AI Winners and Losers
Who gets Chegged?
ON THE POD: Getting Chegged, Episode 124
Online education company Chegg is suing Google for AI Overviews and might become the first major company felled by AI. We go over the hitlist of others at risk of getting Chegged, including SEO-dependent publishers, SaaS companies and even the email newsletter industrial complex. Plus: Why Lenny Rachitsky has succeeded, the case against all-inclusive resorts and a debate on whether reading is dying or just in a format transition.
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PVA CONVERSATION
Winners and losers
TROY: Warren Buffett once regarded newspapers as possessing “franchise value”, attributed to dominant, often monopolistic, market positions and essential role in information distribution. I like this idea. Franchises trump mere “good businesses” for reasons of customer loyalty, pricing power, recurring revenue, barriers to entry. We could put a lot of brands from the media's lost “oligopolistic era” in the franchise bucket. These were glory days when dysfunctional media owners and fat management could stumble to the office off a long martini lunch and still bag 20% margins. Sadly few remain. Franchise value has been replaced by the “network effects” enjoyed by platforms, not content creators.
Education tech company Chegg may never have reached franchise status but they did have a decent business for a time. How quickly they have become AI roadkill, watching a billion dollar market cap evaporate since the launch of generative AI. Chegg may blame Google for AI summaries reducing traffic to their site, but the AI replacement potential is a total eclipse scenario here. Why pay Chegg for textbook summaries and homework help when ChatGPT offers an infinite, personalized source of knowledge in your palm for free.
Chegg is a lethal case of ebola. Look around the digital media space and witness an endless list of companies suffering a less lethal case of Chegging — WebMD, WIkipedia, recipe sites, Quora, Stack Overflow, Yelp, Khan Academy, Duolingo, Investopedia, Wolfram Alpha. Make your own list.
Let’s take solace in a new wave of media models that turning change into tailwinds:
The ultra-lean, email-driven niche publishers that turn decent cash flow with tiny cost structures… Nate Silver’s lean and mean post-Disney Silver Bulletin (Nate’s live discussion with Paul Krugman on Substack says alot about where things are going), Lenny’s wildly successful product manager newsletter (just hit 1 million subs), our friend Emily Sundberg Feed Me rocketship;
The AI innovators like HolyWater Media, turning out short-form vertical video romance series with radical cost efficiency, spinning interactive character universes around their media with AI;
Latvian makers of Animated Oscar winner, Flow. Made on open source 3D software Blender for $4 million dollars, besting big budget blockbuster Inside Out 2.
A perennially struggling local media company, Patch, expanding reach from 1,100 to 30,000 local communities over a few months with the help of AI;
A new generation of powerful multi-platform podcasters, sustaining trad-media sized audiences, replacing old forms of radio and late-night talk with small but mighty margin businesses. See TCG’s latest investment in Audiochuck;
NerdWallet turns in a decent quarter.
Related…I love change, but AI is pushing into anxiety territory, if you take the time to contemplate broad implications coming our way. Ezra Klein added to the feeling on last week’s pod, “The Government Knows A.G.I. Is Coming”, with former Biden AI advisor Ben Buchanan:
If you’ve been telling yourself this isn’t coming, I really think you need to question that. It’s not web3. It’s not vaporware. A lot of what we’re talking about is already here, right now.
I think we are on the cusp of an era in human history that is unlike any of the eras we have experienced before. And we’re not prepared in part because it’s not clear what it would mean to prepare. We don’t know what this will look like, what it will feel like. We don’t know how labor markets will respond. We don’t know which country is going to get there first. We don’t know what it will mean for war. We don’t know what it will mean for peace.
Brian…give me your take. Who is next to fall and what will thrive? Will we ever see new franchise media businesses?
BRIAN: I missed the three-martini lunch era. There are some Condé veterans with great stories of the free luxury cars, mortgage forgiveness and wardrobe budgets.
I know we talked about who is getting Chegged, but there are some better business models out there in media, only they have different mechanics.
B2B, which was always the scruffier, duller and more profitable part of media, is the healthiest sector. There’s a lot of B2B envy now. The business models are far sturdier and advertising was never a massive part of those businesses, at least the kind of brand advertising that fueled consumer media. Look at where Dow Jones makes acquisitions. The FT this week bought Invissio, an events organizer for the structured finance market. Hearst wants everyone to know a majority of its business is B2B.
