Why does Apple keep pulling its own ads?

Plus: The music industry is building the tech to hunt down AI songs

Hey there—Ryan here in sunny LA ☀️. Here’s what I’m tracking today across entertainment, tech, and marketing:

Real connection is back in style—at least if Hinge has anything to say about it. CEO Justin McLeod is calling out AI romance as “emotionally dangerous,” doubling down on helping users find love offline. Meanwhile, Boardroom (yes, Durant’s media baby) just dropped a $3,600 invite-only club that blends sports, culture, and access—it’s Soho House for the power set.

At Apple, the marketing misfires keep piling up. The company just pulled another campaign—an 8-minute Mac promo aimed at teens—after backlash over its manipulative tone and cringe humor. That’s four takedowns in a year for a brand known for creative precision, suggesting even Apple isn’t immune to the culture-check gauntlet.

Over in Cannes, AI companies may have skipped the beachside panels, but their shadow loomed large. Execs from Perplexity and Anthropic were quietly wooing CMOs as brands brace for a world where AI agents control the consumer journey. And publishers? They’re bracing too—as search bots skim content without sending traffic back, threatening the business model of the open web.

And in the streaming war’s latest twist, Apple TV+ just inked a first-look film deal with North Road, locking in prestige cinema as it eyes its own Oscar lane. Meanwhile, Pixar’s Elio struggled at the box office—highlighting just how tough it’s become to launch original stories in a market where familiar IP still rules the game.

Let’s get into it. 👇

1. 🎯 Rich Kleiman is building Boardroom into a membership club, and it's all about legacy

What’s happening: Boardroom, the media and lifestyle brand co-founded by NBA star Kevin Durant and his longtime business partner Rich Kleiman, is expanding into real-world experiences with the launch of the Boardroom Members Club. As reported by Fiona McIntyre for Fast Company, the invite-only membership costs $3,600 annually and offers exclusive access to high-profile events like NBA All-Star Weekend, Art Basel, and Paris Fashion Week. Members will also receive strategic support from figures like Michael Strahan, Taylor Rooks, and Mark Ronson. The initiative aligns with Boardroom’s evolution from a content studio to a cultural authority across the intersections of sports, business, and entertainment. Applications are open now, with the first members set to be admitted in June.

Why it matters: Boardroom is moving beyond storytelling into gatekeeping—positioning itself as the connective tissue for a generation of power players at the nexus of sports and culture. This isn’t just a media play; it’s a status-layered business model betting on access as a premium product. The club format caters to athletes, entrepreneurs, and creators who don’t just want visibility but meaningful, curated proximity. As more brands explore IRL extensions and community-as-product models, Boardroom’s move exemplifies how culturally fluent media brands can evolve into full-fledged platforms for influence and opportunity.

2.🧠 The internet of agents is rising fast, and publishers are nowhere near ready

What’s happening: AI search agents are rapidly reshaping how content is accessed on the web—and publishers are unprepared for the fallout. As reported by Pete Pachal for Fast Company, new data from TollBit reveals that AI-driven bots, especially those tied to real-time user queries (known as user agent bots), are increasingly bypassing traditional access controls like robots.txt. Unlike humans, these bots don’t engage with ads, sign up for subscriptions, or boost on-site traffic—undermining key revenue streams for media companies. Major AI platforms including Google, Meta, and Perplexity are now asserting that bots acting “on behalf of users” should be treated as human, a loophole they’re using to ignore opt-out mechanisms and scrape content. As bot traffic surges and user traffic wanes, publishers are left scrambling to build new defenses, including paywalls and bot detection tools, to preserve monetization.

Why it matters: This shift signals a fundamental breakdown in the unspoken deal that’s long underpinned online publishing: public content in exchange for attention. As AI agents increasingly “shop” the internet without generating traffic or revenue for content creators, media companies face a business model crisis. The rise of agentic browsing may not just reduce pageviews—it threatens the entire ad- and subscription-supported infrastructure of journalism. If AI can impersonate users and extract value without giving any back, publishers may be forced to erect higher walls, demand licensing, or exit the open web altogether. In this emerging “internet of agents,” attention may no longer be the currency—and that changes everything.

4. 🤖 CMOs say AI platforms’ low profile at Cannes won’t happen again

What’s happening: AI was the dominant topic at Cannes Lions 2025—but the major AI platforms themselves kept a surprisingly low profile. Despite their physical absence from the beach, companies like Perplexity and Anthropic were quietly present, sending key execs to meet with top marketers. As Krystal Scanlon and Seb Joseph report for Digiday, CMOs now anticipate these platforms will play a much more visible role going forward, especially as they explore monetization through advertising. Leaders like TripAdvisor CMO Matthew Dacey predict that AI players will soon introduce brand-safe marketplaces and client councils to guide integration. The question isn’t if AI platforms will sell ads—but how they’ll make those placements feel native to utility-driven, conversational environments.

