Get ready for a double feature of inspiration and innovation on this special episode of Thrive LouD with Lou Diamond! Recorded live from the buzzing floor of the Wall Street Conference in Palm Beach, Florida (May 2025), Lou sits down with two dynamic guests: seasoned Wall Street pro and financial media expert Marc LoPresti, and entrepreneurial visionary Matthew Levenson, co-founder of both StubHub and Pepper, an AI-powered shopping assistant.
First, Marc LoPresti shares his lively journey from his Italian Brooklyn roots and early days at Lehman Brothers, to becoming a well-known financial commentator and CEO of Market Rebellion. Marc dives into the evolution of Wall Street, market volatility in the face of political tape bombs, and what it really takes to thrive both behind the scenes and on camera.
Then, Lou connects with Matthew Levenson, whose experience building and selling StubHub helped spark his latest venture: Pepper. Matt explains how Pepper’s AI assistant is disrupting the way we shop, making it possible for anyone—not just obsessive bargain hunters—to get personalized recommendations and the best prices, all while driving real ROI for retailers.
Both guests open up about their passion for their work, the challenges they’ve faced, and what motivates them to keep pushing boundaries. Plus, stick around for the rapid-fire speed round, including insights about family, food, yoga, and more.
Don’t miss: — Marc’s powerful remembrance of his uncle, a Wall Street legend lost on 9/11 — How media has changed the NYSE (and what it’s like on the trading floor now) — Matt’s behind-the-scenes StubHub story and the origin of the “buyer guarantee” — Why AI is the future of online shopping—and how Pepper aims to simplify your life
To learn more about the guests: Marc LoPresti — @mxlesq on X and MarketRebellion.comMatthew Levenson — coach@gopepper.com and GoPepper.com
If you love stories about resilience, business evolution, and the intersection of technology and humanity, this episode is for you!
Hit subscribe and join the Thrive Loud community for more episodes featuring leaders who are taking life, business, and passion to the next level!
Timestamped Overview
00:00 "Thrive Loud: Wall Street Conference"
05:35 Financial Markets: From Trader to Media
06:27 NYSE: From Commerce Hub to Museum
12:26 Economic Warning: Irreversible Trade War Impact
14:01 Earnings Season's Market Impact Analysis
16:41 Broadcasting Thrills Persist
21:36 Simplifying Fragmented Supply Online
23:27 "Pepper: AI Shopping Assistant Revolution"
28:20 Optimized Shopping Discount Integration
32:58 "Entrepreneurship: Legacy Over Easy Profits"
35:04 "Startup Pitch for Investment"
39:03 Customer Experience: Key to Success
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