The Profile: The CEO behind knockoff weight-loss drugs & the king of sports betting

This edition of The Profile features Russell Wilson, Andrew Dudum, Skrilla, and others.

Good morning, friends!

I recently watched the documentary Tell Me Everything, which offers a fascinating look into the extraordinary life of Barbara Walters.

At one point, Oprah says: “There really is no place for a Barbara Walters interview now because everybody’s on social media. Nobody needs an interviewer to get them to tell their story anymore because they’ve already told it.”

I paused the documentary right there.

That one quote hit me hard. I straddle two eras — the one I grew up in, the ’90s and early 2000s, when interviewers were gatekeepers of narrative. And the one I live in now, where everyone tells their own story on their own terms, in their own words, across their own platforms.

It made me question: Is there still room for the profile writer? Do people need someone to tell their story when they can just tell it themselves?

I’ve been sitting with those questions for weeks. And here’s where I’ve landed: I believe profiles are more essential today than they were before social media.

Yes, Oprah’s right — we each have the tools to tell our own story. But in a world of performative curation, the truth often hides behind carefully filtered posts and rehearsed soundbites. Self-curation is image management. That’s quite different from storytelling.

Readers crave tension, contradiction, vulnerability. They want to know what it felt like in the moment everything fell apart and how someone rebuilt after the spotlight faded. (See my profile on Anthony Scaramucci.)

My job is to explore the internal machinery and try to uncover who they are privately— sometimes even to themselves.

I recently shared a video about how I approach profiles, and how I try to go beyond the surface and get to the core.

Would love to hear what you think.

The Art of Getting People to Open Up

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PROFILES.

— The CEO behind knockoff weight-loss drugs [**HIGHLY RECOMMEND**]
— The king of sports betting
— The NFL star’s final act
— Philly’s great rap star
— The designer reinventing Calvin Klein

PEOPLE TO KNOW.

The CEO behind knockoff weight-loss drugs: Hims CEO Andrew Dudum is shaking up the U.S. healthcare system by turning his telehealth startup into a distribution engine for personalized, direct-to-consumer drugs, including controversial weight-loss GLP-1s. As the FDA clamps down on compounded versions of drugs like Wegovy, Dudum has doubled down, forging and then feuding with Big Pharma while cultivating a meme-stock fanbase that sees him as a disruptor. Critics call his tactics reckless, regulators are circling, and even his doughnut shop got caught in the crossfire of controversy. But for Dudum, controversy is part of the playbook. (Bloomberg; alternate link)

“The playbook is: Exploit the gray area and build a user base.”

The king of sports betting: Self-proclaimed “Sports Betting King” Mazi VS flaunted a high-roller lifestyle — flashy cars, luxury shopping, million-dollar bets — while selling $1,500 picks to tens of thousands of followers convinced he had cracked the code of gambling. But behind the Instagram stunts and winning tickets was a cloud of questions: Was he truly beating the sportsbooks or just cashing in on selling the dream? Then, he vanished. Weeks later, rumors confirmed the twist: Mazi VS was allegedly Darnell Smith, now facing 14 felony counts tied to fake IDs and awaiting trial in a Las Vegas jail. (The New York Times; alternate link)

“What are they really selling? Are they selling sports picks or are they selling lifestyle?”

The NFL star’s final act: Russell Wilson, once a Super Bowl-winning star and now a quarterback on his fourth team in five years, is staging a hopeful comeback in New York with the Giants — returning to the same locker where he once hoisted the Lombardi Trophy. Despite public skepticism, memeification, and a rocky stretch in Denver and Pittsburgh, Wilson still exudes unshakable belief in his ability to lead, inspire, and win. In a city built on reinvention, Wilson is betting big on one final act. (Sports Illustrated)

“Honestly, I feel like I’m 25 years old all over again.”

Philly’s great rap star: Philly rapper Skrilla has become a cult figure by channeling the raw chaos of the Kensington neighborhood of Philadelphia into hypnotic, drug-laced tracks and viral visuals. With a haunted voice and pirate swagger, he blends eccentricity, pain, and street wisdom into an unsettling but magnetic persona. His music is both a love letter and a protest — honoring the community while confronting the neglect and gentrification threatening it. (Passion of the Weiss)

“If I find a song I like, I listen to that same song for a week straight, nothing else.”

The designer reinventing Calvin Klein: After a six-year hiatus, Calvin Klein has returned to the runway with designer Veronica Leoni at the helm — its first woman creative director and a bold new voice balancing Roman ease with New York edge. Leoni, a self-described perfectionist with a taste for deconstructed glamour, is reinventing the brand’s minimalist DNA with precise tailoring, ultrafeminine silhouettes, and a whisper of sensuality. Her mission? To make Calvin Klein instantly recognizable again. (Vogue)

“I’m not nostalgic. I try to be seduced by the past, but not to be taken away.”

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