I recently sat down with Tommaso (Tommy) Chiabra, founder and chairman of Royal Yacht International, co-founder of Mangusta Capital and Neat Burger, Head of Culture Brand Advisor at Ray-Ban, and Fundraising Chairman at UNICEF Italia, at The Long Game’s Miami studio. Based in Monaco, raised in Genoa, educated in Milan, and operating globally, Tommy is one of the most quietly influential figures in the ultra-high-net-worth world, a man who moves between billion-dollar yacht transactions, venture capital, and the highest stakes of global wealth with the kind of precision most people only read about.
He started his entrepreneurship journey at 19 with a food and beverage supply company servicing yachts during the Monaco Grand Prix. He saw a bigger business in brokerage, pivoted fast, and built Royal Yacht International into a global operation doing over $1.5 billion a year in sales, with 60% of transactions happening completely off-market. Today, his firm has over $2 billion in new builds under construction, scheduled for delivery between 2027 and 2031.
Tommy launched his career during the 2008 financial crisis. His philosophy: if you can build in a downturn, the rest comes easy.
How the global billionaire population has grown from 1,800 to over 3,000 in a decade, and why Tommy's positioning at the ultra-high end is a deliberate, long-term bet on where the world is heading.
The stories behind Royal Yacht International - from a $60 million first sale to a $1.5B+ annual operation, to why new builds always win on economics, and what separates North European shipyards from Italian builders.
The $300 million yacht sold completely off market to a buyer who never once stepped foot on board, and how a junior broker six months into the job walked away with $1.2 million in commission.
Why every mega yacht transaction closes in international waters, 12 nautical miles from any coastline, with lawyers on board and wire transfers executed in the open ocean.
The vision for building Mangusta Capital, a $75M San Francisco-based venture fund, and how he sees yachting, real estate, and venture as one interconnected ecosystem, not separate industries.
Advice for entrepreneurs in 2026: pivot relentlessly, fall in love with the process, protect your sleep like you protect your revenue, and build with someone you'd choose as a friend.
What Tommy has built isn't a brokerage.It's an ecosystem consisting of yachts, venture capital, consumer brands, and charitable work, all connected by one philosophy: the access to information is available to everyone, but what you do with it is the only thing that separates the people at the table from the people watching from outside.
