limits in the market, that's where it breaks down. The people who want the money don't care about the long term values of Apple, they want paid now, they want growth now, they want more innovation now.
Under the assumption that the people at Apple don't care about money, it might seem that draining the cash reserves to benefit the stockholders would be ok. It wouldn't matter to the people at Apple what happens with it and the money-grabbers get their loot/growth. But rewarding short-term investors over long-term investors runs counter to their values and Tim's primary responsibility is in making sure Apple is on a steady course to stay around because Apple is one of the diamonds in the rough that needs to stay around. Bending to the whims of greedy individuals doesn't set a good precedent for this.
The problem remains that they have a lot of cash and are not doing anything with it. That's the problem that needs to be solved. Stock buybacks are fine as long as the company trades below its intrinsic value. Apple isn't really trading below this any more. If they want to spend for long term stability then they should be buying into timeless business models like content creation/distribution. They can do some crazy things like buying Disney but they should be sensible about where technology is going and make suitable purchases. It's a lot about the people at the companies too rather than what they do. I'd much rather see them use the cash to do buyouts because one of the most recent resulted in the fingerprint sensor so that gets filtered down to customers and what customers love. Stock buybacks do no such thing. It's fine when cash is excessive but $150b can be put to far better use.