Jeremy Stern writes long-form profiles of influential technology founders and investors for Colossus, approaching each piece by starting with a thematic question rather than a person, then finding the subject who best illuminates that question; his profiles of Mark Zuckerberg, Palmer Luckey, Scott Wu, and Josh Kushner reveal how he uses literary craft to explore the psychology, competitive drive, and historical self-conception of figures shaping the present.
The Zuckerberg profile: Augustus, competitive drive, and the last founder standing
Stern was surprised when Zuckerberg’s team reached out after Stern’s earlier profile of Palmer Luckey cast Zuckerberg as the villain who fired Luckey; they met off-record for lunch, and over five to six months Stern spoke with Zuckerberg and nearly 40 others.
Stern initially felt Zuckerberg was overexposed, but came to see him as the last man standing from his founder generation — Larry Page, Sergey Brin, Jeff Bezos, Bill Gates all stepped away; Jobs died — and as a singular millennial founder whose company dwarfs the next closest (Stripe at roughly one-tenth Meta’s value).
Zuckerberg’s long-standing identification with Augustus Caesar shapes his self-conception: he studied Latin in high school, still recites Virgil, ended early Facebook meetings with “Carthage must be destroyed” (until Sean Parker stopped him for antitrust reasons), and recently referred to his personal AI agent as “Agrippa,” Augustus’s indispensable lieutenant.
Zuckerberg’s reading of Augustus is selective: he emphasizes Augustus turning a pillage-based economy into a trade-based economy and bringing peace, while downplaying the standing army and elimination of political liberty that made it possible — a revealing idiosyncrasy in how Zuckerberg sees his own role.
People who know Zuckerberg consistently say two things are underestimated: his ruthless competitive drive (a former AI researcher called him “the Terminator — he just doesn’t stop, always discontent, always unhappy, but not an asshole”), and his personal decency toward people around him.
Zuckerberg frames his edge as methodically improving a single product over decades without needing to raise money or ask permission — a classical American mogul model distinct from AI founders who believe their company is the last thing humanity will ever build.
The bull case for Meta in AI rests on distribution (roughly half of humanity uses WhatsApp, Instagram, Facebook, Messenger, Meta AI), owned infrastructure built through 20 years of unsexy government negotiations, and attention dominance — advantages pure AI labs lack.
Stern believes Zuckerberg will never voluntarily step away; the 2006 Yahoo offer ($1 billion, entire management team and board urging acceptance, 21-year-old Zuckerberg owning ~70% and saying no immediately) is the canonical proof — he will likely die as CEO.
The Palmer Luckey profile: defense tech, integrity, and the first profile
Stern’s first profile subject emerged from a question after October 7, 2023: is defense tech real, or did Israel’s technological overmatch fail against Hamas’s low-tech invasion? Palmer Luckey, founder of Oculus and Anduril, was the legend who could answer.
The piece expanded from a planned 3,000-word interview into a 15,000-word cradle-to-grave profile as Stern spent time with Luckey, his family, friends, and colleagues — a universe of relationships, psychosis, successes, and failures opening up.
Luckey’s support for Trump in 2016 cost him everything: fired by Facebook (which had acquired Oculus), lost the company he built — a rare case of integrity where the stance was taken when it was maximally costly, not when it was popular.
The profile published in August 2024, shortly after the Trump assassination attempt triggered a wave of Silicon Valley alignment with Trump, making Luckey’s earlier lonely stance newly salient.
Stern finds it hard to retain details after a piece is done; he describes a “hole in the brain” that never refills, and deliberately exits the subject’s psychology to avoid “going insane” — unlike podcasting which strip-mines insights for listeners, Stern’s aim is understanding the individual life on its own terms.
The Scott Wu profile: authenticity, genius, and the “Michael Jordan” competitive gene
Stern sought an AI founder who wasn’t grating, unself-aware, or irritating — someone a humanist might trust with the technology; Scott Wu (Cognition) was the name that came up most often.
Wu is not stage-managed, lacks PR layers, and showed willingness to be introspective in a way that felt moving and genuine; Stern felt turning him into a character would be worse than letting readers hear him directly — the piece reads more like a transcript of their conversations.
Among International Math/Physics/Informatics Olympiad gold medalists, Wu is considered the GOAT: top competitor, top coach/mentor, godfather figure — despite not yet being 30, he radiates natural leadership; in a group photo of 12 Olympiad alumni, strangers immediately identify him as the leader.
Wu’s competitiveness differs from Zuckerberg’s: Zuckerberg is maximally competitive at his life’s work; Wu is competitive at everything — “who can eat this salad fastest,” dice games during downtime, a Michael Jordan-like need to destroy people at something in every idle moment.
Wu has rejected massive acquisition offers (including from xAI/Cursor); Stern believes him when he says he wants to ride Cognition all the way — the gap between who Wu is and who he presents to the world is plausibly the smallest of anyone Stern has profiled.
The Josh Kushner profile: Holocaust legacy, the American dream, and Rick Rubin
Stern’s interest in the Kushner family predated Jared’s White House role: the grandparents’ Holocaust survival (grandmother part of the Bielski partisans in the Belarusian forests, inspiring Defiance and Inglourious Basterds), the father’s legal troubles, and the arc from “literally nothing” to Bill Clinton and Netanyahu dining at the grandmother’s table asking favors.
As the Jewish grandson of Holocaust survivors, Stern uses these profiles to “check in on the American dream” — whether the supra-tribal identity (Constitution, individual liberty, freedom) that lets people be as Irish, Sikh, or Korean as they want while remaining American is still alive or fraying.
Josh Kushner rejects the “VC” label; he sees himself as a builder and founder who looks to other founders, not investors, for reference — Stern opened the piece with Kushner visiting Rick Rubin during a personal crisis, asking “What do I do if I lose the magic?” — a fear Stern recognized as distinctly Holocaust-family: everything built can be taken overnight, even in America.
Kushner’s vulnerability about impermanence and his drive to make himself invulnerable while he can contrasts with investors who act like they’re on a rollercoaster just having fun.
Stern’s craft: literary ambition applied to the most culturally central figures
Stern came from politics, foreign policy, and literature (fiction, poetry) — not business or tech; he entered this space because technologists and businesspeople became the most interdisciplinary, culturally central figures in American life (as physicists were in the 1940s, artists in the 1960s-70s).
He saw a market gap: the best prose stylists with literary ambition weren’t covering this beat; most business/tech writing isn’t built to last beyond the news cycle. He and Patrick (Colossus) aimed to revive the great American long-form magazine tradition (New Yorker 1940s-50s, Esquire 1960s, Vanity Fair/Harper’s 1980s-90s) and apply it to today’s central figures.
Stern doesn’t “strip-mine” subjects for applicable lessons; he tries to understand and reveal individual lives that seem unreal from the outside due to power, fame, or historical weight — and to see the larger cultural/historical patterns sweeping them up.
He resists the idea that his work changes him; he focuses on the craft’s success rather than personal absorption, citing David Foster Wallace on writers as “natural-born watchers and lurkers” who covet being witnesses and fear the tables being turned (as in this interview).
A formative mentor: his Russian professor Natalya Shansky (his daughter’s namesake), who at 18 told him that if you have a gift, you have an obligation to exploit it fully — failing to do so is sinning against yourself and God. She pulled him from drinking, drugs, and aimlessness; they corresponded weekly during his 1.5 years in Russia; he kept her voicemails from his 8-month pre-boot-camp wait (sequestration had dried up slots) and wrote her letters by hand from basic training. She died of ALS in 2015; he still has the recordings.