Lenny Rachitsky has built a lean juggernaut with how-tos and guides newsletters and podcasts. It’s hardly pulse racing. It’s also a new form of B2B. That’s usually where you’ll find the money.
Community models are very hot right now. In Austin, I spoke to Sam Parr, who built The Hustle. It’s telling he’s now building an entrepreneurs community with Hampton. Sam makes the point that many publishers pretend to have communities when they really have audiences. And it’s true. Just because you put on some events doesn’t mean you have a community.
We will see all kinds of niche communities pop up. They’ll use media as part of the model, not the central role. Hampton uses a podcast Sam does called Moneywise. He gets rich people to talk about how they spend their money. It’s a great conceit. People love the elicit, and talking about money is elicit. And it does the member-acquisition for Hampton.
Sean Griffey, founder of Industry Dive, told me communities were most interesting to him. That’s not worth because he sold Industry Dive for $530 million. Professional communities are already big businesses, and I do not think AI is going to change that.
ANONYMOUS BANKER
Rise of the Regime Media
It’s not all doom and gloom for traditional media; capital is flowing into businesses with the right alignment. Earlier this week, Newsmax, a traditional media company known for a cable news channel positioned further to the right than Fox, successfully completed a $225mm preferred financing round. While this level of funding was inconceivable before the November election, Trump-aligned media businesses now have the wind at their backs and are taking advantage of positive investor sentiment. One quirk of Newsmax’s financing, highlighted in the press release, is the participation of over 8,000 accredited investors. If this were measured as a crowdfunded round, it would probably rank towards the top of the list for the number of investors and total size of funding.
Where else might regime media deals materialize?
Last month, Fox acquired Red Seat Ventures, a firm that partners with “old-media stars” (many of whom used to be on Fox) such as Megyn Kelly and Tucker Carlson, offering content production services and ad sales. Expect to see a few other regime media companies like The Daily Wire or The Chosen use the positive market sentiment to their benefit to seek additional funding, liquidity, or larger strategic transactions.
In the manosphere realm, at least one of the core creators should be able to score a Rogan-like deal with a platform. While some may desire to stay independent, guaranteed cash can change minds. Theo Von, Shawn Ryan, and Andrew Schulz are at the top of my list, with someone like Shane Gillis building a more multi-faceted media business. In this same realm, MAGA-aligned pundits are also benefiting, with Oliver Darcy reporting that CNN’s Scott Jennings is wrapping up negotiations on a new contract that includes a significant pay bump.
Links from our group chat
AI is killing some companies, yet others are thriving - let's look at the data. (Elena’s Growth Scoop)
AI catharsis
The LA Times adds AI counterpoints to opinion content. (Neiman Lab)
And this week, Patrick Soon-Shiong, owner of The Los Angeles Times, announced that the paper has added AI-powered “alternative perspectives” — dubbed “Insights” — to much of its opinion content. (The Opinion section is also being rebranded as “Voices,” and anywhere in the paper that “a piece takes a stance or is written from a personal perspective, it may be labeled Voices.”)
“The purpose of Insights is to offer readers an instantly accessible way to see a wide range of different AI-enabled perspectives alongside the positions presented in the article,” Soon-Shiong wrote on Monday in a letter to readers.
Surprised this isn’t the norm. Why do kids need phones at school? I seem to remember it went fine. (Guardian)
In an interview with the Guardian, Meyer said all European countries should ban mobile phones in schools and called for EU regulation on it, adding: “And if we find out in five years that it was better with the phones, we can reintroduce them. But I don’t think that will be the case.”
Tyler Cowen on writing with AI
AI generated fashion campaigns for Gucci, Prada, Jil Sander. (BoF)
How long will rich SEO traffic last? NerdWallet had a good quarter and thinks the marketplace page experience is still important in AI chat world. (LinkedIn)
Sergei Brin urges staff to come to office and get hardcore (NYT)
“I recommend being in the office at least every weekday,” he wrote in a memo posted internally on Wednesday evening that was viewed by The New York Times. He added that “60 hours a week is the sweet spot of productivity” in the message to employees who work on Gemini, Google’s lineup of A.I. models and apps.
