How Mark Zuckerberg, Palmer Luckey, Josh Kushner & Scott Wu Think | Jeremy Stern
Jeremy Stern discusses his long-form profile writing process, covering his pieces on Mark Zuckerberg, Palmer Luckey, Scott Wu, and Josh Kushner. He explains how he approaches profiling major tech figures by starting with a question or theme rather than the person, conducting extensive interviews, and using literary techniques to reveal deeper truths about their psychology and motivations.
Summary
Jeremy Stern, a long-form profile writer for Colossus, shares insights into his process of writing in-depth profiles of major tech entrepreneurs and investors. He describes how his Zuckerberg profile came about after initial skepticism—Zuckerberg's team reached out despite Stern's previous critical profile of Palmer Luckey that cast Zuckerberg as an antagonist. Stern spent five to six months on the piece, interviewing nearly 40 people, and gradually discovered that Zuckerberg's lifelong fascination with Augustus and Roman history was more significant than surface-level interpretations suggested.
Stern explains his methodology: he typically begins with a theme or question he's interested in exploring, then finds the right person to use as a vehicle for that exploration. For the Zuckerberg piece, he was interested in examining whether Zuckerberg was overexposed or underexplored, ultimately concluding that while extensively covered, his internal thinking about product building and company creation remains largely unknown. Stern contrasts this with guest Jeremy's interest in those exact operational details, highlighting different approaches to profiling.
On his Palmer Luckey profile—his first ever person profile—Stern started with a question about whether defense technology actually works, prompted by observing the October 7th attack on Israel and the Ukraine conflict. The piece evolved into a cradle-to-grave biography exploring Luckey's willingness to support Trump when it cost him everything (his position at Facebook/Meta), which Stern saw as evidence of genuine integrity rather than calculated image management.
For the Scott Wu profile, Stern took an unconventional approach, using more direct transcript rather than third-person narrative. He was seeking a major AI figure who wasn't grating or self-aggrandizing—someone who could be trusted with transformative technology. Wu stood out for his lack of media training, authenticity, and genuine introspection. Stern notes Wu's ruthless competitiveness extends beyond business into every domain (the Michael Jordan comparison).
On Josh Kushner, Stern began with longstanding interest in the Kushner family dating back before their Trump-era prominence. He was drawn to their Holocaust survival story—how the grandmother escaped the Belsky partisans in Eastern Europe and eventually built a family dynasty. Stern, himself a Jewish grandson of Holocaust survivors, was interested in checking the current state of the American dream through these figures. He describes a pivotal moment where Kushner asked Rick Rubin what happens if he loses his magic, which Stern interprets as a specifically Holocaust-family fear of having everything stripped away overnight.
Stern discusses his own formative mentor relationship with Natalia Lashonskaya, his Russian professor, who taught him that having a gift creates an obligation to that gift—that failing to exploit it is sinning against oneself. This philosophy now shapes how he approaches writing about other people and their potential.
On Zuckerberg specifically, Stern notes that while Zuckerberg may seem like he's behind in AI, his actual competitive advantages are formidable: a global user base of billions across Meta's platforms, infrastructure built over 20 years through boring municipal contracts and tax negotiations, and the ability to deploy AI to his existing user base. Stern contrasts Zuckerberg's ideological coherence about Meta being a business (not humanity's salvation) with AI lab leaders who overestimate their companies' historical importance.
Stern resists the suggestion that his profile writing changes his own thinking, noting instead that he's fascinated by the craft of storytelling and understanding individual human lives rather than extracting lessons for personal application. He frames his interest in tech founders as stemming from their current centrality to American life and global futures, not from intrinsic interest in technology itself.
About this episode
Jeremy Stern is the editor-in-chief of Colossus, where he writes long-form profiles of leading entrepreneurs and investors. He goes behind the scenes of his reporting on Mark Zuckerberg, explaining how months of interviews revealed Zuckerberg’s fascination with Augustus, relentless competitive drive and commitment to building Meta for decades. Jeremy discusses why Meta’s distribution and infrastructure could give it an advantage in AI and why some founders seem incapable of walking away. He explains how a question about defense technology became his first profile, on Palmer Luckey, and why he brings the craft of fiction and poetry to writing about business. Jeremy also describes Scott Wu’s combination of mathematical genius, natural leadership and authenticity, and how Josh Kushner’s family history shaped his exploration of Thrive Capital and the American dream. The conversation closes with the story of Jeremy’s Russian professor, whose belief that people have an obligation to their gifts changed his life and helped shape how he sees the people he writes about. Show notes: https://www.davidsenra.com/episode/jeremy-stern Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra Learn more about your ad choices. Visit megaphone.fm/adchoices
Key Insights
- Stern argues that Zuckerberg's interest in Augustus reveals his selective interpretation of history—focusing on the transition from pillage to trade-based economy while overlooking how Augustus eliminated political liberty and concentrated power, suggesting insight into how Zuckerberg sees his own role
- Stern claims that despite Zuckerberg being overexposed in media, his actual thinking about product building and organizational development remains largely unexplored and locked in his head
- Stern contends that Zuckerberg differs from pure AI lab leaders by viewing Meta pragmatically as a business rather than as humanity's last or most important invention, showing ideological coherence about his company's real role
- Stern states that Palmer Luckey's willingness to support Trump when it cost him his company (forced out by Facebook) demonstrated genuine integrity that couldn't be faked, rather than calculated positioning
- Stern observes that Scott Wu exhibits Michael Jordan-level competitiveness where winning extends to trivial matters (dice games, salads), not just business, distinguishing him from Zuckerberg's more narrowly-focused competitive drive
- Stern argues his mentor Natalia Lashonskaya taught him that possessing a gift creates a moral obligation to exploit it—failing to do so constitutes sin against oneself and God
- Stern identifies that Meta's bull case for AI dominance rests on having a ready-made distribution platform (billions of users) and infrastructure built over 20 years through unglamorous municipal negotiations, which pure AI labs must rent
- Stern claims that Josh Kushner's question to Rick Rubin about losing his magic reflects a specifically Holocaust-family anxiety about having everything stripped away overnight, rooted in generational trauma
- Stern contends that his writing process involves entering another person's psychology for a finite period but that staying too long causes him psychological distress, requiring him to exit once a piece is complete
- Stern argues that successful people often find value in unexpected places by thinking from first principles, noting his own path from political analysis to tech profiling was contingent rather than predetermined
- Stern observes that he is more interested in understanding individual human lives and revealing messy psychological truths than in extracting actionable insights he personally applies
- Stern claims that the most talented prose stylists tend not to cover technology and business despite these being the most culturally central figures, creating an opportunity he and Colossus are filling
Topics
Transcript
All right, you're here because I'm a massive fan. I think you are the best in the world at what you're doing right now, which is writing these incredible long form profiles on a lot of the top investors and entrepreneurs in the world. I just finished reading the one you did on Mark Zuckerberg. I thought it was so good. I actually did an episode on it for my other podcast founders. So I want to just like jump into what it was like spending. If you just like go behind the scenes of like, okay, how long did that piece take to write? How much time did you spend with him and his entire world? So his team…
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