The C.E.O. Other C.E.O.s Turn To for Advice

What’s happening?: The U.S. workforce is experiencing a surge in “polyworking”—the practice of holding multiple jobs simultaneously—which hit a 30-year high in March 2025 with over 8.9 million Americans participating. As reported by Emma Goldberg in The New York Times, this isn’t just side hustling: polyworkers juggle part-time, full-time, and freelance roles across sectors. The trend is especially prominent among Millennials and Gen Z, fueled by rising living costs, economic uncertainty, and the normalization of remote work.

Why it matters: Polyworking is a micro-level response to macroeconomic instability. With inflation outpacing wages and traditional employment failing to provide financial security, workers are diversifying their income like investors diversify portfolios. It’s a structural adaptation to a labor market that no longer guarantees upward mobility through a single employer. For brands and employers, this means a shift in how work is structured, managed, and valued—demanding more flexible policies, clearer boundaries, and recognition that today’s workforce is optimizing for resilience, not just routine.

What’s happening?: The rapid rise of artificial intelligence is decimating entry-level job opportunities for recent college graduates—particularly in the tech sector. Major companies like Google, Meta, Amazon, and Apple have cut new grad hiring by more than half since 2022, with only 7% of new hires in 2024 coming straight from college, down from 25% the year before. As reported by Kashmir Hill in The New York Times, AI is automating tasks that once defined junior roles—coding, debugging, customer service, and financial analysis—effectively locking many young job seekers out of the traditional career pipeline.

Why it matters: We’re witnessing a structural collapse in how careers are built. AI is gutting the entry-level tier—automating the very roles that once served as proving grounds for emerging talent. Without that first rung on the ladder, companies risk weakening their future leadership pipelines and losing institutional memory. For recent graduates, this isn’t just about fewer jobs—it’s about fewer chances to grow, to be seen, and to gain trust inside organizations.

In this landscape, having a strong personal brand isn’t optional—it’s essential. When AI can do the work, your perspective, voice, and visibility become the differentiators. Whether through a portfolio, thought leadership, or creative side projects, young professionals who can clearly signal their value—and be discoverable doing it—will have a distinct edge. AI may be rewriting the rules of work, but storytelling and self-definition are how the next generation will break through.

What’s happening?: A new survey reveals a significant gap between Gen Z’s ambitions and their preparedness for adult life. While 90% of recent high school graduates still plan to attend college, 56% say their schools encouraged them to consider alternative paths—like trades, gig work, and especially content creation. Only 32% feel their education prepared them for the “real world,” with top concerns including money management, independent living, and communication skills. As reported by Sarah Bregel in Fast Company, 34% of grads feel pressure to pursue content creation or entrepreneurship, reflecting a growing cultural shift where influencer careers are not only mainstream, but institutionally endorsed.

Why it matters: What was once a fringe aspiration—becoming an influencer or content creator—is now a cultural expectation for many teens. The pressure to build a personal brand starts younger than ever, amplified not just by social platforms but increasingly by schools themselves. Teens don’t just want to create content—they feel they should. Yet this ambition is unfolding alongside a widespread lack of preparation for financial independence and real-world responsibilities. Without critical support, education, or guardrails, the push toward online visibility risks turning into anxiety and burnout for a generation still trying to find its footing.

What’s happening?: On May 31, 2025, Netflix hosted its most ambitious Tudum event yet — a live, globally streamed fan celebration held at the Kia Forum in Los Angeles. Hosted by Sofia Carson, the two-hour spectacle blended exclusive content reveals, celebrity appearances, and musical performances, all designed to engage Netflix’s worldwide audience.

A Live, Immersive Experience:
For the first time, Tudum was broadcast live on Netflix, marking a shift from previous years’ pre-recorded or YouTube streams. The event transformed the Kia Forum into a fan-centric arena, complete with an N-shaped red carpet, themed fan pits, and interactive photo opportunities. This immersive setup allowed fans to engage directly with the content and stars they love, echoing the energy of events like Comic-Con or Disney’s D23.

