Weekend Briefing No. 617

Your Ambition’s Dark Fuel -- Selling Through Restraint -- The Productivity Mirage

Welcome to the weekend.

Today in the first story, I’m linking to my most recent Forbes article about startups, identity, and mental health based on my conversation with Jane Chen. Jane built a company that saved a million babies and nearly destroyed herself doing it. Our conversation stuck with me for days. I kept thinking about my own drive, where it comes from, what it costs. If you’ve ever felt like your self-worth rises and falls with your company, this one’s for you.

Additionally:

• Watch my full conversation with Jane Chen.

• Buy Jane’s book Like a Wave We Break to read the full story.

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Prime Numbers

417,000 — Greece has culled 417,000 sheep and goats (roughly 4-5% of its total herd) due to sheep and goat pox outbreaks, threatening production of feta cheese, of which the country exported €785 million last year with 80% of its sheep and goat milk dedicated to the protected cheese.

573 — Authorities globally seized the equivalent of 573 tigers between 2020 and mid-2025 (averaging nine per month), reflecting escalating trafficking that threatens wild tiger populations now estimated at just 3,700-5,500 compared to 100,000 a century ago.

42 — Nearly half of Americans believe aliens have definitely or probably visited Earth at some point, with 42% saying aliens have visited in recent years, though Americans are twice as likely to think alien contact would negatively impact human civilization than positively (29% vs. 14%).

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Your Ambition’s Dark Fuel

Most founders believe their relentless drive comes from vision or opportunity, but research reveals a pattern called “wounded striving”—early experiences of powerlessness or inadequacy create a core belief that you’re not enough, which becomes rocket fuel for achievement. The paradox is brutal: Jane Chen saved a million babies and earned global recognition, yet suffered crippling panic attacks because no external achievement can heal an internal wound. Trauma increases risk tolerance (making you more likely to leap into entrepreneurship) while keeping your nervous system in permanent fight-or-flight, overriding every signal to slow down. The shift from “wounded striving” to “healed striving” isn’t about losing your edge—it’s about ambition that expresses your values rather than proves your worth, which means you can build impact without destroying yourself in the process. Forbes (7 minutes)

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Don’t Buy This Jacket

Most companies tell customers to buy more; Patagonia’s most successful campaign ever told people to buy less—and sales soared. The “Don’t Buy This Jacket” ad seemed suicidal: a full-page New York Times spread on Black Friday discouraging purchases, risking revenue during retail’s most critical moment. Yet this apparent contradiction unlocked something profound: when you publicly wrestle with your own paradoxes instead of hiding them, customers don’t see hypocrisy—they see integrity worth paying for. That $57,000 ad generated $50 million in free publicity and record sales because it transformed Patagonia from a retailer into a belief system, proving that the brands willing to challenge their customers’ consumption are the ones customers trust most with their dollars. David Gelles (7 minutes)

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42x: The ROI of Newsletters

Email delivers $42 for every $1 spent—if you do it right. Most newsletters get lost in the noise. The ones that don’t? They solve problems for readers. They build trust. They tell unique stories in an authentic voice. A few strategic changes can transform your newsletter from something people ignore to one they don’t want to miss. Take the Newsletter Health Check: 10 proven ways to boost open rates, engagement, and ROI. Future Forest (Sponsored)

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Toyota’s Innovation in Africa

Toyota is shipping partially assembled trucks to Africa for local assembly—not because it’s cheaper, but because it solves a problem most manufacturers never think about: the vehicle itself becomes the job creator. Traditional automakers chase efficiency by centralizing production in massive factories, but Toyota’s IMV Origin flips this logic by treating the assembly process as the product’s primary value, not just its means of production. By designing trucks that rural communities can finish building themselves, Toyota isn’t just selling transportation—they’re distributing manufacturing capability, technical skills, and employment into areas where formal jobs are scarce and infrastructure makes traditional supply chains impossible. This matters because the future of manufacturing in emerging markets isn’t about replicating Detroit; it’s about designing products that embed economic development into their DNA, where every truck sold creates more value through the assembly work than through the vehicle itself. Nikkei Asia (5 minutes)

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The Productivity Mirage

Every tech revolution promises explosive growth, yet AI’s $50 billion investment wave is producing zero returns for 95% of companies—and this might not be a timing problem. The conventional wisdom says we’re just in the “lag phase” before productivity soars, like it did with computers in the 1990s, but there’s a darker precedent: digital technology since 2005 has delivered smartphones, social media, and countless apps while productivity growth collapsed. AI’s fundamental issue isn’t adoption speed—it’s that the most sophisticated models are trained on internet data to impress consumers, not solve the unglamorous problems in manufacturing, healthcare, and education where real productivity gains hide. The companies slashing jobs and citing AI aren’t boosting productivity; they’re just cutting costs, and until AI is rebuilt to augment workers rather than replace them, we’re investing billions into technology that makes headlines but not GDP. MIT Technology Review (8 minutes)

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Cashless Segregation

Digital payments feel like pure progress—faster, cleaner, more efficient—until you realize they’re quietly dismantling an entire parallel economy. When 60% of wealthy Americans stop carrying cash while only 24% of lower-income people go cashless, we’re not just seeing a technology shift; we’re watching economic segregation play out through payment methods. Street vendors miss sales because they can’t afford the multi-day settlement delays of digital systems, while panhandlers watch crowds of shoppers pass by with nothing to give, creating what one anthropologist calls “enclosed, gated communities” where human connection requires compatible apps. The invisible cost of convenience is that we’re building a city where spontaneous generosity—tipping a saxophonist, helping someone buy lunch—requires planning ahead, and the people who depend on those tiny transactions are being designed out of public space entirely. NYT (6 minutes)

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Success Without Compromise

The Grateful Dead became one of the world’s highest-paid entertainers by doing everything wrong: they encouraged bootlegging, refused corporate sponsorship, changed setlists nightly to prevent repetition, and built their empire not on record sales but on endless touring to audiences who followed them like a traveling circus. Most bands chase mainstream success by adapting to trends and maximizing commercial appeal, but the Dead’s power came from the opposite strategy—they created such an uncompromising, authentic subculture that fans didn’t just buy tickets, they built their identities around following the band from city to city. This wasn’t accidental; it was the logical extension of their origins in LSD-fueled psychedelic experiments where improvisation and mind-altering communion mattered more than polish or profit. If you’re building something that lasts, the lesson isn’t to give people what they think they want—it’s to commit so deeply to your weird vision that you create a tribe who can’t imagine life without it, turning devotees into evangelists and turning cultural outsiders into $33 million underground empires. BBC (8 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

The greatest sources of our suffering are the lies we tell ourselves. -Bessel Van Der Kolk