Why it matters: Cannes has always functioned as a bellwether for what's next in media—and this year marked the quiet emergence of AI platforms as serious commercial players. Their understated presence belied their influence: everyone was talking about them, even if they weren’t on yachts. As AI-driven interfaces reshape how people search, shop, and solve problems, brands must prepare for ad formats that fit these new behaviors. That means moving beyond banners and toward more adaptive, context-rich engagements. CMOs will need to rethink their media strategies—not just for scale, but for fluency in experiences where AI agents are the new gatekeepers.

5. 🤖 AI is screening job applicants. But who is it leaving out?

What’s happening: AI-powered applicant tracking systems (ATS) are increasingly dominating the earliest stages of hiring—often filtering out résumés before any human involvement. As Lauren Weber reports in The WSJ, these systems use scores and keyword filters that can unfairly penalize candidates with employment gaps or nonstandard formatting. A high-profile lawsuit filed in 2023 against Workday highlights the growing ethical and legal concerns. Meanwhile, The New York Times (Evans & Shapiro) adds that many companies are now using AI tools that go beyond keyword matching—evaluating applicant “fit,” analyzing tone, and even predicting personality traits. But these systems often replicate or intensify bias around race, gender, socioeconomic background, age, and language proficiency.

Why it matters: The rise of AI in hiring is exposing a critical tension between efficiency and equity. While AI promises speed and scale, it risks sidelining qualified candidates and reinforcing systemic bias when oversight is lacking. For employers, the adoption of opaque AI screening tools isn’t just an HR issue—it signals how they value fairness and inclusion, with real implications for brand trust and reputation. These systems don’t just scan resumes—they shape who gets seen and who’s shut out. Both articles underscore the need for systemic change: hybrid approaches that combine human review with bias-audited automation, transparent communication with applicants, and intentional design that supports equity in candidate selection. As AI becomes the first touchpoint in hiring, its impact ripples far beyond HR—it’s a mirror of a company’s values, design choices, and long-term talent strategy.

6. 🤖 The music industry is building the tech to hunt down AI songs

What’s happening: AI-generated music is flooding platforms, and the industry is racing to adapt. What’s happening: As reported by Jack Buehrer for The Verge, the music industry is rapidly deploying AI-powered tools to identify, track, and manage synthetic songs. Platforms like Deezer and YouTube are flagging AI-generated tracks at upload, while startups such as Vermillio (with its TraceID framework) and Musical AI are developing technology that analyzes song components—like melody, lyrics, or vocals—to determine whether AI was involved. These tools embed traceability into metadata and allow platforms and labels to monitor song origins before they go live. The goal is not just takedown after the fact, but preemptive identification and licensing at the source. The effort is proactive: instead of scrambling to remove infringing content after it spreads, companies want to verify origins and assign rights before a track is even distributed.

Why it matters: AI-generated music is no longer fringe—it’s becoming a volume and copyright risk. Deezer estimates around 20% of daily uploads are AI-made, and a significant share of listens are potentially from fake or manipulated streams. Rather than chase violations, the industry is building an infrastructure of proactive enforcement—ushering in a new era of music governance. This shift could also birth an entirely new licensing economy for AI-generated content, where value is exchanged upfront through attribution instead of lawsuits. For rights holders, artists, and brands, the lesson is clear: if you want to protect creative value in the AI age, detection must be embedded into the foundation—not applied after the song has already gone viral.

7. 🎬 Apple seals movie deal with media mogul Peter Chernin

What’s happening: Apple has signed a multi-year, first-look film deal with Peter Chernin’s North Road Company, the studio behind hit titles like Ford v. Ferrari, Hidden Figures, and The Greatest Showman. As reported by Lucas Shaw for Bloomberg, this agreement marks a significant win for Apple TV+, which now gains first access to a pipeline of prestige films with box office and award-season credibility. The deal ends North Road’s previous partnership with Netflix and aligns it with Apple’s premium content ambitions. Chernin’s studio is known not just for hits, but for combining commercial appeal with critical acclaim—making it a prized partner as streamers seek standout original films. Apple will also collaborate with Chernin’s production team to potentially develop original IP and high-impact theatrical releases that can elevate Apple’s brand beyond streaming into broader entertainment influence.

Why it matters: This deal is about more than content acquisition—it’s a strategic signal. Apple is staking its claim not just as a tech company dabbling in TV, but as a long-term player in high-end Hollywood storytelling. As competition for subscriber loyalty intensifies, exclusive access to award-caliber films becomes a differentiator. Chernin’s track record provides Apple with both prestige and proven commercial viability—a blend many streamers struggle to balance. Moreover, this illustrates a shift in power dynamics: tech platforms are no longer just buyers; they’re shaping the upstream development of culture-driving narratives. For marketers and founders watching the entertainment space, Apple’s move shows how deeply tech is embedding itself into legacy storytelling ecosystems—and how “first-look” deals are becoming the new battleground for relevance in a saturated media landscape.

