Thank you to everyone who read, shared, and reached out about my Kevin O’Leary profile.

I spent several days following him through New York City to try to understand the man behind the ruthless capitalist persona.

The response to the story has meant so much to me, and it reinforced why I love writing profiles. I am constantly reminded that the most interesting part of a person is usually the part they aren’t famous/known for.

READ THE FULL PROFILE HERE:

BOOK LAUNCH:

The paperback launch of my book, HIDDEN GENIUS, is Aug 11. Writing this book changed my life, and my hope is that it changes the way you think about your own potential.

If you haven’t read it yet, now is the perfect time.

Pre-order here

— Polina

THE PROFILES.

— America’s favorite capitalist villain [**HIGHLY RECOMMEND**]
— The investor betting on the rebels
— The billionaire working to save his daughter’s life
— The CEO who turned around GE
— The ultra-rich buying dinosaur bones (gift link)

THE PEOPLE.

America’s favorite capitalist villain: Kevin O’Leary built one of television’s most memorable personas by embracing the role of ruthless capitalist “Mr. Wonderful.” The version of him I kept encountering between television appearances and business pitches didn’t quite match the one millions of viewers knew. By the end of several days together, I found myself wondering whether Mr. Wonderful was the real Kevin O’Leary — or simply the most successful role he ever played. (The Profile)

The investor betting on the rebels: As AI power, money, and talent concentrate inside a handful of giant labs, venture capitalist Sarah Guo is betting there is still room for rebels. Her firm, Conviction, backs founders building specialized companies the labs can’t (or won’t) create themselves, from legal software to medical tools used by most American doctors. It’s a big wager against near-trillion-dollar rivals. (Colossus)

The billionaire working to save his daughter’s life: Bill Ackman has built his career on an unshakable faith in capitalism. Now, as he argues that every American should own a stake in the market, his most consequential fight is also very personal. He’s helping his 26-year-old daughter recover from a devastating brain hemorrhage. True to form, Ackman is turning his helplessness into action. He’s planning a major brain institute and redefining success by how many lives he can improve. (FORTUNE; reply to this email if you can’t access the article)

The CEO who turned around GE: When Larry Culp took over GE in 2018, the once-iconic company was drowning in debt and flirting with bankruptcy. By dismantling its bureaucracy, splitting it into three focused businesses and rebuilding its culture from the factory floor up, he transformed a $96 billion wreck into companies worth nearly $700 billion. Here’s how he pulled off what may be the greatest corporate turnaround in modern history. (FORTUNE; reply to this email if you can’t access the article)

The ultra-rich buying dinosaur bones (gift link): The ultrarich have discovered dinosaur bones as a new status symbol. But those bones are part of a largely unregulated market rife with questionable claims, legal threats, and fierce disputes over how much of a multimillion-dollar T. Rex is actually real. (Bloomberg)

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Minutes before he is scheduled to appear on Fox Business, he whips out a diamond-encrusted chain from a nondescript green bag and drapes it around my neck.

“It’s heavy, right?” he says.

It is.

The necklace — designed by Tiffany & Co. — is made from 2.2 pounds of white gold and contains 110 carats of diamonds and rubies. Dangling from the center is a one-of-one Jalen Brunson trading card signed by the Knicks star himself.

I keep waiting for O’Leary — the sharp-tongued investor, entrepreneur, and Shark Tank star — to tell me why the necklace is valuable, but he doesn’t. Instead, he tells me why it’s beautiful.

He traces his finger along the chain, explaining why the links taper from large to small toward the center. Then he starts talking about rubies — how difficult they were to match, how many stones were rejected, and how long the process took.

I give it back, and he puts it around his own neck. “It’s a real showstopper,” he says.

A producer begins to clip a microphone to his lapel. O’Leary glances down at the necklace.

“Oh,” he says. “I guess I should take this off now.” He does, but carries it with him onto set.

O’Leary goes on the Fox Business show Varney & Co. to talk about AI, Bitcoin, and the Los Angeles mayoral race. But during the last commercial break, he asks host Stuart Varney if he can spend the final 30 seconds talking about the necklace.

“Fine. But you only have 30 seconds,” Varney shoots back.

The New York Knicks are in the middle of their historic playoff run, and O’Leary has borrowed the Jalen Brunson trading card for the day, hoping to draw attention to the booming sports card market.

The cameras roll, and he turns it on. “Go Knicks! Go Jalen! I’m wearing you tonight,” he says as he holds up the pendant for the audience. “Look at this baby in Tiffany diamonds and rubies.” He kisses the card. “This is a winner right here.”

Varney cuts in: “OK, time’s up buddy.”

For most people, this performative, over-the-top version of Kevin O’Leary is the only one they know. It is the character that made him rich and famous — and, in some circles, deeply disliked.

Today, the 72-year-old investor has a reported net worth of roughly $400 million. He has built and sold companies, spent nearly two decades on the hit TV show Shark Tank, and become one of the most recognizable faces in business television.

Along the way, he earned the nickname “Mr. Wonderful” for his brutally unsentimental approach to entrepreneurs seeking investment. On Shark Tank, he has likened founders to “cockroaches,” dismissed products as “poo-poo on a stick,” and, after one entrepreneur rejected his offer, snapped: “You’re a human tragedy. You’re dead to me when you say no to my deal. You’re dead. You’re gone. You’re vapor.”

On multiple occasions, O’Leary told me he enjoys playing the villain. Heroes are expected to be flawless. Villains are allowed to be human. Audiences may not always like them, but they remember them and connect with their flaws.

“The antagonist is a great role,” he says. “It’s always bringing energy to something. It’s conflict-management — turning on the pressure when necessary. It’s a lot of fun.”

When I ask him how it feels to be seen as the face of ruthless capitalism, he says, “I love it. Yes, I am a capitalist, and I wear it as a badge of honor.”

It was exactly the answer I’d expect from Mr. Wonderful. But the more time I spent with O’Leary, the more that carefully cultivated persona began to feel incomplete. The version of him I kept encountering between television appearances and business pitches didn’t quite match the one millions of viewers knew.

By the end of several days together, I found myself wondering whether Mr. Wonderful was the real Kevin O’Leary — or simply the most successful role he ever played.

When O’Leary was seven years old and his family was struggling financially, he made a promise to himself: he would never feel that frightened or powerless again.

Many of the most important life lessons he’s learned came from his mother, Georgette. Born in Montreal to Lebanese parents, she was pulled into her family’s clothing business at a young age and learned early on that financial independence meant freedom.

She married a charismatic man named Terry and together they had O’Leary and his brother, but the marriage unraveled after his gambling addiction pushed the family into financial trouble. In his book, Cold Hard Truth, O’Leary writes that his mother’s anxiety about money “moved through my bloodstream, and I think it changed my very DNA.”

After divorcing Terry, Georgette married George Kanawaty, O’Leary’s stepfather. Practical and disciplined, George taught him many of the principles that still guide him today. He introduced O’Leary to watches, insisted that luxury items should be purchased only with cash, and warned him never to take on debt for something he couldn’t afford.

In college, O’Leary fell in love with photography and filmmaking. He showed his work to George and told him he wanted to pursue it professionally.

George looked at the photos and said: “You’re not good enough. You’ll never make it,” before urging him to pursue business.

O’Leary listened. “It was the cold hard truth to tell me: ‘Look you’re not going to cut it,’” he says.

Business was the practical choice. After earning his MBA in 1980, O’Leary co-founded Special Event Television, an independent sports production company that he later sold. He then launched the educational software firm SoftKey, which acquired The Learning Company and adopted its name. The business grew into one of the largest educational software companies in North America, producing popular titles such as Reader Rabbit, Carmen Sandiego, and Myst.

In 1998, Mattel acquired The Learning Company in a stock and debt deal valued at roughly $4 billion. The toy giant hoped the acquisition would transform it from a traditional manufacturer into a technology-driven children’s entertainment company.

Instead, the deal became one of the most infamous acquisitions in corporate history. Mattel struggled to integrate the business, sales disappointed, losses mounted, and billions of dollars in shareholder value were wiped out.

O’Leary didn’t last long, either. Up to this point, he had only spent his career building companies, and now, he had to play by the rules of a large corporation. “I got fired after six months,” he tells me. “I kept barking orders at everybody because I wasn’t used to working for anybody.”

He remembers Mattel’s chief financial officer pulling him aside and explaining that wasn’t how things worked at a large organization. Looking back, O’Leary laughs and says: “Can you imagine listening to that insubordinate guy?”

In the decade that followed, O’Leary rebuilt his career as an investor rather than an operator. He backed companies, launched investment funds, and sat on corporate boards — roles that allowed him to shape strategy without running the day-to-day business. He emerged as one of North America’s best-known investors.

It looked as though his stepfather had been right. O’Leary was a businessman, not an artist. After watching him work, however, I wasn’t so sure.

O’Leary and I are riding through Midtown in a black Escalade on the way to Christie’s, where he will pitch Wondercare, the watch insurance company he hopes will become the auction house’s insurer of choice.

He receives a message and turns to me: “I’ve got to show you this.”

It’s a video of his business partner Justin Aronoff handing him a custom Marty Supreme guitar, inspired by the film in which O’Leary plays a financier. “Look at that,” O’Leary says, holding the phone between us but unable to get the sound to play. “It’s the exact orange color from Marty Supreme.”

He pauses the video and murmurs to himself: “It’s a beautiful guitar.”

O’Leary keeps a guitar and amplifier waiting for him at hotels around the world. When he’s not filming Shark Tank or going to meetings, he’s often alone in a hotel room practicing. Every Fourth of July, he attends a gathering in Nantucket where he plays in a band for an audience of a thousand people.

O’Leary doesn’t see himself as just an investor. The problem, he says, is that investing still takes up most of his life. “Yes, I’m an investor. Yes, I’m on Shark Tank, but I do a lot of other stuff,” he says. “I’d like to spend some time doing the other stuff — photography, guitar, the watches.”

A few minutes later, the Escalade pulls up to Rockefeller Center. The moment the car door opens, O’Leary snaps into performance mode.

A group of women in matching T-shirts scream in unison: “Hi, Mr. Wonderful!” A family runs up to ask if their son can snap a quick photo: “We watch you every day!” As we search for the entrance to Christie’s, two men follow us and ask if “Mr. Wonderful needs directions.”

Inside, the lobby features soft lighting, minimalist decor, and hushed voices — a stark contrast to the commotion outside. O’Leary seems relieved. “It’s so peaceful in here,” O’Leary says.

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We head to a private room, and he is in full salesman mode. Years earlier on CNBC, O’Leary laid out his formula for a successful pitch: articulate the opportunity in 30 seconds, explain why you’re the right person to execute, and prove you understand the economics.

He follows his own playbook perfectly.

First, he outlines the problem. O’Leary tells the Christie’s team that his watch collection was stolen and, like many collectors, he discovered that high-value watches were typically bundled into homeowners insurance policies. After filing the claim, his premiums jumped.

Then, he shares his personal edge. People told him a watch insurance business would never work because customer acquisition costs were too high. “I said, ‘Everybody knows I’m a watch collector. I’ve got more than 12 million followers on social media, so we’ve never paid for a customer,’” he explains.

Finally, he nails the numbers. He starts talking about the financials, sharing several confidential growth metrics that seem to impress the people in the room.

The entire pitch takes 3 minutes and 17 seconds.

During the meeting, conversations about insurance often drift into craftsmanship. As things are wrapping up, O’Leary reaches into his bag and pulls out his Jalen Brunson diamond necklace and shows the Christie’s executives how the trading card at its center can be displayed vertically or horizontally. “It’s very flashy, so it’s great on television,” he says.

The executives nod along and promise to arrange follow-up meetings with senior leadership to discuss a potential partnership.

The next morning, I arrive at Phillips Auction House in Midtown Manhattan where O’Leary is giving a fireside chat about its latest watch collection.

The room looks like a museum for people with very expensive hobbies. Glass cases display F.P. Journe, Patek Philippe, Cartier, and Rolex watches worth more than most cars.

At the moment, O’Leary is not admiring any of them. He’s hunched over a tripod frenetically arranging chairs, tapping his wireless microphone, and setting up the perfect camera angle.

“Kevin, what … are you doing,” I ask, my eyes scanning the room for a 20-something social media manager who I assume is not doing his job.

Without looking up, he adjusts the frame another time. “This may be valuable content to post on my social media,” he tells me.

O’Leary had told me that he personally edits one social media video a week using Adobe Premiere Pro. I assumed he was exaggerating. “I’ll take the raw material, and I’ll create it myself,” he says. “And then I’ll just post it — much to the chagrin of my social media team.”

Satisfied with the shot, he steps in front of the camera, and begins: “First, some shameless promotion for my watch insurance business…” The audience laughs.

Wondercare CEO James Walter tells me that O’Leary is deeply involved in the business and promotes it every chance he gets. He joins the company’s weekly status call and, according to Walter, has missed only two in the last three years. “When he was on the Marty Supreme tour, I’d see him changing outfits in the background while on the call so he could hear what was going on and offer input,” Walter says.

Last year, O’Leary landed a role in Marty Supreme, which stars Timothée Chalamet as Marty Mauser, an ambitious table-tennis prodigy willing to do almost anything to win. The casting team was looking for “a real asshole” to play Milton Rockwell, the ruthless financier who bankrolls Marty’s rise. O’Leary was an obvious choice.

O’Leary tells me he couldn’t help himself. He immediately started suggesting changes to the script.

He improvised the now-famous “I am a vampire” line in which his character ominously warns Marty never to cross him. O’Leary even pitched director Josh Safdie on a darker ending in which Milton Rockwell would reveal himself to be a literal vampire by biting Marty on the neck.

