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. 1 day ago

    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

  2. 13 Aug

    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

  3. 7 Aug

    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

  4. 30 Jul

    Michelle Cordeiro Grant | The Long Game w/ Jay Roberts #29

    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 Michelle Cordeiro Grant, founder and CEO of Gorgie, one of the fastest-growing better-for-you energy drink brands in the United States. Michelle shares her journey from growing up in rural Pennsylvania as the daughter of Indian immigrants to building a career at companies including Macy’s, Victoria’s Secret, and Thrillist Media Group. She explains how those experiences helped her launch Lively, grow it into a powerful community-driven brand, and sell the company for more than $100 million just four years later. Jay and Michelle discuss raising her first $1.5 million, learning startup financing in real time, finding mentors, and building teams that could support rapid growth. Michelle also shares how she created Gorgie through focus groups, taste tests, social media, and constant customer feedback. Today, the brand is sold in more than 15,000 stores nationwide, has achieved 600% year-over-year retail growth, and counts Jon Bon Jovi and Alix Earle among its investors. The conversation explores entrepreneurship, consumer brands, grassroots marketing, customer retention, resilience, and why progress over perfection is essential when playing the long game. 🎯 TAKEAWAYS: • How Michelle built and sold Lively for more than $100 million• Why experience, mentorship, and curiosity are essential for founders• How customer feedback shaped Gorgie from the beginning• Why community is more powerful than traditional marketing• How Gorgie expanded into more than 15,000 stores nationwide• Why retention and repeat purchases matter more than attention alone• How Jon Bon Jovi and Alix Earle became investors in the brand• Why founders should choose progress over perfection Stay up to date with Jay Roberts: Instagram: @jayrobertsWebsite: ProsperGroup.com

  5. 23 Jul

    Jay Parker | The Long Game w/ Jay Roberts #28

    On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Jay Parker, CEO of Douglas Elliman’s Florida region and President of Douglas Elliman Development Marketing in Florida. Jay shares how moving from Toronto to Miami, attending the University of Miami School of Law, and building a career in real estate helped shape his approach to leadership, relationships, and business. He explains how Douglas Elliman grew from a small Florida operation into one of the state’s leading luxury real estate platforms, with more than 1,000 agents and a new development pipeline approaching $20 billion. Jay and Jay also discuss the rise of branded residences, what makes luxury developments successful, why Florida’s real estate growth is not a bubble, and which South Florida markets still offer major opportunity. The episode offers valuable lessons on leadership, market expertise, team building, adaptability, and why playing the long game means staying passionate, disciplined, and committed to the process. 🎯 TAKEAWAYS:• How Jay Parker helped grow Douglas Elliman’s Florida operation• Why Florida remains a major luxury real estate opportunity• What makes branded residences and new developments successful• Why South Florida’s current market is different from past bubbles• How agents can build lasting careers through expertise and consistency• Why strong relationships and leadership matter in business Stay up to date with Jay Roberts: Instagram: @jayrobertsWebsite: ProsperGroup.com

  6. 16 Jul

    Melissa Medina | The Long Game w/ Jay Roberts #27

    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 Melissa Medina, Co-Founder and CEO of eMerge Americas, the global technology platform that has helped transform Miami into a major hub for innovation, entrepreneurship, and investment. Melissa shares how growing up as a first-generation Cuban American and watching her father, Manny Medina, build and sell Terremark Worldwide shaped her approach to leadership, risk, reputation, and business. Jay and Melissa discuss how a simple conversation about Miami’s lack of a technology ecosystem became eMerge Americas, a global conference and year-round platform connecting founders, investors, corporations, universities, and government leaders from more than 50 countries. They also explore the early skepticism surrounding Miami’s technology potential, the challenges of surviving the pandemic, the migration of capital and companies into South Florida, and why Miami’s growth has become impossible to ignore. Melissa also shares how eMerge supports early-stage founders through accelerator programs, pitch competitions, investor connections, and educational initiatives, helping create thousands of jobs and billions of dollars in economic impact. The episode offers valuable lessons on entrepreneurship, resilience, community building, investing, leadership, and why playing the long game means believing in a vision before the rest of the world sees it. 🎯 TAKEAWAYS: • How Melissa Medina helped build eMerge Americas into a global technology platform • How Miami became a rising destination for technology, capital, and entrepreneurship • Why reputation, consistency, and keeping your word matter in business • How eMerge connects founders with investors, corporations, and opportunities • Why resilience and adaptability are essential when building something new • How AI, quantum technology, fintech, and national security are shaping innovation • Why in-person relationships are becoming more valuable in an increasingly digital world Stay up to date with Jay Roberts: Instagram: @jayroberts Website: ProsperGroup.com

  7. 9 Jul

    Alfonso Costa JR. | The Long Game w/ Jay Roberts #26

    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

  8. 2 Jul

    Kamal Hotchandani | The Long Game w/ Jay Roberts #25

    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

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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
    33
  • Rating
    Explicit
  • Copyright
    © Prosper Group
  • Show Website
    The Long Game

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