The Long Game

Prosper Group
  • 5.0 (2)
  • Entrepreneurship
  • Updated Weekly

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. 2d ago

    Louis Birdman | The Long Game w/ Jay Roberts #37

    On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Louis Birdman, Co-Founder of 1000 Group and one of the developers behind One Thousand Museum, the iconic Miami residential tower designed by legendary architect Zaha Hadid. With more than three decades of experience in real estate development, Louis has helped shape Miami’s skyline through some of its most ambitious residential projects. He shares how his family's early work in condominium conversions evolved into large-scale luxury development, and how a former gas station site became one of the most recognizable architectural landmarks in the world. Jay and Louis discuss the vision behind One Thousand Museum, the story of bringing Zaha Hadid to Miami, and the extraordinary challenges of constructing one of the city's most complex skyscrapers. Louis also shares how his team navigated the 2008 financial crisis, why they took a chance on downtown Miami before it became a global luxury destination, and what it takes to deliver projects that redefine a city's skyline. They also dive into Louis' latest developments, including Villa Miami and Anantara, the growing influence of hospitality and branded residences, and how luxury buyers are prioritizing lifestyle, privacy, and service. From navigating financing and construction challenges to building lasting relationships and exceeding expectations, Louis shares the lessons he's learned from decades of playing the long game. 🎯 TAKEAWAYS: • How Louis Birdman went from condominium conversions to developing Miami's most iconic luxury towers• The story behind One Thousand Museum and its transformation from a former gas station site• How Louis and his partners convinced legendary architect Zaha Hadid to design the project• The engineering, construction, and logistical challenges behind One Thousand Museum• How Louis navigated the 2008 financial crisis and Miami's changing real estate cycles• Why larger residences, exclusivity, and architectural design became central to his development strategy• Inside Villa Miami and its partnership with Major Food Group• Bringing the Anantara luxury hospitality brand to Miami• Why hospitality, lifestyle, privacy, and service are shaping the future of branded residences• The realities of financing, competition, and managing complex real estate developments• How Miami evolved from a seasonal destination into a global city• Louis' advice on consistency, exceeding expectations, and playing the long game Stay up to date with Jay Roberts: Instagram: @jayrobertsWebsite: ProsperGroup.com

  2. Sep 24

    Manny Angelo Varas | The Long Game w/ Jay Roberts #36

    On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Manny Angelo Varas, Founder, President and CEO of MV Group USA, the luxury builder known as the “Billionaires’ Builder.” Manny has spent more than two decades building and renovating some of South Florida’s most extraordinary homes, with projects for high-profile clients including Rick Ross, Lil Wayne, Jennifer Lopez, and members of the Bezos family. He shares how he went from taking on a $200,000 government housing renovation early in his career to leading projects that now range from $50 million to $100 million. Jay and Manny discuss the power of “terminal value thinking,” relationship economics, and why focusing on long-term value instead of short-term profit helped build MV Group into one of South Florida’s leading luxury construction firms. Manny also breaks down the financial strategy behind ultra-luxury homes, how he approaches building for billionaires and family offices, and why great design can completely change the value of a property or neighborhood. They also dive into Manny’s work on Rick Ross’ Star Island estate, the evolution of Miami’s luxury market, what the world’s most successful people have in common, and MV Group’s new partnership with legendary Italian design house Pininfarina to create a limited collection of branded luxury homes. 🎯 TAKEAWAYS: • How Manny went from small interior build-outs to $50M–$100M luxury projects• Why he believes in “terminal value thinking” over transactional thinking• How relationship economics helped grow MV Group• The story behind the Coral Gables estate purchased by the Bezos family• How Manny transformed Rick Ross’ Star Island estate and created significant additional value• What billionaires and family offices actually look for when building homes• Why carrying costs, efficiency, and pre-construction planning matter so much• How Miami’s luxury neighborhoods and buyer demands are evolving• What the world’s most successful people have in common• Inside MV Group’s new Pininfarina branded-home concept• Manny’s advice for building relationships, creating value, and playing the long game Stay up to date with Jay Roberts: Instagram: @jayrobertsWebsite: ProsperGroup.com

