Jordan Belfort Trained an AI to Sell Like Him 🤖 E161

On this episode of The Money Mondays Podcast, Dan Fleyshman sits down with Jordan Belfort (The Wolf of Wall Street) and Hollywood super-connector Gavin Navarro for a rapid-fire masterclass on the three Money Mondays pillars: how to make money, how to invest it, and how to give it away. Jordan breaks down what really holds people back from earning more: it’s not just “mindset”—it’s missing skills, missing mentorship, and not putting in the reps. He shares why sales is the ultimate life skill, how to treat rejection as a numbers game, and why top performers don’t waste time trying to “convert” hard no’s. Then Gavin pulls back the curtain on turning relationships into real opportunities—without becoming the person who pitches everyone every day. He explains how to bring deals to high-profile people the right way, how to filter constant incoming pitches, and how he built a career by being the guy who can connect the right people in the right cities at the right time. On the investing side, Jordan shares his long-term approach (including S&P 500 and Bitcoin ), while Dan lays out his 40/40/20 framework for balancing low-risk stability, medium-risk growth, and high-risk “shots at glory.” They also explain why businesses like beverages can require serious capital even when demand is booming. Finally, they talk about why charity matters—not just for optics, but for trust, culture, and legacy—and Dan closes with his signature question that always gets a different answer: what percentage of your net worth should go to your family?