When I was fifteen, I hacked my school’s computer system. Not for malice, but for mischief—and yes, to impress a boy. With a little curiosity and a lot of nerve, I got hold of the official letterhead and sent out a notice giving the entire school a day off. Teachers were baffled, my classmates were ecstatic, and I thought I was a hero. Instead, I was expelled.

My IT teacher, who knew I’d never been in trouble before, appealed on my behalf, and I was allowed back. But the lesson stuck: systems are fragile.

That curiosity about how things work has always been how I’ve learned—teaching myself, experimenting, following instincts. And in the last two years, working deeply in yachting and the UHNW world, I’ve realised just how fragile privacy has become. What once required intelligence agencies can now be done by anyone with a laptop, an AI toolkit, and time.

Family office surveys show the scale of it. 

In 2019, barely a third of UHNW families listed cybersecurity as a top concern; by 2024 it was over 70%. 

Deloitte reports that one in four billion-dollar family offices has already suffered a direct cyberattack. The World Economic Forum projects the global cost of cybercrime will reach $10.5 trillion annually by 2025. The numbers aren’t abstract—they’re the scaffolding of a new reality, where privacy is the rarest and most expensive luxury of all.

From Curiosity to Real Danger

What shocked me when I first experimented with AI search tools was how easily the fragments connect. Upload a photo to various apps and you can trace someone across years of the internet. 

Clearview AI has scraped over 30 billion images from social media and beyond, capable of identifying strangers from a single candid shot. A guest leaning on the rail of a yacht in Monaco can be matched to their LinkedIn profile and even their home address. 

The Risk to the Industry

I’ve seen it firsthand: from the CEO of a large brokerage house appearing on an adult site because his corporate photo was scraped, to yacht managers photographed in nightclubs with escorts—images freely available for anyone to see.

DeepFakes the new threat

And then there are the deepfakes. A Hong Kong man was tricked into wiring $622,000 to what he thought was a friend’s urgent plea, the voice was fake. A London firm was conned out of $25 million after criminals used a fabricated CFO in a video call. These are not hypotheticals; they are happening.

I tested it myself: using nothing more than a grainy YouTube thumbnail, I deepfaked a shipyard 

CEO. When I shared the clip in a closed group, people genuinely thought I’d started doing his PR — they believed the interview was real. The AI version had him saying things so outrageous a Scouser half-cut in the pub wouldn’t dream of.

Superyachts were designed as sanctuaries. Distance equalled safety. But Starlink has collapsed that illusion. One captain told me he runs 167 devices simultaneously on board. Connectivity has become oxygen for owners and guests, but it also means the hull is digitally porous. 

And then there are the stories of failure. Jeff Bezos’ phone was compromised by a single WhatsApp video file. GPS spoofing demonstrations in the Mediterranean proved crews can be misled into believing they’re anchored when they’re drifting miles away. Reports surfaced of one yacht owner spending $4 million on an anti-drone system after paparazzi drones kept circling his sundeck. And a luxury travel agency was hacked, with UHNW flight itineraries leaked to criminals who then turned up at airports pretending to be chauffeurs.

Privacy isn’t something you buy. It’s something you practice.

So where does that leave us? I’ve come to believe that privacy is no longer about disappearing. It’s about choosing when to be visible. For the ultra-wealthy, the true luxury isn’t the yacht itself, or the propulsion system, or the interior marble. It’s the privacy and safety that only a yacht can provide in this day and age.

And the truth is, invisibility can still be practised. This is not about living in paranoia. It takes discipline and the structure of solid digital hygiene, yes, but also culture on board—the unglamorous choices: no Instagram geotags, verification of voices, and a collective pride in discretion from everyone.

Written by Claire Hagen, digital consultant for UHNW clients and luxury brands, specialising in AI, creative marketing, and innovative solutions.

Insta @theartofyachts @this.is.odyssey