O’Leary’s role was minor, but the casting generated praise from critics. When accepting the Golden Globe for Best Actor, Chalamet thanked O’Leary before thanking his own family. “If you had told me when I was 19 years old that I’d be thanking Mr. Wonderful from Shark Tank...”

For his part, O’Leary was just as interested in what was happening off camera as on it. Between takes, he wandered around the set photographing Chalamet and the rest of the cast. “I love that behind-the-scenes kind of thing,” he tells me.

O’Leary enjoyed learning what it takes to make a movie. More than anything, he says, he loves the challenge of creating something from scratch. That’s why he still spends hours editing videos in Adobe Premiere Pro.

When he gets stuck, he calls his daughter Savannah, who has made filmmaking her career. She says O’Leary’s questions are usually about some technical editing problem, and that she still can’t believe he edits the videos himself. “It’s not efficient,” Savannah says. “But I think he enjoys it.”

Business, O’Leary tells me, is binary: You either make money or you lose it. But the best entrepreneurs pair financial discipline with creative instinct. The numbers matter, but building a great business requires a feel for marketing, storytelling, and product design.

“You need the discipline of business but the chaos of the arts,” he says.

O’Leary first met television producer Mark Burnett, the creator of Shark Tank, over lunch in Los Angeles. He wasn’t entirely sure why Burnett had extended the invite.

The two men spent hours talking about the marital difficulties they were each navigating. What was supposed to be a quick lunch passed the three-hour mark.

Finally, O’Leary asked, “Why am I here, Mark?”

As O’Leary remembers it, Burnett laughed. “Oh shit,” he said. “I forgot. Tomorrow I’m testing a new show called Shark Tank.”

The next morning, O’Leary was seated alongside fellow investors Daymond John and Barbara Corcoran. Eighteen seasons later, he is still on the show.

On Shark Tank, millions of viewers came to know Kevin O’Leary as Mr. Wonderful. He became known for delivering what he called the “cold hard truth.”

But Anna Skaya, the founder of the cat DNA testing company Basepaws, came to know a different Kevin O’Leary. During her 2019 pitch, O’Leary initially dismissed the idea. “Why spend $29 for a cat testing kit when you can buy a new cat for five bucks?” he says.

O’Leary changed his mind after realizing Skaya wasn’t building a pet testing company so much as a data company with room to expand beyond cats.

O’Leary and Robert Herjavec invested. Three years later, Basepaws was acquired by Zoetis for more than $50 million, making it one of O’Leary’s best-performing Shark Tank investments.

Skaya says O’Leary’s greatest value came after the cameras stopped rolling. “I was the squeaky wheel in his portfolio,” she says. “’Kevin, I need help getting into WIRED. Kevin, do you know someone at Vogue? Kevin, can you do an Instagram Live with me? Kevin, can you hold a cat and take a picture?’”

The effort paid off: O’Leary made a 25x return on his initial investment.

Mark Cuban has watched O’Leary’s television persona and the real person behind it coexist for nearly two decades. “He may be Canadian, but he truly believes in helping people achieve their American dream,” Cuban tells me. And despite the character O’Leary plays on television, Cuban insists, “he does have a heart.”

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Not every Shark Tank entrepreneur has come away with that impression. In Season 7, entrepreneur Maneesh Sethi appeared on the show to pitch Pavlok, a wearable device that delivers small electric shocks to help users break bad habits. O’Leary was the only Shark to make him an offer.

“Mr. Wonderful, I can’t work with you,” Sethi replied. “I would take an offer from anybody besides Mr. Wonderful.”

O’Leary immediately fired back: “Maneesh, you’re an asshole. Get the fuck out of here. Fuck you.”

After his episode aired, Sethi wrote that O’Leary prioritized profits over customers and told me that his view of capitalism leaned “too far toward the villainous end.”

I ask O’Leary whether his outburst was an act for television. “No, that was not an act,” he says. “When we’re in the eighth hour of taping, I don’t even see the cameras. I don’t give a shit. That guy was a dick.”

Moments like these transformed Mr. Wonderful from a television character into a celebrity brand of his own. “I’d never been famous before,” O’Leary says. “Everything was crazy, and that gets to your head. I went to the dark side for a while.”

He tells me about spending a year living what he describes as “a debaucherous life” full of parties and excess. Eventually, a business partner pulled him aside. He said, “Kevin, people are starting to talk. How long will you do this for?”

The consequences of fame became harder to ignore. One day, O’Leary was heading to his car from a restaurant when a stranger grabbed him and put him in a headlock. He managed to break free, but the incident rattled him.

Not long after, the president of ABC called him into his office and asked, “How are you liking fame now?”

“Okay,” O’Leary remembers thinking. “I see the double-edged sword now.”

O’Leary can’t remember the first death threat, only that they’ve become a recurring part of his life. They arrive in every form imaginable — handwritten letters, emails, direct messages, and public social media posts. “I mean, it’s fucking nuts,” he says.

The latest wave started after O’Leary decided to enter the AI race.

While many investors are betting on artificial intelligence software, O’Leary is betting on the infrastructure that underpins it. His proposed Stratos Project would build a massive AI and cloud-computing campus in Box Elder County, Utah — a development supporters see as essential to America’s technological future and critics see as an existential threat to the region’s land, water, and power resources.

As the fight intensified, the dispute became increasingly personal. O’Leary accused several prominent critics, including Utah political strategist Gabrielle Finlayson, of acting as proxies for the Chinese government.

Weeks later, he publicly acknowledged he had “no evidence” to support the allegation. Finlayson is one of the plaintiffs now suing O’Leary and Fox News for defamation over the allegations. “I spent years building my reputation, my business, and the trust of my community,” Finlayson said in a statement announcing the lawsuit. “In just weeks, Kevin O’Leary tore it all down with lies.”

In a statement, O’Leary’s attorney Jeffrey Neiman said O’Leary intends to “defend this lawsuit vigorously” and may bring counterclaims. He called the suit a “cash grab,” arguing that the plaintiffs declined O’Leary’s invitation to discuss the project and used his remarks to raise money. “We look forward to discovery and uncovering the facts related to the misinformation campaign against the data center in Utah,” Neiman said.

Finlayson has referred to O’Leary as “the Canadian who is trying to ruin Utah.” Speaking on a podcast, she said opposition to the proposed AI data centers had become “so strong and so severe,” adding: “These folks don’t always know what’s going to come for them when they decide to put a giant thing no one wants in the middle of people’s homes.”

It’s not the first time O’Leary has landed at the center of a public firestorm. He tells me that he says exactly what he thinks and accepts whatever follows.

When cryptocurrency exchange FTX collapsed in 2022, O’Leary became one of its most visible casualties. FTX had paid him $15 million to serve as a spokesperson, and suddenly he found himself answering questions on national television about one of the largest financial scandals in recent memory.

O’Leary remembers seeing the word “fraud” in relation to FTX flash on the screen during a Fox News segment, and he checked his account to find the money was gone. He called FTX co-founder and CEO Sam Bankman-Fried and reportedly asked, “What’s going on with the accounts, Sam?”

O’Leary was one of the last people to speak with Bankman-Fried, so he had to testify to Congress about what he knew. “It was the first crisis that I’d ever been through,” he says. “And then I remembered something my mother said: ‘Just tell the truth, and you never have to remember what you said.’”

The first few days were brutal. “When shit was flying everywhere and the phone was just ringing, ringing, ringing, I said, ‘Fuck, what a nightmare,’” he says. “Why am I the poster boy for this when there’s 20 other guys that took money?”

Many celebrities who promoted FTX distanced themselves after the collapse. But O’Leary doubled down. He was on TV every day defending his prior involvement with the company.

When I ask him why he kept going on air, he answers as if stating the obvious: “Because I hadn’t been charged with anything.” The experience, he says, taught him to distinguish the signal from the noise. “The media cycle for the big stories is 48 hours,” he says. “After that, it starts to burn off.”

In interviews immediately after FTX failed, he refused to condemn Bankman-Fried.

CNBC’s Andrew Ross Sorkin pressed him directly: “Kevin, you are an actor in this drama, and you had a front-row seat to Bankman-Fried up until the very end. What do you think happened? Do you think this was a fraud?” To which Kevin responded that he doesn’t have all the facts yet.

Financier Anthony Scaramucci, who was also caught in the fallout from FTX’s collapse, remembers feeling “shell-shocked” by the backlash. O’Leary, he says, remained steadfast. “He defended Sam, and he didn’t care about the public opinion,” Scaramucci says.

In a 2022 Senate hearing, O’Leary argued that FTX competitor Binance had intentionally driven FTX out of business while benefiting from what he viewed as lax regulatory oversight that allowed it to dominate the market.

I ask whether experiences like FTX and the death threats surrounding the Stratos Project have made O’Leary more cautious about what he says publicly.

They have not. “The brand is about being authentic — even though it’s controversial,” O’Leary says. “That’s the brand.”

O’Leary and I are sitting in the restaurant of a swanky New York hotel. He orders a Caesar salad with cooked tuna and a glass of Montrachet.

He sets the menu aside, reaches into his bag, and pulls out the Tiffany necklace again. After laying the diamond chain on the table, he takes out a tiny screwdriver and removes the trading card from the pendant. It needs to be returned to its owner.

People start to recognize him. Their eyes shift from O’Leary to the diamond necklace. He’s right — it is flashy. A few diners not-so-discreetly raise their phones to take a picture of the scene. A woman walks past our table and whispers to me, “That’s Mr. Wonderful, right? Love him.”

The interruption doesn’t make O’Leary lose his train of thought. Before he started unscrewing the necklace, I’d asked him how he defines success at this stage of his career.

“I don’t measure it by money anymore,” he says. “I don’t need more money, you know? I just want to make really good use of my time. That’s what matters.”

Now, he wants to make room for the pursuits he once thought he’d left behind. Maybe one day he’ll be known as an artist — a musician, filmmaker, or photographer. But that day is not today.

Today, he is content to be known as Mr. Wonderful, the villain.

O’Leary says playing the villain gives him more freedom than playing the hero. “The bad guy is always scheming,” he says. “He’s always got a subplot. It has the audience thinking, ‘What is he really doing? Why is he saying that?’”

So what is Mr. Wonderful’s subplot?

He thinks for a moment, and takes a sip of wine.

“There’s nothing more motivating to me than someone saying I can’t do something,” he says. “Fuck you, watch this.”

The irony is that the first person to tell O’Leary he couldn’t do something was his stepfather, who told him he wasn’t good enough to become a professional photographer. O’Leary accepted the advice, abandoned the dream, and went into business instead.

Or at least that’s what it looks like from the outside looking in.

Because now, decades later, after turning himself into one of the most recognizable capitalists in America, he still spends his free time photographing strangers, editing videos, collecting watches, and playing guitar.

We are in the car on the way to a keynote speech he has to deliver at Delmonico’s steakhouse on Wall Street. I keep asking him: How does it not wear him down — the criticism, the death threats, the endless scrutiny? He’s rich — why not walk away and spend the rest of his life making art on a beach somewhere?

“No, you can’t let that get you. You just can’t,” he says, looking out of the car window. “Every 30 minutes, there’s something catastrophic and something euphoric happening — every single day. It’s to the bottom and then it’s to the top — over and over and over again.”

He pauses.

“So my attitude is, why don’t I just — “

The car comes to a stop. “Oh, this is it, I guess.”

He never finishes the sentence.

He steps out of the car, adjusts his jacket, and goes on to give a presentation on quantum computing to a room full of people who came to see their favorite capitalist villain — Mr. Wonderful himself.

-

Written by Polina Pompliano | Edited by Laura Entis | Photos & video by Stephen Yang

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Tomorrow, I’m publishing my Kevin O’Leary profile.

I’ve spent the past several weeks thinking about how to explain why this may be my favorite profile I’ve written. I think it’s because I really feel like I uncovered the real person behind the persona.

Most people know O’Leary as the ruthless capitalist who tells entrepreneurs their ideas are worthless and seems perfectly content to be the villain. That person is real. But he is also a character O’Leary has spent nearly two decades perfecting.

I shadowed him through TV appearances, business pitches, and private moments. I spoke with the people who have invested beside him, worked with him, fought with him, and watched him navigate the biggest crises of his career.

I can’t wait for you to read it, and I look forward to hearing your feedback. (I’ll be publishing clips and behind-the-scenes moments on my Instagram. You can follow me here.)

In your inbox tomorrow morning.

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— Polina

THE PROFILES.

— The modern athlete redefining his sport
— The TikTok influencer-turned-entrepreneur
— The rock icon stepping off stage
— The teenager who took on Meta — and won
— The startup that rebuilt itself from the inside out [**HIGHLY RECOMMEND**]

THE PEOPLE.

The modern athlete redefining his sport: LeBron James has spent more than two decades proving his greatness on the court. But his most enduring legacy may be the way he changed what athletes believe they’re allowed to become — turning fame into ownership, influence into leverage, and a playing career into something far bigger than basketball.

The TikTok influencer-turned-entrepreneur: Alix Earle built one of the most influential personal brands on the internet by making millions of followers feel like close friends. But behind the viral “Get Ready With Me” videos is a meticulous entrepreneur who obsesses over product decisions, audience psychology, and long-term career building. Here’s how she turned authenticity into a business empire. (TIME)

The rock icon stepping off stage (gift link): At 82, Mick Jagger speaks with surprising warmth about the strange bargain of a life in the spotlight. The conversation explores the space between performance and identity, and what remains when one of the world’s greatest showmen steps off the stage. (The New York Times)

The teenager who took on Meta — and won (gift link): At 17, Kaley Glenn-Mills became the face of a landmark lawsuit against the biggest social media companies in the world. This is a fascinating profile about how even at even after helping expose how these platforms hook young users, she still can’t stop scrolling. (Bloomberg)

THE COMPANIES.