Star-Studded Appearances:
The event featured appearances from a plethora of Netflix’s biggest stars, including the casts of Stranger Things, Wednesday, Squid Game, and more. Notably, the young adult (YA) genre was well-represented, with a crossover of popular YA casts from Ginny & Georgia, Outer Banks, Forever, and My Life With the Walter Boys. Actors like Antonia Gentry, Chase Stokes, Nikki Rodriguez, and Lovie Simone engaged with fans through live Q&A sessions and a playful “YA class photo.”

Major Reveals and Announcements:
1. Stranger Things Season 5
Final Season Release Schedule: Volume 1 premieres November 26, Volume 2 on December 25, and the finale drops December 31, 2025.
Teaser Trailer: A nostalgic and emotional look back set the stage for Hawkins’ final battle.

2. Wednesday Season 2
Release Dates: Part 1 arrives August 6, and Part 2 follows on September 3, 2025.
Lady Gaga Joins Cast: Gaga plays Rosaline Rotwood, a mysterious new professor at Nevermore Academy.
New Cast Members: Steve Buscemi, Billie Piper, and Haley Joel Osment also join the ensemble.

3. Squid Game Season 3
Premiere Date: June 27, 2025.
Trailer and Cast Appearances: Lee Jung Jae, Lee Byung Hun, Park Sung Hoon, Kang Ae Shim, and T.O.P previewed the new season live.

4. Film Reveals
Happy Gilmore 2: Trailer dropped with Adam Sandler and Bad Bunny.
Frankenstein: Guillermo del Toro’s gothic adaptation starring Oscar Isaac and Jacob Elordi.
Wake Up Dead Man: A Knives Out Mystery: Premieres December 12 with Daniel Craig, Jeremy Renner, Josh Brolin, Mila Kunis, and Kerry Washington.
The Rip: A satirical preview from Ben Affleck and Matt Damon involving Cookie Monster set the tone for their upcoming police thriller.

5. Other Series and Surprises
ONE PIECE: Debut of Tony Tony Chopper via CGI/motion-capture, voiced by Mikaela Hoover.
YA Series Updates: New content from Emily in Paris, Outer Banks, Love Is Blind, and WWE kept longtime fans engaged.

Why it matters: Tudum 2025 wasn’t just a fan event — it was a strategic play for cultural endurance and everyday relevance. By spotlighting Stranger Things, Wednesday, Squid Game, and Knives Out, Netflix positioned these titles as more than shows — they’re long-term franchises with world-building potential. Tudum becomes the annual ritual to keep those worlds alive, tease what’s next, and reinforce Netflix’s commitment to developing IP that lasts beyond a single season. At the same time, the event was built for virality. With Lady Gaga’s coffin entrance, Jenna Ortega’s return, and meme-ready cameos from stars like Bad Bunny, Tudum generated high-impact, easily shareable content. In an attention economy where streaming services compete for screen time as much as subscriptions, Netflix isn’t just dropping content — it’s creating cultural flywheels. Tudum proves Netflix can spark conversation and sustain momentum in between releases, turning fandom into fuel.

What's happening?: A newly surfaced internal strategy document reveals OpenAI’s roadmap for transforming ChatGPT into a personalized AI “super-assistant” by mid-2025. The vision goes far beyond chat—ChatGPT will plan, transact, email, and manage calendars while adapting to each user’s preferences. It will be available across platforms, from chatgpt.com and mobile apps to integrations like Siri and email. Growth and monetization plans are staged:
Short-term: Focus on driving daily active use and delivering clear value.
Mid-term: Prepare to monetize new agentic capabilities and integrations.
Long-term: Pursue new business models as super-assistant capabilities mature.

Why it matters: This strategy reframes ChatGPT as a platform-level interface—positioned not just against other AI tools, but against search engines, browsers, and native OS assistants. OpenAI is betting that users will shift from siloed, manual workflows to seamless, AI-driven ones. By prioritizing personalization and actionability, it aligns with how people want to interact with technology today: through assistants that can actually do things. Culturally, it’s a shift from informational AI to functional AI.

