Jun 9, 2025 · 58m · big-technology
Apple’s AI 'Gap Year' at WWDC?, Elon Vs. Trump Goes Nuclear, NYTimes’ OpenAI Attack
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In this episode of the Big Technology Podcast, Alex Kantrowitz and Ranjan Roy dissect Apple's AI vulnerabilities ahead of WWDC, the explosive public breakdown between Elon Musk and Donald Trump alongside its business fallout, and significant legal battles surrounding generative AI data retention.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 59.7% of the talking time here. How this is scored →
Alex as informed peer 6.6 Guest teaching 2.1 Guest disagreement 1.8 Alex pushing back 1.9
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 55:17 Ranjan pushes back on Alex's framing of the New York Times as a bad actor
Ranjan rejects the idea that the Times is acting improperly, asserting that OpenAI could never realistically license all publisher content individually and embracing the aggressive legal stance.
Hardest push from Alex ▶ 54:45 Alex challenges Ranjan on whether the New York Times' lawsuit imperils user privacyAlex directly questions Ranjan's enthusiasm for the lawsuit by asking if forcing OpenAI to retain user chats makes the Times a bad actor harming millions of users.
Biggest teaching moment ▶ 6:21 Ranjan reframes Apple's on-device model strategy as missing the pointRanjan explains that while on-device inference was once viewed as an advantage, latency and privacy are no longer Apple's real issue compared to delivering a functional product that reliably retrieves email data.
Alex holds their own ▶ 25:04 Alex lays out comprehensive strategic rationale for Apple acquiring PerplexityAlex displays detailed industry command by combining query volume metrics, Apple's buyback capacity, antitrust vulnerability with Google, and regulatory clearances to build a compelling acquisition thesis.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| Apple's AI Challenges and On-Device Models at WWDC | 7 | 3 | 2 | 2 | Alex demonstrates strong domain knowledge by quoting reporting from Mark Gurman and detailing technical parameters of Apple's 3-billion-parameter on-device models. Ranjan agrees with the premise of Apple's struggles but reframes on-device efficiency as irrelevant compared to basic product functionality. The tone is highly collaborative and conversational. | |
| Apple's AI Roadmap, Siri Overhaul, and Health Ambitions | 6 | 2 | 2 | 2 | Alex walks through Apple's internal product roadmaps including LLM Siri and Project Mulberry, comparing challenges to Amazon's Alexa rollout. Ranjan complements the analysis by detailing the agentic shortcut developer ecosystem and criticizing Apple Health's native functionality. The exchange remains friendly and analytical. | |
| WWDC Operating System Updates and Apple Ecosystem Stagnation | 7 | 1 | 1 | 1 | Alex cites IDC market data showing declining iPhone shipments and explains how average selling prices are masking hardware stagnation. Ranjan builds on this with cultural anecdotes about green bubble stigmas eroding as Android Pixel features improve. Both hosts are in broad agreement. | |
| The Case for Apple Acquiring Perplexity for Twenty Billion | 8 | 1 | 1 | 1 | Alex presents an extensive, data-backed thesis for Apple acquiring Perplexity for $20B, citing query growth numbers, buyback reserves, and antitrust testimony from Eddy Cue. Ranjan enthusiastically endorses the thesis and riffs on the branding. The dynamic showcases host analysis with minimal conflict. | |
| The Musk and Trump Bromance Implodes on Twitter | 5 | 3 | 2 | 2 | Alex acknowledges being mistaken in his prior prediction that Trump and Musk would maintain an alliance, quoting their respective public attacks. Ranjan playfully highlights his own earlier tweet predicting their split in March. The discussion is lighthearted and reflective. | |
| Fallout for Tesla, SpaceX, and the Tech Right | 7 | 2 | 1 | 2 | Alex provides detailed context on Tesla's market cap loss, European sales declines, and SpaceX's multi-billion dollar Starlink and ISS contracts. Ranjan adds perspective on how government dependency differs sharply between Tesla and SpaceX. Both hosts explore the tech-right political fallout constructively. | |
| Elon Musk's Legacy and the DOGE AI Contracting Fiasco | 7 | 2 | 1 | 1 | Alex summarizes ProPublica reporting regarding Doge's flawed AI tool that miscalculated Veterans Affairs contract values. Ranjan reflects on how this represents the worst-case scenario for careless enterprise AI deployment. The segment features strong journalistic synthesis from Alex. | |
| The New York Times versus OpenAI Chat Retention Lawsuit | 6 | 3 | 4 | 4 | Alex questions whether the New York Times' chat retention demand makes them a bad actor imperiling user privacy. Ranjan pushes back, arguing that OpenAI's business model cannot feasibly negotiate with every publisher and admiring the Times' aggressive legal maneuvering. This represents the liveliest debate of the episode. |
Statements from this episode (16)
Roy: The Elon Musk and Donald Trump Bromance Is Dead
“Bromances are dead, Alex. Musk and Trump, the bromance is dead.”
