The Long Game
The Long Game is a conversational podcast hosted by Jay Roberts, CEO of Prosper Group. It features billionaire investors, world-class operators, and elite capital allocators who have built enduring wealth through discipline, conviction, and resilience. The show explores how real fortunes, brands, and companies are created over cycles by those who understand risk, survive setbacks, and compound trust, capital, and judgment over decades.
Episodes
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
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 w
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 accomplish
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
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
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
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. De
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 int
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 Bea
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
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 include
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 Relate
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 reg
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 Tula
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 hardworki
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,
Allie Eichner | The Long Game w/ Jay Roberts #16
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
Tommaso Chiabra | The Long Game w/ Jay Roberts #15
$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
MJ Green | The Long Game w/ Jay Roberts #14
$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 develop
Fredrik Eklund | The Long Game w/ Jay Roberts #13
$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 Ne
Don Peebles III | The Long Game w/ Jay Roberts #12
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
Margit Brandt | The Long Game w/ Jay Roberts #11
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
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 unpreceden
Leonard Chinchay | The Long Game w/ Jay Roberts #009
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
70% Cash in Miami… While NYC Raises Taxes?
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
Brian Gale | The Long Game w/ Jay Roberts #008
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 deal
Michael Simas | The Long Game w/ Jay Roberts #007
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 inn
Mathieu Massa | The Long Game w/ Jay Roberts #006
In this episode of The Long Game, we sit down with Mathieu Massa, the founder behind some of Miami’s most iconic hospitality concepts, to break down his journey from growing up in the south of France to building a multi-million dollar hospitality and real estate portfolio in Miami.Mathieu shares how he moved to Miami in 2007, raised capital from Europe, and began investing in distressed real estat
Kobi Karp | The Long Game w/ Jay Roberts #005
In this episode of The Long Game, we sit down with internationally acclaimed Architect Kobi Karp who has spent more than four decades shaping Miami’s skyline and delivering some of the market’s highest-value luxury developments.In this episode of The Long Game, we break down the mindset behind longevity, the evolution of high-end real estate, record-breaking price points, and what it takes to desi
Kevin Peake | The Long Game w/ Jay Roberts #004
On this episode, we sit down with Kevin Peake, president and co-founder of NEXT Health, one of the fastest-growing brands in health optimization and longevity. We explore how Kevin helped launch and scale the company, what’s driving the shift toward proactive, data-driven medicine, and his bold vision for living well beyond 150 years. A powerful conversation on performance, prevention, and designi
Alvaro Nuñez | The Long Game w/ Jay Roberts #003
In this episode, Jay sits down with ultra-endurance athlete, entrepreneur, author, and high-performance trailblazer Alvaro Nunez. Together they unpack the mindset that drives Alvaro to tackle feats most people wouldn’t attempt — from running marathons across seven continents in seven days, conquering the harshest races on Earth, to using extreme challenges as tools for mental toughness, purpose, a
Dina Goldentayer | The Long Game w/ Jay Roberts #002
In this episode of The Long Game, Jay Roberts sits down with Dina Goldentayer, a leading Miami Beach luxury real estate expert. They discuss her career, the realities of operating at the highest level of a competitive market, and the long-term mindset required to build sustained success in real estate and beyond.
Isaac Toledano | The Long Game w/ Jay Roberts #001
Isaac Toledano is a real estate developer and the Founder & CEO of BH Group, with active projects across Florida and partnerships with some of the most established developers in the country.Isaac joins Jay to talk about what separates long-term winners from short-term thinkers, why he only invests in prime real estate, and how conviction, speed, and selectivity shape his decision-making. He br
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