The startup that rebuilt itself from the inside out: Most companies are bolting AI onto old products. Notion did something much harder. It rebuilt itself from the inside out. This behind-the-scenes look reveals how a decade-old startup transformed its culture, product, and way of working to become one of the few pre-ChatGPT companies thriving in the AI era. (Colossus)

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This week, I’m publishing my new profile of Kevin O’Leary — or, as most people know him, Shark Tank’s Mr. Wonderful.

Over the course of several days, I shadowed O’Leary through New York City, following him from Fox News studios to Christie’s auction house, sitting in on business pitches, watching him make million-dollar decisions, and asking him about the moments that have defined his career.

He told me about the biggest mistake of his life, the crisis that almost destroyed his reputation, the childhood promise that still drives him, and the legacy he hopes to leave behind.

Spending time with him dismantled assumption after assumption. If all you see is a ruthless capitalist, you’re only seeing the character — not the person. I realized that Mr. Wonderful — the television character millions recognize — is only one part of the story.

Yes, this is Kevin O’Leary:

Most of all, this profile is about identity. It’s about what happens when the world decides who you are before you get the chance to tell your own story. How much of ourselves do we choose, and how much becomes a role we can never escape?

I think you’ll come away seeing Kevin O’Leary — and perhaps a little of yourself — a bit differently. In your inbox this week.

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— Polina

THE PROFILES.

— The billionaire soccer icon [**HIGHLY RECOMMEND**]
— The creator of the Founders podcast
— The founder who created an army of AI influencers
— The concierge gynecologist
— The self-made billionaire who saved Clear

THE PEOPLE.

The billionaire soccer icon: David Beckham was once one of the most famous athletes on the planet. Somehow, he’s become even more successful in retirement. The soccer icon has turned his fame into a $1 billion empire spanning brand deals, documentaries, startups, real estate, and a 26% stake in Inter Miami — the MLS club he spent more than a decade fighting to build. Beckham’s second act is a masterclass in turning celebrity into ownership. (Forbes)

The creator of the Founders podcast: For five and a half years, David Senra read one business biography a week, recorded a podcast about it, and published each episode to almost no one. Today, Founders is a cult obsession among some of the world’s most powerful CEOs and billionaires, and a one-man business generating millions in annual profit. Senra has turned down acquisition offers, refuses to chase a mass audience, and still reads, records, edits, and publishes every episode himself.

The founder who created an army of AI influencers: At 21, Zuhair Lakhani is building a business designed to manufacture virality. His startup, Doublespeed, operates thousands of smartphones that run armies of AI-powered social media accounts — watching, commenting, posting, and promoting products while posing as real people. Backed by Andreessen Horowitz, Lakhani has embraced the dystopian implications as a marketing strategy: Why pay human influencers when fake ones can work around the clock? (alternate link)

The concierge gynecologist: Silicon Valley’s obsession with optimization has found its next frontier: women’s sex lives. Dr. Sally Greenwald has built a wildly sought-after concierge gynecology practice treating sexual health as seriously as sleep, exercise, and nutrition. Her approach combines hormone therapy, emerging research, and frank advice on everything from libido to orgasms. (The New Yorker)

The self-made billionaire who saved Clear: In 2010, Caryn Seidman Becker bought Clear out of bankruptcy for $6 million. Today, the airport security company is worth $7.6 billion, making her one of America’s few self-made female billionaires. Now she’s trying to turn Clear into a universal identity company that uses your face to verify who you are everywhere from hospitals and government accounts to workplaces and stadiums. (Forbes)

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The United States of America turned 250 this weekend. And yet, according to this CBS poll, just half of Americans say they’re even somewhat confident the American Dream is still attainable. Most believe that only a select few people have a real chance to get ahead anymore.

I looked up the actual definition of “The American Dream,” and it says: “The American Dream is an ideal that the United States offers the possibility of upward mobility, freedom, and equality for all individuals who work diligently and possess the will to succeed.”

This country has allowed my family upward mobility that would be inconceivable anywhere else on this planet. And I’m not talking about generations — I’m talking about the difference in life of one generation.

When my dad was in 6th grade in Bulgaria, he wrote ‘USA’ on his backpack. The teacher saw it, reported it to the principal, and they called his parents. He got in major trouble because he lived in a former communist country that doled out punishments for those who dared deviate from the government’s ‘allowed’ speech. (Not to mention that my dad’s family members who had spoken out against communism were killed, imprisoned, and sent to labor camps.)

His daughter (me) would go on to become a journalist working for some of the most prestigious news organizations in the world: CNN, USA TODAY, and FORTUNE magazine. One day, she would own her own media business & work for herself. Inconceivable.

This country is far from perfect, but it’s a nation of self-improvers. When something is wrong, people take to the streets, protest, and make sure their voices get heard.

I think about this a lot. The people I profile come from wildly different backgrounds, but they all believed their future could be bigger than their circumstances. As simple as that sounds, it’s a big freaking deal because it’s one of the few places on Earth where people are still free to build, create, question, fail, and voice their opinion without fear.

I’ll never forget what Evan Mwararire, the pastor who stood up to a dictator in Zimbabwe, told me: “Freedom means you can talk to your friend, criticize the government, and then forget about it and go home. Where I’m from, if you criticize the government, you’re not going to make it home.”

The ability to speak freely — and then forget what you said because you’re not worried that your words will cost you your life — is one of the greatest freedoms we take for granted.

Happy Fourth of July, friends. I hope you had a wonderful weekend with the people you love.

— Polina

A WORD FROM OUR PARTNER ✨: Have you ever read about a founder building the next great consumer brand and thought — I wish I could invest in that? Most people can’t. The best startup deals go to a handful of elite VC firms, and everyone else hears about them years later.

Alumni Ventures changes that. As one of TIME’s Top Venture Capital Firms, AV gives accredited investors access to curated Next-Gen Consumer deals — startups like Oura, Quince, and Bluesky — already co-invested alongside brand-name investors including a16z, Forerunner, and Khosla.

No cost to see deals. No obligation to invest. Just access to the deal flow that used to be off-limits.

See Next-Gen Consumer Deals →

Disclosure: Not an offer to sell securities. Example portfolio companies for illustrative purposes only and not available to future investors except potential follow-on investments. Venture capital investing involves substantial risk, including risk of loss of all capital invested.

PROFILES.

— The founder of Barstool Sports telling all [**HIGHLY RECOMMEND**]
— The mom using AI agents to run her house
— The founder who built a $5.5 billion athleisure startup
— The Today star reeling from a tragedy
— The hottest ghost kitchen in NYC

THE PEOPLE.

The founder of Barstool Sports telling all (complimentary link): Dave Portnoy built Barstool Sports by ignoring conventional management advice. Instead of rigid strategy, he hires interesting people, gives them freedom to create, and embraces controversy rather than running from it. The result is a media empire built on constant experimentation, strong personalities, and an instinct for capturing attention. (WSJ; complimentary link)

The mom using AI agents to run her house: Jesse Genet wakes up to groceries she never ordered and books she never bought. That’s because an army of AI agents is running her household — shopping, teaching her children, handling paperwork, and building software on command. While most people debate whether AI will take their jobs, Genet is already treating it like a personal staff. (New York Magazine; alternate link)

The founder who built a $5.5 billion athleisure startup: Joe Kudla thought he’d become an accountant. Instead, a brief and miserable modeling career unlocked his creative side and ultimately inspired him to build Vuori into a $5.5 billion activewear company. The profile shows how Kudla combined artistic obsession, financial discipline, and a relentless focus on product to create one of the biggest challengers to Nike and Lululemon. (Bloomberg; complimentary link)

The Today star reeling from a tragedy: Savannah Guthrie has spent her career reporting other people’s tragedies. Then, overnight, she became the story. When her 84-year-old mother vanished without a trace, Guthrie found herself balancing unimaginable personal grief with the impossible task of returning to the Today show as conspiracy theories swirled, cameras followed her every move, and millions of viewers watched her navigate a mystery that remains unsolved. (New York Magazine; alternate link)

THE COMPANIES.

The hottest ghost kitchen in NYC: Most ghost kitchens have struggled to live up to the hype. Goop Kitchen has done the opposite. Gwyneth Paltrow’s healthy takeout brand just pulled off its most successful launch ever with its first New York location, proving that celebrity may spark interest, but operational excellence and attention to quality are what turn a delivery-only restaurant into a breakout business. (Inc)

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I recently went to a talk where was discussing his new book, Wired on Wall Street: The Rise and Fall of Tipper X, One of the FBI’s Most Prolific Informants.

Hardin has jaw-dropping story. He went from rising Wall Street analyst to “Tipper X,” the FBI informant whose cooperation helped expose one of the largest insider trading rings in U.S. history.

In his talk, he used the phrase “character gap” to describe the space between who you appear to be (your reputation) and who you actually are (your true character). The goal, he said, should be to close that gap.

In a Substack post, he wrote: “Your reputation is who you are based on everything someone thinks they know about you. Your character is who you are even if you’re the only one who knows. And your integrity, the real measure, is how closely those two things align.”

Damn. It reminded me of Martha Beck’s idea of an “integrity cleanse,” the process of practicing honesty in thoughts, words, and actions. Beck realized that she wasn’t lying about big things — she was lying about the small, everyday things. “I didn’t tell lies about my taxes or anything in my personal life even,” she says. “I was telling lies about how I felt.”

Here’s how she suggests we can conduct an integrity cleanse: For the next three days, try to be aware every time you say something you don’t believe. “Most lies are told to smooth social interactions,” she says.

And every time you tell a small fib or you say something you don’t actually mean, write it down in a journal.

Beck offers the following example: Imagine someone says, “We’d love you to come out and visit us.” And to be polite, you respond with something you don’t mean: “Sure, sometime.”

But then in your journal, you write: “Okay, that was a lie. I would rather die a thousand times than go to stay with these people.”

By writing down the truth, you start noticing the situations in which you lie. And then you start lying less and becoming more in alignment with who you really are. Truth breeds integrity and integrity breeds respect.

Why is this important? Because many of us choose conformity instead of integrity until we look in the mirror and no longer recognize ourselves.

Beck writes, “We lie our way through our lives to get people to like us, and then we find out they didn’t like us because we were lying.”

We all know that living in alignment with our truth is what we ultimately want. But it’s so hard to do — especially if you’re a person who seeks external validation.

Beck offers a warning: “Depart from your truth in any way — offer a fake smile, flatter your awful boss, marry for money — and you become two people: the truth knower and the lie actor. That’s duplicity. And duplicity, not social noncompliance, is the real enemy of joy.”

— Polina

PROFILES.

— The CEO making Eli Lilly huge [**HIGHLY RECOMMEND**]
— The founder bringing robots to life
— The king of New York
— The Elle Woods of Seattle
— The billionaire taking over the North Fork

THE PEOPLE.

The CEO making Eli Lilly huge: Dave Ricks inherited a struggling, unpopular pharmaceutical company and transformed it into the world’s most valuable healthcare business. Under his leadership, accelerated drug development, bet aggressively on GLP-1 obesity treatments, invested billions in manufacturing before approval, launched a direct-to-consumer business, embraced AI, and reshaped Lilly into a faster, more consumer-focused company. The story explores how Ricks built a trillion-dollar giant — and whether he can avoid the boom-and-bust cycle that has defined nearly every great pharmaceutical company before him. (Bloomberg; gift link)

The founder bringing robots to life: Jeff Cardenas is building one of the world’s most ambitious humanoid robotics companies, but he’s unusually honest about how far the technology still has to go. While rivals hype robot butlers and AI breakthroughs, Cardenas argues the future will arrive gradually, starting in factories before expanding into everyday life. The story explores how Apptronik is trying to balance enormous expectations with the messy reality of building robots that actually work. (Bloomberg; gift link)

The king of New York: Jalen Brunson spent two months carrying New York on his shoulders and emerged with the Knicks’ first championship in more than 50 years. Now, amid parades, television appearances, and a citywide victory lap, the Finals MVP is still trying to process what happened. The story explores how the incredibly disciplined star, shaped by his demanding father and unshakable belief in himself, became the face of New York sports. (New York Magazine; alternate link)

The Elle Woods of Seattle: A year ago, Lexi Minetree was a recent college graduate with a handful of acting credits. Today, she’s the handpicked successor to one of the most beloved characters in modern pop culture: Elle Woods. The story follows how an unknown actress from Atlanta manifested, auditioned for, and ultimately landed the role that could change her life. (Cosmopolitan)

The billionaire taking over the North Fork: Stefan Soloviev inherited one of New York’s great real-estate fortunes, then spent decades trying to escape its shadow. Now the billionaire land baron, father of 22 children, and one of America’s largest private landowners is reshaping Long Island’s North Fork — whether locals like it or not. The story explores what happens when a man with virtually no limits collides with a community determined to preserve its identity. (New York Magazine; alternate link)

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On the day of my college graduation, my dad gave me a letter.

In it, he recounted the story of when he, my mom, and I moved to the United States from Bulgaria. When we came 26 years ago, my dad was a 33-year-old with a master’s degree in chemical engineering and more than a decade of work experience.

But in the U.S, he was starting over.

In the letter, he wrote:

“I was working at Marriott, and the money I was making was not enough to cover the bills for the first few months we lived here. I begged my manager to give me extra shifts so we could pay rent. At that time, we literally had nothing. My dream was to be able to buy you something to make you happy, so you could see that the U.S. is a happy place.

“For better or worse, you remember everything we went through in those first few years, but please never forget that I’ve always loved you more than anything in the world.”

Along with the letter, he enclosed a check so I could buy something I wanted now that he couldn’t afford to buy me then.

I still think about that moment often. It reminds me that my life would look completely different if my parents hadn’t been willing to take an enormous risk, put their egos aside, and start over from scratch in a brand-new country.

Now, as I watch my husband with our kids, I think about how some of the most important things dads do are rarely noticed in the moment. The opportunities children have are often built on sacrifices they never see.