What's happening?: In a new profile by Jordyn Holman for The New York Times, Steve Stoute—founder of UnitedMasters and Translation—emerges as one of the most quietly influential figures at the crossroads of music, tech, and marketing. At 54, he’s the person leaders like Jay-Z, NBA commissioner Adam Silver, and Google’s Lorraine Twohill call when they need to make sense of culture, brand, and strategy. From launching iconic campaigns for Beats by Dre and McDonald’s to building a global distribution platform for independent artists, Stoute has built a career out of connecting the dots between creativity and commerce. At Sadelle’s in Miami, where he’s an investor, the article paints a picture of Stoute as a magnet for power players—Miami’s mayor Francis Suarez even calls him “the guy people turn to.” With UnitedMasters, Stoute continues to champion a model where artists own their work, access brand deals, and bypass traditional gatekeepers. His reach spans continents, generations, and industries.

Why it matters: Steve Stoute isn’t just advising from the sidelines—he’s reshaping how influence flows in a world where culture leads business. His model challenges the old playbook: that power resides in institutions. Instead, he proves it can live in individuals who understand both creative instincts and boardroom dynamics. In an age where authenticity, identity, and cultural fluency drive value, Stoute is building infrastructure—through UnitedMasters—for creators to control their futures. He’s also emblematic of a larger shift: the rise of cross-industry translators who help brands, artists, and platforms move at the speed of culture. As the walls between tech, music, and marketing continue to blur, people like Stoute—who can synthesize across domains—aren’t just helpful. They’re essential.

What's happening?: Meta is developing a suite of AI tools that will allow advertisers to generate entire ad campaigns—visuals, video, copy, targeting, and budget optimization—using only a product image and a marketing goal. These tools are designed to make campaign creation nearly hands-free and highly personalized, with the system dynamically tailoring ad creative for individual users in real time.

In a report by The Wall Street Journal’s Meghan Bobrowsky and Patrick Coffee, the company detailed its goal to launch these tools by the end of 2026, backed by a massive infrastructure investment. Meta plans to spend between $64 billion and $72 billion next year to support its AI roadmap. Shares of major advertising agencies have already dropped in response, signaling broad industry concern about the disruptive potential of this technology.

Why it matters: Meta isn’t just iterating on its ad tools—it’s rewriting the rules of digital advertising. With this move, it’s turning its platforms into end-to-end ad engines, potentially displacing creative and media planning roles long held by agencies. For brands, this means faster, cheaper, and more precise campaigns. For small businesses, it means access to high-performance marketing without an agency or in-house team. And for the broader industry, it raises a high-stakes question: when AI controls not just delivery but also creation, what happens to the human layer of storytelling, strategy, and craft?

What's happening?: Pinterest, long cherished by Gen Z for its personalized and human-curated aesthetic, is encountering user frustration due to an influx of AI-generated content. As reported by Annabelle Choi for Fast Company, users have observed that searches for inspiration in areas like hair color, nail art, and interior design are increasingly dominated by AI-created images, making it challenging to find authentic, human-generated content. In response, Pinterest is piloting new tools aimed at helping users filter out unwanted AI content from their feeds.This shift has led some users to seek alternatives. For instance, the curation app Cosmos has experienced a surge in new users, particularly after being highlighted by popular TikTok creator Lois (@dandydemon), who expressed concerns over the prevalence of AI content on Pinterest. Cosmos reports gaining tens of thousands of new users in the days following the mention.

Why it matters: Pinterest's appeal to Gen Z has been rooted in its role as a safe, personalized space for inspiration and self-expression. The growing presence of AI-generated content threatens this unique positioning, potentially eroding user trust and engagement. As Gen Z users seek authenticity and human connection in their digital experiences, platforms like Pinterest must balance the integration of AI technologies with the preservation of the human-centric qualities that attracted users in the first place. Failure to do so could result in a migration of users to alternative platforms that better align with their expectations for genuine, curated content.

What's happening?: In a new Financial Times interview, Laurene Powell Jobs and former Apple design chief Jony Ive reflect on their enduring friendship and the unintended consequences of the tech revolution they helped shape. The conversation comes as OpenAI moves forward with its $6.5 billion acquisition of Ive’s AI hardware startup, io. While Powell Jobs is not a collaborator on the secretive new device, she has invested in both io and Ive’s design firm LoveFrom, and she voices strong support for his mission to build more humane, emotionally intelligent technology.

Ive acknowledges the unintended downsides of his Apple-era work—particularly the iPhone—and says his new efforts with OpenAI are driven by a desire to “own the consequences” and do better. “Humanity deserves better,” he tells the FT, referencing the growing unease many feel toward technology. Powell Jobs echoes that concern, pointing to the dark potential of tools never meant to harm. Her investment reflects belief not just in the business, but in the possibility of a more mindful tech future.

