A public service announcement for the denizens of Silicon Valley: The increasingly violent ground tremors you are likely experiencing aren’t foreshocks indicating looming earthquakes. The unrest is merely Apple founder and former CEO Steve Jobs spinning ever faster in his Palo Alto grave. Jobs would be appalled by Apple’s disastrous AI missteps and if he returned to life, his first order of business would be to return to the innovative Cupertino headquarters he spearheaded and fire CEO Tim Cook.
Even as he transformed Apple into a blue-chip company, Jobs was always an entrepreneur at heart who never rested on his laurels or wanted to become an empty turtleneck. He was a radical innovator who swung for the fences, and his myriad successes included the consumer-friendly iMac, the iPod, the iTunes store, the iPhone, the iPad, and the App Store.
Not much to be wowed about under Cook’s leadership in the ensuing 14 years he’s run Apple since succeeding Jobs, unless you consider the Apple Watch, AirPods, and the Apple Silicon chip head-spinning innovations.
Of course, Wall Street would prefer Cook’s cautious and disciplined management to Jobs’ disrespectful and dismissive ways, particularly his refusal to compromise product quality or innovation to satisfy quarterly earnings expectations. Cook prefers to coddle investors and shower them with stock buybacks that boost the value of Apple’s shares and bolster the investment banking revenues of the lucky firms that execute the legalized stock manipulation.

Stock buybacks, also known as share repurchase programs, occur when companies buy their shares in the open market. Fewer shares outstanding means profits are distributed across fewer shares, thereby increasing their individual value in the short term. Under Cook’s leadership, Apple has squandered more than $500 billion in stock buybacks, making it the leading stock repurchaser in the S&P 500. In May of last year, Apple authorized an additional $110 billion stock buyback, a new record for the company.
Here’s a new Starkman Approved maxim I’ve coined: “Stock buybacks don’t make for great companies, but great companies are destroyed by stock buybacks.”
Cook, to his credit, leveraged Jobs’ innovations into mega volume cash printing machines, generating so much money that he hasn’t the faintest idea what to do with all the moolah, hence the hundreds of billions in stock buybacks. But to keep Apple humming, and Wall Street salivating, Cook needs to ensure the company remains on the cutting edge of innovation, particularly with products that are critical to its ecosystem.
One of those products is artificial intelligence, and on that front, Apple is not only way behind, but it has also suffered a very public and humiliating defeat. If Jobs were still alive, you wouldn’t want to go anywhere near Apple’s headquarters for fear of getting hit by some of the bodies he’d be throwing from the building’s rooftop.
Eureka moment
As a longtime admirer and early adopter of Apple products (yes, yours truly, the technophobe, embraced Apple when it was a fringe company because of its consumer friendly interface and software), I could never imagine buying a computer, tablet, or mobile phone that wasn’t part of the Apple ecosystem and supported by the company’s customer care, which is unrivaled in the tech industry. But reading this article about ChatGPT’s Sam Altman partnering with famed designer Jony Ive to create a device from the ground up specifically intended for AI was a Eureka moment.
Altman told a Japanese news service the device would be “the greatest evolution in technology devices since the iPhone.”
That might sound like the typical Silicon Valley braggadocio, but given Ive’s involvement Cook should be running scared. Ive was Apple’s former Chief Design Officer and was instrumental in creating the iconic designs of the iMac, iPod, iPhone, and iPad. Ives redefined consumer electronics design and without him, Jobs might not have achieved his legendary status.

