The Long Game

Épisodes

• Kamal Hotchandani | The Long Game w/ Jay Roberts #25 02.07.2026 46min

  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
• Matthew Whitman | The Long Game w/ Jay Roberts #24 26.06.2026 55min

  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 evolutionStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com
• Elizabeth Macbride | The Long Game w/ Jay Roberts #23 21.06.2026 47min

  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 lifeStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com
• Sam Nazarian | The Long Game w/ Jay Roberts #22 18.06.2026 1h 17min

  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
• Carlos Rosso | The Long Game w/ Jay Roberts #21 12.06.2026 37min

  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
• Ralph Choeff | The Long Game w/ Jay Roberts #20 04.06.2026 45min

  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
• Brad Meltzer | The Long Game w/ Jay Roberts #19 29.05.2026 38min

  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
• Mike Neal | The Long Game w/ Jay Roberts #18 23.05.2026 1h 16min

  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 industryStay up to date with Jay Roberts:Instagram: @jayroberts
• Ben Van Leeuwen | The Long Game w/ Jay Roberts #17 21.05.2026 35min

  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 internationallyStay up to date with Jay Roberts:Instagram: @jayroberts
• Allie Eichner | The Long Game w/ Jay Roberts #16 15.05.2026 47min

  On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Allie Eichner, President of Continuum Companiesand one of the leading voices shaping luxury waterfront development in Miami today.Allie grew up around one of the most iconic real estate development families in the country and is now leading the next generation of the Continuum brand — the team behind the legendary Continuum South Beach towers, widely considered the gold standard for oceanfront luxury living in Miami. Today, she’s spearheading major waterfront projects including Continuum Club & Residences in North Bay Village and several other transformative developments across South Florida.We dive into the evolution of Miami luxury real estate, legacy development, waterfront living, and what it takes to build projects that stand the test of time. Allie also opens up about her unconventional upbringing, competitive mindset, early independence, and the lessons that shaped her approach to leadership and business.🎯 TAKEAWAYS:• How the Continuum brand became one of the most iconic names in Miami luxury real estate• The vision behind Continuum Club & Residences and Miami’s next wave of waterfront development• Why experiential amenities and “boat-in, boat-out” living are reshaping luxury housing• How Allie’s upbringing and competitive tennis background built resilience and independence• The realities of carrying on a legacy brand in a rapidly evolving Miami market• Why Miami continues attracting global wealth, entrepreneurs, and ultra-high-net-worth buyersStay up to date with Jay Roberts:Instagram: @jayroberts
• Tommaso Chiabra | The Long Game w/ Jay Roberts #15 08.05.2026 41min

  $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
• MJ Green | The Long Game w/ Jay Roberts #14 30.04.2026 36min

  $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 M.J. Green, Chief of Economic Development & Strategy at the Miami Downtown Development Authority.MJ brings a unique background—from wealth management at major financial institutions to building community development funds that have deployed capital across the U.S.—before stepping into one of the most important roles shaping Miami’s future.We dive into what’s really driving Miami’s explosive growth—from downtown development and infrastructure to the influx of capital, talent, and global attention. MJ breaks down the strategy behind transforming Miami into a true 24/7 urban core—and why the job is far from finished.We also get into the numbers behind the boom, the evolution from a tourism-driven city to a diversified business hub, and what it will actually take for Miami to compete on a global level over the next decade.🎯 TAKEAWAYS:Why Miami is in a once-in-a-generation “timing window” for growthHow the DDA is using grants and incentives to attract restaurants, retail, and startupsThe real impact of 500,000+ monthly cruise passengers on downtown economicsWhy downtown Miami now has three built-in customer bases (residents, workers, tourists)How projects like Flagler Street, the Baywalk, and the Underline are reshaping connectivityWhy Miami shouldn’t try to become Silicon Valley—and what it should be insteadHow rising wages and population growth are stabilizing the city’s economyThe role of relationships and community in building long-term business successWhy global capital, logistics, and lifestyle are all converging in Miami right nowWhat needs to happen next for Miami to fully become a world-class business hubStay up to date with Jay Roberts:Instagram: / jayroberts
• Fredrik Eklund | The Long Game w/ Jay Roberts #13 23.04.2026 1h 2min

  $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 Fredrik Eklund, one of the most successful real estate brokers in the world.Fredrik has sold nearly $30 billion in real estate, sold out over 140 buildings, and became a global name through Million Dollar Listing New York - but he started in New York with no clients, no network, and no safety net.We dive into his journey from early startup failures to breaking into real estate and using TV to build one of the most powerful personal brands in the industry. He explains how he went from his first deal to becoming a go-to broker for developers worldwide.We also cover what separates elite brokers, why authenticity wins, and how building a strong team has kept him at the top for over two decades.🎯 TAKEAWAYS:Why Fredrik believes being fully yourself is the ultimate sales advantageHow he used reality TV as a strategic tool to build trust at scaleThe real story behind his first deal—and why he still remembers every detailWhy new development is the highest level of real estate and how he dominates itHow timing, luck, and preparation combined to launch his careerWhy the best brokers think like developers—not just salespeopleThe importance of building a team that feels like family (and why solo agents fall behind)What ultra-wealthy buyers actually want—and how it differs by marketWhy long-term success in real estate takes at least 5 years of real commitmentHow exposure from TV turned into daily inbound listings and deal flowStay up to date with Jay Roberts:Instagram: https://instagram.com/jayroberts
• Don Peebles III | The Long Game w/ Jay Roberts #12 16.04.2026 35min

