Weekend Briefing No. 622

Rising Strong -- The History of Rolex -- Fake News Powered by AI

Welcome to the weekend.

Here’s my January playlist featuring Gracie Abrams, The Lone Bellow, Olivia Dean, Jon Bellion, Bruce Springsteen and others.

The first story this week is a briefing on the history of Rolex as told on the Acquired podcast. It’s not a story about jewelry. It’s a story about branding, survival, and the brilliance of Hans Wilsdorf.

As you may know, I have another newsletter called Acquired Briefing, where I take in-depth notes on Acquired episodes. Over the next month or so, I’m covering some of their most popular episodes, and some of my favorites. Rolex was this week; the surprisingly fascinating story of IKEA is next. I think you’ll really dig it, so sign up to get those briefings directly.

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Prime Numbers

82 — The top 19% of American readers—those who read at least 10 books in 2025—account for 82% of all books read in the U.S., while 40% of Americans didn’t read any books at all, revealing stark inequality in reading habits.

62 — Americans rank nursing as the top college major for students entering today, with 62% calling it a very good decision, followed by engineering (58%) and computer science (57%), though 74% say student interest should be the most important factor when choosing a major.

7.2 — Goldman Sachs projects the live entertainment business will grow 7.2% annually, prompting tour companies to recruit roadies by marketing the work as recession-proof, creative, and resistant to automation amid rising audience demand for high-quality production.

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The History of Rolex

Rolex is a series of paradoxes. They sell obsolete and objectively inferior mechanical devices for 10-1000x the price of their superior digital successors… and demand is stronger than ever in history! Their products are comparable to a Hermès Birkin bag in price, luxury status and waitlist times… yet they produce over 1m units / year (roughly 10x annual Birkin production). They make the most universally recognized and desired Swiss watches… yet their founder wasn’t Swiss and didn’t start the company in Switzerland! If Rolex were publicly traded, they’d almost certainly be among the top 50 market cap companies in the world… yet they’re 100% owned by a charitable foundation in Geneva that (among other things) literally just gives away money to local people in the city. This is one of the most fascinating and admirable companies Ben and David have ever covered on Acquired and one of my favorites. Check out my briefing on Rolex including some iconic Rolex print ads. Acquired Briefing (18 minutes)

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Rising Strong

Rising Strong by Brene Brown is one of my favorite books on living a whole-hearted and courageous life, I read it every January. Most of us think courage is about not falling—but everyone from Fortune 500 leaders to artists to clergy who live brave lives fall just as hard as anyone else. What separates them is that they’ve learned to treat emotional upheaval not as something to avoid but as raw material: they 1) reckon with what they’re feeling, 2) rumble with their stories until they find truth, then 3) turn that process into daily practice. The pattern holds whether you’re grieving a divorce or nursing a workplace slight—the magnitude changes but the method doesn’t, and it’s in that repetition where you stop performing resilience and start becoming someone who actually gets back up. This isn’t about bouncing back to who you were before; it’s about using the fall to forge what you’ll become next. Amazon (8 minutes)

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Fake News Powered By AI

A Reddit whistleblower claimed a food delivery app calculates “desperation scores” to exploit drivers, amassing 86,000 upvotes and fooling a tech reporter with an 18-page AI-generated technical document and a fake Uber Eats badge. What used to require days of effort to fabricate—convincing internal documents, employee credentials, corroborating materials—now takes minutes with AI, turning every anonymous source into a potential hoax that still demands hours of verification. The old journalism rules still work (if it’s too good to be true, get a second source, beware outrage bait), but they require time and skepticism that AI-generated lies are specifically designed to overwhelm. If you’re building anything that depends on verified information—journalism, due diligence, trust and safety—the cost of verification just went up while the cost of fabrication dropped to zero, and “I don’t have time to check this” is exactly the exploit the hoaxsters are counting on. Platformer (14 minutes)

