The Anti-Status Watch: Why Men in Finance Love Cheap, Cheesy Watches
The ultimate trading-floor flex? A Snoopy Swatch. Or a Casio calculator. Why lots of money men (still) favour novelty watches.
The ultimate trading-floor flex? A Snoopy Swatch. Or a Casio calculator. Why lots of money men (still) favour novelty watches.
How do you tell the time? Neal W. McDonough, the COO of a finance and policy startup in Ho-Ho-Kus, N.J., looks to Charlie Brown, the loveable, miserable “Peanuts” protagonist. An illustration of the character occupies the exec’s watch dial, Brown’s stout arms acting as the minute and hour hands.
McDonough, 55, bought the kooky Timex for a Valentine’s Day trip about five years ago, along with a matching model depicting Lucy van Pelt (Brown’s frenemy) for his then-girlfriend. To his surprise, he kept wearing the $150-ish ticker after the trip. “It’s now my business watch,” he said, adding that such a non luxury model can telegraph that he’s under no obligation to be flashy. “I have nothing to prove to anyone,” he said. “And the fun thing is, a lot of people notice [my watch].”
Though finance guys famously flaunt Rolexes or Patek Philippes on their wrists, an established subspecies of money men goes the other way entirely. In place of a sleek steel case and elegant ceramic dial? Mickey Mouse. SpongeBob SquarePants. Fanta-orange rubber straps.
Over the years, highfliers have made headlines for sporting Swatches. (See: Blackstone Group CEO Stephen A. Schwarzman or former Goldman Sachs CEO Lloyd Blankfein .) That “wealthy guy, cheap watch” ethos continues to resonate in boardrooms and on trading floors, with men of all seniority levels embracing plasticky, offbeat designs, from superhero models to calculator Casios. Many resemble something you might win in a claw machine. Priced from $30 to a few hundred bucks, they’re a bit of fun and a different sort of flex, conveying an “I don’t need a Rolex” bravado that comes from having made it. Call them anti-status watches.
Patrick Lyons, the managing partner of a family office in New York, rotates two contrasting watches: a 1988 Santos de Cartier and a Nickelodeon “SpongeBob SquarePants” model with a tangerine strap.
The Cartier, a family heirloom, is a slice of French sophistication; the Nickelodeon dial features a giant image of a pink starfish named Patrick Star who lives under a rock. Lyons, 35, likes that the second watch is idiosyncratic—and that its starfish shares his name. “I wear that more often than my Cartier,” he said, adding that he hopes to pass down both models to future offspring.
Leroy Dikito, 42, an executive director at JPMorgan Chase in New York, chose his $450 “Avengers” watch from Citizen because it reminds him of his father, who loved comic books. Though its stainless-steel strap reads urbane enough, its cheerfully garish dial slices together images of the Hulk, Iron Man, Captain America and other superheroes. Working in finance, you need to be “serious all the time,” so a fun watch brings welcome levity, said Dikito. “People need to know there is more than the big job and the title.”
Since a suit can only inject so much color, a watch offers that rare opportunity to “show off your personality,” said Eli Tenenbaum, 36, the director of corporate development for a New York private-equity firm. Plus, he noted, “If you wear a fancy watch, chances are someone else may be wearing the same one.” Tenenbaum runs little risk of twinning with a colleague when he straps on his Mickey Mouse or Snoopy Swatches, worn with premium Brioni or Zegna suits.
Evan Vladem, 37, considers his Casio calculator watch a neat “ice breaker” when schmoozing, a professional obligation for the partner at a financial advisory in Fort Lauderdale, Fla. “It came in handy to break up awkward moments,” he said of the black, $30-ish design, a Casio classic. At a dinner with an insurance partner a few years ago, he recalls, the conversation petered out after an exchange about a client’s situation, which involved some financial arithmetic. “I pulled out my wrist and said, with a smile, ‘Well, I’m happy I have my trusty calculator watch to help me here,’” said Vladem. “We both laughed. [It] kicked off another conversation.”
Even men who have invested heavily in high-end horology seem to be falling for cheap, kitschy designs. Scott Jay Kaplan, 44, a film producer and financier for Brooklyn company CoverStory, owns pricey models from Rolex and Audemars Piguet. But for daily wear he’s currently favouring a super-chunky $25 watch he bought in Argentina this past winter, a model similar to a G-Shock but by an unfamiliar brand. He says he has received a lot of compliments on it, and it has held up surprisingly well. “I bought it because it looked silly,” he said. “Not for clout.”
McDonough, the Charlie Brown fan, urges anyone considering a novelty ticker to follow just one rule: Don’t splurge. “I think the whole idea of luxury watch brands coming out with ‘kitsch’ watches is…a little bit absurd,” he said. “So anything over, say, $500 would be out.”
Prop styling by Marina Bevilacqua
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Artificial intelligence is making it easier than ever to build a business without building a team. As AI takes over coding, customer support, marketing, administration, and other day-to-day tasks, a growing number of solo founders are scaling startups to millions in revenue with few—or even no—employees. While the trend is lowering barriers to entrepreneurship, it is also reshaping hiring, raising questions about the future of work and how businesses will grow in the AI era.