Happy Father’s Day to all the incredible dads out there!

— Polina

PROFILES.

— The FTX founder’s life behind bars [**HIGHLY RECOMMEND**]
— Sam Altman’s executive coach
— The entrepreneurs looking to cash in on peptides
— The creator fighting the ‘tradwife’ label
— The podcaster whose media empire is crumbling

THE PEOPLE.

The FTX founder’s life behind bars: Sam Bankman-Fried’s prison years have done little to change the way he sees himself. In this deeply reported profile, he comes across as the same hyper-rational, endlessly analytical figure who built FTX — still convinced he was misunderstood rather than fraudulent, still plotting a return, and still viewing life through a utilitarian lens that prioritizes outcomes over process. While fellow inmates often find him likable and eccentric, the question remains whether he is a visionary brought down by mistakes or a man whose belief in his own judgment led him to justify catastrophic risks with other people’s money. (Bloomberg; alternate link)

Sam Altman’s executive coach: Joe Hudson, the executive coach trusted by Sam Altman and leaders across Silicon Valley, believes the AI race will make human skills more valuable, not less. His core idea is that the most successful leaders are the ones who can navigate difficult emotions, build deep trust, and connect with others. As AI commoditizes knowledge, Hudson argues that wisdom, self-awareness, and emotional intelligence will become the ultimate competitive advantage. (Bloomberg; alternate link)

The entrepreneurs looking to cash in on peptides: The peptide boom is turning a niche black market into a multibillion-dollar industry. What began with bodybuilders and biohackers ordering experimental drugs from China has exploded into a mainstream wellness craze fueled by GLP-1s, longevity culture, and social media. Now, with the FDA considering legal pathways for some peptides, entrepreneurs, telehealth companies, compounding pharmacies, and investors are racing to cash in. (Bloomberg; alternate link)

The creator fighting the ‘tradwife’ label: Hannah Neeleman, the creator behind Ballerina Farm, says the internet has spent years trying to turn her into a symbol, but she just sees herself as a woman who loves babies, big dreams, and building businesses. In this candid interview, she defends her choices, embraces the chaos of raising nine children while growing a farm empire, and argues that women shouldn’t have to pick between ambition and family—they should be free to define success for themselves. (New York Magazine; alternate link)

The podcaster whose media empire is crumbling: Alex Cooper built Call Her Daddy into one of the most successful media brands of her generation by positioning herself as a champion of ambitious young women. But according to interviews with dozens of current and former employees, the culture inside her company, Unwell, often looked very different from the empowering image she projected publicly. The story explores allegations of high turnover, fear-driven management, and the outsized influence of Cooper’s husband and business partner. (Vanity Fair; alternate link)

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As many of you know, I love New York.

I don’t follow sports particularly closely, but basketball is one of the few games I can actually understand and enjoy. My husband is a diehard Knicks fan, so over the years I’ve tagged along to plenty of games and always had a great time.

But the Knicks making the Finals (and now WINNING THE NBA CHAMPIONSHIP) has transformed the city’s already-electric energy into something I can’t even describe. It feels like New York has been plugged into a power outlet.

People are outside watching together. A united front. (It also helps that Knicks fans are delightfully unhinged. I can’t stop watching the “man on the street” interviews on Instagram.)

We went to Game 4 at Madison Square Garden hopeful.

Then the Spurs took a small lead. Then a bigger one. By halftime, they were up 27 points. The cheers turned into groans, and the groans turned into silence.

And then — a miracle. The Knicks didn’t take their first lead until just under a minute remained in the game.

Thousands of fans experienced the same emotional sequence. Everyone went from “it’s over” to “wait…” to “maybe?” to “oh my God what did I just witness?”

Jalen Brunson missed the potential game-winning three-pointer. The Knicks won only because OG Anunoby tipped it in with 1.2 seconds remaining. One point two seconds!

Moments like that are rare because they force us to confront something we spend most of our lives trying to avoid: uncertainty. We want certainty. We want to know how the story ends.

By halftime, most of us were convinced we knew exactly how the Knicks’ story would end. Then, in the span of a few minutes, that certainty left and the hope returned. The comeback was a reminder that the improbable happens more often than we’d like to admit — and that even when the odds look overwhelming, it ain’t over til’ it’s over.

As a storyteller, I love that. I love hearing my normally-pragmatic husband talk about destiny. I love hearing a lawyer who demands evidence in every other aspect of her life talk about serendipity.

It’s equal parts absurdity and magic — the combination that makes New York City extraordinary.

CONGRATULATIONS TO THE KNICKS AND ALL THE KNICKS FANS! As one of the commentators said when Jalen Brunsen hugged his dad: “Life is not perfect, but there are perfect moments. And there’s one right there.”

Here is a video I took from the stands of the game-winning shot of Game 4:

— Polina

PROFILES.

— The world’s most likable celebrity [**HIGHLY RECOMMEND**]
— The trailer park billionaire
— The king of New York
— The ultra-athlete competing in Antarctica
— The modern conservative woman

THE PEOPLE.

The world’s most likable celebrity: If you read one thing today, let it be this profile on Dwayne ‘The Rock’ Johnson. Beneath one of the world’s most carefully managed public personas is a man increasingly preoccupied with the scars of his past. Through long, tequila-fueled conversations, Johnson reflects on marriage struggles, his fear after discovering a potentially serious health issue, the pain of childhood poverty and abandonment, and his evolving view of masculinity, politics, and fame. Such an entertaining read. (Esquire) (For more, check out my Profile Dossier on Dwayne Johnson here)

The king of New York: Jalen Brunson’s rise from an overlooked second-round draft pick to the face of the New York Knicks is a story of relentless work, self-belief, and humility. Long doubted because of his size and athleticism, Brunson steadily proved skeptics wrong at every level before arriving in New York, where his grit, leadership, and clutch performances have made him the city’s unlikely basketball king. (ESPN)

The trailer park billionaire: Bob Bull turned Britain’s trailer parks into a billion-pound empire by convincing lenders they were luxury housing developments, borrowing heavily to fuel rapid expansion. But inflated valuations, questionable business practices, and mounting debt eventually caused the company to collapse, leaving creditors owed billions and raising questions about where much of the money went. (Bloomberg; alternate link)

The ultra-athlete competing in Antarctica: Stephanie Case, a 43-year-old lawyer and ultramarathon runner who famously won a race while breastfeeding her infant daughter, is attempting something no woman has ever done before. She will compete in — and potentially break the overall record for — the 100-mile Antarctic Ice Ultra. Despite admitting that she “genuinely hates the cold,” Case will face brutal -13°F temperatures and fierce Antarctic winds in a challenge she says is about more than endurance. (The Athletic; alternate link)

The modern conservative woman: At Turning Point USA’s Women’s Leadership Summit, attended by roughly 3,000 women, Erika Kirk outlined a vision of conservative Christian womanhood centered on faith, marriage, motherhood, and family over career ambition. The conference reflected a broader shift within the movement away from overt politics and toward cultural and religious values, with speakers promoting traditional gender roles, criticizing feminism, and encouraging young women to prioritize family life while framing conservative communities as a refuge from increasingly hostile mainstream institutions. (WSJ; complimentary link provided)

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Last week, I hosted a live Q&A with premium members of The Profile.

A reader asked me about my process for getting to the deeper, harder questions. Do I start with small talk or do I just dive right in?

Here’s what I said: Small talk earns you a bit of trust, which you can then use to ask the hard questions. But even then, sometimes, it can backfire and get really, really awkward. Sometimes a subject gets defensive or angry or visibly uncomfortable.

During one of my shadowing sessions, I asked a question that struck a nerve. The subject became upset, and the entire energy of the interview changed. In moments like that, every instinct tells you to retreat and make the awkwardness disappear.

But I often remind myself that the topics that make people uncomfortable are usually the ones that matter the most. So instead of backing away, I did the only thing I know how to do — I tried to understand.

Eventually, we got through it. I understood where he was coming from, and he understood why I was asking the question. Although I could tell that some of the trust evaporated after that moment, the exchange taught me something important about him.

I saw the mask drop, and for a brief moment, the polished answers disappeared, and I got to see the real person underneath. To me, that was a win.

One of the biggest lessons I’ve learned from profiling people is that genuine curiosity can diffuse almost any emotionally-charged situation.

And in the end, the quality of the answers you get is usually a reflection of the trust you’ve earned.

— Polina

—

A WORD FROM OUR PARTNER ✨: Have you ever read about a founder building the next great consumer brand and thought — I wish I could invest in that? Most people can’t. The best startup deals go to a handful of elite VC firms, and everyone else hears about them years later.

Alumni Ventures changes that. As one of TIME’s Top Venture Capital Firms, AV gives accredited investors access to curated Next-Gen Consumer deals — startups like Oura, Quince, and Bluesky — already co-invested alongside brand-name investors including a16z, Forerunner, and Khosla.

No cost to see deals. No obligation to invest. Just access to the deal flow that used to be off-limits.

See Next-Gen Consumer Deals →

Disclosure: Not an offer to sell securities. Example portfolio companies for illustrative purposes only and not available to future investors except potential follow-on investments. Venture capital investing involves substantial risk, including risk of loss of all capital invested.

THE PROFILES.

— The Murdoch seceding from his family [**HIGHLY RECOMMEND**]
— The billionaire who fell from grace
— The celebrity-backed AI shopping startup
— The billion-dollar beauty brand
— The anti-corporate hero of the games industry

THE PEOPLE.

The Murdoch seceding from his family: James Murdoch is buying New York magazine and Vox Media in a move that looks like a declaration of independence from his father’s legacy. While Rupert Murdoch built a media empire by giving audiences what they wanted, James is betting that in an AI-saturated world, trusted journalism and original ideas will become even more valuable — even if they generate less profit. The irony is that both father and son are building media empires around distinct audiences. They just have very different visions of the world. (The New York Times; alternate link)

The billionaire who fell from grace: Few people have spent more time managing their public image than Bill Gates. But after years of successfully recasting himself from tech villain to global philanthropist, his association with Jeffrey Epstein is threatening to unravel one of the most remarkable rebrands in business history. (WSJ; complimentary link provided)

THE COMPANIES.

The celebrity-backed AI shopping startup: Phoebe Gates is building an AI shopping startup with a cap table that looks more like a Met Gala guest list. Phia has raised $43.5 million, attracted dozens of celebrity investors, and already serves 1.5 million users. Gates wants Phia to become a personalized shopping agent that knows your taste, curates what you should buy, and eventually predicts what you’ll want before you do. (Vogue)

The billion-dollar beauty brand: Rhode has become one of beauty’s fastest-growing brands, reaching $390 million in annual sales and setting its sights on $1 billion in global retail revenue. Hailey Bieber’s strategy is simple but difficult to execute: turn a skincare brand into a lifestyle universe through viral products, immersive pop-ups, and carefully curated experiences that make customers feel part of a world. The challenge now is staying culturally relevant in an industry where consumers move on quickly and attention is the scarcest resource. (Vogue)

The anti-corporate hero of the games industry: Valve spent decades cultivating the image of an anti-corporate gaming utopia — a quirky, flat organization run by gamers for gamers. But as Steam grew into the dominant marketplace for PC games, critics began to see a company with enormous power, a 30% tax on developers, and rules that competitors say are impossible to escape. Now, antitrust lawsuits in the U.S. and U.K. are testing whether Valve is the benevolent backbone of PC gaming or simply another monopoly hiding behind a beloved brand. (Bloomberg; alternate link)

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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:

Subscribe now

I’ll see you there.

— Polina

THE PROFILES.

— 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 PEOPLE.

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 COMPANIES.

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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My first book, Hidden Genius, published exactly three years ago. I still remember how surreal it felt to walk into a bookstore and see something that had lived in my head for years sitting on an actual shelf.

Here is the moment I saw it for the very first time:

What I didn’t expect was how many messages I’d receive from readers saying the book changed the way they think about success, talent, and their own potential. That has meant more to me than I can properly express.

The book was born from a question I became obsessed with as a reporter: Why do some people build extraordinary lives and companies while others — with just as much talent — never quite break through? Over years of interviews with founders, athletes, investors, and operators, I realized that what separates people is in the hidden advantages — thed mindsets, habits, emotional patterns, and ways of seeing the world that compound quietly over time.

✨ And now, three years later, I’m excited to share that the paperback edition of Hidden Genius launches this August. ✨

Pre-Order Hidden Genius Here

This new edition is incredibly special to me because it gives the book a second life, and hopefully introduces these ideas to a whole new group of readers.

How you can help:

If you’ve ever wanted to support my work, pre-ordering the paperback is one of the most meaningful ways to do it. Pre-orders genuinely matter in publishing more than most people realize. They help determine how much attention a book receives, where it gets placed, and how far it travels.

You can preorder it here:

Pre-Order Hidden Genius Here

Thank you for reading my work, supporting The Profile, and allowing me to spend my life chasing stories and ideas that fascinate me. None of this exists without you.

— Polina

PROFILES.

— Silicon Valley’s AI tycoon [**HIGHLY RECOMMEND**]
— The Amazon CEO making AI-era bets
— Comedy’s breakout star
— The company building a $200-billion data center
— The billion-dollar skincare line

PEOPLE TO KNOW.