Kantrowitz: Apple Intelligence cross-app contextual features failed to ship in 2025
“I mean, if you think back to last year's event, we were promised effectively a contextually aware assistant, Apple intelligence that could combine signals from your apps and make your life easier by doing things like searching your Gmail and telling you when y…”
Roy: Apple's on-device AI doesn't matter because latency isn't the issue
“I don't think it matters at all, because latency is not the problem. Privacy, maybe some could argue, and we're going to get into OpenAI and chat retention in a little bit, but like, that's not the issue Apple's having right now. Just making a barely functiona…”
Ranjan Roy: Gemini within Gmail still fails at searching user email history
“Gemini within Gmail still is not good at searching through your Gmail, so the data problem of taking a massive data set like your entire email history is a lot harder than maybe we should give it credit for”
Roy: Vision Pro Is Incredible Technology, Unlike Apple Intelligence
“Vision Pro, maybe DUD, but Amazing piece of technology. I actually think that was very different than Apple Intelligence. That was almost like too forward looking a piece of technology or too niche, but still an incredible piece of technology. Apple Intelligen…”
Kantrowitz: Apple iPhone Shipments Fell from 234M to 232M in 2024
“IPhone shipments down. Twenty-twenty-four, according to IDC, 232 million? Is it million? Yeah, million iPhone shipments. Twenty-twenty-three, 234. So actually, iPhone shipments are down. Market share, 20% in twenty-twenty-three, 18.7%. In 2024. The only reason…”
Kantrowitz: Perplexity Is Raising at a $14B Valuation
“Now perplexity is out raising 14 at a fourteen billion dollar valuation right now.”
Kantrowitz: Perplexity Is in Talks to Integrate into Samsung Devices
“And perplexity is also right now in talks for a wide ranging deal to integrate its technology into Samsung devices.”
Kantrowitz: Google-Apple Search Deal Threat Is Big Tech's Most Underrated Liability
“I think it's one of the most underrated liabilities for big tech companies. It's a company, it's one of the most underrated liabilities for a big tech company today, if not the biggest.”
Roy: Apple Spent $410B on Buybacks Over Past Five Years
“Four hundred ten billion dollars spent in share buybacks over the last five years. Expected ninety billion this year.”
Kantrowitz: An Apple Acquisition of Perplexity Would Clear Antitrust Review
“Apple has a negligible share of the search market, and perplexity has a negligible share of the search market. Deal will sail through.”
Kantrowitz: SpaceX has $4.5B in federal contracts and eyes rural internet funds
“Beyond its existing 4.5 billion in federal contracts. SpaceX is also poised to get a slice of the forty two billion in contracts to provide internet connections to rural areas through Starlink.”
Kantrowitz: Tech right will side with Trump over Musk if pressed
“I think many will land with Trump over Musk if you really press them. He is the president after all”
Roy: Tech right will move toward Musk and reject Trump
“I think overall, like, people move back towards Musk and definitely not choose Trump over Musk”
Kantrowitz: Judge orders OpenAI to preserve ChatGPT chats for NYT lawsuit
“The New York Times is telling OpenAI, has gotten a judge to rule in favor of this position, that OpenAI has to preserve its chats, because people who are using OpenAI's ChatGPT to, ah, go around the New York Times paywall, ah, may delete those chats. And there…”