A rich guy had a very bad day on the internet. An embarrassing incident involving a flashy car went viral. TMZ picked it up, as did local news. On Reddit, one commenter called the centimillionaire a "douchebag." That's all according to Div Churiwal, who runs Nexus Multimedia, a California-based reputation-management company that caters to wealthy clients. Churiwal won't tell me the client's name, so I try to reverse-engineer it from the clues he gives me.

Google gets me nowhere. Neither does ChatGPT nor Gemini. Making unwanted information harder to find is what his clients pay him for, especially at a time when AI is changing how people search for one another. "All we have to do is release a whole army of other information that would overpower what's trending," Churiwal says, citing podcasts, news articles, and Reddit threads as tools at their disposal. To do that, he employs two dozen Gen Z staffers who work to master the new rules of AI search, which is fast becoming the default.

They're familiar with Reddit threads and a variety of other social media platforms, and fluent in the vernacular of the Extremely Online. While wealthy people have always paid professionals to manage their reputations, today, they face a new threat: managing what chatbots say about them. And the firms I speak with say that as a legion of young global elites emerges, they are finding new value in advisors who grew up in the digital world. "You don't want boomers writing Reddit threads where Gen Z is the audience," Churiwal, 34, says.

Three reputation-management firms tell me that ultrawealthy clients are increasingly concerned about how chatbots portray them, as more people use AI tools to research someone before meeting them, doing business with them, or inviting them onto a board.

"I've had clients where a single negative article has cost them, in one case, we think about $200 million US within just a few months," says Michael Macfarlane, the founder of London reputation firm Michael Macfarlane Associates. In this shifting landscape, his job has become "can you create an information environment in advance that mitigates the impact of that?"

The good old-fashioned Google search that dominated recent decades provides a list of ranked links for users to click through and form opinions, often prioritizing major publications. Chatbots and AI search instead perform multiple related searches and synthesize a wealth of information from across the web into a write-up that spoon-feeds an impression of the person searched.

When Macfarlane was coming up, the ideal reputation manager was a seasoned PR operator with a thick contacts book, someone who knew which newspaper editor to call and could try to land a flattering profile in The Wall Street Journal over a boozy lunch. Increasingly, though, Macfarlane finds himself relying on the judgment of employees born after the dot-com boom.

"I'm 43," Macfarlane says. "There's stuff that I would admit that I'm not fully across that younger people are." He has a blunt name for his recruitment strategy: "Hire the children."

His younger employees audit what LLMs say about clients, monitor the themes and sentiment associated with their names, and decide what sort of content could strengthen their reputations online, be it a podcast appearance or a series of long-form posts on social media.

At Nexus, Churiwal puts his legion of Gen Zers to work on one particular reputation-shaping platform: Reddit. They spend most of their work hours starting and participating in Reddit threads about wealthy clients and the businesses they run.

Reddit is a "huge tool," he says, because "it's one of the easiest peer-to-peer communication platforms for gauging how people feel about things." Churiwal believes that getting involved in those conversations can influence what AI chatbots surface about his clients, helping to overpower dirty laundry with freshly laundered content. On a negative post, he says, they might ask a dissatisfied customer or anonymous hater what went wrong, or respond on the client's behalf. Churiwal says they always disclose their affiliation. His workers' fluency in online culture, gives them an advantage over millennials like himself, he says. "Like, what's LARPing?"

Around a boardroom table in London's Canary Wharf neighborhood, two of Macfarlane's "children" sit across from each other. Icy Wong, a 22-year-old analyst, spent her childhood between China, Hong Kong, and London. She wrote her undergraduate thesis on trust and credibility on RedNote, the Chinese social media platform. For Macfarlane, her multilingual background and fluency across Asian and Western online platforms make up for her lack of traditional experience.

Opposite her sits Megan Shears, a 25-year-old associate who studied history at King's College London before doing freelance work in social media and fashion PR. Last year, Macfarlane messaged her on LinkedIn about a job. She recalls telling him, "I don't have the experience you're looking for." He hired her anyway. A year into the job, Shears has come to see her youth as an asset. An emerging generation of international wealth holders makes up a significant share of Michael Macfarlane Associates' clients. "The great wealth transfer is happening, and it's underway," she says.

"You're going to be dealing with a lot of young billionaires and millionaires who are much more native than maybe their advisors give them credit for." A record 35 Gen Zers appeared on Forbes' 2026 World Billionaires' List, a rise that Forbes attributes to large startup funding rounds, the AI boom, and inheritances. By 2040, the children of billionaires will inherit at least $5.9 trillion, according to the UBS Billionaire Ambitions Report 2025.