  3. Sep 10

    Alicia Cervera | The Long Game w/ Jay Roberts #35

    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 Alicia Cervera Lamadrid, Managing Partner of Cervera Real Estate and one of Miami’s most experienced real estate leaders. Alicia has worked through every major Miami real estate cycle since 1980 and helped lead the sales of more than 115 condominium projects. She shares how Miami evolved from a young regional market into a global destination for capital, luxury real estate, business, and culture. Jay and Alicia discuss her family’s legacy in Miami real estate, her longtime work with Jorge Pérez and Related, the rise of neighborhoods like Brickell and South of Fifth, and how today’s pre-construction market differs from the cycles that came before it. Alicia also explains why she remains bullish on Miami and West Palm Beach, what makes a great real estate agent, and why relationships, work ethic, and resilience still matter most. 🎯 TAKEAWAYS: • How Alicia built a four-decade career in Miami real estate • How Cervera helped pioneer the developer sales model • Alicia’s work with Jorge Pérez and Related • How Miami recovered from 9/11 and the 2008 financial crisis • Why today’s pre-construction market is structurally different • How Miami’s neighborhoods have evolved • Why Alicia remains bullish on Miami and West Palm Beach • What it takes to become a top real estate agent Stay up to date with Jay Roberts: Instagram: @jayroberts Website: ProsperGroup.com

  4. Sep 3

    Joe Magazine | The Long Game w/ Jay Roberts #34

    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 Joe Magazine, Miami Beach City Commissioner and Senior Partner at Fortuna Investments, a venture capital firm focused on technology, energy, critical resources, and national security. Joe brings more than two decades of experience in finance, beginning his career on Wall Street at Merrill Lynch and later holding roles at firms including Deutsche Bank, Barclays, and Loop Capital. He shares how the work ethic and perspective he developed in New York ultimately shaped his approach to business, investing, public service, and leadership. Jay and Joe discuss his unexpected path into politics, including the grassroots campaign that saw him knock on thousands of doors and ultimately win his Miami Beach election by just 67 votes. Joe explains why accessibility, community involvement, and simply listening to residents became central to the way he governs. The conversation also explores Miami’s transformation into a global center for capital, technology, entrepreneurship, and luxury development, along with the challenges that come with rapid growth — including housing affordability, infrastructure, education, public safety, and maintaining Miami Beach’s unique character. Joe also breaks down his work at Fortuna Investments, including investments in aerospace, uranium, nuclear energy, rare earth minerals, and other industries he believes will become increasingly important to America’s economic and national security. Jay and Joe also discuss fiscal discipline in government, Miami Beach’s approach to homelessness and spring break, bringing new education options to the city, the future of property taxes in Florida, health and wellness, padel, and why giving back to your community can ultimately be more fulfilling than professional success alone. 🎯 TAKEAWAYS: • How Joe went from Wall Street to Miami Beach City Commissioner • How knocking on thousands of doors helped him win an election by just 67 votes • Why Wall Street taught him the value of work ethic, humility, and preparation • Why Joe believes Miami is building a real economy beyond traditional boom-and-bust cycles • How Miami Beach is balancing economic growth with housing, infrastructure, and quality of life • Why fiscal discipline and responsible government spending matter • How Fortuna Investments is investing in aerospace, uranium, nuclear energy, and rare earth minerals • Why rare earth minerals and domestic energy production are becoming national security issues • How Miami Beach is approaching public safety, homelessness, education, and community development • Why Joe believes giving back and staying connected to your community are essential to a meaningful life Stay up to date with Jay Roberts: Instagram: @jayroberts Website: ProsperGroup.com

