The Profile: The founder who built the most profitable startup & the investor who bet ever
May 31, 2026
Good morning, friends!
I’ve spent a decade researching the most extraordinary people in the world — spending time with them, watching hundreds of hours of interviews, combing through old blog posts, and trying to understand what makes someone truly remarkable.
The most important thing I’ve learned is that pretty much no one is who they appear to be in public.
Here’s a small example. When I profiled Jake and Logan Paul, I expected indifference. Their entire brand is built on being loud, reckless, and seemingly impossible to embarrass.
But on set, during a podcast taping, a joke about Logan’s daughter lands a little too close to home. For a moment, the mask drops. He recoils, pushes back, tells the host to cut it. Later, when I ask about reputational hits, the warm, gregarious version of him disappears.
What I found is that Logan obsessively reviews and edits every single video, clip, and post before it goes out. Jake hired a celebrity attorney to pursue legal action against anyone who questions the legitimacy of his boxing matches. These are not men who don’t care. These are men who have built an empire on performing like they don’t.
How someone presents themselves and what’s actually true is often at the core of my profiles. I’ve developed something close to a methodology for it. There are signals I look for, questions I ask, sources I go to, and clues that help me read what someone is not saying as much as what they are.
This Wednesday, June 3 at 12 p.m. EST, I’m hosting a live, members-only session called “How to Read People” and I want you there.
For one hour, I’ll walk you through exactly how I research someone, what I look for in the first five minutes of an interview, and the psychological tools I use to read them. Then I’ll open it up to you. Bring me questions, and I’ll give you techniques.
This session is for paid members only.If you’ve been on the fence about upgrading, this is your sign. You can sign up & upgrade below:
I’ll see you there.
— Polina
— The CEO who revived a struggling bookstore[**HIGHLY RECOMMEND**]
— The founder who built the most profitable startup
— The investor who bet everything on ChatGPT
— Hollywood’s most polarizing actor
— The ‘buy here, pay here’ auto dealer
The CEO who revived a struggling bookstore: Barnes & Noble CEO James Daunt seems to have pulled off one of retail’s most surprising turnarounds. It explores the story of how a struggling big-box bookstore chain became a thriving, highly localized retail experiment under private equity ownership. Rather than relying on rigid corporate strategy, Daunt empowered individual stores to behave more like independent bookstores — letting staff curate inventory for their specific communities, redesign displays around “pyramids” instead of publisher-driven “blocks,” and prioritize passionate booksellers over traditional retail managers. (Remember this profile when he first started making the changes?) (Bloomberg)
The founder who built the most profitable startup: Jeffrey Yan is a hyper-intense former quantitative trader who walked away from a lucrative crypto trading operation to build what he believes could become the infrastructure layer for a new financial system. This profile details how Yan and his tiny team of 11 built Hyperliquid into one of the most profitable startups per employee in the world — rejecting venture capital, refusing to pay insiders, and distributing billions of dollars worth of tokens directly to users instead. It reveals a portrait of a founder who views traditional finance as outdated, works with near-monastic intensity, and believes that truly transformative systems must be public, decentralized, and owned by the people who use them. (Colossus)
The investor who bet everything on ChatGPT: Sarah Guo became one of the most influential AI investors by betting aggressively on artificial intelligence years before ChatGPT made the industry mainstream. After leaving Greylock in 2022 to launch her AI-focused fund, Conviction, Guo built a concentrated portfolio of companies like Harvey, Baseten, and Mistral AI that are now collectively worth tens of billions of dollars. The piece portrays Guo not as a passive investor but as an intensely hands-on operator obsessed with long-term technological shifts, willing to ignore conventional venture capital wisdom in favor of deeply researched, conviction-driven bets on the future of AI. (Forbes)
Hollywood’s most polarizing actor: In this interview, Nicolas Cage reflects on the artistic philosophy that made him one of Hollywood’s most original and polarizing actors. Cage describes his performances as intentionally risky, grotesque, and emotionally extreme, drawing inspiration from sources as varied as Francis Bacon paintings, comic books, Bruce Lee films, and pop art. He discusses his willingness to be misunderstood in pursuit of originality, the strange afterlife of becoming an internet meme, and how his larger-than-life mythology eventually took on a life of its own. (New York Times; alternate link)
The ‘buy here, pay here’ auto dealer: This investigation into Byrider examines the harsh economics of America’s “buy here, pay here” used-car industry, where people with poor credit often end up paying double — or more — the actual value of a vehicle through high markups, steep interest rates, and aggressive collection tactics. (Bloomberg)
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