Silicon Valley’s AI tycoon: Is Cognition founder Scott Wu a new kind of Silicon Valley genius? Wu is hyper-competitive, mathematically gifted, and less interested in academic prestige than in building world-changing AI products at extreme speed. This profile details the transformation of the “nerd genius” from isolated academic outsider into founder-king — someone whose intelligence now translates directly into power, capital, and infrastructure. Wu argues that AI coding agents like Devin could eliminate much of the friction and “sludge” of modern life, while also hinting at a future where human creativity matters more than execution itself. (Colossus)

The Amazon CEO making AI-era bets: Andy Jassy is trying to turn Amazon from the company that dominated e-commerce and cloud computing into the infrastructure backbone of the AI era. This profile portrays him as a disciplined operator cleaning up Bezos-era excess while making some of the biggest AI bets in corporate history — spending hundreds of billions on chips, data centers, satellites, and partnerships with OpenAI and Anthropic. Can Jassy preserve Amazon’s culture of invention while transforming it into a mature, tightly managed corporate empire? (Bloomberg; alternate link)

Comedy’s breakout star: Robby Hoffman has quickly become one of comedy’s breakout stars through her hit Netflix special and role on Hacks, building a reputation for provocative, deeply personal humor that divides audiences. Raised in poverty in a strict Hasidic Jewish community, Hoffman channels her chaotic upbringing, outsider identity, and blunt worldview into comedy that rejects polished Hollywood norms in favor of radical honesty, emotional openness, and unapologetic self-belief. (The Guardian)

COMPANIES TO WATCH.

The company building a $200-billion data center: Meta’s $200 billion Louisiana data center shows what happens when the AI boom collides with small-town America. This profile frames the project as a lifeline for a struggling farming community now being reshaped by billionaires, politics, and massive energy demands. Residents want economic revival, but many fear they had little say in the transformation of their home. (Bloomberg; alternate link)

The billion-dollar skincare line: Hailey Bieber turned Rhode from a celebrity skincare line into a billion-dollar beauty empire by combining obsession and internet-native storytelling. Rather than relying solely on fame, she and her team built a “360 world” around Rhode — using YouTube, social media, aesthetics, and lifestyle marketing to cultivate demand long before products launched. The brand that sold out instantly, broke Sephora sales records globally, and was acquired by e.l.f. Beauty for up to $1 billion. (TIME)

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I know all of you read a ton of newsletters, articles, posts, and updates every day, so I want to make sure The Profile continues to feel genuinely worth your time and attention.

If you have a few minutes, I’d really appreciate if you took this short survey. I’m trying to better understand what resonates most with you, what you want more (or less) of, and how I can make the publication more valuable over time.

Thank you for reading week after week, sharing the stories, replying to emails, and supporting The Profile. Your feedback genuinely means a lot to me.

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PS: I haven’t been posting a lot on X or Instagram because I’ve turned my focus to Substack Notes, which I love. You can follow me on Notes here.

PROFILES.

— Comedy’s newest star [**HIGHLY RECOMMEND**]
— Silicon Valley’s pro-tech Democrat
— The reality TV star building a real estate empire
— The influencer selling longevity hacks to women
— The struggling celebrity media company

PEOPLE TO KNOW.

Comedy’s newest star: Marcello Hernández is emerging as Saturday Night Live’s breakout Gen Z star — a hyper-energetic Miami comic whose charisma feels built for both TikTok-era fame and old-school stand-up. This GQ profile paints him as relentlessly “on,” turning every interaction into material while grinding obsessively at comedy even as Netflix specials and movie roles pile up around him. Hernández wants to become the next crossover comedy star in the mold of Kevin Hart or Adam Sandler. (GQ)

Silicon Valley’s pro-tech Democrat: Ro Khanna is reinventing himself from Silicon Valley’s favorite pro-tech Democrat into one of its loudest critics — backing a billionaire wealth tax, attacking the “Epstein class,” and openly antagonizing donors like Peter Thiel. Khanna believes distancing himself from tech elites could make him a credible 2028 presidential contender at a moment when public distrust of AI, billionaires, and Silicon Valley is surging. (Bloomberg)

The reality TV star building a real estate empire: Ryan Serhant says the real villain of his Netflix show Owning Manhattan isn’t a rival broker — it’s himself. The profile frames Serhant as a reality-TV savant who understands that fame comes from “creating noise,” whether that means jumping naked into a pool on camera or turning his own ambition and ego into storyline fuel. (New York Magazine; For more, check out my profile on Ryan Serhant here.)

The influencer selling longevity hacks to women: Kayla Barnes-Lentz is building a female-focused longevity empire on the idea that the biohacking world was built by men, for men. This profile portrays her as part wellness guru, part human experiment — turning blood tests, sleep tracking, saunas, and hormone data into a booming business for women who feel left out of Silicon Valley’s “live forever” movement. How much of modern longevity is real science, and how much is elite wellness theater?

COMPANIES TO WATCH.

The struggling celebrity media company: Once valued at $650 million, Kevin Hart’s media company has faced layoffs, executive turnover, stalled projects, and internal conflict as Hollywood spending slowed and the business remained overly dependent on Hart himself. The profile suggests Hart’s new deal with Authentic Brands Group — which moves his endorsement business outside Hartbeat — may signal the slow unraveling of the company’s original vision.

✨ The rest of this newsletter is only available for premium members of The Profile, whose support makes this work possible. If you’re not already a premium member, consider upgrading your subscription below for access to an additional section of weekly audio + video recommendations. ✨

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Last week, I published my latest profile on Jake and Logan Paul.

I spent months reporting it — sitting in on LP meetings, watching how they operate behind the scenes, digging into their businesses and investments, and trying to answer this question: Can internet attention actually be converted into longstanding wealth and power?

One thing I’ve learned from profiling people is that we’re all driven by some unspoken need. Why do we keep doing what we do every single day? Usually, there’s something we’re trying to prove, resolve, escape, or heal within ourselves.

So when I profile someone, I really try to understand their worldview. What drives them? What scares them? What are they chasing?

With Jake and Logan, I could tell that they seem to genuinely want to be taken seriously while simultaneously having become wildly successful by being unserious.

That was the crux of my story. So instead of only asking, “Why do you want to be billionaires?” I kept approaching the question in different ways:

• “What would billionaire status actually change for you?”

• “Would it change how people see you?”

• “Does it bother you that people underestimate you?”

Eventually, both brothers arrived at the same idea: At the highest levels of wealth and power, people care less about how you got there and more that you made it there at all.

If you read the piece, I’d love to know what you thought. And if you have questions about the reporting process, profiling, or anything behind the scenes, reply and send them my way. (I’ll be answering the questions in a live AMA soon.)

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Disclosure: Not an offer to sell securities. Example portfolio companies for illustrative purposes only and not available to future investors except potential follow-on investments. Venture capital investing involves substantial risk, including risk of loss of all capital invested.

PROFILES.

— The influencers turning attention into a billion dollars [**HIGHLY RECOMMEND**]
— The engineer-CEO building America’s $31 billion defense startup
— The NFL commissioner going to Hollywood
— The obsessed investor
— The $2 billion brand rejecting the Victoria’s Secret playbook
— The companies driving renewed interest in nuclear energy

PEOPLE TO KNOW.

The influencers turning attention into a billion dollars: Jake and Logan Paul are trying to turn internet outrage into a billion dollars. The same traits that made the brothers impossible to ignore online — provocation and attention-seeking — have evolved into a deliberate business strategy centered around their venture firm Anti Fund and stakes in companies like Prime Hydration, Betr, and Whatnot. (The Profile)

The engineer-CEO building America’s $31 billion defense startup: Brian Schimpf is the engineer at the center of Anduril’s rise — a technical, intensely operational CEO trying to build the next great American defense company by applying Silicon Valley speed and software thinking to modern warfare, while avoiding becoming the bloated military bureaucracy he’s trying to replace. (FORTUNE)

The NFL commissioner going to Hollywood: Roger Goodell has turned the National Football League into the most valuable force in modern media, with giants like Netflix, Amazon, and YouTube fighting to pay billions for live football rights because the NFL still commands mass real-time attention. The profile argues that in a fragmented media landscape, live sports have become the ultimate power asset, and Goodell is the executive sitting at the center of it. (Vanity Fair)

The obsessed investor: This profile of Kima Ventures investor Jean de La Rochebrochard is all about obsession, insecurity, and endurance. The piece follows Jean through founder meetings, nonstop dealmaking, emotional setbacks, and Ironman races, revealing a man driven by a constant need to prove himself. This profile reveals something we can all understand: the fear of never quite being good enough. ()

The $2 billion brand rejecting the Victoria’s Secret playbook: Jennifer Foyle is the retail executive who turned Aerie into a nearly $2 billion brand by betting early that women wanted comfort, authenticity, and “realness” over the hypersexualized fantasy pushed by Victoria’s Secret. Now she’s trying to turn that same instinct into an advantage in the coming backlash against AI-generated beauty. (FORTUNE)

COMPANIES TO WATCH.

The companies driving renewed interest in nuclear energy: This is the ****story of how Three Mile Island — once the symbol of America’s nuclear disaster fears — is being revived to power the AI boom. As companies like Microsoft race to build energy-hungry AI systems, nuclear power is suddenly becoming strategically valuable again. The piece frames it as a remarkable collision of two high-risk technologies reshaping the future. (Bloomberg)

✨ The rest of this newsletter is only available for premium members of The Profile, whose support makes this work possible. If you’re not already a premium member, consider upgrading your subscription below for access to an additional section of weekly audio + video recommendations. ✨

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“Oh — hi Jake Paul?” His face makes clear he has just encountered someone in a place where they don’t belong.

“What are you doing down here?”

Jake steps into character. “Hustling, bro. Empire State of mind. What are you guys doing?”

They laugh and state the obvious: “Working.”

“Same, bro. Same.”

Upstairs, in a glass conference room overlooking the Hudson River, Jake is about to meet with investor Rudy Sahay, whose firm is the largest limited partner in his venture fund, Anti Fund. Geoff Woo, Anti Fund’s co-founder, slides into a chair. They are there to talk about capital — whether Sahay will commit more money to the fund.

It’s not the version of Jake Paul most people are used to seeing. Before I began reporting this story, my understanding of the brothers Jake and Logan Paul was surface-level at best. I remembered Logan’s 2017 “suicide forest” vlog, which showed a dead body and sparked global backlash. I remembered that Jake’s Calabasas mansion was raided by a SWAT team in 2020.

But mostly, I remembered them as the internet’s first “influencers” on the now-defunct social media site Vine, where they posted stunts and skits featuring all sorts of teenage debauchery. I dismissed them as recurring characters in the internet’s endless outrage cycle.

I thought they would eventually fade into obscurity like so many in their cohort, but they never did. In fact, they’re more present than ever. The behavior that makes Jake and Logan hard to take seriously is the same behavior that has kept them at the center of everything.

Over the past two decades, Jake and Logan built a social media empire in public, amassing a combined following of more than 150 million and becoming a case study in growing up in the attention economy.

Even their biggest critics can’t seem to look away from the escalating stunts, the public feuds, the diss tracks (remember “It’s Everyday Bro?”), and the steady drip of controversy.

It’s all part of the Paul brothers’ playbook: declare a bold ambition publicly, repeat it often, direct attention toward it, position themselves as the underdog, introduce just enough controversy — and, over time, the performance starts to tilt toward reality. By the time Jake was pitching his fund at the Aquarian office, he was reinforcing a brand he had been building for two decades.

Today, that Paul brothers brand shows up in some not-so-obvious places. Jake and Logan have each separately co-founded companies like sports drink brand Prime Hydration, boxing promotions company Most Valuable Promotions, personal care startup W, and sports betting platform Betr.

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At the center of that strategy is Anti Fund, the venture firm Jake launched with Geoff Woo. Logan has since joined as a general partner, helping invest in and promote companies through their combined audience.

Anti Fund’s investment thesis is that capital is abundant, attention is not. At their scale, attention can act as leverage by bringing awareness, shaping a company’s narrative, and driving user growth. Traditional venture firms tend to specialize in a specific industry or sector, while Anti Fund’s portfolio spans everything from consumer brands to frontier AI and defense.

The portfolio includes OpenAI (currently valued at $852 billion), Anduril ($60 billion), Ramp ($32 billion), Whatnot ($11.5 billion), Cognition ($10.2 billion), Physical Intelligence ($5.6 billion), and Modal Labs ($1.1 billion).

The Profile has exclusively learned that Anti Fund’s stake in OpenAI has more than doubled, while an early-stage check into robotics startup Physical Intelligence could turn into a 100x outcome if the company’s next round lands at the rumored $11 billion valuation. Even smaller consumer bets, like soda brand Olipop, have already multiplied several times over.

Jake and Logan understand that brand deals and YouTube revenue won’t make them billionaires. Building companies and investing in startups might. They’re trying to turn attention into ownership — real equity they can eventually cash out — rather than relying on fleeting brand deals.

The Paul brothers forced their way to the center of YouTube and entertainment, where performance eventually evolved into strategy. Logan pivoted to professional wrestling, and Jake to boxing. “All those performances are a vehicle for us to build big businesses,” Logan tells me.

They’ve even turned that ambition into content. I opened YouTube to find Jake and Logan posted a video titled “Jake & Logan Paul Expose Their Billion Dollar Business Plan,” laying out their intent to become billionaires and stake a claim in the world of business.

And now, after spending time with them, I came away with the sense that they genuinely believe billionaire status is within reach — even if declaring it publicly makes it part of the performance.

Logan, 31, says, “It just seems like an accomplishment that Jake and I can both independently achieve in this life. So why not try to achieve it?”

When I ask Jake, 29, when he expects to become a billionaire, he thinks for a moment and lands somewhere around his 35th birthday. But there’s a difference, he notes, between a billionaire on paper and one with a billion in liquid assets.

So which does he mean?

“I’m saying liquid [by] 35 years old,” he says in a way that sounds like he’s making a bet.

“It’s over, it’s over,” Logan says, out of breath, leaning on auctioneer Ken Goldin behind a long wooden table stamped with the Ripit logo — his new company built around Pokémon cards and premium collectibles. Three cans of Prime Hydration, his sports drink, sit in full view.

He watches the screen in disbelief as the auction for his rare illustrator Pikachu card comes to an end. Someone had made the winning bid for $16,492,000.