Pearl Lam, a 58-year-old gallerist with a signature deep-purple bouffant, is one of the eight children of the late billionaire real-estate tycoon Lim Por-yen. Hong Kong-born, Lam began curating exhibitions in her 20s and has since built a prominent career in the art world. When Michael Macfarlane Associates first audited Lam's online reputation, she says, it found that the version of her dished out by AI was stuck in an earlier chapter of her career.

"My profile was still largely about my work bringing Chinese abstract art into the international mainstream," she says. "That was true, and I am very proud of it, but it was no longer the whole truth."

Lam wants her online identity to catch up with her ambitions: to be known not only as an art dealer, but as a global cultural voice. Traditional PR firms, she says, had often left her "disappointed." She finds them obsessed with "press clippings." Michael Macfarlane Associates, however, encourages her to lean into newer formats. Her online presence now includes a podcast, a video channel, and a RedNote account for her gallery.

"If you leave an empty space, the internet will fill it for you," Lam says. "So we needed to create enough serious, substantive work to demonstrate who I actually am and what I stand for."

Lam says she has seen the strategy yield positive effects in the art world. At major art fairs, collectors increasingly approach her, feeling as though they know her from what they've encountered online. She credits some of that success to advisors less than half her age.

Michael Macfarlane Associates' Gen Z advisors, she says, understand the "language, behavior, and unwritten rules" of social media and AI because "they live with them every day." Michael Macfarlane Associates' retainers start at $25,000 a year. Lam sees it as a normal cost of doing business, like hiring good accountants and attorneys. "Resources give people access to professional help," she says. "It would be dishonest to pretend otherwise."

Still, there are limits to what money can buy. "You cannot control the internet, and you should not be able to buy a false version of yourself," she says. "What you can do is invest in making sure that truthful, substantive information exists and can be found."

I got a taste of what that investment looks like. Without my prompting, UK-based firm Pavesen ran my name through Claude, ChatGPT, Gemini, Perplexity, and Google AI, and provided me with a 17-page assessment of my online presence. The verdict: B+. I thought that sounded mediocre, but Tony McChrystal, Pavesen's managing director, calls it "top of the range." None of the platforms had anything adverse to say about me.

I was relieved, but McChrystal points out that I was still vulnerable. The chatbots relied heavily on material from my employer, book publisher, and agent. There was little independent coverage of me online and no authoritative profile I controlled. The LLMs' answers were also inconsistent, producing materially different biographies when asked twice who on earth I was.

Pavesen offered to use me as a test case, expanding my online presence to show how this process typically works for its ultrawealthy clients, who pay upward of $20,000 for a project lasting six months or more.

For all the talk about reputation management in a quickly changing landscape, my prescription was surprisingly old-school. I sent over my CV, biography, and photographs. A week later, I had a professional website.

Over the following weeks, I filled out questionnaires that asked about everything from my most controversial takes to my guilty pleasures. The emerging industry focused on AI search is often called generative-engine optimization, or GEO, but Google, for one, cautions against assuming its methods actually work. "As generative AI search evolves, so have the theories and practices — and sometimes, the misconceptions — surrounding it," the company says in guidance published on its official documentation hub for website owners and SEO professionals.

"From Google Search's perspective, optimizing for generative AI search is optimizing for the search experience, and thus still SEO," the company says. Alex Connock, a professor of media and AI at Oxford University's Saïd Business School, is similarly skeptical that anyone has cracked the code. "The way to optimize those results, whether for a family office or any other entity, is not fully known," Connock says, advising caution with "various snake-oil vendors claiming to do just that."

Connock describes AI optimization and generative-engine optimization as, at some level, "fancy new ways" of describing search-engine optimization. Connock says he is also skeptical that LLMs can be swayed simply by flooding the internet with new material: "The idea that the machines are dumb enough to prioritize alone the volume of AI-generated slop posted at scale to social channels is probably naive." Churiwal, the reputation manager who relies heavily on Reddit threads, remains confident that his strategy can influence how AI portrays his clients, but the ground is constantly shifting.

PromptWatch data published in August showed Reddit's share of ChatGPT citations plunging 86% in a matter of weeks. Seven weeks after I'd fed the internet a slew of new content about me, Pavesen ran its assessment again. My B+ became an A-.

The new material I controlled was surfacing more prominently, replacing the information from my employer and publisher at the top of the list of sources. "Now your website is the anchor reference," McChrystal says. "It's the most-cited source and can be updated by yourself when you want." I'm not sure the exercise will have much impact on my career or social standing, but it gave me a better idea of what clients with more to lose pay for, and who to turn to should an anonymous critic ever call me a douchebag on Reddit: not a PR veteran, but a twenty-something who knows what LARPing means.