The Long Game

Prosper Group
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The Long Game is a podcast hosted by Jay Roberts, CEO of Prosper Group. It is a conversational podcast series featuring billionaire investors, world-class operators, and elite capital allocators who have built enduring wealth through discipline, conviction, and resilience. This podcast explores how real fortunes, brands and companies are created - not overnight, but across cycles - by those who understand risk, survive setbacks, and compound trust, capital, and judgment over decades.

  1. hace 12 h

    Matthew Whitman | The Long Game w/ Jay Roberts #24

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com. On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Matthew Whitman Lazenby, President and CEO of Whitman Family Development and fourth-generation steward of one of Miami's most influential real estate families. Matthew shares the remarkable story of how his family's journey began in Miami Beach in 1912 and evolved into developing some of the country's most iconic luxury destinations, including Bal Harbour Shops and Brickell City Centre. He discusses the vision behind Bal Harbour Shops, why his grandfather rejected the traditional enclosed mall concept, and how a century of long-term thinking helped build one of the highest-performing retail destinations in the world. Jay and Matthew also explore the challenges of expanding an iconic property, the future of mixed-use development, Florida's Live Local Act, workforce housing, and the realities of navigating community opposition while planning for the next generation. The conversation offers valuable lessons on family businesses, leadership, patience, and what it truly means to play the long game when your family's legacy spans more than 100 years. 🎯 TAKEAWAYS: • The 100+ year history of the Whitman family's real estate legacy • How Bal Harbour Shops became one of the world's premier luxury shopping destinations • Why long-term thinking beats short-term decision making in real estate • The philosophy behind curating unforgettable retail experiences • The challenges of expanding landmark developments in today's regulatory environment • How Florida's Live Local Act is reshaping workforce housing • Lessons on leading a multi-generational family business • Why preserving a legacy requires constant innovation and thoughtful evolution Stay up to date with Jay Roberts: Instagram: @jayroberts Website: ProsperGroup.com

    55 min

  2. hace 5 días

    Elizabeth Macbride | The Long Game w/ Jay Roberts #23

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com. On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Elizabeth MacBride, financial journalist, national bestselling author, and co-author of Capitalism Evolution: The New American Economy and What It Means for Your Business and Our Future. Elizabeth shares insights from nearly three decades as a journalist covering entrepreneurship, business, and economic systems. The conversation explores how capitalism has evolved over the last 50 years, the rise of shareholder-driven corporate thinking, and why new ownership models may help create stronger companies and broader prosperity. Jay and Elizabeth discuss employee ownership, long-term thinking, startup culture, AI's impact on entrepreneurship, the future of work, and why successful leaders must balance speed in execution with patience in achieving meaningful results. The episode also dives into the principles behind playing the long game, drawing lessons from Warren Buffett, Charlie Munger, Jack Bogle, Vanguard, Wealthfront, and some of the most successful business leaders of the modern era. 🎯 TAKEAWAYS: • Why capitalism is constantly evolving and what comes next• The difference between short-term and long-term business thinking• How employee ownership can create stronger companies• Lessons from Warren Buffett, Charlie Munger, and Jack Bogle• Why startup success requires both speed and patience• The impact of AI on entrepreneurship and company creation• Building businesses that create value for employees, customers, and shareholders• Practical advice for playing the long game in business and life Stay up to date with Jay Roberts: Instagram: @jayrobertsWebsite: ProsperGroup.com

