The Profile: The Enron parody that turned into a real(-ish) business & the people who train AI to sound more human

This edition of The Profile features Enron, Bobbi Brown, Olivia Munn, and others.

Good morning, friends!

One of the most surprising things I discovered about Philadelphia Eagles star Saquon Barkley when writing my longform profile, Saquon Barkley Is Playing for Equity, was how he thinks about risk and money.

Early on, I kept circling a contradiction: Saquon wants permanence in the form of ownership and equity yet he’s pursuing it partly through venture investing, an asset class defined by volatility. As my editor Laura asked me, “Curious about why, if his goal is building a stable foundation for his kids, he doesn't just invest in an index fund?”

That was a great point, and one that led me down a road of nuance and detail to better figure out his relationship with risk.

Laura’s point was that even late-stage companies with dazzling valuations can go to zero. Why would someone obsessed with durability choose a risky path?

The answer revealed itself in how Saquon thinks about control. Football taught him fragility: one injury, one franchise decision, one bad week can flip a narrative.

Investing, on the other hand, is a form of risk he believes he can shape. When Saquon backs a company, he lends his reputation, shows up in ads, talks to customers, and does whatever he needs to move the odds closer in his favor.

That’s the tension I chased in this piece, and it’s also what this ‘Ask Me Anything’ unpacks: how I found the heart of the story, captured his humanity and contradictions, and what non-athletes can borrow from his playbook.

I hope you enjoy it by watching the video at the top of this article.

Here is an excerpt:

Q: What are the key elements in a profile that you must have and are never optional?

One thing that I always have to have in one of my profiles is a contradiction. No one is fully perfect in the regard of, ‘I believe this, and I only believe this in every area of my life.’

This is why the Saquon story came out so well, I think, is because he has so many contradictions. The contradictions in someone's life are what make them human. For example, you can want to be great while also believing you don't entirely deserve what you have.

With Saquon, for example, I found it fascinating that he hadn’t consciously connected some of the forces shaping him. His father was a talented boxer whose career ended after a shoulder injury he couldn’t afford to repair.

Naturally, it makes sense that Saquon became so focused on long-term wealth and ownership because one injury can end a career. But when I asked him about it, he said he’d never really thought of it that way. His father, on the other hand, has previously talked about how his own lack of access to capital drove him to tell Saquon to never give up and to build something lasting.

Watch the full video here:

How I Wrote the Saquon Barkley Profile

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PROFILES.

— The Enron parody that turned into a real(-ish) business [**HIGHLY RECOMMEND**]
— The cosmetics mogul who started over
— The people who train AI to sound more human
— The actress dominating the small screen
— The iconic auto brand that fell from grace

PEOPLE TO KNOW.

The Enron parody that turned into a real(-ish) business: Enron is back … or at least a satirical version of it. Performance artist Connor Gaydos, co-creator of “Birds Aren’t Real,” has relaunched the disgraced energy giant with slick ads, a fake home nuclear reactor called The Egg, and even a $ENRON crypto token that briefly hit a $700M market cap. The project blurs parody and reality, filing actual energy applications in Texas while running wild PR stunts endorsed by Paris Hilton and plastered on trucks. What started as a joke about corporate greed has morphed into a real-ish company, raising the uncomfortable question: in today’s meme-stock era, is there really a difference between performance art and business? (Bloomberg; alternate link)

“I think I’m more a CEO than most CEOs. Everyone’s an actor at this point.”

The cosmetics mogul who started over: Bobbi Brown’s memoir Still Bobbi champions “normal” as beautiful, the same ethos that built her billion-dollar makeup empire. After selling her first, eponymous brand to Estée Lauder and chafing under corporate control, she reinvented herself with Jones Road — a scrappy, authentic beauty company built on social media and candor. (NYT; alternate link; For more, check out my Profile Dossier on Bobbi Brown here.)

“I’ve had three kids and I drink vodka.”

The people who train AI to sound more human: Behind every chatbot conversation is a hidden workforce of human annotators who train AI with prompts that swing from silly to deeply unsettling. For some, it’s a flexible side hustle that can bring in thousands of dollars a month, but for others, it’s grueling, unpredictable, and emotionally taxing work. These invisible workers shape how AI cracks jokes, gives career advice, or avoids dangerous responses — even as they worry their own jobs will disappear once the bots get too smart. (Business Insider; alternate link)

"Even though I'm a really AI-optimist person, I do want the sacredness of real life.”

The actress dominating the small screen: Olivia Munn has fought through childhood chaos, Hollywood backlash, and a breast cancer battle — and now she’s back on screen in AppleTV+’s Your Friends & Neighbors. Known as both a fighter and a truth-teller, she’s reshaped her public image into one of resilience and advocacy. Today, Munn is focused on motherhood, her marriage to John Mulaney, and protecting her peace while still wielding her voice with power. (Bustle)

“My entire childhood was survival mode. Like being on the edge of a cliff with somebody running after you.”

COMPANIES TO WATCH.

The iconic auto brand that fell from grace: Jeep rolled out Harrison Ford in a Super Bowl ad to celebrate “freedom” just as its parent company was spiraling from collapsing sales and a botched strategy. With factories in chaos and tariffs piling up, leadership turned to an insider to slash prices, revive stalled models, and steady the ship. The brand’s comeback now hinges on fixing Jeep fast while its billionaire chairman looks to shift the family empire from rusted pistons to sleek tech and luxury bets. (Bloomberg; alternate link)

“Tariffs are just an excuse.”

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