AI has fast become a critical part of my life, so much so that I wonder how I survived without it. I’d liken the product to Google on steroids, significantly reducing the time I spend researching this blog and dismissing in mere seconds thesis ideas I mistakenly thought were credible. I’m preparing my medical records so that AI can analyze them and recommend treatments and activities for all that ails me. As I get my financial affairs in order, I will use AI to test my asset allocations and my choice of ETFs.
Apple’s botched AI
Apple so far has botched its foray into artificial intelligence and fallen behind, leading to delays, technical issues, and calls in the tech world for Tim Cook’s resignation.
Apple last June announced Apple Intelligence, a suite of AI-driven features aimed at enhancing user experience across its devices. Initially slated for release with iOS 18 and the iPhone 16, the features were postponed due to stability concerns. Reports indicated that Apple needed additional time to address software bugs and ensure a smooth user experience.
Even after the delayed release, Apple Intelligence faced technical hurdles. The AI-powered notification summaries, designed to provide concise news updates, generated inaccurate and misleading headlines. In one instance, the program falsely reported that murder suspect Luigi Mangione had shot himself, incorrectly attributing the false information to BBC News.
The New York Times reportedly experienced a similar issue when Apple Intelligence incorrectly summarized an article about Israeli Prime Minister Benjamin Netanyahu, creating a notification claiming he had been arrested when the original article discussed an arrest warrant from the International Criminal Court.
Even some analysts on Wall Street are skeptical of Apple’s AI rollout plans, and its ability to introduce a new iPhone design in a timely manner. The iPhone’s design hasn’t changed all that much since Jobs died.
“We do not expect a material change in the [handset shape] or a significant improvement to Apple Intelligence over the next 12 months even with the upcoming [iPhone] 17 series…in the fall of 2025 dampening demand,” wrote UBS analyst David Vogt in a research note.
UBS calculates that the average age of a consumer’s iPhone, excluding China, is now around 37 months, up from 34 months a year ago. That means consumers didn’t perceive the iPhone 16 as a must have product.

Corporate America is returning to the era of the a-hole CEO, no longer touting DEI and singing Kumbaya but rather demanding that employees return to their office cubicles and order them to put up and shut up. Chase CEO Jamie Dimon and Meta CEO Mark Zuckerberg have excitedly embraced the return of their real selves, and Elon Musk never changed his managerial spots.
It’s an unfortunate truth that a-holes are the ones who can innovate and get things done. Uber founder Travis Kalanik was an uber-a-hole and notably his supposedly warm-and-cuddly successor Dara Khosrowshahi has yet to pioneer one innovation in his nearly eight years on the job, pocketing $134 million for himself while shafting his drivers. It should come as no surprise that Uber has implemented an $8.5 billion share repurchase program.
Jobs was a certifiable a-hole, a description I doubt he’d mind or dispute. Tim Cook has always struck me as a nice and decent guy, but unfortunately nice guys too often finish last, which is where Apple is headed if it can’t quickly get its AI act together.
A reader sent me this post by David Heinemeier Hansson, a tech entrepreneur whose views are very much akin to my own. Below are some of his compelling insights. Apologies for publishing his vulgarity, but I suspect he’d have a few choice words for me if I cleaned it up.
Apple needs a new asshole in charge
When things are going well, managers can fool themselves into thinking that people trying their best is all that matters. Poor outcomes are just another opportunity for learning! But that delusion stops working when the wheels finally start coming off — like they have now for Apple and its AI unit. Then you need someone who cares about the outcome above the effort. Then you need an asshole.
In management parlance, an asshole is someone who cares less about feelings or effort and more about outcomes. Steve Jobs was one such asshole. So seems to be Musk. Gates certainly was as well. Most top technology chiefs who’ve had to really fight in competitive markets for the top prize fall into this category.
Apple’s AI management is missing an asshole:
Walker defended his Siri group, telling them that they should be proud. Employees poured their “hearts and souls into this thing,” he said. “I saw so many people giving everything they had in order to make this happen and to make incredible progress together.”
So it’s stuck nurturing feelings:
“You might have co-workers or friends or family asking you what happened, and it doesn’t feel good,” Walker said. “It’s very reasonable to feel all these things.” He said others are feeling burnout and that his team will be entitled to time away to recharge to get ready for “plenty of hard work ahead.”
John Gruber from Daring Fireball dug up this anecdote from the last time Apple seriously botched a major software launch:
Steve Jobs doesn’t tolerate duds. Shortly after the launch event, he summoned the MobileMe team, gathering them in the Town Hall auditorium in Building 4 of Apple’s campus, the venue the company uses for intimate product unveilings for journalists. According to a participant in the meeting, Jobs walked in, clad in his trademark black mock turtleneck and blue jeans, clasped his hands together, and asked a simple question: “Can anyone tell me what MobileMe is supposed to do?”
Having received a satisfactory answer, he continued, “So why the fuck doesn’t it do that?”For the next half-hour Jobs berated the group. “You’ve tarnished Apple’s reputation,” he told them. “You should hate each other for having let each other down.” The public humiliation particularly infuriated Jobs.
Can you see the difference? This is an asshole in action.
Apple needs to find a new asshole and put them in charge of the entire product line. Cook clearly isn’t up to the task, and the job is currently spread thinly across a whole roster of senior VPs. Little fiefdoms. This is poison to the integrated magic that was Apple’s trademark for so long.