  5. Aug 27

    John Parsiani | The Long Game w/ Jay Roberts #33

    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 John Parsiani, founder and CEO of Parsiani Real Estate**, a developer advisory firm behind some of South Florida’s largest luxury projects. John has personally closed more than **$1.6 billion in sales**, while his team has surpassed **$5 billion**.John shares his journey from fleeing Iran as a child and growing up in Sweden to building a career in Miami real estate. He explains how those early experiences shaped his mindset, resilience, and pursuit of the American dream.Jay and John discuss the **“Seal Team Six” approach** behind Parsiani Real Estate, why preparation and trust matter more than chasing transactions, and how putting relationships first helped John build a career in luxury development sales.John also tells the story of meeting **Marc Anthony** after a mysterious phone call and ultimately advising him *not* to buy a penthouse — despite having a major commission on the line — because it wasn’t the right property for him.The conversation also explores Miami’s transformation, personal development, Ferrari culture, material success, and why John believes **trust, relationships, and knowledge compound more than capital**.🎯 **TAKEAWAYS:**• How John built more than $1.6 billion in personal real estate sales• Why he built Parsiani Real Estate like a specialized “Seal Team Six”• Why preparation and trust are critical in real estate• The story behind John’s relationship with Marc Anthony• Why relationships matter more than short-term commissions• Why John believes Miami is still early in its growth• How mindset and self-development shaped his career• Why patience and long-term thinking are essential to successStay up to date with Jay Roberts:**Instagram:** @jayroberts**Website:** ProsperGroup.com

  6. Aug 20

    Matthew Baron | The Long Game w/ Jay Roberts #32

    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 Baron, founder and president of Baron Property Group, a vertically integrated development and investment firm building across New York City and Miami. Matthew shares lessons from more than two decades in real estate development, from navigating complex financing and market cycles to building a pipeline totaling nearly 4 million square feet, more than 3,600 residential units, and over $2 billion in value.He takes Jay inside the refinancing of Metro parc, a 559-unit rental development in Hialeah, including how a lender pulled out just days before a $225 million refinancing was expected to close and how his team was forced to replace hundreds of millions of dollars in capital. Jay and Matthew also discuss the Amazon HQ2 deal in Long Island City that could have generated substantially over a quarter of a billion dollars for Matthew and his partners before Amazon abandoned its plans for New York City in 2019. The conversation explores the challenges facing real estate development in New York, the impact of rent stabilization and proposed rent freezes, why capital and developers are increasingly looking toward Miami, and the dramatically different experience Matthew had developing in South Florida.Matthew explains why he prefers rental developments over condominiums, how long-term ownership can help developers withstand market downturns, and why successful real estate development requires patience, resilience, strong relationships, and the ability to constantly adapt. He also shares lessons from one of the worst deals of his career, why entering unfamiliar markets without deep local knowledge can destroy a project, and why failure and experience remain two of the greatest teachers in business. 🎯 TAKEAWAYS: • How Matthew built a real estate development pipeline valued at more than $2 billion • What happened when a lender pulled out days before a $225 million refinancing • The story behind Matthew’s Amazon HQ2 deal in Long Island City • Why Matthew believes failure is an unavoidable part of long-term success • Why relationships, communication, and transparency matter during difficult deals • Why Matthew believes New York has become increasingly challenging for developers • How Miami’s approach to development and investment differs from New York • Why Matthew prefers rental developments over for-sale condominiums • How market cycles and long-term ownership can create opportunities for developers • Why local knowledge is critical when entering a new real estate market • Why resilience, adaptability, and the ability to pivot are essential in development • How Matthew thinks about playing the long game in real estateStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com