    47 min

  3. 18 jun

    Sam Nazarian | The Long Game w/ Jay Roberts #22

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Sam Nazarian, one of the most influential entrepreneurs in hospitality, nightlife, and real estate.Sam shares his journey from immigrating to the United States after the Iranian Revolution to building a global hospitality empire that included more than 100 hotels and 150 restaurants. He discusses the early lessons that shaped his career, how his family’s success with Qualcomm led to opportunities in real estate, and the story behind launching his first nightclub in Beverly Hills.The conversation also explores the growth of SBE, identifying opportunities before they become mainstream, the evolution of luxury hospitality, and why wellness, longevity, and lifestyle are becoming increasingly important in the future of luxury real estate and hospitality.🎯 TAKEAWAYS:• Sam’s family’s journey from Iran to the United States following the 1979 Iranian Revolution• How Qualcomm transformed his family’s financial future• Why his father chose to diversify into real estate• The story behind launching his first nightclub in Beverly Hills• Building SBE into a global hospitality platform• The intersection of luxury hospitality, wellness, and longevity• Why certain luxury real estate ecosystems continue to thrive even during market downturnsStay up to date with Jay Roberts:Instagram: @jayroberts

    1 h 18 min

  4. 12 jun

    Carlos Rosso | The Long Game w/ Jay Roberts #21

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts joins Carlos Rosso, Founder & CEO of Rosso Development and one of the most influential real estate developers shaping Miami’s urban landscape, for an exclusive tour of The Standard Residences Midtown Miami.After spending more than two decades at Related Group, where he rose to become President of Condominium Development under Jorge Pérez, Carlos launched Rosso Development and has since become the driving force behind transformative projects across South Florida.In this special walkthrough episode, Carlos takes viewers behind the scenes of The Standard Residences Midtown Miami and shares the vision behind Midtown Park, a multi-phase mixed-use development helping connect Wynwood, Midtown, and the Design District. As they tour the property, Carlos discusses the importance of walkability, public spaces, community-driven development, and why Miami continues to attract residents, investors, and businesses from around the world.🎯 TAKEAWAYS:• An inside look at The Standard Residences Midtown Miami• Carlos Rosso’s journey from Related Group to launching Rosso Development• The vision and master plan behind Midtown Park• How Midtown Miami evolved into one of the city’s most desirable neighborhoods• Why walkability, parks, and public spaces increase long-term value• The future of Miami real estate and continued population growth• Lessons learned from developing some of South Florida’s most successful projects• Why long-term thinking remains the key to real estate investingStay up to date with Jay Roberts:Instagram:LinkedIn:Website:Follow Prosper Group:Instagram:LinkedIn:Website: ProsperGroup.com

    37 min

  5. 4 jun

    Ralph Choeff | The Long Game w/ Jay Roberts #20

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Ralph Choeff, Founding Partner of Choeff Levy Fischman Architecture + Design and one of the leading architects behind South Florida’s luxury residential boom.From immigrating to the United States after leaving Cuba to building one of the region’s most respected architecture firms, Ralph shares his journey, the rise of Tropical Modern architecture, and the lessons learned from more than four decades in the industry.We also discuss some of his most notable projects, including the North Bay Road home later purchased by David and Victoria Beckham for $72.5 million, residences designed for Alex Rodriguez, and the $285 million Manalapan estate that has captured worldwide attention.🎯 TAKEAWAYS:• Ralph’s journey from Cuba to becoming a world-renowned architect• The evolution of Tropical Modern architecture• Why Miami has become a global destination for luxury real estate• The story behind the Beckham and Alex Rodriguez homes• How technology and wellness are shaping luxury home design• Ralph’s advice for aspiring architects and entrepreneursStay up to date with Jay Roberts:Instagram: @jayroberts