Logan, who often speaks in hyperbole, is about to say something that sounds outlandish but is actually true. He had sold “the most expensive trading card of all time.” Logan bought the card in 2021 for $5.275 million, tripling his money in five years.

Suddenly, AJ Scaramucci, investor, collector, and son of financier Anthony Scaramucci, steps on stage and says, “Logan, I bought your card, baby.”

The Pikachu card auction, which generated 2.5 million views on Logan’s YouTube channel, got covered in CNN, FOX, The Los Angeles Times, the BBC, and countless other outlets.

“They know we can’t look away, and they keep escalating the level of insanity,” Scaramucci says. “They tap into that primal, amygdala, fight or flight, animalistic craziness that is society.”

And nothing is more primal than getting punched in the face. Once the Paul brothers discovered combat sports, they started turning the online performance into a business with real money at stake.

Six weeks after the auction, Logan is in New York City for WWE’s “Monday Night Raw.” He’s in a black Escalade being driven between podcast stops ahead of his match at Madison Square Garden.

As we weave through traffic, he explains the difference between his private self and his public persona. “Jake and I have a secret weapon in that we’re not actually the dumbasses that we’re perceived to be,” he says. “This is a façade. This is all a façade.”

I stop him. “Are you performing right now?”

“Kind of, yeah.”

Minutes later, he’s heading into Caleb Pressley’s comedic podcast, “Sundae Conversation.” Logan tells me he’ll conduct the interview “in character” as a “fucking dumbass dickhead that people love to hate,” before beelining toward a jar of lollipops, grabbing a pink one, and walking on set.

The transformation is jarring. Logan turns from the reflective, almost philosophical version of himself in the car into the jockish character I had seen on the internet — yet off camera, he tells me he’s into sci-fi, animé, Pokémon, collectibles, and dinosaur documentaries.

When the podcast ends, he drops the persona. He’s in the elevator debriefing with his team — breaking down what worked, what didn’t, and how it could be better next time. “I have really high standards for the content we put out,” he says. “Maybe unrealistically high sometimes.”

Professional wrestling has a word for this: “kayfabe.” It’s the practice of treating performance as reality, never breaking character, and protecting the illusion at all costs. The Paul brothers have been refining this skill for most of their lives.

In 2007, two years after YouTube launched, Logan, 12, and Jake, 10, created a channel where they uploaded prank calls, backyard stunts, and low-budget sketches to an audience of strangers.

The views began growing, and brand deals followed. In college, Logan asked his dad, who worked as a commercial roofer, how much he had made in his best year.

$120,000.

“I was like, ‘Dad, I made that much this year, and I’m 18,’” Logan says. “I think this internet stuff has some legs. I’m going to pursue it.”

He dropped out of college and moved to Los Angeles. Jake followed, leaving high school to do the same.

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When influencer Amanda Cerny first met Jake and Logan, they were living in the same apartment building. “From the very beginning, they wanted to launch businesses,” Cerny says, recalling how Jake tried to convince the Vine influencers to start a clothing brand together. “They saw that eyeballs meant dollar signs, so attention was really valuable.”

In 2016, Jake launched Team 10, a content house and talent management agency where creators collaborated on videos and tried to make them go viral every day.

Justin Roberts joined at age 14. “I went over to the Team 10 house, and [Jake] was filming a video where he was going to blow up a car in the desert,” Roberts says. “We were building homemade water slides, pulling pranks on each other, [creating] dating gossip — all to get the attention of the audience.”

As Jake reflects on that period now, he calls it “the YouTuber Disease” — the compulsive cycle of feeding the algorithm, each video more extreme than the last. He takes responsibility, saying he feels “guilty” for helping to perpetuate an internet culture of constant escalation.

“I didn’t know anything about life,” he says. “I was just full steam ahead. I didn’t care about consequences. I didn’t understand my impact. I didn’t understand emotional intelligence.”

Things came to a head in 2020, when FBI agents, accompanied by a SWAT team, raided his home and seized multiple firearms. The raid followed charges in Arizona for misdemeanor criminal trespassing and unlawful assembly — both of which were later dropped.

After Team 10 disbanded in 2020, Jake turned to boxing where the performance and the attention are central to the business. With his combat sports promotion company Most Valuable Promotions, he is the owner, not the talent. He controls the narrative and the economics.

By April 2021, Jake had beaten two YouTubers and a former NBA player, but few in boxing took him seriously, dismissing him as a showman. His match against Olympic wrestler and MMA champion Ben Askren was seen as his first real test, and Jake leaned into his “Problem Child” boxing persona by provoking Askren and calling him “a pussy ass bitch.”

“At that point, no one knew how good Jake was,” Askren tells me. “Unfortunately, he was better than what I anticipated, and the fight didn’t go so well for me.”

Jake knocked him out in under two minutes. Soon after, Jake appeared on Logan’s podcast and focused on the metric that mattered most to him: the earnings.

The match generated a whopping 1.3 million pay-per-view buys at $50 each — a roughly $65 million event.

Even when he’s losing, he’s still winning. More recently, 33 million viewers tuned in to watch Anthony Joshua knock out Jake and break his jaw. It was a brutal defeat, but Jake still reportedly made $92 million. By some estimates, his total boxing earnings now fall between $170 million and $200 million.

All across social media, critics insist that Jake isn’t a real boxer, that he handpicks his opponents, and that his career is more entertainment than sport.

And yet, here we are all watching, putting millions of dollars in his pocket.

In a TikTok video, Jake Paul smiles and counts down: “3, 2, 1 … I’m gay!” A makeup palette appears in his hand. “I’ve got a makeup set, guys. Oh my gosh, it looks amazing.”

The nine-second clip racked up 25 million views. It’s Jake, but not exactly. He had licensed his name, image, and likeness to OpenAI’s text-to-video platform Sora, allowing users to generate hyperrealistic deepfakes of him.

To many people’s surprise, it was later revealed that Jake was advising OpenAI on the development of the Sora product. After meeting Sam Altman at Donald Trump’s second inauguration, he began working closely with the team, weighing in on everything from high-level direction to details as granular as button design.

As both investor and distribution engine, Jake helped OpenAI garner more than one billion views on the Sora product in six days — an estimated $57 million in organic media value for the company.

Six months after Jake’s videos went viral, OpenAI shut Sora down because running it proved to be astronomically expensive for the company.

A similar dynamic played out during the early days of Jake’s personal care brand W (the name is a nod to “winning”). The launch drew millions of eyeballs and brought in customers, but it couldn’t make them like the product.

Users of the W deodorant criticized the glide (“shit is so dry and hard to put on”), the scent (“it smells like alcohol wipes”), and some even made a bizarre claim that it ripped out their armpit hair.

“Normally, companies start with something and build, grow, change, iterate and continue to refine — and then they get more and more customers,” Jake says. “W had a ton of exposure on day one.”

In March, W debuted a “new and improved” formula as an answer to the customer feedback. “It’s fair to say that not everything we touch turns to gold, but I think it’s standard for an early stage venture firm,” Anti Fund co-founder Geoff Woo says. “You try, you launch, and then you run it back.”

As a Stanford computer science graduate and a seasoned operator, Woo brings institutional credibility to the partnership. In conversations with founders and investors, he is consistently described as the one driving deals — “an absolute stud,” “a sharp investor,” and “an ultimate brain.”

Though Woo and Jake had met years earlier, they reconnected at a Miami tech party in 2021. The two formalized their personal investing into a $10 million rolling fund, which has returned roughly half of investors’ capital within five years.

Anti Fund has since scaled. Its first early-stage venture fund was $30 million, and it is now raising a second expected to reach $50 million, according to people familiar with the matter. It is also reportedly raising a $150 million growth vehicle targeting more mature companies.

Anti Fund’s limited partners consist of individuals, entrepreneurs, and institutions, including Marc Andreessen and Chris Dixon of a16z, as well as Aquarian Holdings and Autilus Partners.

When I ask Jake if it bothers him that some people see Woo as the dealmaker and him as the distribution engine, he pauses for a long time before responding. “Um, I mean, I’ve never even heard someone say that, but I don’t give a shit,” he says. “As long as our LPs — and we — are making money, and the flywheel is working, that’s all that matters.”

That flywheel is most visible at the company level. When Joey Levy was building Betr, Jake’s involvement extended beyond capital.

He kicked off an 8-minute YouTube video by explaining Betr’s model and revealing he’d gotten the company’s logo tattooed on his leg. The stunt generated 2 million views, giving Betr instant visibility without a traditional marketing budget. The $50 million fundraise that followed was covered across major news outlets.

When the alignment between the company and the Paul brothers’ audience is strong, the model starts to make sense. Logan’s early investment in the live-shopping platform Whatnot, which mirrors his audience’s interest in collectibles, has multiplied significantly.

The founders approached Logan during their Series A round. Logan invested $100,000 in 2021, when the company was valued at $90 million. Today, Whatnot is valued at $11.5 billion, which would put his stake somewhere in the $10 to $12 million range, depending on dilution. His name is listed beside investing heavyweights Andreessen Horowitz, Sequoia Capital, Lightspeed Venture Partners, and CapitalG.

Harry Stebbings, investor and host of the 20VC podcast, explained it this way: as technology gets cheaper to build, founders will increasingly prioritize distribution. In other words, the ability to get a product in front of millions of people quickly may matter as much as the product itself.

That approach has produced both breakout successes and volatility. Prime Hydration, the sports drink Logan co-founded, produced more than $1.2 billion in revenue in 2023 before projections dropped sharply in the following years.

Media reports have pegged Logan’s stake at around 20%, though the company has never confirmed the exact ownership split. Majority control sits with Congo Brands, which handles manufacturing and distribution, while Logan’s role is to drive attention.

Anti Fund is built on a similar premise, and not everyone in venture buys the strategy. Several investors described it as thin — more narrative than substance — arguing the fund’s approach lacks specificity. One investor, speaking anonymously, said his conversations with the group felt unsubstantiated, with little evidence of an original approach beyond access and amplification.

That amplification only intensified in December, when Logan attached his brand to Anti Fund, announcing he was joining as a general partner. “I have two of the top five American tastemakers of the millennial and Gen Z [demographic],” Woo says. “We’re not afraid to talk a little shit and shake things up.”

When I first heard Jake and Logan say they want to be billionaires, I dismissed it. It’s an audacious goal under any circumstances — let alone by age 35. But I still decided to pressure-test this claim. What would it actually take?

As a teenager, Jake thought about becoming a billionaire as a game — almost like Monopoly, where the objective is simply to win. Over time, he says, it became more about what the number represents. “It’s freedom,” Jake says, describing it as the ability to say what he wants and provide long-term security for his family.

The path to a billion dollars is inherently difficult because it requires generating — and holding on to — an inordinate amount of wealth. Jake and Logan have to earn cash, convert it into ownership, let that ownership compound, and eventually turn it into liquidity.

The brothers have already proven the first step. Between YouTube, boxing, WWE, and brand deals, they’ve earned hundreds of millions of dollars in cash.

The second step is underway. Instead of relying solely on sponsorships, they have taken ownership stakes in companies like Prime and Betr, while investing through Anti Fund.

The numbers, however, show how far there is to go. Betr, which is valued at $375 million, might make Jake tens of millions depending on his stake, which is meaningful but not transformative. For it to matter at a billionaire scale, it would need to become a multibillion-dollar company and compound over time.

Similarly, W was last valued at more than $150 million in 2024. If Jake still owns a sizable piece, that stake could be worth real money on paper. But unless the company grows far beyond that mark, it’s unlikely to close the gap to a billion.

Logan comes closer. Estimates have placed his sports drink brand Prime between $3 billion and $8 billion at its peak, according to CB Insights — which would have put his ownership stake at around $1 billion on paper back in 2023.

But he’s not a billionaire yet. The valuation isn’t confirmed, his stake isn’t liquid, and the business itself has already proven volatile, with revenue projections declining from their 2023 peak.

This is where it gets complicated. Compounding is what creates billionaires, but it takes time, and most investments don’t work. The bet Jake, Logan, and Geoff Woo are making is that attention can compound into real equity, and that a few outliers will be big enough to matter.

The risk isn’t purely financial either. In 2023, Jake settled with the SEC over touting a cryptocurrency without proper disclosure, which underscores that reputation may be the most fragile piece of the entire strategy.

Ryan Serhant, the real estate entrepreneur known for turning attention into business, frames the challenge more broadly: “Durable brands have to outlive algorithms, and that’s hard.”

Even if they clear that bar, there’s one final hurdle: liquidity. Jake explicitly says that he’s not aiming to be a billionaire on paper. He’s aiming to be liquid.

But time is the constraint. Whether the Paul brothers become billionaires won’t depend on their ability to make money. They’ve already proven they can do that. The question is whether they can turn something as fleeting as attention into something that lasts.

When I suggest that some still see Jake as nothing more than an entertainer, he tells me a story about hosting people at his house for a recent event.

“I start talking about Anti Fund, our investment strategy, the markups, and you can tell they’re like, ‘What the fuck? I didn’t expect that,’” Jake says. “Some of the people there were telling my team, ‘Oh, he’s actually smart?’”

I ask if that bothers him.

“I guess the results will speak for themselves,” he says.

It’s a question I was asked repeatedly while reporting this story: Are they actually smart? By traditional measures of intelligence — credentials and pedigree — they’re easy to underestimate.

Their advantage is a more creative form of judgment in that they know how to manufacture moments, turn them viral, and convert that attention into tangible opportunities like deal flow.

More importantly, they have shown an ability to stay culturally relevant while anticipating where the world is heading — backing companies like observability firm Chronosphere and drone startup Aerodome early, before they were acquired for $3.35 billion and $300 million, respectively.

