EPISODE · May 8, 2026 · 41 MIN
Tommaso Chiabra | The Long Game w/ Jay Roberts #15
from The Long Game · host Prosper Group
$2.8B real estate development pipeline. Become an investor here: https://prospergroup.com/invest/On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Tommaso Chiabra, CEO and founder of Royal Yacht International and founder of Mangusta Capital.Tommaso built one of the world’s leading superyacht brokerage firms from the ground up—going from yacht supply operations during Monaco Formula 1 weekends to brokering some of the largest yacht transactions in the world. Today, Royal Yacht International works with ultra-high-net-worth clients globally and oversees billions in yacht transactions and construction projects.We dive into the hidden world of superyachts, billion-dollar wealth, off-market deals, and how ultra-wealthy buyers operate behind the scenes. Tommaso breaks down the business of yacht brokerage, venture investing, global entrepreneurship, and what it takes to build relationships at the highest level of business.🎯 TAKEAWAYS:How Tommaso built Royal Yacht International during the 2008 financial crisisThe story behind a $300 million yacht purchased sight unseenWhy relationships and information are the real leverage in luxury brokerageHow billionaires structure yacht purchases and off-market transactionsWhy Miami has become a major global hub for entrepreneurs and investorsTommaso’s philosophy on longevity, discipline, and sustainable performance.Stay up to date with Jay Roberts:Instagram: @jayroberts
What this episode covers
$2.8B real estate development pipeline. Become an investor here: https://prospergroup.com/invest/On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Tommaso Chiabra, CEO and founder of Royal Yacht International and founder of Mangusta Capital.Tommaso built one of the world’s leading superyacht brokerage firms from the ground up—going from yacht supply operations during Monaco Formula 1 weekends to brokering some of the largest yacht transactions in the world. Today, Royal Yacht International works with ultra-high-net-worth clients globally and oversees billions in yacht transactions and construction projects.We dive into the hidden world of superyachts, billion-dollar wealth, off-market deals, and how ultra-wealthy buyers operate behind the scenes. Tommaso breaks down the business of yacht brokerage, venture investing, global entrepreneurship, and what it takes to build relationships at the highest level of business.🎯 TAKEAWAYS:How Tommaso built Royal Yacht International during the 2008 financial crisisThe story behind a $300 million yacht purchased sight unseenWhy relationships and information are the real leverage in luxury brokerageHow billionaires structure yacht purchases and off-market transactionsWhy Miami has become a major global hub for entrepreneurs and investorsTommaso’s philosophy on longevity, discipline, and sustainable performance.Stay up to date with Jay Roberts:Instagram: @jayroberts
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Tommaso Chiabra | The Long Game w/ Jay Roberts #15
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