    45 min

  6. 29 may

    Brad Meltzer | The Long Game w/ Jay Roberts #19

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Brad Meltzer, President & Partner at Two Roads Development, one of the leading luxury real estate developers shaping South Florida and beyond.Brad began his career in construction in New York City after studying architecture at Tulane University, eventually rising through the ranks to become CEO of Plaza Construction. Over the past three decades, he has helped deliver some of the most iconic projects in Miami, including the Mandarin Oriental Miami, W South Beach, One Hotel South Beach, and 1000 Museum by Zaha Hadid.Today at Two Roads Development, Brad is leading large-scale luxury projects across Miami, Tampa, Las Vegas, and the Bahamas, including Four Seasons and Pendry-branded developments totaling billions of dollars in construction and investment.We dive into the evolution of Miami real estate, the importance of long-term relationships in business, the realities of managing billion-dollar developments, and the lessons Brad has learned from building some of the most ambitious projects in the country.🎯 TAKEAWAYS:• How Brad went from framing houses in New York to leading billion-dollar developments• The importance of relationships, trust, and reputation in construction and development• What Brad learned building iconic Miami projects like W South Beach and 1000 Museum• Why pre-construction planning and “zero allowance” budgeting reduce risk on major projects• The differences between developing luxury projects in Miami, Tampa, Las Vegas, and the Bahamas• Why Four Seasons remains the gold standard in branded residences• How Miami has evolved into a global city attracting top talent and capital• The biggest challenges facing Miami’s future growth and development• Why long-term relationships matter more than ever in business and lifeStay up to date with Jay Roberts:Instagram: @jayroberts

    38 min

  7. 23 may

    Mike Neal | The Long Game w/ Jay Roberts #18

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com. On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Mike Neal, CEO of KAST Construction, one of South Florida’s most respected builders with decades of experience shaping the region’s skyline and luxury real estate market. Born and raised in Hollywood, Florida, Mike grew up in a hardworking middle-class family where discipline, accountability, and work ethic were instilled at an early age. From mowing lawns and delivering newspapers as a kid to working difficult construction jobs alongside his father, a union electrician, Mike learned firsthand what it takes to build something from the ground up. Today, Mike leads KAST Construction, a premier South Florida construction firm responsible for delivering some of the region’s most notable residential and commercial projects. In this conversation, we dive into leadership, construction, business growth, South Florida development, and the mindset required to succeed in one of the toughest industries in America. 🎯 TAKEAWAYS: • How Mike Neal’s blue-collar upbringing shaped his leadership and work ethic• The lessons he learned working construction jobs as a teenager alongside his father• Why discipline, accountability, and consistency matter in business and life• The realities of operating in the construction industry and managing large-scale projects• How South Florida’s explosive growth is changing development and construction• What it takes to build a long-term business and reputation in a highly competitive industry Stay up to date with Jay Roberts:Instagram: @jayroberts

    1 h 16 min

  8. 21 may

    Ben Van Leeuwen | The Long Game w/ Jay Roberts #17

    Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com. On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Ben Van Leeuwen, Founder & CEO of Van Leeuwen Ice Cream, one of the most recognizable premium ice cream brands in America. Ben started with a simple idea, a used 1988 Chevy postal truck, and just $60,000 raised from friends, family, and a college professor. Nearly two decades later, Van Leeuwen has grown into a national brand with 100+ stores across the U.S., millions of customers, and international expansion underway in Korea. We dive into the early days of building the business, the reality of raising capital, why location changed everything on day one, how Van Leeuwen built a cult following around high-quality ingredients, and what it takes to scale a brand without losing the product quality that made it special. 🎯 TAKEAWAYS: • How Ben turned a used postal truck into a national ice cream brand• Why every wealthy person told him no before he raised his first $60,000• The day-one lesson that changed how he thought about foot traffic• Why premium ingredients became the foundation of the Van Leeuwen brand• The unsexy operational details that make or break a growing business• How Van Leeuwen is expanding nationally and internationally Stay up to date with Jay Roberts:Instagram: @jayroberts

    35 min
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The Long Game is a podcast hosted by Jay Roberts, CEO of Prosper Group. It is a conversational podcast series featuring billionaire investors, world-class operators, and elite capital allocators who have built enduring wealth through discipline, conviction, and resilience. This podcast explores how real fortunes, brands and companies are created - not overnight, but across cycles - by those who understand risk, survive setbacks, and compound trust, capital, and judgment over decades.

Información

  • Creador
    Prosper Group
  • Años de actividad
    2 k
  • Episodios
    25
  • Clasificación
    Explícito
  • Copyright
    © Prosper Group
  • Mostrar sitio web
    The Long Game

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