Both brothers are careful with their words, intentional about how they present themselves, and acutely aware that declaring a path to billionaire status is both a goal and a form of content. Jake, in particular, has built a team of experienced operators, allowing him to focus on attention while they handle the sourcing and execution of deals.

The structure isn’t unusual, but the reaction to it is. Athletes like NFL star Saquon Barkley invest in a similar way, surrounding themselves with seasoned partners to manage the details. The difference is perception. Jake, with years of internet baggage, is still treated as an outsider.

“Everyone my whole career underestimates me, and then I surpass expectations, and they’re like, ‘Oh, okay, well,’” Jake says. “I think anytime you start to break out of the norm and do something different in life, you’re always going to have haters.”

What surprised me most about Jake and Logan is how much they care. On set, during the Sundae Conversation podcast taping, a joke about Logan’s daughter lands a little too close to home. For a moment, the mask drops, and he recoils and pushes back, telling the host to cut that part.

When I ask about times when he has taken a reputational hit, his demeanor changes from warm and gregarious to a much more guarded version of himself.

For most of their adult lives, Jake and Logan have been defined by the internet as “obnoxious assholes” and “famous for being famous.” They are not as indifferent to it as I expected.

They are still intent on controlling how they come across — even if that control provokes more hate and, in turn, more attention. Logan obsessively reviews and edits every single video, clip, and post that goes out on his social media channels. Jake hired celebrity attorney Alex Spiro to pursue legal action against people who question the legitimacy of his boxing matches.

“There’s a certain sector of the audience that still thinks I’m the 21-year-old YouTube kid,” Jake says. “A lot of my haters don’t know enough about me. I think people react to different versions of who they think I am.”

That gap between perception and reality is part of what attracts them to business. It’s one of the few areas where they can prove the work is real, and, by extension, that they are too. The problem with applying their attention playbook to business is that it leans on traits — like cockiness and provocation — that run counter to a field that tends to reward restraint (or at least the appearance of it).

As Jake’s driver parks in front of the Aquarian Holdings office, he tells me he wishes fundraising could be reduced to a five-sentence pitch: “I just want to walk in the room and be like, ‘Hey, you’re going to make a fuck ton of money. Bet on me. I have a great track record. I’m putting all my money into it. If you don’t want to do it, peace out.’”

It’s a pitch that has worked on the internet for two decades: bet on me. And in some ways, the room he’s walking into isn’t as different as it seems. Even here, the attention of the most traditionally successful people in the office bends toward him.

During my time with them, Jake and Logan both kept returning to the same idea: at the highest levels of wealth, the path you took to get there matters less than the fact that you made it.

Eventually, the winners all end up in the same room.

–

Written by Polina Pompliano | Edited by Laura Entis | Photos & video by Stephen Yang

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Can internet fame be turned into a billion dollars?

I spent the last few months inside the world of two of the most polarizing figures on the internet who are trying to do exactly that.

Tomorrow morning, I’m publishing a deeply reported profile that pressure-tests whether it actually works. If you’ve ever wondered whether attention can be converted into something real, this story may change how you think about it.

This piece took five months of reporting — dozens of interviews, days of shadowing my subjects, and a close look at the actual numbers behind their business empire.

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I appreciate you always.

— Polina

PROFILES.

— The podcaster letting you eavesdrop on the AI elite [**HIGHLY RECOMMEND**]
— The conservative media figure breaking with Trump
— The actress reframing aging
— The ‘free’ social casino games
— The startups allowing you to choose your ‘best baby

PEOPLE TO KNOW.

The podcaster letting you eavesdrop on the AI elite: Dwarkesh Patel went from a bored college sophomore to the go-to interviewer for the people building A.I. — with CEOs and researchers treating his podcast as required listening. He wins access by going deeper than anyone else, mastering the material and speaking the insiders’ language. That proximity gives him real influence, shaping how the industry talks about its own future. He’s an embedded operator who documents power from inside the room. (The New York Times; alternate link)

The conservative media figure breaking with Trump: Tucker Carlson has broken with Donald Trump over the Iran war, arguing the president was pressured into a disastrous conflict that betrays his core promises. He now casts himself as a critic of both the administration and the broader Republican establishment, framing the war as morally wrong and politically ruinous. At the same time, Carlson’s worldview has grown more ideological — blending anti-interventionism, skepticism of U.S. alliances, and a belief that deeper cultural and even spiritual forces are at play. (The New York Times Magazine)

The actress reframing aging: Anne Hathaway is reckoning with what comes after the “have it all” era. And she has found that it’s … harmony. After two decades of fame, motherhood and sobriety have shifted her from relentless ambition to a more grounded, self-aware version of success. She’s still intensely driven, but now less interested in proving herself and more focused on how she moves through her life. (Harper’s Bazaar)

COMPANIES TO WATCH.

**The ‘free’ social casino games:** “Free” social casino games are generating billions by mimicking gambling — hooking players with virtual coins they can’t cash out but can endlessly pay to keep using. A small group of heavy spenders drives the business, sometimes losing tens of thousands — or even millions — while companies actively target and retain them. Apple, Google, and other platforms profit from the model, taking cuts of in-app purchases while avoiding many gambling regulations. Fascinating. (Bloomberg; alternate link)

**The startups allowing you to choose your ‘best baby:’** Startups are selling $50,000 tests that promise to help parents pick the “best” embryo, but the science behind them is still shaky. The real appeal is control, tapping into deep parental anxiety about risk and uncertainty. For now, the benefits appear marginal, but the ethical stakes, from inequality to “designer babies,” are enormous. (New York Magazine)

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My husband Anthony went on The New York Times’ podcast, “Interesting Times” to talk about the future of Bitcoin.

What I found compelling is that the conversation sidesteps the usual “Is Bitcoin a fad?” debate. Instead, it gets at the much more fascinating question of, “How does the financial system actually work, and who does it work for?”

Anthony’s core argument is that the system is structurally designed to erode the value of cash, and that’s why he believes bitcoin is a long-term digital savings mechanism.

Having watched and learned about Bitcoin since I met Anthony in 2016, it feels like the debate has changed. For years, the question was whether it had value at all. Now, the argument is over what kind of asset it is — currency, commodity, tech bet, insurance policy, or some combination of the four.

Anyway, it’s a fascinating conversation, and I hope you give it a listen.

Check it out here

— Polina

PROFILES.

— The CEO buying struggling airlines [**HIGHLY RECOMMEND**]
— The TV anchor who went independent
— The billionaire trying to build the newsroom of the future
— The sports stadium surveilling you
— The AI startup helping reverse denied health insurance claims

PEOPLE TO KNOW.

The CEO buying struggling airlines: Scott Kirby has reshaped United Airlines by aiming to build an ecosystem that keeps customers spending. Known for his sharp edges and outsize confidence, he’s paired bold strategic moves — like massive plane orders during Covid — with a push into higher-end travel and loyalty economics. This has resulted in a stronger, more competitive United, even as it chases Delta and flirts with industry-shaking mergers. (Bloomberg; alternate link)

The TV anchor who went independent: Katie Couric has embraced her post-network “no filter” era and built a thriving independent media business to match. Free from corporate constraints, she’s leveraging newsletters, social media, and podcasts to reach millions while speaking more bluntly about politics and the media than ever before. At the same time, she’s deeply skeptical of legacy news, arguing that corporate pressures, polarization, and the push for “both sides” coverage are eroding journalistic integrity. (Variety)

The billionaire trying to build the newsroom of the future: A billionaire media veteran is making a high-stakes bet on Washington journalism — again. After sensing an opening created by turmoil at The Washington Post, Robert Allbritton is aggressively hiring top reporters and rebranding his startup as “The Star,” aiming to build the capital’s next dominant newsroom. Backed by a $10 million investment and a plan to double staff, he’s betting that a focused, insider-driven publication can thrive in an already crowded market. (WSJ; complimentary link provided)

COMPANIES TO WATCH.

The sports stadium surveilling you: Madison Square Garden may be watching you. A new investigation reveals an expansive surveillance operation under owner James Dolan, using facial recognition, watchlists, and private security to track critics, employees, and even ordinary fans, sometimes in extraordinary detail. What’s framed as security often blurs into personal score-settling, with allegations of profiling, intimidation, and overreach extending beyond the arena itself. Dolan may be an early example of a broader shift toward corporate “private armies” powered by biometric surveillance. (WIRED; alternate link)

The AI startup helping reverse denied health insurance claims: When insurers deny care, most patients give up, but one startup is betting AI can change that. Claimable helps patients generate legal-grade appeals to fight coverage denials, flipping the script as algorithms increasingly drive those decisions in the first place. Early results are striking, with a majority of cases overturned, often by combining automation with public pressure and escalation tactics. (Bloomberg; alternate link)

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My next profile is on two people who have spent most of their lives as targets for public scrutiny. In response, they’ve become highly skilled at controlling what you see.

I went in expecting to spend the day with the characters I’d seen online. That’s not who showed up. In their place were two people who were more thoughtful, more self-aware and more human than I anticipated. I found a constant negotiation between the person and the persona, and the question of whether, after two decades, any real separation remains.

I’ve spent the last four months working on this one, and I’ll be sharing more soon.

(This is the crowd that formed outside once one of them walked inside an office building in NYC.)

— Polina

PROFILES.

— The OpenTable CEO reinventing the business
— The new Mrs. Bezos who is unapologetic about being uber-rich
— The secretive wealth adviser to tech billionaires [**HIGHLY RECOMMEND**]
— The $10 billion startup training AI to take our jobs
— The AI school bus camera company

PEOPLE TO KNOW.

The OpenTable CEO reinventing the business: When Debby Soo took over OpenTable, restaurants — its real customers — were fed up, calling the company expensive, out of touch, and stuck in the past. She rebuilt the business by flipping its focus: serve restaurants first, or lose them entirely. The turnaround meant reworking pricing, rebuilding products, and winning back trust—often by sitting through angry meetings across the country. Now, as competition and AI loom, OpenTable is growing again with the idea that better data and better alignment with restaurants can fill every empty seat. (Bloomberg; alternate link)

The new Mrs. Bezos who is unapologetic about being uber-rich: Lauren Sánchez Bezos has turned her marriage to Jeff Bezos into a full-throttle embrace of wealth, visibility, and influence. From the morning gratitude lists to the headline-making appearances by night …. she’s living it up. She wants you to know she’s truly happy, even as critics see excess and provocation. I don’t know what to say about this one except you need to read it for yourself. (The New York Times)

COMPANIES TO WATCH.

The secretive wealth adviser to tech billionaires: Iconiq built its fortune managing money for billionaires, and now it’s using those relationships to become a major power broker in the AI boom. The firm is pouring billions into startups like Anthropic, leveraging its elite network to open doors that traditional VCs can’t. Its strategy is concentrated and high-stakes: pick a few winners, go deep, and use access as an edge. If it works, Iconiq will help shape who gets to build our AI future. (Bloomberg; alternate link)

The $10 billion startup training AI to take our jobs: A social worker logs on every night to train the very AI that could one day replace her. She’s part of a fast-growing startup, Mercor, that pays professionals to break their expertise into data — turning real-world judgment into machine intelligence. For many, it’s a lucrative side hustle born out of job insecurity; for others, it feels like monetizing their own obsolescence. The bet is that AI will create more opportunity than it destroys, but the transition may be awfully messy. (Bloomberg; alternate link)

The AI school bus camera company: A company promises safer streets by installing AI cameras on school buses, but the real engine may be fines, not safety. Across the country, drivers are racking up tickets by the thousands, while violations barely decline and cities often keep only a fraction of the revenue. Confusing road design rather than reckless driving appears to be racking up many infractions, trapping ordinary residents in a costly system. When enforcement becomes a business model, is it protecting children or profiting from confusion? (Bloomberg; alternate link)

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The artist, Alex Mebane, told me the cartoon chicken was once real. His daughter named it “Marzipan,” eventually shortened to “Little Marzi,” and it became his muse.

I’ve written before about “weak social ties” — the casual relationships with people you encounter in coffee shops, bookstores, or on your daily walk — and how they can magnify your happiness. This felt like one of those moments.

I stood there longer than I expected. There was something paradoxical about it — the simplicity of the image paired with the weight of the words.

When I asked Alex how much the paintings cost, he told me: “You pay me whatever you want. This is such a weird gift from God that he knows what I need.”

Today is Bulgarian and Greek Orthodox Easter, and it made me think about the nature of faith. I saw its power firsthand when my newborn twins were in the NICU. I’ve seen it again in friends going through difficult seasons.

And now, I saw it in the way Alex had turned his hardest moments into something unexpectedly bright. A belief in God carried him through the darkest stretches of his life.

For me, believing in God has always been a source of strength — the kind you don’t realize you have until you need it.

Of course, I asked Alex more questions, and I’ve shared his answers below. If you feel inclined, you can check out his work here or find him in Central Park.

Q: How did this become your life’s work?

ALEX: In 2016, my family had moved to Austin from Santa Monica and getting backyard chickens seemed like a fun idea. Marzipan (named by my youngest daughter), the main character to my paintings, was the only yellow chicken and a bit odd. Granted, ALL chickens are odd but she was more so. After a year, I moved back to Santa Monica to resume my career in entertainment. Then Covid happens, and I’m not working. A friend was painting water colors live on Facebook and I joined purely out of “something to do.” I envisioned perhaps writing a children’s book with Marzi (that’s usually what we called her) as the main character. I broached the subject with my painting friend and he responded, “I’ll teach you how I do watercolors.” So in 2020, my life as an artist began. The first couple of hundred looked like I had painted them with my foot. But they got better.

What drew you specifically to New York City and Central Park?

ALEX: Julia Cameron’s The Artist’s Way profoundly influenced both my painting and my move to New York. One of her exercises was to do a vision board and unfortunately, nothing I chose for it was in California. My grandparents had lived here in NY when I was young, and I always thought of NYC as a magical place. And still do. I figured I would just get a new agent and go back to working in entertainment.