Ben Broca launched a company last December that offers AI tools to entrepreneurs. He’s already added 10,000 paying customers and is on track to bring in $10 million in revenue this year.
One thing he hasn’t added: any other employees.
The 40-year-old is part of a class of entrepreneurs who are launching, and then often running, new companies on their own. Artificial intelligence tools answer Broca’s emails, help write and debug code, field requests from customers, sign up new subscribers and grant refunds when issues arise.
Broca relishes his ability to make whatever decisions he wants on his own, often from his sun-drenched Sausalito, Calif., living room. “I think compromises make lukewarm results,” he said.
Once upon a time, running a business of a certain size required a team. AI is turning that assumption upside down, and more aspiring entrepreneurs are going it alone.
An analysis by the payments company Stripe shows there are thousands of solo operators on the company’s platform that are generating over $1 million in revenue, with their ranks doubling between 2023 and 2025. The number of solo operators crossing the $10 million threshold nearly tripled in that same span.
In the past, people without business contacts or particular savvy might not have known how to get their ideas off the ground, said Ernie Tedeschi, Stripe’s chief economist. “Now, AI can be a built-in business partner,” he said.
AI’s ability to handle various administrative tasks makes it potentially useful for launching solo businesses in many fields. But the technology’s ability to also handle key tasks in tech, like coding, make that field a particular hot spot.
Analyzing Census Bureau data, Bank of America Institute economist Taylor Bowley found that among all industries, new business applications in the information sector have seen the biggest percentage increase—nearly 45%—over the past year. At the same time, the rate of information-sector applicants saying they plan to hire workers has experienced the sharpest decline of any measured industry.
This Census dataset doesn’t track solo-operated businesses. But the numbers broadly show—in tech and beyond—that applications are flat among businesses likely to hire workers, but generally rising elsewhere. Economists say that’s a strong sign that solo operators are on the upswing.
“The bar for getting started has never been lower,” said Julian Weisser, who runs a San Francisco-based accelerator for solo founders working in tech. The accelerator—which offers founders seed money and mentorship in exchange for an equity stake—attracted 4,500 applicants for 10 slots made available in its most recent cycle, nearly five times the number it drew when it launched last May.
Going it alone with AI can still be surprisingly expensive. Broca said he was losing money on many customers’ accounts while paying to access Anthropic’s Claude to run his clients’ requests—that AI company, as well as others, charges based on usage. He has since switched to free open-source AI models from China.
Broca said he has raised $30 million from investors and, at the same time, has saved millions in salary since he hasn’t needed a team of software engineers.
Another risk: If it’s easy for one entrepreneur to launch an AI-assisted business, copying them can be easy, too. This creates anxiety for founders like Troy Johnston, who runs an AI-assisted business alone in Orlando, Fla.
“Everybody has the sword and we all have the ability to unsheathe Excalibur now,” said Johnston, 40, who used AI to code an app that helps people get the most out of credit card benefits. The company makes around $3,000 a month in profit, with no employees, and is continuing to grow.
What one-person businesses will mean for the labor market remains to be seen. Polling has shown Americans are worried that AI will replace jobs, and top economists are wrestling with that possibility, too. But AI is also creating lots of new jobs, and the go-it-alone entrepreneurs show how the technology can both open doors and limit employment opportunities.
“If everyone’s hiring less, but you get four times more firms, what does that do to head count?” said Rembrand Koning, an associate professor at Harvard Business School who studies entrepreneurship. He co-authored a recent study that found that among 50,000 startups the researchers examined, those focused on AI tended to operate with 25% fewer employees.
Koning also believes a soft hiring environment that’s left some people mired in long job searches has encouraged more to try their hand at launching businesses.
Some founders cite different motives. “It’s a perfect storm of post-pandemic burnout and a re-evaluation of one’s priorities, and also booming AI and a sense of what’s possible,” said Samir Ahmad, 39, who lives in Breinigsville, Pa.
Two years ago, Ahmad decided to leave the corporate job he had worked at Verizon for almost two decades to start a solo coaching and consulting business. He had been seeing social-media posts touting the ease and virtues of AI, which he used to chart a business plan and help with marketing. “It was like my chief of staff, a second in command,” he said.
The business ultimately petered out within months, though, and Ahmad is now back to a full-time corporate role with a utility company.
For Claire Vo, 41, AI helped her turn a passing impulse into a business. She was working full-time as a tech executive when she tapped AI in late 2023 to help code an app that would help her manage documentation and design for new products, with customers ranging from financial services to healthcare firms.
“I was copying and pasting from ChatGPT,” said Vo, who lives in San Francisco.
She put the app online for $1 a month, and within weeks people downloaded it thousands of times. Nearly three years later, Vo’s company—which she ran solo for nine months before hiring an engineer—now has 100,000 users and is on track to make seven figures in profit this year. AI handles the company’s marketing, sales and customer support.
While AI is a shortcut, Vo said her network and credibility in the industry were key. “I think people over-index on how easy AI is and under-index on how much I did to get to this point,” she said.
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