8. 💘 Hinge CEO Justin McLeod: “Dating AI chatbots is playing with fire”

What’s happening: In a candid and wide-ranging interview, Hinge CEO and founder Justin McLeod laid out the dating app’s evolving philosophy, making clear that Hinge isn’t chasing screen time—it’s optimizing for real relationships. As reported by Nilay Patel for The Verge, McLeod explained that the company has moved away from the engagement-driven models that dominate the dating app space, instead focusing on helping users find meaningful, offline connections. AI is part of the toolkit—used to improve matchmaking, recommend stronger profile content, and assist with messaging—but Hinge draws a hard boundary when it comes to emotional substitution. McLeod issued a strong warning about the rise of AI companionship and romantic chatbots, calling them “emotionally dangerous” and likening them to junk food: easy to consume, temporarily satisfying, but ultimately hollow and harmful. He emphasized that forming bonds with machines risks eroding our capacity for genuine human relationships, especially among younger generations. For Hinge, the message is clear: AI should support connection, not replace it.

Why it matters: McLeod’s stance is a noteworthy signal in an industry increasingly experimenting with AI-driven intimacy. While some apps flirt with full-on AI companions, Hinge’s decision to use AI only to support—not supplant—human interaction marks a critical point of brand differentiation. For marketers, founders, and product strategists, it’s a case study in ethical AI integration: acknowledging the power of the technology while resisting its more seductive, but possibly corrosive, applications. As AI tools become more emotionally intelligent, brands will face pressure to define not just what they can do with AI, but what they should do. Hinge is making its bet: that long-term brand value lies in enabling genuine human experiences, not digital surrogates. This move could resonate deeply with a generation increasingly wary of artificial connection and hungry for real-world meaning.

9. 🖥️ Apple Keeps Pulling Its Own Ads

What’s happening: Apple has quietly pulled another ad—an 8-minute short titled The Parent Presentation, starring comedian Martin Herlihy, aimed at helping students convince their parents to buy them a Mac. As reported by Wes Davis for The Verge, the ad was released and then swiftly removed from YouTube and Apple’s college site within 24 hours. While the accompanying 81-slide deck remains live, the full video was taken down amid growing criticism. Viewers described the ad as “cringe,” manipulative, and ethically questionable for encouraging teens to emotionally sway their parents into making a major purchase. Others noted the campaign mocked both students and parents, casting them as either scheming or gullible. This marks the fourth time in a year that Apple has pulled a high-profile ad following public backlash.

Why it matters: For a brand celebrated for its creative precision, Apple’s recent pattern of releasing and retracting campaigns points to a misalignment between ambition and cultural sensitivity. The Parent Presentation misfired by combining Gen Z–style humor with overt sales tactics—creating a tone that felt off-brand and ethically murky. In today’s hyper-responsive media landscape, audiences are quick to flag tone-deaf content, especially when it targets minors or relies on manipulation. This latest removal underscores the importance of audience calibration, ethical storytelling, and pre-launch testing. Even for brands with Apple’s cachet, misjudging tone can lead to rapid retreat.

10. 🎥 MrBeast used AI to generate YouTube thumbnails, and creators aren’t happy

What’s happening: MrBeast (Jimmy Donaldson), YouTube’s most-subscribed creator, launched an AI-powered thumbnail generator through his analytics platform Viewstats, which could automatically swap faces and styles from popular videos. As reported by Chris Stokel-Walker for Fast Company, the rollout, promoted in tutorial content and social posts, was quickly met with backlash when creators like Jacksepticeye discovered their likenesses and branding had been used without consent—sparking concerns around creative theft and brand appropriation. Jacksepticeye took to social media to condemn the tool, calling it “deeply unethical and harmful to the creative community,” and stating, “I hate what this platform is turning into. Fuck AI.” Other YouTubers echoed his outrage, accusing the product of undermining original work and reinforcing an ecosystem that increasingly favors high-volume, high-reach creators over those who build value through distinct creative identity.

Why it matters: This incident crystallizes the tension between AI convenience and creative integrity. When high-profile creators like MrBeast deploy automation tools, they risk widening the gap between established influencers and smaller channels—reinforcing power imbalances rather than democratizing opportunity. Backlash underscores a growing sentiment in the creator economy: AI should serve as an augmentation tool, not a shortcut for replicating others’ creative work. Brands and platforms face rising pressure to integrate AI responsibly—protecting original creators, ensuring ethical usage, and preserving the value of human-driven artistry.

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