Private Lives, Public Eyes

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%. 
According to Deloitte’s Family Office Cybersecurity Report 2024, 43 % of family offices globally have experienced a cyberattack in the past 12-24 months, with about 25 % of those suffering three or more attacks.
And according to Cybersecurity Ventures (cited via World Economic Forum) the global cost of cybercrime could reach US$10.5 trillion annually by 2025. World Economic Forum+1
These 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.