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Kenya’s Great Energy Valley

Kenya’s Great Rift Valley produces vast geothermal energy—steam that currently escapes unused into the atmosphere—and startups like Octavia Carbon are betting they can harness it to power direct air capture machines that suck CO₂ from the air and lock it underground in volcanic rock. The central tension is whether DAC can scale from removing 10,000 tons annually worldwide to the billions needed for climate impact, especially when carbon credits cost $450 per ton versus $84 for alternatives, Trump is killing US funding, and corporations are quietly abandoning their climate pledges. For Kenya, the promise is green industrialization and jobs for 6 million underemployed youth, but the Maasai communities displaced by geothermal plants still lack electricity themselves, and critics argue the entire premise gives polluters an excuse to delay transitioning off fossil fuels while Africa deepens its debt financing someone else’s climate solution. If you’re building climate tech, the lesson cuts both ways: find the places where natural advantages intersect with real problems (geothermal energy meeting carbon removal need), but understand that “solving climate change” means nothing if the people living on top of your solution can’t turn on their lights. MIT Technology Review (12 minutes)

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Humans Want Humans

AI seems poised to replace every job—coding, manufacturing, even content creation—yet the author argues the doomsday scenario of extreme inequality misses what humans actually value: other humans. The economic logic is sound: once AI builds self-replicating robots that harvest their own materials and work at zero marginal cost, capital owners would capture all value while labor gets nothing, creating permanent dynastic wealth—except this assumes humans will accept robot-generated abundance over human-made imperfection. History shows humans constantly invent new work (podcasters didn’t exist thirty years ago), and right now individual creators uniquely reach audiences at scale while AI scales compute to individuals—opposite dynamics that suggest humans will keep paying premiums for human-made things precisely because they’re human-made, from sex to art to cathedrals, status games that persist regardless of material abundance. If you’re building anything in AI, the paradox cuts deep: you’re creating tools that might devalue human labor while humans demonstrably prefer human-created content (Sora ranks 59th while human social apps dominate), which means the real opportunity isn’t replacing humans but freeing them to do what only humans can—create the imperfect, unique things other humans actually want, even when perfect robot versions exist for free. Stratechery (10 minutes)

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What Now for Liberals?

Liberalism’s 1980s dreams became reality, from poverty reduction to gay marriage to expanded healthcare. Then it became progressivism and overreached into failure: discrimination-fighting became institutionalized discrimination, environmental mandates underperformed deregulation, education standards collapsed, academia chose activism over truth. Conservative implosion left no check on excess. But the ideals still have power. Diversity will only increase, economic security remains unfinished, tolerance and free expression are still necessary for any future worth wanting. You learn from dead-end paths and try again. Noahpinion (7 minutes)

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Expensive Pain

George Bell walked out of his brownstone at nineteen, saw more squad cars than he’d ever seen in his life, and didn’t return for twenty-four years. A detective threatened to use his head as a hockey puck until the terrified teenager confessed to a double homicide he didn’t commit—no gun residue, no physical evidence, just a lying informant seeking reward money and cops who needed someone Black to blame for killing one of their own. Now he drives a $300k Lamborghini between his suburban mansion and the maximum-security prison where he visits friends still inside, depositing cash in their commissary accounts because he knows what it’s like when the world forgets you exist. The old-timers on Astoria Boulevard shake their heads—”he blowin’ all his money”—but George has wealth advisors at the biggest banks, seven college credits earned by studying with earplugs in while chaos erupted around him, and teeth reconstructed because prison dentists just pull them out. The $17.5 million settlement made headlines, the largest wrongful conviction payout New York City ever gave, but George calls his cars and clothes and house “expensive pain.” What George needs isn’t your judgment about diamond Cartier sunglasses or how a wrongly convicted man should perform gratitude for compensation that can never return what was stolen. He needs you to understand that he still showers thinking about being attacked, still sleeps with his head away from where bars used to be, still can’t process that his phone talks back or that people walk around with invisible earbuds. He tries to live every day like Christmas—the holiday he spent twenty-four years crying through in his cell, replaying the arrest—which means living with open heart and generosity, even though Christmas 1996 lives in every single day and no amount of joy erases the hockey stick, the confession beaten out of a teenager, the moment society decided a Black kid from Queens was guilty before anyone bothered with evidence. Esquire (18 minutes)

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Should We Work Together?

Hi! I’m Kyle. This newsletter is my passion project. When I’m not writing, I run a law firm that helps startups move fast without breaking things. Most founders want a trusted legal partner, but they hate surprise legal bills. At Westaway, we take care of your startup’s legal needs for a flat, monthly fee so you can control your costs and focus on scaling your business. If you’re interested, let’s jump on a call to see if you’re a good fit for the firm. Click here to schedule a one-on-one call with me.

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Weekend Wisdom

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat. - Theodore Roosevelt