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.
The Long Game
Claim This Podcastby Prosper Group
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27 episodes
Updated Daily
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Podcast Overview
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.
Language
🇺🇲
Publishing Since
1/28/2026
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Recent Episodes
July 9, 2026
Alfonso Costa JR. | The Long Game w/ Jay Roberts #26
<p>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 Alfonso Costa Jr., Chief Operating Officer of The Falcone Group, one of South Florida’s leading real estate development firms.Alfonso shares his journey from Yale, Harvard Law School, and Oxford to serving as a senior official at the U.S. Department of Housing and Urban Development during the Trump administration, where he helped advance major housing and economic development initiatives including Opportunity Zones.Jay and Alfonso discuss the power of discipline, education, athletics, public service, and long-term mentorship in shaping a high-performance career. Alfonso also shares how his work in government led him into private real estate development, where he now helps oversee a portfolio of large-scale projects across South Florida.The conversation explores Opportunity Zones, the Live Local Act, workforce housing, public-private partnerships, Miami Worldcenter, and the long-term vision behind major mixed-use developments that reshape cities over decades.Jay and Alfonso also dive into Miami’s rise as a global destination for capital, real estate, and development, as well as the importance of patience, flexibility, and staying power in both business and life.The episode offers valuable lessons on leadership, real estate, policy, long-term investing, community impact, and why playing the long game means building with vision, discipline, and purpose.🎯 TAKEAWAYS:• How Alfonso Acosta Jr. built a path from elite academics and athletics into government and real estate• Why discipline, teamwork, and lifelong learning are critical to long-term success• How Opportunity Zones are driving investment into underserved communities• Why the Live Local Act is changing the future of workforce and attainable housing in Florida• The strategy behind Miami Worldcenter and large-scale mixed-use development• Why patience and flexibility are essential in real estate cycles• How public-private partnerships can unlock new housing, jobs, and community growth• Why Miami continues to attract major domestic and international capital• The importance of asking questions, staying humble, and learning from people around youStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com</p>
July 2, 2026
Kamal Hotchandani | The Long Game w/ Jay Roberts #25
<p>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 Kamal Hotchandani, Co-Founder and CEO of Haute Media Group, the luxury media company behind Haute Living, Haute Residence, Haute Jets, Haute Beauty, Haute Wealth, and more.Kamal shares how he built a single Miami-based luxury publication into a global media platform spanning more than 20 markets, serving some of the world's most influential entrepreneurs, investors, developers, celebrities, and luxury brands. He discusses the power of long-term relationship building, creating value before asking for anything in return, and how community became the foundation of Haute Media's success.Jay and Kamal also explore the evolution of luxury media, the rise of AI-powered search and generative engine optimization (GEO), Miami's emergence as a global capital for wealth and real estate, and why the next decade belongs to businesses that adapt early to artificial intelligence.The conversation offers valuable lessons on entrepreneurship, branding, relationship capital, innovation, and why playing the long game means creating opportunities that compound over decades.🎯 TAKEAWAYS:• How Kamal built Haute Living into one of the world's leading luxury media brands• Why leading with value creates long-term business opportunities• The importance of building authentic relationships and community• How luxury brands create lasting customer loyalty• Why Miami has become a global hub for wealth, luxury, and entrepreneurship• How AI and generative search are transforming media, marketing, and business• The strategy behind expanding into luxury real estate, aviation, and lifestyle businesses• Why patience, consistency, and long-term thinking are the foundation of lasting successStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com</p>
June 26, 2026
Matthew Whitman | The Long Game w/ Jay Roberts #24
<p>Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.</p><p>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.</p><p>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.</p><p>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.</p><p>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.</p><p>🎯 TAKEAWAYS:</p><p>• The 100+ year history of the Whitman family's real estate legacy<br />• How Bal Harbour Shops became one of the world's premier luxury shopping destinations<br />• Why long-term thinking beats short-term decision making in real estate<br />• The philosophy behind curating unforgettable retail experiences<br />• The challenges of expanding landmark developments in today's regulatory environment<br />• How Florida's Live Local Act is reshaping workforce housing<br />• Lessons on leading a multi-generational family business<br />• Why preserving a legacy requires constant innovation and thoughtful evolution</p><p>Stay up to date with Jay Roberts:</p><p>Instagram: @jayroberts<br />Website: ProsperGroup.com</p>
27 total episodes available
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- What is The Long Game?
- How often does this podcast release new episodes?
This podcast updates daily.
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This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
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Yes, this podcast regularly features guests.
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