Why it matters: This conversation isn’t about nostalgia—it’s about reckoning. Ive and Powell Jobs are among the few figures in tech with the perspective, track record, and influence to publicly challenge the industry’s trajectory. Ive’s comments mark a rare moment of introspection from a designer whose products defined an era. His partnership with OpenAI suggests a future where design isn’t just about elegance—it’s about ethics, wellbeing, and long-term impact.

Powell Jobs, while not directly involved in the product’s development, brings moral clarity to the conversation. Her financial backing of projects like io signals that values-aligned capital still has a place in shaping next-gen tech. Together, their shared narrative underscores a larger shift: from building for utility and status to building for trust, emotional resonance, and human good.

What's happening?: Disney’s live-action Lilo & Stitch is quickly becoming one of the most profitable films in years, thanks to a series of smart strategic choices. Originally developed as a Disney+ exclusive, the film was rerouted to a wide theatrical release—a decision that unlocked massive earning potential. Over Memorial Day weekend, Lilo & Stitch shattered records, bringing in more than $182 million domestically and crossing $610 million globally after just two weekends. With a modest $100 million production budget, the film broke even early and is now on pace to top $950 million in ticket sales.The success goes beyond box office numbers. The film has seen exceptional international performance, especially in Mexico, the UK, France, and Brazil. It’s also captured a multigenerational audience: while families showed up, over half of opening weekend viewers were adults, driven by Gen Z and millennial nostalgia. Add in merchandise sales and a strong CinemaScore (“A”), and it’s clear Lilo & Stitch is a standout success across revenue streams and demographics.

Why it matters: Disney’s success with Lilo & Stitch is more than a box office win—it’s a strategic case study in how to maximize IP value in a shifting media landscape. At a time when major studios are questioning the ROI of direct-to-streaming content, this film shows the power of theatrical-first distribution when paired with beloved, multi-generational IP. The modest production budget sharpened its profit potential, while the reroute to theaters allowed Disney to tap into premium pricing, event-style marketing, and global audience turnout.

Culturally, the film hits a sweet spot: a mix of millennial nostalgia, Gen Z engagement, and family accessibility. Competitively, it signals that Disney still holds a unique advantage in cross-demo storytelling—especially when it leans into emotional, character-driven narratives. Lilo & Stitch also reinforces a broader trend: audiences are showing up for theatrical releases that feel meaningful, shared, and culturally resonant. For Disney, it's validation that strategic agility—paired with the right story—can still deliver extraordinary commercial upside.

What's happening?: In a new piece for The New York Times, Priya Krishna explores how artificial intelligence is quietly transforming the restaurant industry—from behind-the-scenes recipe development to real-time kitchen operations. Chefs and operators are using AI to generate new dishes, simulate flavor combinations, forecast diner preferences, and even automate parts of the cooking process. AI platforms like Climax Foods and Analytical Flavor Systems are already helping develop plant-based alternatives and predict how specific demographics will respond to a dish.

Some restaurants are using AI to analyze vast amounts of customer feedback, helping chefs refine menus based on taste trends and dietary preferences. Others are experimenting with AI-generated recipes, sometimes incorporating them into fine dining menus. While most chefs still see AI as a collaborative tool rather than a replacement, its growing role in inventory tracking, menu optimization, and personalized dining experiences signals a deeper integration of tech into the culinary craft.

Why it matters: The rise of AI in kitchens represents a pivotal moment for an industry traditionally rooted in hands-on skill, intuition, and creativity. For restaurants, the technology offers tangible operational benefits—reduced food waste, streamlined staffing, and faster innovation cycles. For consumers, it opens the door to highly personalized meals and faster service. But it also challenges long-held ideas about what makes food meaningful: Is a recipe less authentic if it was optimized by an algorithm?

More broadly, AI in restaurants reflects a growing trend of automation entering emotionally resonant, sensory-rich spaces once thought to be uniquely human. The fine line between enhancement and erasure of craft is being tested. How the food industry responds—balancing efficiency with artistry—may serve as a bellwether for other creative industries navigating the same tension.