  7. Aug 13

    Vicki Lopez | The Long Game w/ Jay Roberts #31

    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 Miami-Dade County Commissioner Vicki Lopez, who represents District 5, including Brickell, Downtown Miami, Little Havana, Miami Beach, and surrounding communities. Vicki shares her journey from earning an accounting degree at Notre Dame and working as an investment banker to entering public service, first as a county commissioner and later serving in the Florida House before returning to local government. Jay and Vicki discuss Miami-Dade’s housing affordability crisis, the influx of new residents and capital into South Florida, and why increasing housing supply and incentivizing developers are critical to keeping Miami accessible to working families, first responders, teachers, nurses, seniors, and young professionals. Vicki also breaks down her work on Florida’s Live Local Act and explains how the legislation has evolved to encourage more attainable housing while accounting for the unique needs of communities such as Miami Beach. The conversation also explores the condominium reforms passed in the wake of the Surfside tragedy, including stronger reserve requirements, structural inspections, special assessments, and the realities of maintaining aging condominium buildings throughout South Florida. Jay and Vicki discuss property tax reform, government spending, Miami International Airport, the future of transit between the mainland and Miami Beach, PortMiami’s continued expansion, the Fisher Island fuel facility, the I-395 Signature Bridge, and the transportation challenges facing Miami’s rapidly growing urban core. Vicki also explains why she believes effective government requires collaboration between residents, developers, capital markets, community organizations, and public officials—and why local government gives her the opportunity to directly address the issues affecting the people she represents. 🎯 TAKEAWAYS: • How Vicki Lopez went from investment banking to public service • Why housing affordability remains one of Miami-Dade’s biggest challenges • How the Live Local Act incentivizes developers to build more attainable housing • Why Miami needs more housing for teachers, nurses, firefighters, first responders, seniors, and young professionals • How the Surfside tragedy reshaped Florida’s condominium safety laws • Why condo reserves, structural inspections, and special assessments have become major issues for Florida homeowners • Vicki’s perspective on property tax reform and government spending • Why Miami International Airport and PortMiami need continued investment and expansion • The transportation challenges connecting Downtown Miami, Miami Beach, and the surrounding urban core • Why collaboration, negotiation, and listening to constituents are essential to effective local government Stay up to date with Jay Roberts: Instagram: @jayroberts Website: ProsperGroup.com

  8. Aug 7

    Fred Voccola | The Long Game w/ Jay Roberts #30

    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 Fred Voccola, former CEO and current vice chairman of Kaseya and chairman and CEO of simPRO Group.Fred shares his journey from teaching himself to code and starting his first software company in college to becoming one of the most accomplished operators in the technology industry.He explains how he sold his first company during his senior year, helped take another company public, built and exited multiple software businesses, and eventually transformed Kaseya from roughly $50 million in revenue into a $1.5 billion global business valued at approximately $15 billion.Jay and Fred discuss scaling companies, acquiring and integrating businesses, developing high-performance teams, and why successful founders must remain deeply involved in the details of their organizations.Fred also shares the inside story of the 2021 Kaseya ransomware attack, including the decision to immediately shut down the platform, work alongside the FBI, communicate transparently with customers, and protect millions of businesses around the world.The conversation explores artificial intelligence, cybersecurity, preventative medicine, Miami’s entrepreneurial culture, and Fred’s vision for simPRO, an AI-powered field service platform helping trade businesses dramatically improve their efficiency and profitability.🎯 TAKEAWAYS:• How Fred started and sold his first software company while still in college• How he helped build and exit multiple successful technology companies• How Kaseya grew from roughly $50 million to $1.5 billion in revenue• Why obsessive, hands-on founders build the strongest organizations• How transparency helped Kaseya navigate a major ransomware attack• Why Fred believes Miami is uniquely suited for entrepreneurship• How AI could transform medicine, cybersecurity, and field service businesses• Why entrepreneurs must love the journey rather than focus only on an exit• How simPRO is using AI to improve profitability for trade contractors• Why grit, accountability, customer service, and long-term thinking are essential for successStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com

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Ratings & Reviews

5
out of 5
2 Ratings

About

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.

Information

  • Creator
    Prosper Group
  • Years Active
    2026
  • Episodes
    38
  • Rating
    Explicit
  • Copyright
    © Prosper Group
  • Show Website
    The Long Game

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