Despite near-unlimited capital and distribution, Apple's most impressive innovation in the last decade has been a thinner iPhone. This is viewed as a major failure of vision and a massive missed opportunity for a company positioned to lead in new technological frontiers.

Cook's potential retirement isn't about failure but preserving his legacy. He could exit after a record-breaking quarter, before the high-stakes AI bets of competitors either collapse the market or prove Apple is too far behind, protecting his track record.

The young Steve Jobs famously vilified IBM in the iconic "1984" ad. However, upon returning to a failing Apple, the older Jobs recognized his own operational weaknesses. He hired a wave of talent from IBM, including Tim Cook, to instill the discipline in logistics, procurement, and manufacturing that he had previously disdained.

When a clear number-two executive like Jeff Williams retires unexpectedly, it's often a signal they were passed over for the top job. This pattern was seen at Amazon when Jeff Wilkie left right before Andy Jassy was named CEO, suggesting Tim Cook's replacement has been chosen.

Even with full board support, a successor CEO may lack the intrinsic 'moral authority' to make drastic 'burn the boats' decisions. This courage is harder to summon without the deep-seated capital a founder naturally possesses, making company-altering transformation more challenging for an outsider.

Sierra VC Shashank Saxena finds Steve Jobs most inspiring not for Apple's initial founding, but for witnessing its dramatic reinvention with the iPod and Mac. This perspective highlights that a leader's ability to execute a successful turnaround can be a more powerful source of inspiration than their original vision alone.

Tim Cook, at the height of his success, is planning his exit. This stands in stark contrast to aging political and corporate leaders who cling to power, creating instability. The biggest problems often trace back to a powerful man who "won't fuck and leave."

Successor CEOs cannot replicate the founder's all-encompassing "working memory" of the company and its products. Recognizing this is key. The role must shift from knowing everything to building a cohesive team and focusing on the few strategic decisions only the CEO can make.

Thompson critiques Apple's lucrative services strategy as a shift from creating the best products to "harvesting the profits from other companies' innovations." The argument is that this rent-seeking behavior is corrosive to the company's core DNA of product excellence and innovation.