I loved Central Park as a child and visited here not long before I moved here in 2022 and met a girl near the Bethesda Fountain doing poetry for strangers. She told me a permit wasn’t required to vend there along the Mall, so after I moved here in June of 2022, I gave it a shot. And oddly enough, people responded in a way that I didn’t expect.

Faith seems central to what you do. Has that always been true, or did it emerge over time?

ALEX: I’ve been a Christian for 50 years, and it’s always found its way into what I create. More than a few of my paintings I sell here in the Park came from struggle. LA was a hard period for me. I had some success (I sang on some Disney children’s albums, won a Los Angeles Emmy for a children’s show I’d help produce), yet consistent work was difficult to find.

Also, during the pandemic, I read an article by a pastor from Philadelphia, Paul David Tripp, about dealing with hopelessness, from which I was struggling. One of the suggestions was, “Be the encouragement you need to hear.” So some of what I paint is that. Hope my own heart needed to hear.

You let people pay whatever they want for your work? Why do it that way?

ALEX: Honestly it’s such a weird gift from God, (I had never painted anything before the pandemic other than a wall) and the reality, God knows what I need. It’s how I’ve made a living for the past 4 years. I often joke, following the Lord is a lot like the mapping app Waze. It takes you on paths that seem totally opposite of where you want to go, but you end up exactly where you were supposed to be, at exactly the right time.

My dad often tells me: “Sometimes God helps us, and other times, He uses us to help others.” I’ve come to believe that the highest form of faith is the kind that extends beyond yourself — helping others, even in the smallest ways.

Below is a ‘day in the life’ video of how Alex makes a living selling chicken paintings:

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On a recent walk through Central Park, I stopped in front of a display of watercolor paintings of a chicken — a small, yellow, wide-eyed bird, each one paired with a line of scripture or a simple, handwritten quote.

The artist, Alex Mebane, told me the cartoon chicken was once real. His daughter named it “Marzipan,” eventually shortened to “Little Marzi,” and it became his muse.

I’ve written before about “weak social ties” — the casual relationships with people you encounter in coffee shops, bookstores, or on your daily walk — and how they can quietly magnify your happiness. This felt like one of those moments.

I stood there longer than I expected. There was something paradoxical about it — the simplicity of the image paired with the weight of the words.

When I asked Alex how much the paintings cost, he told me: “You pay me whatever you want. This is such a weird gift from God that he knows what I need.”

Today is Bulgarian and Greek Orthodox Easter, and it made me think about the nature of faith. I saw its power firsthand when my newborn twins were in the NICU. I’ve seen it again in friends going through difficult seasons.

And now, I saw it in the way Alex had turned his hardest moments into something unexpectedly bright. A belief in God carried him through the darkest stretches of his life.

For me, believing in God has always been a source of strength — the kind you don’t realize you have until you need it.

Of course, I asked Alex more questions, and I’ve shared his answers below. If you feel inclined, you can check out his work here or find him in Central Park.

Q: How did this become your life’s work?

ALEX: In 2016, my family had moved to Austin from Santa Monica and getting backyard chickens seemed like a fun idea. Marzipan (named by my youngest daughter), the main character to my paintings, was the only yellow chicken and a bit odd. Granted, ALL chickens are odd but she was more so. After a year, I moved back to Santa Monica to resume my career in entertainment. Then Covid happens, and I’m not working. A friend was painting water colors live on Facebook and I joined purely out of “something to do.” I envisioned perhaps writing a children’s book with Marzi (that’s usually what we called her) as the main character. I broached the subject with my painting friend and he responded, “I’ll teach you how I do watercolors.” So in 2020, my life as an artist began. The first couple of hundred looked like I had painted them with my foot. But they got better.

What drew you specifically to New York City and Central Park?

ALEX: Julia Cameron’s The Artist’s Way profoundly influenced both my painting and my move to New York. One of her exercises was to do a vision board and unfortunately, nothing I chose for it was in California. My grandparents had lived here in NY when I was young, and I always thought of NYC as a magical place. And still do. I figured I would just get a new agent and go back to working in entertainment.

I loved Central Park as a child and visited here not long before I moved here in 2022 and met a girl near the Bethesda Fountain doing poetry for strangers. She told me a permit wasn’t required to vend there along the Mall, so after I moved here in June of 2022, I gave it a shot. And oddly enough, people responded in a way that I didn’t expect.

Faith seems central to what you do. Has that always been true, or did it emerge over time?

ALEX: I’ve been a Christian for 50 years, and it’s always found its way into what I create. More than a few of my paintings I sell here in the Park came from struggle. LA was a hard period for me. I had some success (I sang on some Disney children’s albums, won a Los Angeles Emmy for a children’s show I’d help produce), yet consistent work was difficult to find.

Also, during the pandemic, I read an article by a pastor from Philadelphia, Paul David Tripp, about dealing with hopelessness, from which I was struggling. One of the suggestions was, “Be the encouragement you need to hear.” So some of what I paint is that. Hope my own heart needed to hear.

You let people pay whatever they want for your work? Why do it that way?

ALEX: Honestly it’s such a weird gift from God, (I had never painted anything before the pandemic other than a wall) and the reality, God knows what I need. It’s how I’ve made a living for the past 4 years. I often joke, following the Lord is a lot like the mapping app Waze. It takes you on paths that seem totally opposite of where you want to go, but you end up exactly where you were supposed to be, at exactly the right time.

—-

My dad often tells me: “Sometimes God helps us, and other times, He uses us to help others.” I’ve come to believe that the highest form of faith is the kind that extends beyond yourself — helping others, even in the smallest ways.

Below is a ‘day in the life’ video of how Alex makes a living selling chicken paintings:

Share The Profile

PROFILES.

— The OpenAI CEO who may control our future [**HIGHLY RECOMMEND**]
— The nuclear engineer who started the sports betting revolution
— The people who live on an isolated island
— France’s tech hub trying to win the AI race
— The luxury reading retreats

PEOPLE TO KNOW.

The OpenAI CEO who may control our future: At OpenAI, the question isn’t just what Sam Altman is building, but whether he can be trusted to control it. Inside the company, allies see a brilliant operator; critics see a leader willing to bend the truth to win. As A.I. inches toward world-shaping power, that tension has turned one man’s judgment into a global risk. (The New Yorker; alternate link)

The nuclear engineer who started the sports betting revolution: A bored engineer turned a mainframe into a money-printing machine while accidentally rewriting the rules of sports betting. Mike Kent’s algorithm gave his crew an edge so powerful it drew the mob, the FBI, and millions in wagers into its orbit. But as the winnings piled up, so did the risks, until the operation collapsed under betrayal, paranoia, and federal scrutiny. (Bloomberg; alternate link)

The people who live on an isolated island: On Tristan da Cunha, the most isolated inhabited island on Earth, there’s no such thing as a quiet life. With just 221 residents and no way in or out except by sea, survival is a full-time, all-hands operation. Everyone does everything—and the island only works because no one opts out. What a fascinating article. (NPR)

COMPANIES TO WATCH.

France’s tech hub trying to win the AI race: At Station F, France built a startup campus to showcase its tech talent. Now, it’s trying to win the global AI race. Backed by political power, elite founders, and deep-pocketed partners, the campus has become a magnet for ambition and capital. But turning that momentum into lasting global dominance means closing the gap with Silicon Valley’s speed, scale, and mindset. ( Substack)

The luxury reading retreats: Reading, once a social ritual, is being reinvented as a luxury escape. Across the US and UK, people are paying up to $1,000 to sit in silence with strangers. The appeal is supposedly about reclaiming attention, community, and the rare feeling of being fully present. (Bloomberg; alternate link)

✨ The rest of this newsletter is only available for premium members of The Profile, whose support makes this work possible. If you’re not already a premium member, consider upgrading your subscription below for access to an additional section of weekly audio + video recommendations. ✨

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One Christmas a few years ago, my mom gave me a book titled, Life Stories. It’s a compilation of The New Yorker’s greatest longform profiles.

The first line of the book reads, “One of art’s purest challenges is to translate a human being into words.” That sentence has been on my mind ever since I read it, and as a writer who specializes in profiles, there’s no greater challenge.

There are layers on layers to a human being. And to think that you could deconstruct someone’s essence into 4,000 words is naive, and frankly, silly. But there are some profiles that capture the complexities of that elusive je ne sais quois in a way no one has been able to before*.*

One writer who is able to capture it is named Wright Thompson. He wrote this epic 2016 ESPN profile on Tiger Woods.

Let me preface this by saying that it’s about Tiger Woods, but it’s not really about Tiger Woods. It’s about anyone who has ever experienced profound loss, grief, and inexplicable loneliness.

In the 10 years since his father died, Tiger lost his greatness at golf, while becoming obsessed with the military and indulging in a dozen or more affairs — both reflections of his dad Earl. All kids, the story says, whether they love or hate their fathers, want to shake free of the past and overcome any inherited weakness. Tiger’s father seemed to evoke conflicting emotions: The best and worst things that have happened in his life happened because of Earl.

Tiger grew up without any siblings or many friends and spent his childhood with his father, either on the golf course or hitting balls into a net in the garage. They often butted heads, but their biggest, most serious fight centered around Earl’s love for women. Tiger hated that his dad cheated on his mom. Yet somehow, Tiger’s life unraveled in a way much like his father’s, and he found himself repeating the same mistakes.

We never see the past coming up behind because shaping the future takes so much effort. That’s one of those lessons everyone must learn for themselves, including Tiger Woods. He juggled a harem of women at once, looking for something he couldn’t find, while he made more and more time for his obsession with the military, and he either ignored or did not notice the repeating patterns from Earl’s life. “Mirror, mirror on the wall, we grow up like our daddy after all,” says Paul Fregia, first director of the Tiger Woods Foundation. “In some respects, he became what he loathed about his father.”

And that’s the thing — the past always sneaks up on us when we least expect it. We unknowingly pick up our parents’ habits, fall into old patterns, and get nostalgic about how things used to be.

The thing that struck me about the profile is that so many people expected Tiger to act a certain way because of his status. But he almost never behaved in accordance with social norms, and that made him, well, “a weird f---ing guy,” as one Navy SEAL put it.

This is a remarkable story of early success, a meteoric rise, a catastrophic fall, and an uncertain future. But it’s mostly a reminder that humans are complex creatures, and the unpredictable forces of life can bring anyone to their knees.

Wright Thompson — the writer of the piece — recently appeared on a podcast in which he discussed what a profile’s really about. He said: “Profiles are about figuring out what is a central complication of somebody’s life and how, on a daily basis, they go about solving it.”

It sounds simple, almost obvious, until you realize how rarely profiles actually do this. The best profiles reveal the problem the subject is trying to solve, and why a person’s decisions that seemed erratic start to feel inevitable.

Right now, I’m working on a profile of two people who have spent their entire adult lives in public. On the surface, their story seems like it is about attention. I was struggling to write the piece until I realized that the attention is actually not the complication of their life. It’s a need for a scoreboard that’s concrete enough to silence the doubters, the haters, and all the people who want to see them fail.

And so every day becomes a kind of experiment in solving that problem.

Thompson’s framing becomes useful because it forced me to look past the spectacle and ask: “What are they trying to fix?”

My hope is that the profile answers it.

— Polina

PROFILES.

— Apple’s next CEO [**HIGHLY RECOMMEND**]
— The billionaire who wants to reshape Miami
— The most prolific reporter in media
— The woman who alerts the world when an asteroid could hit
— The designer helping men dress better

PEOPLE TO KNOW.

Apple’s next CEO: Apple is entering a leadership transition as longtime executives retire, with John Ternus emerging as the top candidate to succeed Tim Cook. Ternus is a respected operator who has helped steady Apple’s core products, but his rise raises this question: Can a company built on iteration find its next breakthrough, especially as it falls behind in AI?

The billionaire who wants to reshape Miami: Ken Griffin is betting Miami is the future of American capitalism, citing its speed, pro-business culture, and openness to growth. The Citadel CEO has turned that belief into power by building Citadel into a financial giant while emerging as a key voice in shaping Republican economic policy. Now, he’s pushing a broader vision of low-regulation, pro-immigration capitalism and positioning himself to help lead it. (FORTUNE)

“The fight in America is all about protecting the cultures in places like Miami or Silicon Valley, and keeping us a nation of entrepreneurs.”

The most prolific reporter in media: Nick Lichtenberg is using AI to produce more stories in days than many reporters do in months. At Fortune, his AI-assisted work now drives a significant share of traffic, offering a glimpse into how legacy media is adapting to survive. His approach is all about scaling speed and output while risking accuracy, trust, and the very definition of reporting. (WSJ; complimentary link)

“It’s like a sports car that you can crash if you’re not careful. You’ve got to be like a Formula One driver.”

The woman who alerts the world when an asteroid could hit: Aarti Holla-Maini, the little-known UN official in charge of planetary defense, found herself confronting a real “Armageddon” scenario when an asteroid briefly threatened Earth. Trained for simulations, she had to quickly coordinate a global alert to 193 countries — testing, for the first time, the world’s response system to a potential space disaster. The moment revealed how much responsibility rests on a small, under-the-radar team—and how thin the line is between routine monitoring and global crisis. (The Guardian)

“This wasn’t a simulation or a drill. It was real.”

The designer helping men dress better: Todd Snyder has built a thriving fashion brand by offering high-quality, Italian-crafted style at prices that don’t feel absurd. As luxury brands lose millions of customers amid soaring prices, Snyder is winning by occupying the middle — delivering classic, wearable clothes that feel elevated but attainable. His bet is that most men want to dress better, just not at the cost — or risk — of high fashion. (Bloomberg; alternate link)

“I’ve always been about creating something that is attainable.”

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