  On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Don Peebles III, Chief Operating Officer of The Peebles Corporation, the largest Black-owned real estate development company in America.We dive into his origin story—growing up at the dinner table learning cap rates before long division, being immersed in the family business from an early age, and building his own credibility inside one of the most respected development firms in the country.Our conversation explores how The Peebles Corporation has built a four-decade track record across major U.S. cities by targeting both ends of the market—ultra-luxury and affordable housing—while most developers compete in the middle. Don breaks down the story behind the Bath Club, one of Miami Beach’s most historic private clubs and now a cornerstone asset in the firm’s portfolio.He also shares why off-market relationships are the only deals worth doing, what the next generation of real estate development looks like, and the mindset that has kept The Peebles Corporation at the top for over 40 years.This episode reveals what it looks like when legacy, credibility, and the right market thesis compound across generations.🎯 TAKEAWAYS:Why The Peebles Corporation targets both ends of the barbell—ultra-luxury and affordable housing—and why chasing the middle is a losing strategyThe full story behind the transformation of the Bath Club into one of the firm’s most iconic assets as it approaches its 100th yearWhy a 12-seat omakase restaurant inside the club could be on the verge of a Michelin starHow nearly 5,000 affordable housing units could define the firm’s next chapter—and why affordability should be a stepping stone to ownershipHow Peebles wins deals by going directly to sellers and avoiding marketed listings entirelyWhy information is more valuable than money—and how transparency builds long-term investor trustHow AI is reshaping real estate and why interpersonal skills now matter more than technical expertiseIf you’re interested in investing with Prosper Group, visit https://prospergroup.com/invest/Stay up to date with Jay Roberts:Instagram: https://www.instagram.com/jayrobertsFor more information about Don Peebles III and The Peebles Corporation:https://peeblescorp.com
• Margit Brandt | The Long Game w/ Jay Roberts #11 09.04.2026 29min

  On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Margit Brandt, Senior Luxury Real Estate Advisor at Premier Estate Properties.If you’re interested in investing with Prosper Group, visit prospergroup.com/investStay up to date with Jay Roberts at instagram.com/jayrobertsFor more information about Margit Brandt, visit https://margitbrandtpalmbeach.com
• Fernando De Nuñez y Lugones | The Long Game w/ Jay Roberts #010 30.03.2026 28min

  In this episode of The Long Game, Jay Roberts sits down with Fernando De Nuñez y Lugones, CEO & Co-Founder of Vertical Developments, to break down the global forces shaping Miami’s real estate market.From investment banking and international markets to building ultra-luxury branded residences, Fernando shares how capital flows, geopolitical shifts, and demographic trends are driving unprecedented growth in South Florida.They discuss:Why global capital is moving into MiamiThe strategy behind branded luxury developmentsHow macroeconomics impacts real estate decisionsThe future of interest rates, debt markets, and investor behaviorWhy Miami continues to outperform global citiesIf you want to understand how wealth, capital, and real estate intersect on a global level—this episode is for you.
• Leonard Chinchay | The Long Game w/ Jay Roberts #009 27.03.2026 21min

  In this episode of The Long Game, we sit down with Leonard Chinchay to break down what actually builds trust in real estate investing and why “skin in the game” isn’t just a phrase, it’s a requirement.From raising capital to executing deals, Leonard explains how alignment between sponsors and investors is what separates sustainable success from short-term wins. This conversation goes beyond theory and dives into the full lifecycle of an investment from acquisition to exit and what serious investors should be paying attention to at every stage.We cover: Why having real capital at risk changes everything.The importance of investor alignment and accountability.What a proven track record actually looks like.How strong investor relations are built over time.The formula that consistently delivers results.This episode is a clear look into how experienced operators think about capital, risk, and long-term performance.
• 70% Cash in Miami… While NYC Raises Taxes? 24.03.2026 8min

  we break down the numbers behind one of the biggest economic shifts happening right now.In 2025, 70% of Miami-Dade $1M+ condo purchases are all cash — and at the highest end of the market, that number jumps to 85%. At the same time, cities like New York are proposing higher income taxes, property taxes, and major changes to estate taxes.So what does the data actually show?We cover:The surge of all-cash buyers in Miami real estateWhat rising tax policies in New York could meanThe growing divide between high-tax and low-tax statesWhy Florida continues attracting capital and high-net-worth individualsThis episode focuses purely on the numbers — and what they reveal about where money is moving in the U.S.
• Brian Gale | The Long Game w/ Jay Roberts #008 19.03.2026 34min

  In this episode of The Long Game, Jay Roberts sits down with Brian Gale to break down what’s happening in today’s real estate market.They discuss how the market has shifted, what agents are seeing on the ground, and how strategies are evolving in response. Brian shares his perspective on staying competitive, adapting to changing conditions, and the role of consistency and marketing in closing deals.The conversation also touches on client expectations, navigating uncertainty, and what it takes to keep momentum in a slower or more complex market.If you're in real estate or paying attention to where the market is heading this is a grounded look at what’s actually going on right now.
• Michael Simas | The Long Game w/ Jay Roberts #007 12.03.2026 47min

  In this episode of The Long Game, we sit down with Michael Simas, CEO of the Florida Council of 100, to discuss Florida’s rapid economic growth and why companies, investors, and entrepreneurs are increasingly choosing the state.Michael shares insights from his career in New York and explains how Florida’s business environment, talent pipeline, and pro-growth policies are attracting capital and innovation. We also discuss infrastructure, affordable housing, and the long-term strategy behind Florida’s continued expansion.GoldCoastFlorida.com