The Long Game

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...

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

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 unprecede...

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 theor...

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...

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 dea...

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 in...

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 esta...

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 des...

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...

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...

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 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 b...