More than 1 billion people watch podcasts on Google every month (Verge)
If people are trying to "watch" podcasts on their phone - this has to be one of the best forcing functions to move people to YT premium. It's the only way to "watch" (+listen to podcasts) with the app in the background.How the ‘Manosphere’ Became Mainstream Entertainment (NYT)
Related: Barstool’s Dave Portnoy says young people don’t trust traditional media, but they trust him (Fox)
"It’s all about trust and I think a lot of young people do not trust the traditional media, and they trust somebody like me because I've been talking to them for 20 years," Portnoy told Fox News Digital.
The world's first "biological computer" that fuses human brain cells with silicon hardware (New Atlas)
These remarkable brain-cell biocomputers could revolutionize everything from drug discovery and clinical testing to how robotic "intelligence" is built, allowing unlimited personalization depending on need. The CL1, which will be widely available in the second half of 2025, is an enormous achievement for Cortical – and as New Atlas saw recently with a visit to the company's Melbourne headquarters – the potential here is much more far-reaching than Pong.
This is “Dark Woke”. Welcome to the new hashtag-resistance, where viral clips of men defacing Cybertucks are channeling the frustrated energy of the online left (GQ)
This is “dark woke.” It’s the newest evolution of what was once labeled, in Trump’s first term, the dirtbag left—a name for young progressives who weren’t afraid to viciously mock their political opponents. It’s things that you wouldn’t normally say or do, made acceptable because they’re directed at Republicans. The idea is to subvert the qualities that people think made wokeness cringe—the virtue policing, the polite “when they go low, we go high” posturing—and go Joker Mode to Make Democrats Cool Again. What qualifies for dark woke, per social media: A kid calling Trump “GAY,” A$AP Rocky calling homophobia in hip-hop “retarded” in 2012, Alexandria Ocasio-Cortez telling the woman behind the Libs of TikTok account to “cry more” and asking if she’s triggered. One viral tweet described a dismal Travis Kelce stat from the Super Bowl—0 RECEPTIONS IN POSTSEASON FIRST HALF FOR FIRST TIME IN CAREER—as dark woke.
It’s a big world. Chinese film Ne Zha 2 becomes the first animated feature to surpass the 2 billion dollar mark (Fiction Horizon)
GOOD PRODUCT
Crossing the uncanny valley of conversational voice
Try this Sesame demo.
More… Eerily realistic AI voice demo sparks amazement and discomfort online (Ars)
Despite decades in the spotlight Donald Trump still continues to defies explanation—at least through the usual lenses. Every day pundits, scholars, and political foes still scramble to pin him down, their analyses buckling under his contradictions. Is he a genius or a chaos agent? A populist savant or a tabloid caricature?
The answer lies not in psychology or ideology, but in a wider more seismic cultural shift: Trump is the first president to operate fully beyond the Gutenberg Parenthesis—a figure whose multi-modal, improvisational mindset upends the print-bound norms of politics and signals a new era of leadership.
The Gutenberg Parenthesis: A Frame for Understanding
The “Gutenberg Parenthesis,” a term from media theorist Lars Ole Sauerberg, captures the historical era dominated by print culture—from Johannes Gutenberg’s press in the 15th century to the digital upheaval of the late 20th. Within this parenthesis, communication is linear, structured, and authoritative. Print privileges permanence—fixed texts, coherent arguments, institutional credibility. Before it, oral traditions thrive: fluid, performative, rooted in emotional resonance. After it, the digital age ushers in fragmentation, immediacy, and multi-modal expression.
Trump’s current reign marks him as an early outlier of this post-parenthesis world. His communication style—wildly effective yet baffling to traditionalists—rejects the Gutenberg playbook entirely. Where print demands logic and consistency, Trump thrives on spectacle and adaptability. Where it reveres the written word, he wields a chaotic blend of speech, image, and digital noise. To grasp him, we must see him as a creature of this cultural pivot—and, crucially, as a product of that first Post-Gutenberg city that primed him for it: New York.
Trump’s Multi-Modal Mastery
Trump doesn’t argue; he performs. His rallies were always less policy lectures than visceral experiences—part stand-up comedy, part revival meeting, part tribal chant. “Make America Great Again” isn’t a thesis; it’s a slogan that sticks, a rhythmic hook echoing the oral traditions of pre-print bards. His gestures—exaggerated shrugs, pointed fingers—amplify his words, while his branding (the hair, the hats) doubles as a visual meme. This is multi-modal communication at its peak, a far cry from the staid text of a congressional report.
His mastery spills into the digital realm. On social media Trump turns 280 characters into a megaphone for provocation—ALL CAPS outbursts, nicknames like “Crooked Hillary,” and half-formed thoughts that spark endless remixes.
These aren’t missteps; they are seeds for a chaotic, self-sustaining ecosystem of attention. Like a medieval storyteller adapting to the crowd, he pivots with the moment, unburdened by print’s demand for permanence or coherence.
Beyond Print’s Sacred Rules
The permanence of print culture embodies consistency—fixed positions, evidence-based arguments, a clear A-to-B. Trump shrugs that off. He claims one thing today, contradicts it tomorrow, and dismisses the dissonance with a grin. Fact-checkers and editorial boards, still tethered to Gutenberg’s legacy, cry foul—but his audience doesn’t flinch. Why? Because he’s not playing their game. In a post-parenthesis world, meaning comes from momentum, not meticulous logic. Trump’s improvisational style—repetitive slogans, emotional jabs—feels closer to folklore or ritual than policy discourse.
In a post-parenthesis world, meaning comes from momentum, not meticulous logic.
This agility explains why traditional media struggle to “get” him. Armed with print-era tools—long-form analysis, calls for “serious debate”—they chase a phantom. Trump isn’t debating; he’s surfing, riding waves of outrage and loyalty that print’s sober linearity can’t touch. His fondness for “Fake News” isn’t just a jab—it’s a rejection of the Gutenberg myth that authority lies in ink.
The NYC Crucible
If Trump is the poster child of a post-Gutenberg era, his origins offer a clue to how he got there. Born in Queens in 1946, he emerges from NYC —a cultural cauldron that is already straining against print’s confines. Like ancient Rome birthing its early emperors, NYC forges Trump in its image: brash, loud, and obsessed with being seen. By the mid-20th century, the city is already proto-digital stew, blending media and madness in ways that prefigure the internet age.
Madison Avenue’s ad men teach Trump that slogans outshine essays—catchy, visceral, and built to stick. The city’s mixed-media artists—Warhol with his pop-art collages, Basquiat with his graffiti sprawls—show him that bold fragments trump subtle strokes. Tabloids like the New York Post and the street’s oral pulse—hawkers, cabbies, headlines—give him a rhythm that is fast, fragmented, and unscripted. Long before X or TikTok, NYC is a multi-modal playground, and Trump is its most eager pupil.
He is the city’s archetype: the swaggering developer, the Page Six fixture, the golden-haired mogul who’d rather build a tower than pen a treatise. His Apprentice fame and Trump Tower glitz aren’t accidents—they are NYC’s excess distilled, a rejection of print’s quiet dignity for something louder and less tethered. If anywhere was going to birth a post-Gutenberg president the Big Apple was it.
A New Political Paradigm?
Trump’s dominance as a post-Gutenberg figure raises an important question: is he a fluke, or a harbinger? His intuitive grasp of attention over accuracy, performance over persuasion, aligns with our ever more digital age’s fractured logic. Social media posts ricochet, memes multiply, and vibes outpace white papers—a world where engagement is the new currency, and in this Trump is definitely a billionaire. Most if not all the political class on all sides remains still half-stuck in Gutenberg’s shadow, probably to be outflanked by leaders who follow his lead—whether populist firebrands or progressive showmen.
The future of influence may belong not to policy wonks but to vibe architects—figures who juggle text, image, and spectacle with same ease as Trump does. If so, his presidency isn’t just an anomaly; it is a preview.
Conclusion: The Chaos King
Donald Trump defies explanation only if we continue to judge him by Gutenberg’s rules. Seen through a post-parenthesis lens makes more sense: a multi-modal mogul, forged in NYC’s frenetic furnace, who rewrites politics as performance art. His contradictions—chaos one day, triumph the next—aren’t flaws but features of a mind unbound by print’s sacred adherence. As the digital age accelerates, Trump stands less as an outlier than a taste of things to come - where we can expect leaders of a world where the stage outshines the page.